If you miss me sliding into your email inbox on a regular cadence, Binge-Worthy GTM is now where you can find me online (it’s double opt-in — so be sure to confirm your email after you sign up). The party continues over there.

I’ll be sending my kickoff post later this week, and there’s plenty more where that came from.

Sign up for Binge-Worthy GTM

Looking forward to seeing you,
Ross

Subscribe now

Let’s boogie:

Let’s talk about gardening. If you want to plant a bountiful garden, there’s a logical process you need to follow. To start, you need to decide what size garden you can manage. Then, you’ll need to figure out what types of vegetables you want to grow. Depending on what you like to eat, you may plant more tomatoes than string beans. You may not even plant carrots or onions at all. Perhaps you love corn, and you decide to dedicate half of your garden to those big lumps of juicy knobs (sorry, I had to do it). Once that all is decided, you gather the correct seeds, water the stalks, provide ample sunlight, wait, wait some more, and finally harvest your creations. Editors Note: I’m sure it’s slightly more complicated, but I’m not a botanist.

Ultimately, what you plant is as important as how you grow it. If you’re looking for a well-balanced diet, you shouldn’t just plant potatoes. If you’re planting a bunch of different types of vegetables, you can be sure they require different quantities of water. And, if you plant a garden and then forget to water it altogether… well, then, you probably won’t have a garden for very long.

Please don’t stop reading to go grab a salad. I promise this is going somewhere.

The collection of friendships you cultivate over your lifetime is a lot like a garden.

You and a particular friend have a unique relationship. You won’t get everything you want or need from each one.

This is a piece of advice my Dad shared with me growing up. You can’t expect every friendship to fulfill every need you have. Likewise, you can’t expect to follow the same formula to nurture every friendship. Each one is like its own vegetable, requiring specific attention and care. However, they are all built on the same foundations of camaraderie, trust, and mutual respect. Some friendships are meant to be simple. Others, like close friends, are meant to be deeper and more intricate.

Different vegetables provide unique nutritional benefits and flavor profiles, and thus you eat them in different quantities and frequencies. So while lettuce may make sense to eat every day, super spicy peppers are probably good for once in a blue moon. Additionally, lettuce doesn’t contain all of the nutritional value we need for a balanced diet, so we naturally choose to diversify what we put in our bodies. In turn, why should we expect one friend to scratch all of the itches we have from non-familial relationships? Reality check. We shouldn’t.

While thinking outside the box is welcome for most things in life, I operate under the impression that friendships are better off placed inside one.

Some friends are great for Friday nights out. Others are there when you’re going through a tough time. In rare cases, you find a smaller group of friends you enjoy immensely and will be there no matter what. These are your close friends. More on them shortly.

Sometimes we get caught expecting more from our friends than we should. This leads to stress and disappointment. In difficult times, we may fault looser friends for not sending a condolence card. On birthdays, we may fault our work friends for forgetting to celebrate. I’d argue we feel disappointed because we set relationship expectations at a higher level than mutually agreed upon for the friendship in question.

For today’s grid, rather than a traditional 2x2 grid—which has been a Gridology staple for more than two years—I’ve opted for a more holistic chart: a Venn diagram with three circles. Yes, Venn diagrams are a type of grid. I make the rules here.

The overlapping areas of this Venn diagram offer us an opportunity to examine common relationship types, assess how to effectively nurture them, and set the right internal expectations to not stimy their growth.

In the first circle, we have reciprocity. Here, I define reciprocity as an approximately equal give and take between you and your friend. Do they text you or call you as much as you call them? Are you the one always trying to make plans to meet up or are they the ones? Strong friendships are like strong romantic relationships—they are two-sided. One-sided relationships build frustration and resentment.

In the second circle, we have fun. This is a rough measure of how much time you spend smiling or laughing with your friend. Do you 100% enjoy yourself when you are hanging out? Do you have fun no matter what you are doing or is it just limited to a specific domain?

In the third circle, we have trust. As Jeff Weiner aptly says, “trust is consistency over time.” Trust is something that takes years to build but can evaporate in a moment. Trust also unlocks deeper connections. There’s no quick way to build trust—it requires continuous commitment. Building trust in a relationship means opening up to others about personal topics and feeling supported to continue doing.

Understanding the Grid

This grid should help classify your friendships to gain greater clarity on where to spend your time and how to set the right expectations.

As I’ve written previously, there are many reasons why you may have conflicts with your friends. However, that prior post failed to mention all how we could set the wrong expectations with our friends, leading to conflict. Today’s grid builds off this work, with an emphasis on how to nurture different relationship archetypes effectively to not have them spoil.

Heavy Hitters

This is where reciprocity and trust overlap. Heavy hitters are often people you see all the time but don’t enjoy their company unconditionally. Typically, this means people at work fall into this category. Given you’re seeing these people almost every day, there are many opportunities to build trust. Reciprocity grows from there. That may mean you and your work buddy instant message each other equally as often. It could also mean you both equally invite each other to do activities outside of work. However, the moment you switch jobs, your relationship is at risk. While you have trust, the reciprocity—the tenet that kickstarted your relationship in the first place—starts to fade.

Outside the office, heavy hitters can come from any place you frequent. Perhaps you go to the same coffee shop every morning. You may start to develop a relationship with the owner of the store. As you continue buying lattes and croissants, trust between you both starts to develop. However, the moment you decide to stop going to that coffee shop, your friendship is as good as done.

Fun is a requirement for taking these friendships to the next level. Without fun, it’s hard to see heavy hitters in your life for the long haul. In situations where fun gets added to a heavy hitter, the relationship has the opportunity to blossom into a close friend relationship or jump to a historical pal (more on that soon).

New Entrants

This is where reciprocity and fun overlap. Some friends are fantastic because they offer reliable opportunities to have fun. When you have reciprocity and fun, it’s easy for each person in the friendship to extract utility from the relationship. For example, you may have friends that are based on doing a specific activity together—that could be working, hitting the gym, going to a sporting event, talking through a tricky career situation, or going to an art class. Because these friends are often activity-based, they tend to be newer to your life. As you try new things, you meet new people.

Because trust isn’t developed yet, you keep your relationship tethered to a single domain. Imagine going out on a Saturday night to a party with your friend from pottery class. It could happen in theory, but it isn’t the norm. I also doubt this person would be the first person you asked to go to the party with you. In this scenario, pottery acts as the glue to your friendship. For as long as you both decide to continue to throw clay, you both will protect the quality of your relationship. However, should one person lose interest in pottery before, I’d expect this reciprocity would fade and soon, too, your friendship.

While trust isn’t the focal point of your friendship, that’s okay. Remember our garden, not every vegetable provides the same utility. Heavy hitters enable us to have a buddy when doing a specialized interest. I had a friend throughout college who I’d frequently go to EDM concerts with on the weekends. We would share new concerts that popped up on the calendar with each other. And for a good year or two, we probably went to 10 or so concerts in downtown Chicago. While we were friends at school outside of that, concerts were the real way in which we enjoyed each others’ company. Nothing wrong with that. Without each other, we’d be at the concert alone or, worse, not at all. However, when we graduated, our friendship, unfortunately, began to fade.

Historical Pals

This is where fun and trust overlap. With historical pals, you enjoy your relationship, but for one reason or another, neither person in the friendship decides to actively communicate or schedule events with the other. This category often is filled with old friends from high school, college, camp, or work. Because you’ve known this person for years, trust is well established. Plus, when you’re together, you both always have fun. However, initeria and societal tropes cause historical pals to stay historical pals rather than transform into close friends. We tell ourselves silly narratives such as “Oh I shouldn’t randomly message this friend because I haven’t spoken to him in six months” or “I can’t randomly ask this person to go grab dinner. That would be weird.” That said, when you finally silence these narratives and make a plan with a historical pal, you are left dumbfounded as to how you let so much time pass before you hung out.

Historical pals have all the kindling and tinder required to become close friends, but old habits and dynamics can be hard to disrupt. Plus, for historical pals to transform into close friends, it needs to be mutual. Reciprocity only works when it is a two-way street.

Close Friends

This is where reciprocity, fun, and trust overlap. From my experience, close friends are historical pals that increase reciprocity over time or new entrants that build enough trust outside of their current domain of overlapping interest. Close friends are individuals who you trust deeply, enjoy unconditionally, and engage equally. There is mutual respect. They’re the people who you’re always texting. You never feel strange about picking up the phone and just giving them a call.

When it comes to nurturing close friendships, maintaining trust and reciprocity is the most important. Given the nature of your friendship, fun with these people is almost guaranteed. However, as life throws more obstacles and responsibilities our way, it can be challenging to schedule the right amount of time to grow your friendships. Close friendships, like romantic relationships, can combust with a single breach of trust. Maintaining your honesty is essential. However, when close friendships continue to get the love and support they need to continue growing, they can blossom into the best friendships you’ll ever have.

Grid Shortcomings

1. This grid fails to account for the negative effects conflict has on relationships. This framework falls apart when conflict arises and causes individuals to act irrationally. If you have a historical pal but are often arguing with this person, it’s safe to say that this longstanding relationship could be in jeopardy. While disagreements are not necessarily considered breaches of trust, they erode all factors that support healthy friendships.

2. This grid doesn’t talk about friendship objectives. Hot take: you probably don’t want every friend you make to become a close friend. Some relationships are best left in their original category. Close friendships require lots of time to grow. At most, I’ve found I can manage five or so close friendships at a time. Again, this is okay. Not every friend needs to become a close friend. Keep people in the categories (or try to nurture them) into the ones that make the most sense for you. Prioritize the people that matter.

Best friends start at one tenet and take time to work their way to the very center of today’s grid. Like our garden, you can’t expect to plant seeds, add water and sunlight, and be able to see a full-grown tomato the next day. These things take time. I hope that this grid helps you keep the right expectations with the friendships you carry. How do you think about building, nurturing, and maintaining your friendships? I’d love to hear your thoughts in the comments.

Life’s only as confusing as you let it be,
Ross

Subscribe now

I’m excited to be behind the keyboard once again. Thank you to many of you for encouraging me to get back to writing (you all know who you are). Much appreciated.

Subscribe now

Let’s party:

“Deep down, nobody really knows anything,” I blurted out matter-of-factly—frustrated with the current direction of the class conversation. I was sitting in one of my final MBA classes (People, Power, and Politics) at NYU Stern. It was a crisp November morning. Plenty of students were gripping their pumpkin-spiced lattes and sharing their grievances about toxic work environments.

At the moment of my boldness, we were talking about leadership and imposter syndrome. As the conversation shifted to the different techniques people use to overcome feelings of self-doubt and anxiety, the class could have been mistaken for a needed therapy session. Student after student shared example after example of times he or she felt like a fraud.

Mind you, I was in a room of 40 high-achieving, mid-career professionals—all hailing from top undergrad schools and employers. How was it possible that so many people had the same experience of anxiously waiting for the moment when everyone found out they don’t belong? Myself included.

As my moment of clarity continued to brush over me, I continued sharing my perspective with my classmates. “Why are we all doubting ourselves when it’s clear nobody knows anything? It’s silly to feel like an imposter when clearly everyone around you feels the same way. Everyone’s just doing their best, and most of the time that’s plenty good enough.”

Socrates is famous for saying:

I am the wisest man alive, for I know one thing, and that is that I know nothing.

“Nobody knows” is Socrates dumbed down and simplified. Feelings of being an imposter should fade upon the realization that if you’re a fraud, then so too is everyone else.

Yet, our minds love to play tricks on us. What’s the modern workplace if not a playground for social politics and a sandbox for figuring out your own self-worth?

I’ve had imposter syndrome many times throughout my career:

• When I moved to San Francisco to start my career at LinkedIn, I thought “I hope the leaders of my rotational program don’t realize they should have accepted these other students from Northwestern.”

• When I changed roles and joined the insights team, I thought “I hope my manager doesn’t regret hiring me when I don’t know how to code as well as the rest of the team.”

• When I was accepted into NYU Stern’s Tech MBA program, I thought “I can’t believe admissions picked me vs the hundreds of others who applied.”

• When I started Gridology, I thought “Will anyone care what I have to say? What on Earth do I actually know?”

• When I became Chief of Staff at Sounder, I thought “I hope I know what I’m doing.”

Realizing that everyone alongside you is winging it is the first step toward putting imposter syndrome behind you. Today’s grid builds on what to do next. Feelings of self-doubt are normal when society has trained us to believe it at every turn.

On the x-axis, we have the people you choose to engage. When imposter syndrome strikes, who do you consult? Choosing the right community to help you build your confidence can cause feelings of imposter syndrome to dissipate quickly. Opting to confront imposter syndrome alone prevents growth.

On the y-axis, we have your ego. In life, are you humble or arrogant about your capabilities? Are you quick to admit your blindspots or do you tend to bullshit your way through things you don’t know? Having the right attitude about professional development is essential in overcoming feelings of self-doubt.

Understanding the Grid

This grid illuminates that the best way to overcome imposter syndrome is with curiosity. When you have a growth mindset and invest in a quality support community, anxiety and stress start to fade.

Curiosity

You seek out community and do so with humility. When I started as Chief of Staff at Sounder, I felt overwhelmed. In classic startup fashion, my role is to wear many hats across the business: marketing, business operations, investor management, and other priority projects that pop up along the way. While I had a strong belief in my skill set to meet deadlines and figure stuff out, many of my day-to-day responsibilities were new for me. So rather than wallow in self-doubt, I sought a community to help. When I joined the On Deck Chief of Staff fellowship, it exposed me to a group of people who had similar roles and dealt with similar feelings. The fellowship even had a session on how to handle imposter syndrome earlier this year.

After many of the conversations I had with my peers, what became clear to me was how everyone had a similar story of self-doubt to tell. With so many people looking to fill in their blindspots with collective group wisdom, I felt less alone. My confidence and—in turn—my effectiveness improved. Imposter syndrome transformed from feelings of self-doubt to an opportunity for accelerated growth.

There are so many different types of valuable communities. My On Deck fellowship is one small example. Whether you invest time in your own personal board of directors, close family, or friends, know that spending time sharing and learning from others about your feelings of imposter syndrome will give you greater confidence in your ability to achieve.

Peacocking

You seek out community and do so with arrogance. If you trade humility for arrogance in a group setting, you’re set up to gain far less wisdom. If I had entered my On Deck fellowship with an ego, it would have prevented me from learning new skills needed to get better at my job. In this setting, being arrogant would have shielded me from others in the program seeing me as incapable or undeserving of my title. If I pretend to know everything, then clearly I know what I’m doing and have a lot to offer! That’s just science.

However, this would have been a massive miss. Peacocking can work but only temporarily. It’s only a matter of time before expectations for your abilities do not match reality. The community could and most likely will reject you for your dishonesty and lack of value.

Overcoming imposter syndrome is not simply convincing others that you know what you’re doing. It is realizing that while nobody expects you to have all the answers, they do expect you to be able to find them and then act accordingly. When you’re pretending to be something you’re not, you’ve actually failed at the assignment. When you engage with a community, gain value from it by being eager to learn. Bring these learnings back with you to your job—making you more productive, successful, and confident.

Doubt

You isolate yourself and act with humility. In this quadrant, negative self-talk runs rampant. You feel out of place and anxious. Oftentimes nothing is actually going wrong at work. However, your lack of confidence is destroying your perception of how you are performing at work. Because you’ve isolated yourself, you don’t have anyone to tell you that these feelings are common. There’s no one there to coach you through difficult moments. Oftentimes the isolation can cause self-loathing, frustration, and inaction. Because you feel out of place at work, you can start disengaging entirely. Feeling alone and undeserving are two key ingredients for an imposter syndrome cocktail.

Posturing

You isolate yourself and act with arrogance. Like peacocking, you are pretending you have skills you don’t actually have. However, when you’re posturing you’re doing so with your colleagues and teammates rather than with an external community. This is a recipe for disaster. If you were hired to do a job and then are all talk and no game, you’re on a path to a quick termination. Arrogance is the kiss of death.

A quality treatment option for imposter syndrome is positive feedback. When you are learning and growing, you—logically—get better at your job. However, when you don’t know what you’re doing and make it as if you do, positive feedback is not headed your way. Posturing saves face in the short-term to only destroy it in the long term. Opt to be open about your shortcomings and eager to learn. Your team will respect you more for it.

Grid Shortcomings

1. This grid doesn’t take into account self-guided learning. While the doubt quadrant is real—I’ve certainly been there—there’s also an alternative to it. Though you chose to isolate yourself, you could have engaged in private learning to build your skill set. Recognizing you don’t have all the skills needed to thrive in your job, you take courses, watch videos, and read books to fill in blind spots and build confidence. Not all growth stems from engaging with a community. However, when it comes to overcoming imposter syndrome, communities help increase the speed at which you can grow. When learning as part of a group, skill gaps are quickly identified and addressed while your emotions are cared for.

2. This grid doesn’t take therapy into account. Talking to a therapist about feelings of self-doubt and anxiety is a powerful tool to help you adjust the narratives you tell yourself. It’s helped me immensely.

The cure for imposter syndrome is a deep devotion to having a growth mindset. The more you believe that you are a work in progress, the less pressure you put on yourself to achieve at all times in every situation. Give yourself some grace. You’re where you are in life because you deserve to be there.

Life’s only as confusing as you let it be,
Ross

P.S. Thank you Fred again.. for powering my 5am writing session to get this post out. Unbelievable what you can accomplish when you can’t sleep and have awesome music.

Subscribe now

If you’re enjoying Gridology, it would mean the world to me to forward today’s post to someone else who may want to subscribe. Have them join 325 curious and growth-minded individuals also receiving 2x2 breakdowns of questions regarding life, business, careers, and (mental) health.

Subscribe now

Let’s boogie:

I always thought I knew what I was doing when it came to setting SMART (specific, measurable, achievable, relevant, and time-bound) goals. Every December, when it came time to review my performance, my list of “achievements” often didn’t match my list of goals.

In fact, I barely accomplished any of the things I thought I wanted to do by the end of the year.

Here are some examples from 2017 and 2018:

This pattern of hitting 50% of my goals (at best) continued through 2020. The routine was clinical:

• December: Think about things I’d love to have said I accomplished by this time next year. Create a laundry list of those items, and make them stretch, but achievable goals.

• January: Set them in stone, and get started planning a few of the items on the list.

• February to November: Status quo as usual. Continue living life the exact same way as I was before I wasted 10ish hours reflecting on my life and setting new goals I won’t achieve.

Maybe this sounds familiar because you may currently do something similar. We all have personal, health, and professional goals we’d like to achieve in the short and long term. Writing them down is a great way to manifest those things into reality.

That said, we can write down anything we want. We all know too well that merely writing down something doesn’t mean anything. I could write down that I want to be in the NBA. Great. So what? It doesn’t make a 5’8 guy with a 6-inch vertical any more likely to ride the bench next to LeBron. In fact, it may mean I have a distorted sense of athletic ability or that I’ve never actually watched the NBA. (Disclaimer: I stink at basketball and this example got out of hand).

While exaggerated, the point is clear: Writing things down is important for you to identify your goals. However, without a real plan—developed in achievable, small daily habits—success is slim to none.

In my last post, I discussed I was in the middle of reading Atomic Habits by James Clear. At the risk of sounding like another Millennial self-help bro who had his life changed by reading Atomic Habits, he does make honest and well-backed points about manifesting change in your life. Throughout the book I felt myself nodding along, wondering if I was Jim Carrey in The Truman Show. Example after example was something I had done: make unrealistic promises, aim big, start for a few days, stop cold turkey.

Had James Clear been watching my life on television and then using what he saw as examples for his book? I’m unconvinced.

At its core, Atomic Habits is about manifesting small actions through strategic planning. Want to lose weight? Make it really, really easy for yourself to go to the gym after you finish work by laying out your gym clothes and shoes so they are waiting for you when you get home. Want to read more? Charge your phone overnight in your living room, and put a book on your nightstand. Want to save money? Set up automatic bank transfers to move $20 a week to a savings account.

As creatures of habit, we gravitate towards the status quo. Only when a new easy alternative is introduced—one that aligns with the identity we want to craft and makes us feel better in our own skin—will we go out and grab it. Even then, habits are hard to maintain. They require nonstop strategic planning through environment design, automation, and practice.

That’s what today’s grid is all about. It’s time we all swap SMART goals for annual charters. While James Clear’s approach is all about setting up small daily habits that compound into massive, annualized gains, my approach is slightly different. It requires you to set your identity (or guiding theme) for the year. What principles will you live by? How do you act on those principles every single day?

On the x-axis, we have the underlying intent for your goal. Deep down, what’s the reason you want to achieve this item? Most goals, hopefully, are because you value them as part of your personal identity. However, some goals are on paper for performative reasons—perhaps a close family member or friend expects something of you which causes you to manifest that expectation into reality.

On the y-axis, we have how you set that goal. While this axis may feel like straight nuance—it is actually the most important aspect of actually achieving your goals. Are you setting them up as milestones—just like I did above? That’s a recipe for failure (we will discuss more).

Understanding the Grid

This grid will help you set and revise your goals to be achievable, rather than being a source of anxiety next year when you inevitably fall short (sorry for the bluntness, but this has always been a no-BS newsletter).

Compounding Growth

Your goals are true to your identity, and you set them as habits. Ink your charter. Identify where you want to make strides for the year and attack it. I started writing my goals in the form of an annual charter for my birthday last year. A friend and previous Gridology collaborator, Guillermo Echarte, introduced me to the idea. It starts with setting an intention for yourself. I spend about three to five weeks crafting this document—allowing it to sit and marinate in the background while I continue to process what should be included, discluded and refined. This year, I chose to focus on Balance. Here’s what the top of my document looks like:

This is my “vibe-check” for the year. Below the paragraph I shared with you all above, are three sections for the key areas of my life: personal, health, and professional. Each section has a guiding mantra, four to five principles, and a few tangible goals. The tangible goals are a mix of items. Some are habits I want to create by year-end. Some are milestone moments that act as a north star. The habits I’m choosing to build should compound and allow me to realize my goals. Whenever I start to feel unbalanced or disorganized, I reread this document. It resets my intentions.

If you’re interested in learning more about this process, I’m happy to chat or provide a template. At its core, this type of annual charter allows you to better define and then attain the goals you set for yourself.

North Star

Your goals are true to your identity, and you set them as major milestone achievements. This quadrant is where the goals I shared from 2017 and 2018 mostly land. They are big goals without a plan. They’re like shooting a bow and arrow with a blindfold on. Unless you’re Hawkeye, you’re going to miss. That said, they directionally serve a powerful point. Together, these goals define your aspirational identity—who you want to become. Once you have your North Star goals, you can easily break them down into more tactical, achievable habits that compound over time.

For example, take two North Star goals that appeared on both of my lists from 2017 and 2018: reading 10 or more books. This is a North Star goal. At the time, I believed I wanted to just read more. Because I didn’t carve out the right space and habit, that reading mostly consisted of low-brow news articles and Twitter threads. However, this year, I introduced a habit-based approach. I’ve already read one book this year, and I’m halfway through another. My North Star goal helped me define the identity I wanted to set for myself: to become a book reader. Thus, my daily habit is now to read a book for 10 minutes either right when I wake up or right when I get into bed before I fall asleep. This habit has a pretty slick reward—it “unlocks” my ability to go on social media. I read in the Apple Books app so there is a convenient reading tracker at the bottom. Here are my results since I started this new habit right before New Year’s Eve:

I’ve never read this consistently before in my entire life. Forty days of reading 10+ minutes in a row already enabled me to read more books in 2022 than I did in all of 2021. What started as a struggle at first has turned into a must-have daily routine. I even seek out to accomplish my 10 minutes of reading outside of the time windows in which it’s scheduled.

Performance Art

Your goals are performative, and you set them as habits. These are autopilot goals that typically begin by accident or for the wrong reason. Simply put, these goals are at odds with your target identity. They cause you to focus on the wrong things. That’s because most of the time these goals are never written down as intentional goals. They operate in the shadows. Performance Art goals are best explained with an example.

While I’ve never written it down on my list of goals for the year, it’s always been important for me to be informed about what’s going on in the country and world. That led to the number of newsletters I read a week to peak in 2020 (without counting, it was at least 20 or 25). However, when I took a closer look at my desire to be informed, I realized it came from a place of thinking I needed to be always connected and informed. So, in 2021, I unsubscribed from a few superfluous newsletters and became less OCD about having to have my email inbox have close zero unread newsletters at the end of the day. Instead, I’ve adjusted my goal to be reading the news on my time. That means I get to reading newsletters whenever I get to them. If they are more than a few days old, then I just delete them (2017 me would have gasped if he read that last line). The best thing to do with Performance Art goals is to audit your behaviors and reflect on why you do the things you do without thinking about them.

Mount Everest

Your goals are performative, and you set them as major milestone achievements. These goals are moonshots—items that typically go unresolved on a bucket list unless they are properly evaluated and acted upon. I had to learn Python on my list of things to achieve for two to three years before I finally did it. While I wanted to learn Python, it wasn’t anywhere close to an item at the top of my list. It was, however, something I thought I should do to become a better analyst. I also thought learning Python could potentially lead to a faster promotion. It wasn’t until I actually needed to learn Python for it to happen (there was a project I was working on in 2019 that forced my hand). Mount Everest goals either move to the North Star quadrant and then to Compounding Growth to be actioned on or, with greater reflection and prioritization, Mount Everest goals fade away from your grid entirely. Mount Everest goals are items that feel awesome in theory but haven’t been properly embedded into your new identity.

Grid Shortcomings

1. This grid doesn’t include joy. While realizing your goals is great, the journey is often more important than the final destination. So while things may be important to achieve personally or professionally, if you don’t have fun while doing it then these goals come at too high of a cost.

2. This grid doesn’t include how to leverage your community. My goals are rarely set alone. This year, Guillermo and I caught up and shared our goals with each other—talking about how last year went and what we wanted to change for this year. While these goals are totally my own, it is great to have to explain them to someone else. Like most things in life, your understanding of any topic becomes greater when you have to explain it to someone else. It causes you to deeply understand why you wrote down the things you did. It forces you to be hyperaware of what you’re doing and why you’re doing it.

This grid helps me think through how I set goals. While I find goalsetting a powerful way to realize your big, hairy, and audacious dreams, I frequently change how I do it. I’d be lying to you in saying that I found the answer that will empower you to achieve your dreams, but I’m confident that my approach to doing so right now is the best it’s ever been.

I expect it only to get better every year.

Life’s only as confusing as you let it be,

Ross

Subscribe now

Let’s dive in:

I’m going to let you in on a little secret. Nobody knows what’s best for you. You’re the only person who knows that. In today’s world, where self-help is as prevalent as a cup of coffee, we may lose sight of that concept.

However, it’s important to keep this in mind while reading today’s post. Every year, we are inundated with hundreds (thousands?) of books, blogs, podcasts, treks, and courses that try to convince you that your life would be better if you listened to their guidance. In reality, much of it is noise. Nobody really knows whether you should quit your job, get a dog, go to business school, finally go gluten-free, or ask your partner to marry you.

And, while Gridology probably falls in the broader category of self-help, I’ve always applied a take-it-or-leave-it approach to this newsletter. I let you all in on how I approach questions, and it’s up to you to apply them to your life, situation, or circumstance. And, as you’ll see in a moment, I try to write every newsletter so that it lands in the Good Habits quadrant.

A few weeks ago, David Perell published a mini-essay regarding the paradoxes of modern life. His definitions are brilliant. I’ve embedded it below. Give it a quick read:

However, I think he missed an important one: The Paradox of Advice. I’ve noticed that when people share advice, it often is a tactic they use to convince themselves they’ve made a good choice. So, in reality, giving advice is a method for them to build self-assurance rather than to provide helpful guidance to others.

Here’s an example: Back in 2019, I was having one-on-one conversations with product managers to learn more about the role and seek clarity on how best to become one. I spoke to a wide range of industry professionals—some at startups and others at big tech. The advice I got was scattered. One said for me to find any role at a startup solving a meaningful problem, and then pivot into product management afterwards (spoiler: that was the path she took). One said for me to pursue a Master’s in Engineering and then I’ll find lots of success job hunting (spoiler: that was the path he took). Another said to find a small company and convince them to let me do product management (spoiler: you get the idea at this point).

Does this mean all of this advice was horrible? Not exactly. The final suggestion on that list ended up being the path that worked for me. When I joined Sounder back in May 2020, I had conversations with the CEO and COO where I discussed the value I could add to the team. A few weeks later, I was managing a big platform release and then planning an upgrade for our creator analytics dashboard.

What this does mean, though, is that when receiving advice that’s merely a regurgitation of someone else’s decision-making, don’t take it as gospel. More on this in a moment.

Without properly evaluating advice, you’re at risk of merely becoming someone else’s supporting detail. Humans are status-seeking animals—any opportunity we have to prove ourselves as smarter, wiser, or more accomplished is one we often take. What looks like assistance may prove to be something else entirely.

So, for today’s grid, I’ll be dissecting the framework I use to evaluate received advice.

On the x-axis, we have the level of specificity for the piece of advice. Published self-help content, for example, often is on the left half of the grid—the creator often fails to tailor the content to a targeted audience, purposefully taking a “one-size-fits-all” approach. One-on-one conversations with individuals you know well often fall on the right half of the grid. These people understand you, your personality, and your background and can offer valuable advice given who you are.

On the y-axis, we have how detailed the explanation is for the piece of advice. Above all, good advice has context. Because nobody truly knows everything about us, we need to understand the background history and reasoning for why people suggest what they do. These details unlock deeper evaluation. With strong explanations, we can assess whether the advice is coming from the right place.

Understanding the Grid

This grid is most valuable when evaluating whether a new piece of life, business, or health wisdom meets the high bar you (should) set for yourself before adjusting your strategy.

Worth Actioning

The advice is targeted and well explained. This is the best type of advice you could possibly receive. Often it comes from family, therapists, close friends, and professional mentors. The advice is given in a one-to-one format. What someone is advising you would not work for anyone else they know—it has that level of specificity. When I was debating leaving LinkedIn for a new job or to go to business school, a mentor I had for four years advised me to try using a different lens to make the decision. Rather than optimizing for the next year of my life—and what would be a better ROI—he told me to think about it in terms of regret and what I could gain outside of a professional context. When I’m 50-years-old, which road would frustrate me more if it was left untraveled? I realized that there will be plenty of jobs in my life but really one opportunity to get an MBA. Given my mentor knew my career goals and my personality, I followed his advice’s reasoning, and it resonated with me.

Further Vetting

The advice is targeted but poorly explained. This is the most dangerous quadrant of the grid because, without careful analysis, advice that should belong in this quadrant accidentally ends up in the Worth Actioning bucket. Too often we seek advice and just take it. We are so desperate for answers that when somebody exudes confidence and prestige, we believe they suddenly know best. Your friend who is kneck-deep in the crypto world and has been flipping NFTs shouldn’t become your financial advisor overnight. Networking conversations with industry professionals shouldn’t be considered prescriptive. In order to confidently take action from guidance, you need to understand the root cause of why someone is offering that advice. In the examples above, is your crypto friend trying to ensure his investments don’t go to zero? Is that connection trying to give himself a needed boost of self-confidence? These intentions are tough to identify. With deeper questioning, greater understanding can be gained. Above all, trust your gut—when something feels too good to be true, it probably is the case. As the quadrant is named, don’t just disregard this advice, continue vetting if the ideas are worth applying to your current strategy.

Good Habits

The advice is universal but well explained. I’m reading James Clear’s Atomic Habits right now, and it has transformed the way I block off my time and carry myself throughout the day. While Clear’s advice is universal, he explains the relevant background information you need to understand his perspective. The book begins with his personal story. When Clear was a sophomore in high school, a baseball bat hit him straight in the face. He needed to be put into a medically induced coma and attached to a ventilator to prevent unintended seizures. He writes:

“I returned home with a broken nose, half a dozen facial fractures, and a bulging left eye… it was eight months before I could drive a car again... I became painfully aware of how far I had to go when I returned to the baseball field one year later.”

However, despite this brutal injury. Clear transformed his life through well-designed habits to help him not only fully recover but also be selected as the top male athlete at Denison University and get named to the ESPN Academic All-American team. He puts real proof behind the systems he preaches later in his book. His explanations give me faith that if I listen to his advice, I can develop good habits.

Clear is just one example in a sea of strong content that can help improve your life. When digesting this information, digest it like a lawyer. Be skeptical. Demand explanations. Question everything. When you do, you will only implement the advice that helps you build good habits over time.

Societal Tropes

The advice is universal and poorly explained. Generalized content and poor individual conversations tend to land in this quadrant. Pithy quotes reign king here.

“Find a job you enjoy doing, and you will never have to work a day in your life.” —Mark Twain

“If you love something set it free if it returns its yours forever, if not it was nevermeant to be.” —Proverb

“Stay hungry, stay foolish.” —Steve Jobs

I’ll stop before I make you vomit. Taken alone, this type of advice is merely just a Societal Trope. They are so well-circulated that they’ve lost their meaning and intention. However, advice in this quadrant can still be useful, directionally speaking. Am I suggesting you listen to Mark Twain, quit the job you hate, and find your passion? Not exactly. However, these quotes won’t die because they represent some ideals worth striving to achieve. Would you rather be in a job you love than hate? Sure, but that’s easier said than done. For guidance that resonates and lands in this bucket, use them as a source of inspiration to go out and find better resources or people that can help.

Grid Shortcomings

1. This grid assumes all advice you are evaluating is directionally positive in nature. This framework breaks down if you’re engaging with objectively bad ideas that could get you hurt or in serious legal trouble.

2. This grid doesn’t mention trust. Having confidence in the places you are receiving advice is the foundation for this grid. You would never action or consider advice from someone who doesn’t care about you.

If this advice helps with evaluating advice (meta… I know), then great! Throw it in the Good Habits quadrant and send it to a friend if you think it would be helpful.

This is the framework I’ve been using for the last few months. I developed it because I found myself to be too trusting of others. When seeking advice, I'd assume everyone was trying to help me make sure I made the right choice. I realized lots of the advice I received from others was coming from a place to help them make sure they already made the right choice. It’s an important distinction that can be the difference maker.

I’d love to hear how you typically think about the guidance you receive. What did I miss? Feel free to comment or shoot me an email.

Life’s only as confusing as you let it be,

Ross

If you want to join 306 curious and growth-minded people in receiving semi-regular updates from me regarding life, business, careers, and (mental) health, then hit that subscribe button.

Subscribe now

Let’s jump in:

One of the most inflammatory things you can say to someone, especially if they’re American, is to call them a quitter.

It breeds antipathy and disgust. If you’ve ever been labeled as a quitter, you know this feeling. It’s like drinking a cocktail that’s two parts guilt, one part shame, and another defeat. The hangover is brutal, too. You feel worthless. Inadequate. Sad.

Growing up, my parents, teachers, counselors, and friends shared the same mantra, “Winners never quit, and quitters never win.” As a child, I interpreted this into an “always try hard even when times are tough” mindset. It means to always power through adversity to reach the other side... where victory is waiting.

This axiom—one I lived by for years and never thought to second guess—began to feel really backwards in 2021.

The “winners never quit” mindset disregards strategy. Sometimes you just can’t bulldoze through the obstacle you’re facing.

It disregards mental and physical health. Sometimes your mind and body shut down and trudging forward is impossible.

It disregards interest. Sometimes you no longer care about the things you start.

Over the summer, some rightfully praised and others wrongfully butchered Simone Biles for her decision to pull out of the gymnastics team and all-around events. Citing a case of the “twisties,” Simone said she couldn’t track herself in the air anymore. For a gymnast, that’s the difference between landing on your feet or getting seriously injured. Above all, continuing would have put her in physical danger… so she didn’t.

Quitting, though, has different connotations depending on the context. For example, quitting a job is commonplace. It’s built into the DNA of what it means to be a corporate employee. It’s so ordinary nowadays that the media has even dubbed all of the employees quitting their jobs in 2021 as The Great Resignation (it even sports its own Wikipedia page).

However, if you quit a hobby or bail on a commitment you run the risk of getting (or feeling) judged. Why is it okay (and considered normal) to quit in some situations yet frowned upon in others?

For today’s grid, let’s disregard all the irrelevant external pressures associated with continuing or stopping any given activity. Let’s focus solely on what it is you’re actually looking to quit. Let’s put everyone else’s opinions where they belong. The trash.

On the x-axis, we have the impact the activity has on your emotional or physical health. When deciding to quit something you should always ask yourself, “Does continuing to do this improve or ruin my life?” The answer here should dictate whether the activity falls on the left or right half of the grid.

On the y-axis, we have how much you enjoy doing the activity. When making a decision to stick with or quit something, it’s important to understand how much you are enjoying both the process of doing the activity and how you feel afterwards. Some activities are a struggle to do (such as going to the gym), but once it’s completed you feel great.

Understanding the Grid

If you’re thinking about quitting something, this grid is immensely valuable. The grid will help you categorize your life’s activities, habits, and relationships in the right frame of reference.

Continue

The activity is healthy and exciting. This is an all systems go quadrant. Blue skies. Clear pastures. The activities in this quadrant are healthy and are enjoyable. For me recently, this has been weight lifting. As a runner for many years, I felt like I needed to take a break from running after completing a marathon back in 2018. My body felt worn down and tired. Weight lifting, however, offers me a chance to feel strong and challenged. When activities make you better physically, mentally, and emotionally there should be no question here: keep going.

Refocus

The activity is healthy but a nuisance. Gridology fell into this quadrant for me by the end of 2020. My laundry list of weekly topics had run dry (or uninteresting for me to write about). Time worked against me—I had commitments as a student and as a part-time startup employee that stretched me too thin (more on that in an upcoming post). So it was time for me to Refocus. Refocusing, or reevaluating the amount of time you spend with an activity, enables you to reflect and make necessary tweaks to your current commitments.

My parents are always quick to remind me of the time where I wanted to quit working for the high school newspaper. While being a member of the newspaper was certainly a positive growing experience for me in high school, when I first joined as a freshman, I found it an anxiety-provoking nuisance. I was intimidated to interview the high school football coach or any of the varsity athletes. Having my name published next to my writing caused real panic. What if my article was horrible? What if I got something wrong? The stakes felt so high. So rather than quitting the newspaper, I refocused my attention into writing articles that didn’t cause as much stress. I eased my way into being a reporter. This led to me becoming the sports editor, then the news editor, then the managing editor, and eventually a journalism student at Northwestern University. Had I not refocused the activity into something more manageable to start, I probably would have quit and failed to cultivate my love for writing.

Pause

The activity is unhealthy but exciting. Most vices fall in this category (or the Quit quadrant). I personally have a self-proclaimed addiction to sweets—just give me a vanilla sheet cake with vanilla icing and I’m a very happy guy. That said, it’s so unhealthy. A big objective for me this year is to build healthy and lasting health habits. Thus, it means taking a pause of many of the sweets I know and love until I can figure out to how to effectively incorporate them into a healthy lifestyle. Being in the pause quadrant is a bit like hitting the reset button with any type of activity. It requires being mindful and reflective about how you treat your mind and your body. This is the Simone Biles quadrant—taking the necessary break from things to ensure you can perform at your fullest potential.

Quit

The activity is unhealthy and a nuisance. In this quadrant, there’s no room for negotiation. The answer here is obvious. If an activity is unhealthy and causing you emotional distress, then why should you continue? As I’ve matured, I’ve realized that several friendships needed to be placed into this quadrant. Sometimes these relationships made me feel bad, anxious, and disrespected. There should be no tolerance for that in your life. Many across the country are quitting their jobs based on the new realities of what it means to be an employee in 2022—to have the ability to work from home or from an office, to have paid parental leave, to have the opportunity to build new skills, etc. When you quit an activity in this quadrant, you feel free. It’s like that feeling of finishing your last exam before break starts—the stress just starts pouring off of you.

Grid Shortcomings

1. This grid ignores dependencies. Some things in life you have to do because people depend on you to do them. Often when I go to my parents house, I shed the “son” title and don the title of “IT repairman.” While it’s not particularly enjoyable—it’s not something I plan on stopping because my folks need the help sometimes. While (hopefully) these required activities aren’t unhealthy, they may force you to operate in the Continue quadrant rather Refocus.

2. This grid ignores external judgment. How other people interpret your decision to stop or continue doing something should have no impact on your decision. The moment you start living out of fear or appeasement, is the moment you know you’ve made a severe wrong turn.

As the new year kicks off, let 2022 be full of meaningful activities, habits, and friendships. When something no longer serves you, cut it out of your life. Let this year be the year where you trust your gut, not your friend, parent, or manager’s opinion. Be ruthless in your prioritization. If you need any help, feel free to reach out—I’m always happy to help.

Life’s only as confusing as you let it be,

Ross

For my first post back from my mini-hiatus, I’m sharing my takeaways from my first completed class at NYU Stern. Special shout out to Professor Nate Pettit for teaching such a terrific course.

And here we go:

Share Gridology

Great leadership is having the courage and ability to drive change in a compassionate, inspiring, and inclusive manner. Great leadership, then, is a lot of things all rolled into one. It’s not a skill you can learn but rather a goal and mindset you can strive to achieve. Becoming a great leader requires many different abilities working together for a higher-order cause.

A younger version of me also wrote a post on leadership. If you want to save the five minutes reading it, here’s younger me’s thesis:

“When your successors outperform you, that's when you know you've done right by them.”

This misses a lot of the nuance. For one, the team could have outperformed you because you were holding them back. It goes without saying that many leaders strive to leave teams better than how they joined them. However, assuming you’re a good leader just because your old team outperforms without your presence misses a few dots between points A and B. There’s more to the story.

I filled in many of these gaps in the last three weeks after finishing my first class at NYU Stern. As you could probably guess, it was a class named Leadership, and it was taught by Nate Pettit. It forced me to rethink many of my views on how to be a great leader. 

Most importantly, I learned being a leader is less about gaining new skills and more about refining ones we practice every day. It’s about being a great listener, having courage, and embracing change. It’s about having the right mindset on how to collaborate with others. These things, right now, are 100% in your control.

Let today’s grid be a tool for us all to strive to be the leaders we want to be.

On the x-axis, we have an individual’s level of emotional intelligence (EQ). I wrote about EQ back in March, but I applied it to the concept of managing your friendships rather than leading people. Great leaders have a high EQ. Full stop. As Professor Pettit puts it, “EQ does not just mean you are nice.” He goes on to say that EQ is characterized by five traits:

1. Self-awareness — How do my actions affect others?

2. Self-regulation — How am I able to monitor and adjust my emotions across different situations?

3. Motivation — Do you have an internal self-drive for improvement?

4. Empathy — Can you know/feel what others are feeling? I’d make the argument here that compassion is probably better to use as it’s based more on your ability to combine action and empathy rather than to just know/feel what others are feeling.

5. Social Skills — Are you generally a tolerable person with good people skills?

For the sake of simplicity, I’d like to narrow the focus for identifying EQ to the most observable indicators: a person’s ability to listen and be honest.

When you listen, and I mean deeply listen, to the point where you provide others the space to solve their own problems just by affording them the opportunity to be heard, it’s an indicator you have strong social skills and are an empathetic/compassionate person. Take any conversation: you have a speaker, and you have a listener. Often when someone speaks, the listener is thinking more about what to say next than what is being said to them. When the listener stops evaluating and starts actually listening, it allows the person speaking to feel more open and cooperative.

When you’re honest—not just with others but with yourself, too—it indicates self-awareness and self-regulation. You can make better decisions from a place of transparency and openness rather than through lies and deceit.

On the y-axis, we have an individual’s tolerance for change and failure. As I alluded to earlier, great leadership is about having the courage to drive change and respond to failure. The best leaders are ones who don’t resist change but seek it. Change is a constant: we can count on the fact that 10 years from now will look nothing like 10 years ago. The best leaders prepare for this reality by shifting priorities, dreaming new strategies, and aligning individuals accordingly. Change, too, is a lot like Rome. It’s not created in a day. Sure, there are seismic, black swan-type events that can rock our system (COVID-19, cough). Those are not the norm, however. That said, great leaders embrace change—however and whenever it comes.

Great leadership also appreciates the power of failing. Not every idea can be a winner, but every failed idea helps lead to winning. Simply put, “failure is a prerequisite to invention.” Great leaders encourage their employees to innovate, fail, and try again. When I worked at LinkedIn, this point was made clear through the company’s culture. Communication from executives to middle managers encouraged every employee to “take intelligent risks.” This provided a safety net for failure. Rather than being scolded for trying an idea that didn’t work, employees were generally recognized for innovating on the status quo.

Understanding the Grid

The objective of this grid is to land in the top right quadrant. The more you can improve your EQ, encourage failure, and embrace change, the more impact you will have as a leader.

Transformation

You have high EQ, and embrace change and failure. Think about the best leaders you’ve known. Here are a few guesses: They don’t only care about your work. They also care about you as a person. When they ask you how you’re doing, responding “good” is considered inadequate... they did deeper. These leaders share their own shortcomings. They don’t pretend to be god-like figures or business messiahs. As Richard Farson and Ralph Keyes wrote in The Failure-Tolerant Leader, “[a]dmitting mistakes show’s a leader’s self-confidence… a blunder admitted is empathy earned.” Transformational leaders build a culture that’s diverse and inclusive—one where all team members can act like themselves and feel like they belong.

These leaders are transformational because of their ability to shape both their business and their people. On the business side, transformational leaders embrace the hunt for new ideas… not necessarily good ideas. Every idea to these leaders can offer essential learnings needed to achieve their vision. When it comes to people, they use their ability to listen and understand rather than speak and demand. This garners respect amongst their team and improves collaboration.

Conservative

You have high EQ, but avoid change and failure. These individuals tend to act more like managers than they do leaders. According to John P. Kotter, managers “cope with complexity” while leaders “cope with rapid change.” This division is profound. When individuals fall in the conservative quadrant, they prefer to resist change rather than embrace it. That’s because the systems they’ve set up to manage current business complexity do not apply to future business complexity. Change creates new obstacles, upsetting the status quo. While these managers care deeply about their team, they don’t accelerate the growth of the business. They prefer to optimize for here and now rather than tomorrow and the future.

Because of their high EQ, these individuals fear upsetting others. However, to enact change, you’re going to upset someone. As Ginni Rometty, former executive chairman and CEO of IBM, says, “growth and comfort do not coexist.” Making people feel comfortable with uncomfortable situations is a large part of being a great leader, and conservative individuals have a hard time operating in uncomfortable environments.

Cures: Demonstrate that doing nothing is more dangerous than pursuing new strategies; showcase how failures are not really failures, but opportunities to learn and find the right solution.

Pushy

You have low EQ, but embrace change and failure. Leadership stereotypes often apply to these people. They can be loud, assertive, demanding, and action-oriented. These traits are considered the “push” elements of leadership—activities that compel others to act. Where these people lack is in the “pull” elements of leadership—activities that build credibility and garner respect through listening. I’m sure you can think of some pushy managers you’ve had… they probably don’t do a good job listening to your feedback. They may be micromanagers. As Maslow said, “To a man with a hammer, everything looks like a nail.” Pushy managers only have a hammer in their toolbox. They must solve problems any way they can. I’ve had managers like this. It’s a painful experience. Things need to be done their way and on their timeline. They do a poor job of listening. When you speak, they evaluate and critique as a means to convince you to see it their way rather than trying to understand your point of view.

Cures: Listening; self-reflection; receiving open, honest, and constructive feedback. 

Stationary

You have low EQ, and avoid change and failure. These individuals believe they know best and are desperate to protect the status quo. After all, the present is the environment where they have thrived. These individuals may be more extrinsically motivated than intrinsically motivated, meaning they care less about seeing the company succeed than they do cashing (large) paychecks. They lean into their titles to assert their leadership ability, too. As a general rule, when you have to tell others to listen to you because you’re the “leader,” you’re not really the leader you think you are. Leadership isn’t bestowed through titles. It’s granted through courage, conviction, compassion, and action. This quadrant could have been named regressive, as these stationary people can cause teams to move backward through intra-team drama and/or poor results.

Cures: Pursue strategies listed in the Stationary & Pushy quadrants.

Grid Shortcomings

1. This grid ignores results. Leaders are ultimately deemed effective when they can drive positive outcomes. Part of driving success is making good decisions. However, every great leader must account for different biases and shortcomings that can negatively affect decision-making (i.e. overconfidence or prospect theory).

2. This grid ignores personality. That’s because it isn’t a strong indicator of what makes for a great leader. Great leaders can be introverted or extraverted, Type A or Type B, ESTJ or INFP. What matters more is someone’s EQ, as discussed.

3. This grid ignores company culture. A strong and healthy culture is a byproduct of great leadership, not an input to it. Transformational leaders build a diverse and inclusive team where everyone has the opportunity to grow.

4. This grid ignores team development. While I didn’t specifically call it out, great leaders help their team become better professionals (and people). As Pettit said in a class lecture, “the higher you go, the more you are judged by the performance of those beneath you.” Great leaders build their team while aligning each member towards achieving a shared and urgent vision.

When you reflect on the best leaders you’ve known, what made them so great? Did you feel like they cared about you as a person and as a professional? Did they listen to you? Did your career accelerate after being on their team? My guess is the answers to all of those questions are yes.

Everyone can be a leader. However, we often default to not rising to the occasion. Being a leader is scary, and it’s not for everyone. However, if you strive to be a great leader there are simple things you can start doing right now to improve.

You can listen better. Rather than interrupting others or “trying to be a good conversationalist,” ask follow-up questions and give them space so they can take their time to speak.

You can pursue the right thing rather than the popular thing. It takes bravery to stand with conviction against the norm for what you believe is right. Conformity is not leadership. It stunts a team’s potential.

While these things are hard, they’re not impossible. All it takes is a bit of courage to get going.

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here or you can check out the podcast.

Click here to take the survey

Nearly nine months ago on March 8, I published the first Gridology post. Every Sunday morning since, there’s been an email from gridology@substack.com in your inbox. That weekly deadline felt like a forgotten friend. From 2007 to 2015, I had an article due nearly every week between my work for the high school newspaper and my journalism classes at Northwestern. However, somewhere along the way after graduation, I stopped writing. The deadline disappeared and so did hitting publish on my work.

There’s something special about writing in public vs. writing in private. The former breeds consistency. The latter breeds intimacy. When others are expecting your work, you actually get something written. When you’re only writing for yourself, it’s easy to procrastinate to the point of avoidance. That said, some of the most important writing I’ve ever done has not been published, nor will it ever be published.

Either way, whether it’s in public or private, writing is cathartic for me. It detangles ideas. It transforms the confusing into the straightforward. It forces me to spend time with my thoughts rather than ignoring them. I’ve missed it. Thank you all for being part of this journey in what has been a wild 2020.

I started this newsletter with just one goal: to give myself a real deadline so I could start consistently writing again. Going in, I had no expectations. Right now, I’m floored at what’s transpired.

Some 2020 Gridology Highlights

• There are 271 people who are subscribed

• I was featured on a podcast

• I spoke on a side projects panel

• I featured six awesome writers and companies through collaborations

• Substack analytics aren’t the best, but Gridology posts have received ~10k views

• Jeff Weiner read and commented on one of my posts

• I made lots of Internet friends through Compound Writing

• I detangled tons of thoughts and ideas by writing consistently for 37 weeks

• My writing improved (I know that because I’ve reread my first 10 posts and would heavily edit them)

• I started a podcast (more to come there)

In an effort to always put out writing I find valuable, I’m going to be taking a short break to refocus, retool, and realign on the type of content I want to publish. While my consecutive writing streak will come to an end, sometimes it’s vital to take a moment to reflect.

With the remaining time I usually occupy on your Sunday morning, I’d greatly appreciate it if you could use it to complete this short reader survey I prepared.

Take the survey

And again, if you have some time and you’d love to jump on a call to discuss Gridology, I’d love that, too.

Wishing you all the best this holiday season. Stay safe.

Life’s only as confusing as you let it be,
Ross

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here or you can check out the podcast.

I wish you all happy and shouting-free Netflix browsing—may you be able to select a movie in five minutes or less.

Let’s dive in:

Share Gridology

It’s 8 pm. You're with your family or your significant other or your kids. You’re in your favorite spot on the couch, smothered in your favorite blanket. A big bowl of Thai food sits on the coffee table in front of you. You’re eager to put something on the television, enjoy it, and crawl right into bed. The problem is you first need to conquer this screen:

Screenshot is taken from Netflix

You can’t dwell on a title for too long. Otherwise, an annoying trailer starts playing (please, oh please, let me press and hold the OK button to preview content). When you move the cursor too slowly, the peanut gallery erupts in a cacophony of grievances to pass the remote. Oh, and don’t even dare navigate this screen too fast, either! That’s a one-way ticket to having the remote snatched from your hand.

This, clearly, is a struggle I know far too well. While I don’t pretend to have all the answers—I’ve been trapped on this screen for the length of an entire Pixar movie just to watch a real Pixar movie (side note: go watch Onward… it’s awesome).

Often, these moments before selecting a group movie can get really heated. You have several people invested in the decision, all with different tastes and past viewing histories. Nowadays, given our lives are filled with dings of distraction and clips of content, it’s a scary proposition for many to put their phone down and watch something for two hours straight. Focus is scary and the reward better be worth it.

To avoid the endless carousel of titles requires focus and finesse. It demands prior preparation. And, hardest and most of all, it requires maturity—something everyone somehow forgets when their movie choice loses to that option they really, really didn’t want to watch.

So, let’s review how to avoid couch conundrums and pick a movie fast.

On the x-axis, we have the environment for how the movie will be selected. Are you operating in a democracy, where everyone has an equal chance to pitch their idea (and have it inevitably shot down)? Or, are you potentially risking the total destruction of the movie night by bestowing full film selection powers to one person? Understanding the rules in which you must operate is essential to picking a winning movie picking strategy.

On the y-axis, we have what type of movie you’re hoping to watch. Are you actually trying to watch a great movie? Are you looking for just some noise in the background to liven up your conversation? Depending on what type of movie night you’re in for should dictate the strategy pursued.

Understanding the Grid

There are two strategies I use that work best (spoiler: they’re the quadrants on the top half of the grid). The Veto Technique works well when you want to give everyone a chance to be the savior of the night. Dealer’s Choice works well when you just want to avoid any bit of debate around what movie to watch.

Veto Technique

You are operating in a democracy, and you want to watch a great movie. Here’s how it works:

• Everyone takes three minutes to come up with a list of five movies they want to watch. These five movies must be ones that you are eager to watch.

• Someone goes first and shares a movie on their list.

• Everyone else has the ability to veto the movie. However, you only have one (or two if you want) “vetoes” to use during the entire selection process.

• If no one vetoes the first movie shared, you just found your selection. Hit play and start watching.

• If someone does veto the film, a veto is selected from that person’s allotment and then the next person suggests a movie.

• The process continues until everyone agrees or a movie is shared and there is no one to veto it.

This method, when you actually follow the rules, is flawless. You spending five to eight minutes picking a movie in a democratic and fun way. Everyone gets along. There’s no arguing. No one stomps out of the room to go watch a different movie.

Hopelessness

You are operating in a democracy, and you don’t really care what movie you watch. This is like trying to pick a restaurant for dinner, asking others in your group where they want to eat, and having them respond, “I don’t care… whatever.” In reality, we all know it’s not whatever. The moment you propose a potential restaurant, someone disagrees. It’s the same deal when picking a group movie. The team is hopeless. Someone will randomly call out a movie to watch only to have it knocked down a moment later. This is how you get caught selecting movies for more than 30 minutes. There are no shared objectives, no boundaries on what the group wants or doesn’t want to watch, and thus no chance of success. Disaster strikes and oftentimes you don’t even end up watching a movie. Go in with focus rather than ambivalence. It makes a world of difference.

Dealer’s Choice

You are operating in a dictatorship, and you want to watch a great movie. This quadrant is simple: one person picks the movie, no questions asked. The rest of the group can certainly put some guidelines around the selection such as no action films, no Tom Cruise movies, no movies released prior to 2010, and no movies below a 70% audience score on Rotten Tomatoes. You can randomly decide who selects the movie or you can set a rotation if you tend to watch movies with the same group. Here you are optimizing for speed. You want to get to a decision quickly. Sometimes, that means letting the selection format be Dealer’s Choice so that the show literally goes on. Not everyone can be happy with the outcome, but it’s just a few hours of your life. Watching something is better than aimless scrolling through title cards.

Background Noise

You are operating in a dictatorship, and you don’t really care what movie you watch. In this quadrant, watching a movie is really the last concern. You are actually just going to talk the entire time anyway, so who really cares what’s playing in the background. Have someone pick a fan-favorite—already-seen comedies fare well in this quadrant—and end the decision making process. It’ll be easier for everyone involved. Another technique that’s effective is someone taking control to force a faster decision from the group. Here’s how it works":

• Whoever has the remote sees any movie they’d watch and, without asking anyone, just starts playing it.

• The room will erupt in anger. This is your cue to give an important ultimatum, “I’m fine not watching this, but everyone has to agree on something different to watch before I turn it off.”

• This acts as an incredible forcing mechanism for the group. With a potentially unapproved movie playing in the background, everyone else begins to focus on new possibilities.

• Once the ultimatum is given, I find it takes five or so minutes to decide a new movie or the team just gives up and watches what was on.

Either way, you end up spending less time on the movie selection screen, which is the goal of this entire post.

Grid Shortcomings

1. This grid doesn’t account for strong personalities. When you are dealing with a Hollywood diva who is extra picky on movies, using any of these strategies may prove ineffective. In these cases, share your plans early. If you want to watch movie with the full group, tell everyone to start thinking and discussing during the day. That way, once it’s time to sit down for a movie, all of the frustrating deliberation will be complete.

Reaching consensus for a group movie night is challenging work. Sometimes it feels like a real battle—something fresh out of Gladiator. Increase your group’s effectiveness during your next movie night by employing some of these strategies. Hopefully it helps the next time you snuggle up for Pad Thai and a movie.

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here or you can check out the podcast.

This is a Thanksgiving week unlike any other. The CDC has recommended a very different type of Thanksgiving, one that's masked, distanced, and outside.

It’s not what any of us want to hear. The last eight months have been a real challenge. That said, there are other ways to celebrate Thanksgiving aside from the entire family on the couch, watching football, and stuffing your face with pecan pie.

Let’s get into it:

Subscribe now

For me, Thanksgiving is family, friends, and loved ones. It’s the crisp autumn air. It’s leaves in red and orange and yellow. It’s flannel shirts and heavy sweaters. It’s pumpkin spiced lattes and pumpkin pie. It’s football. Lots of football. But, above all, it’s an opportunity to take stock of what we have and to stop thinking about what’s missing.

When we pause and reflect, the reality of our lives becomes clear.

Most of us already have what we need. We just forget.

Let this week not just be an opportunity to remember, but to exclaim it. Let this week be your opportunity to let the important people in your life know how much they mean to you. I’ve left important people intentionally vague. Spare no one who matters:

• Family

• Friends

• Colleagues

• Customers

• Doormen

• Mentors

• Role Models

• That person you’re friends with behind the deli counter

Give thanks to anyone and everyone who improves your life. This isn’t a controversial concept. Most people agree that telling people they matter is a worthwhile activity. Where people—myself included—get lost is how to give thanks. Sometimes heartfelt messages feel out of place. Surprise gifts are a challenge to think of and get.

Let today’s grid be a framework for tackling the how to give thanks.

On the x-axis, we have the format of how you give thanks. There are dozens of ways to show others you’re grateful for them. On one end, the simplest thing you can do is use your words—telling people they matter in text or to their face. On the other, you can give someone a meaningful and personal gift. The strength and nature of your relationship should the way to demonstrate to them that you care and they matter.

On the y-axis, we have the forum for how you give thanks. Not every expression of gratitude needs to be on display for everyone to see. Sometimes, however, sharing praise publicly is a simple way to demonstrate high praise.

Understanding the Grid

This grid is most powerful when used as a framework to power your thinking around how to demonstrate gratitude. All four categories below are worthy of your time. Different individuals in your life will fall into one (or multiple) categories. Use what you know about the person’s personality and the nature of your relationship to choose a quadrant that works best.

Awards & Surprises

You give someone a gift in public. Public displays of gift-giving, when done right, can create immeasurable amounts of goodwill and affection. For example, when I left LinkedIn a little more than eight months ago, my team surprised me with a going-away gift featuring a personalized Photoshopped cake, back-to-school supplies, and a marble notebook filled with heartfelt notes. It warmed my heart. The gift assured me I had made a difference as both a colleague and a friend to my coworkers. Because of that warm send-off, I have and will always have a special place in my heart for the Insights team at LinkedIn. Big, public, sentimental gifts are best used to show thanks in milestone moments: farewell parties, marquee birthdays, end-of-year awards ceremonies.

Something Special

You give someone a gift in private. Holidays, birthdays, and anniversaries are perfect opportunities to demonstrate thanks with private, personalized gifts. It allows the person being recognized to know that you listen and care. Sometimes, however, no occasion is needed. This week, George Clooney was in the news for doing something special. In an interview, he explained why he had given each of his closest friends a million dollars.

While this is an extreme example, the sentiment is there. “Why wouldn’t you do that, you schmuck?” When people matter—when they really show up for you—show them you noticed. It’s in these moments, where people go above and beyond, that you should, too. It’s when a gift is worth more than just verbal or written pleasantries.

Digital Love

You share kind words about someone in public. Best reserved for projects with a set start and end date, sharing public words of thanks is a powerful way to quickly show people they matter. However, this format isn’t limited to just projects—any occasion will do. Often it’s easiest (or least awkward-feeling) to publicly share a sentimental message of love on people’s birthdays or relevant holidays. For example, here’s a post I shared about the important women in my life (I believe for International Women’s Day back in 2018):

Publicly expressing how much these women impacted my career trajectory was an easy way for me to demonstrate to them how important they all are to me.

Dwayne Johnson is an even better example of someone who’s mastered Digital Love. You don’t need to look hard to discover that The Rock understands the value of gratitude. It’s all over his Instagram, where he often gives thanks to crew members, co-stars, his team, his family, and ordinary people who are doing awesome things. Giving thanks and recognizing others is in The Rock’s DNA. See for yourself (both Instagram posts are videos, so you have to click on them… and remember to read the caption):

Personal Messages

You share kind words with someone in private. For me, this quadrant is my favorite. I’m always shocked and elated when someone writes me a personal note of gratitude. Email, text message, snail mail… it doesn’t matter. To me, what matters most is that someone took the time to share serious words of praise or thanks. George H. W. Bush did this often. In fact, he was known for it. Frank Blake, former CEO of The Home Depot and deputy counsel to Bush when he was Vice President, said this of Bush’s letter-writing habit:

“Vice President Bush started every day by typing notes to people. You knew they were typed by him because some of the letters were off line and there could be misspellings. I saw the power of taking the time to write a nice word to someone.”

Inspired, Blake took up the practice himself. He says he must have wrote at least 25,000 notes. Personal messages matter. I’m always quick to shoot someone a meaningful text message or email after a favor. While we can debate whether writing notes by hand and sending them over USPS is more meaningful than the immediacy of a sentimental digified note, what we can agree on is writing something is better than writing nothing at all.

Grid Shortcomings

1. This grid doesn’t mention when you should give thanks in multiple quadrants. Oftentimes, both quadrants on the top or the bottom half go together. For example, when giving a personalized gift, it’s common that a sentimental note is also part of the package. Ultimately, there’s no science. Just use your judgment. Bigger, Herculean moments deserve all the thanks they can get.

So, while we all may not be with all of our loved ones this Thanksgiving—this is the first time I won’t be spending Thanksgiving at home with my parents—there are ample ways to show them that they matter and we care. Don’t lose the spirit of the holiday just because the holiday looks a little different.

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here or you can check out the podcast.

Was this post forwarded to you? Why not get Gridology delivered to your inbox every Sunday morning? The subscribe button is just below.

Subscribe now

Let’s jump in:

One of my favorite things to do outside of work is to help my friends with their resumes. A buddy of mine calls me “The Walking Career Office: Open 24/7.” While I consider it an overly nice compliment, I don’t consider myself the de facto authority on what makes the perfect resume. That said, I’ve seen enough examples to know when a resume does an excellent job. I’m eager to share that wisdom with you all today. Please use this guide as an input in a sea of resources available to you online.

At its core, a resume is supposed to prove one thing: That you have professional abilities well-beyond your current job title.

Your resume should demonstrate to a recruiter that you’re an all-star candidate. On just one page, you need to prove to someone (without speaking to them) that your work experience has offered you opportunities to be a leader, stretch outside of your comfort zone (and succeed), and make a big impact on your team, business line, or company.

Easier said than done.

Writing an elite resume takes time. You need to reflect on your unique experiences in your role. What makes you different than every other marketer or investment banker? What can you bring to the table that no one else with a similar profile can bring?

You need to calculate the impact of your work. It’s not enough to share all of your completed projects. What impact did they have on the business? Once you master the formula of how to write a great resume bullet point, the process of writing your resume simplifies.

Here’s the formula:

Bullet Point = Your Contribution + Impact on the Business

That’s it. If you follow this formula, your resume will shine. Sure, there are other components around style, formatting, length, quantity, and what jobs to actually include. However, for the sake of this post, I want to focus on how to write good content for each job on your resume.

On the x-axis, we have how you explain your contribution. The trick to creating an eye-popping resume is being action-oriented. You want to frame your work as being self-driven and autonomous. Let’s say, for example, you want to include a line on your resume about creating a new sales strategy for WidgetProduct. Which way sounds more exciting to read?

1. Implemented news sales strategy

2. Scoped, designed, tested, and launched a new sales strategy to a team of 10 sales reps for WidgetProduct.

Clearly, it’s the second option. While the first option isn’t wrong, it reads more like a completed checklist item than resume text. The second option provides the necessary context for your contribution:

• What did you do, specifically?

• Why did you do it?

• Who/what was impacted?

On the y-axis, we have how specific you are about the impact of your contribution. The more precise you can be with impact, the stronger your resume gets. Of course, we can’t always have access to hard dollar figures, growth rates, or efficiency gain metrics for your projects… but we can do our best. Continuing from our example earlier, let’s finish the bullet point equation with the resulting impact. Which option sounds more impressive?

1. Scoped, designed, tested, and launched a new sales strategy to a team of 10 sales reps for WidgetProduct to drive new client relationships.

2. Scoped, designed, tested, and launched a new sales strategy to a team of 10 sales reps for WidgetProduct, leading to $500k+ new business in the six months after launch.

Again, the second option is clearly the better choice. With option one, we don’t have a strong understanding of how successful this new initiative was in the marketplace. With option two, we do.

So, before we jump into the quadrants, we just transformed a bullet that could have read, “Implemented news sales strategy to drive new client relationships,” to “Scoped, designed, tested, and launched a new sales strategy to a team of 10 sales reps for WidgetProduct, leading to $500k+ new business in the following 6 months after launch.”

Specificity matters. We’ve now framed the work in a way such that it’s more marketable, impressive, and accurate.

Understanding the Grid

As you could have guessed, the goal of this grid is to write bullet points that land in the top right quadrant. That means you’re following the bullet point formula. However, based on the information available to you, ensuring every bullet point is in the Elite quadrant isn’t always possible. Sometimes we have to settle for the Searching or Checklist quadrant.

In the sections below, you’ll find examples of what bullet points sound like in each quadrant so you know what to emulate and what to avoid.

Elite

Your bullet point is action-oriented and specific. Here, you follow the formula. When you have data, metrics, and estimated gains for the projects you’ve worked on, include them. They make your experience come to life and feel more tangible. If you’re a salesperson, you didn’t just “hit quota” you “achieved 102% of your quota by selling $1.4m in new business deals.” Elite bullet points pop. When a recruiter reads what you wrote, they pause, say “wow,” and eagerly move onto the next bullet point. That’s important. They keep reading. There are times where a recruiter or hiring manager will stop reading a resume if it isn’t strong. There’s a stack of dozens to get through. It’s your job as the writer to keep your reader engaged throughout. Every bullet point should have the reader think, “Wow… what else has this person done?!”

Some examples of Elite bullet points:

• Wrote, tested, and shipped 2,000 lines of Python code to launch Groups feature, leading to a 20% increase in user engagement.

• Designed new brand identity (logo, color pallet, typeface) for a local sports retailer, leading to a 15% increase in ad effectiveness and ~5% increase in site-wide traffic.

• Collaborated and led team of four in launching new learning and development course for unconscious bias training, resulting in a course completion rate that was 10-points higher than the average course.

Searching

Your bullet point is action-oriented but vague. As the quadrant name suggests, the resume reader is impressed, but still searching for more information. Bullet points that fall into this category often (and unfortunately) cannot be improved. There are no metrics to gather. The data for the project doesn’t exist. There’s no way to even begin to estimate the impact that your project had on your team or company. Every resume tends to have a handful (read: 1-5 total) bullet points that are in the Searching category. To compensate for the lack of specificity around the impact of your contribution, be sure to fully elaborate on your contribution.

Some examples of Searching bullet points:

• Designed and launched a new sales strategy for WidgetCo’s WidgetBreaker, leading to adoption by 40+ employees to increase sales.

• Built models to perform market and business forecasting for six different industries; model was used to consider 10+ potential deals.

• Created user engagement dashboard using SQL, Python, and Tableau monitored by 15 senior leaders to track the daily health of the company.

Checklist

Your bullet point is task-oriented but specific. In some cases, when the impact of your contribution is so impressive, keeping your contribution short allows the impact to shine. This allows the impact to speak for itself. Over explaining your contribution could dilute the bullet point entirely. However, there are times where the Checklist-style bullet point is ineffective. That’s when the impact is small and the entire bullet point does barely makes it to half of a line on paper. Effective Checklist-style bullet points should be used sparingly, though. When used correctly, they act as a very short sentence in a sea of intense prose. It just works.

Some examples of great Checklist bullet points:

• Managed enterprise sales team in achieving 180% of quota, outperforming by $2.4m+.
  (The numbers here are large and impressive. Keeping it simple allows them to shine)

• Raised $4.3m in Series A funding for WidgetCo.
  (Raising a Series A is no easy feat in and of itself)

Some examples of not-so-great Checklist bullet points:

• Achieved quota of 130%.
  (Leaves room for you to explain how you did it)

• Redesigned marketing website leading to 15-point increase in conversion rate.
  (Leaves room for you to explain what was so novel about the redesign)

Lacking

Your bullet point is task-oriented and vague. These bullet points require a full rewrite. They act more like notes, helping you identify the projects you worked on that are worth highlighting on a resume. They lack the necessary detail in your contribution and impact to make a recruiter keep reading. Elaborating and searching for how your work impacted those around you are essential improvements needed. Using these bullet points can be useful to outline your resume. Elite bullet points are born from Lacking ones. It requires editing and revision to transform vague and task-oriented bullet points into specific and action-oriented ones.

Some examples of Lacking bullet points:

• Managed team of five in generating company sales.

• Modeled industry trends to better inform department employees.

• Identified data inconsistencies and adjusted models to improve accuracy.

Grid Shortcomings

1. This grid doesn’t talk about bullet point length. As a rule of thumb, I strive to have a 50-50 ratio of 1-liner bullet points to 2-liner bullet points (with the 1-liner bullet points primarily landing towards the bottom of the resume). When your bullet point is more than 2-lines, it becomes unreadable. The recruiter or hiring manager gets jumbled in the words and loses the impact of the bullet point. Any shorter than one full line suggests you didn’t actually do all that much (or your contribution was small).

2. This grid doesn’t mention how many bullets you should have per role. The number of bullets per role varies on a few things: how much you did, how impressive your work was, how long you were in that role, and how long ago you were in that role. The oldest role on your resume typically should have two to three bullet points while your most recent role can have anywhere from three to five. When you have more than five bullet points for a role, you need to be certain that every bullet point shares something new about what you did in that job.

3. This grid doesn’t talk about what roles to include. Depending on the job you’re applying for, you may want to tailor your resume differently. That may mean deciding between including skills or your volunteer experience or this previous role over that role. A resume is about arranging your professional experiences in a way that is most eye-popping to the reader for the role you are trying to get. Remember, recruiters have a job, too: They need to hire someone as fast as possible who will be as successful as possible and who will stay at the company for as long as possible. Write your resume such that the risk of a recruiter moving you to the interview round feels negligible.

4. This grid doesn’t mention formatting or style. One big tip here: Allow your text room to breathe. When you zoom out from a resume, it’s all just text. Reading a single page covered in text from end to end can feel like trying to swim across a swimming pool without taking a breath. Use whitespace to your advantage. Don’t suffocate the reader. Whitespace affords the reader the chance to ultimately finish your resume without stopping after the first few bullets. So, when it comes to adding an extra bullet point but reducing your font size to 8.5… just don’t do it.

As we gear up towards the end of the year, the largest hiring season of the year is upon us. Sure, things will be different given COVID-19. I assume that it is even more important to put your best foot forward by creating the best resume you possibly can make.

My hope is this post can act as a resource for those of you or your friends who are getting ready to start looking for a new job. Feel free to forward this to them. I’m also more than happy to take a look at your resume if you’d like a second set of eyes on it. Just shoot me a note.

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here or you can check out the podcast.

Answer: Not enough time to craft a meaningful post this week.

I intend for this newsletter to always be a useful and quality use of your time each and every Sunday morning. This week, for obvious reasons, is a bit different.

Again, I won’t get fully into the politics of the moment, but briefly, I’m relieved. For me, a haze has lifted over the country. I’m excited for a Biden/Harris administration that’s anchored in possibilities, as Biden shared in his victory speech.

If you missed their speeches last night, they’re a must-watch:

However, if you’re looking for some Gridology content, I want to share five earlier posts that capture my current mood and are worth rereading:

What makes a great mentor?

How can I leverage the power of compounding?

How do I maintain my relationships?

How can I sustain my ambition?

How do I deal with adversity?

Gridology will be back next week with normally scheduled programming. If you have any specific topics you’d like me to tackle, as always please shoot me a note.

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here or you can check out the podcast.

That said, I am passionate about voting—so consider this email another voice in the chorus of your inboxes, newsfeeds, and text messages imploring you to vote. And, if the grid framework helps you best understand what to do on November 3, 2020, I made a quick one for you:

And now, let’s jump in:

Subscribe now

This week, my free time has been spent staring at one of two things: FiveThirtyEight election coverage and my fantasy football lineup. A stark contrast. Well, not really—both are based on believing analyst projections. I digress…

Together, the balance between the two somehow works. They are the perfect yin and yang for the moment. I spend time stressing over the election and then—when I reach my limit—I decompress with the best possible distraction… my currently-in-first-place fantasy football squad.

Decompression is essential. To do our best work, we need to turn off. Otherwise, we’ll run out of battery. Our brains need to rest the same way our muscles do after a workout. We can’t just bicep curl every day and expect our arms to still function. Even The Rock takes breaks (side note: his cheat meals look insanely delicious).

So, for today’s grid, I’m sharing a framework you can use to decompress. Relaxation means something different to everyone. For some, it may mean going for a long run. For others, it may mean setting up in your favorite spot on the couch with a blanket and a movie.

On the x-axis, we have your decompression method. I love to decompress through avoidance. It allows me to take a full and complete break. If there’s something stressful going on in my life, often the last thing I want to do to relax is to think about it. For others, confronting stressful situations is a way of reducing their weight. You relax from anxieties by dealing with them.

On the y-axis, we have who’s involved in the decompressing activity. How you choose to decompress is contingent on your mood, the type of stress, and the amount of time available to you. Sometimes it’s best to decompress with a solo activity vs. among others.

Understanding the Grid

We all have a lot going on—both societally and in our personal lives. Decompression hits differently depending on how it’s done. Some activities are needed to blow off steam. Others are needed to grapple with pressing issues. The focus of this grid is to pursue decompression in every quadrant because each offers restoration in its own way.

Discuss

We confront stress, and we do so with others. We seek to decompress through action and conversation. Engaging meaningfully with others helps us feel productive. Think of the person who has a weekend to-do list. Addressing the tasks and problems head-on allows for them to be put to bed. When applying this thinking to this quadrant, it means you handle stresses by consulting others. It’s often through a discussion. You may call a friend to discuss a personal problem or perhaps you have a regularly scheduled appointment with your therapist. The point is you’re addressing your issues to move past them. For me, talking things out with others is a critical way I decompress, especially when my stress is interpersonal or work-related. Sometimes I need to hear someone levelheaded tell me everything is going to be okay or that something isn’t as big of a deal as I had thought. Hearing it from someone else, sometimes, makes it sound true.

Research

We confront stress, and we do so alone. Sometimes we don’t need to talk to anyone about our problems. There are some things we just need to take care of for ourselves. It may mean meditating about the issue, digging into some research around the problem, or doing some reading about it. The focus here should be on spending time alone to assuage your fears and come up with actionable solutions. However, when this type of decompression is done incorrectly, it can look like you are spinning your wheels for nothing. The last thing you want is to be trapped in a tailspin of anxiety. As long as the research serves as a way to proactively respond to future work, go for it. For example, if you have a busy week a work, try spending 20 minutes to decompress by writing a plan for how and when you’re going to accomplish your projects. Though it may feel like work, in this format it does more to relax you than drain your energy.

Socialize

We avoid stress, and we do so with others. When I use socialization as a means of de-stressing, it acts as a hard reset. It’s like when your phone is glitching and you turn it off and on to fix the problem. Going out and hanging with friends or family is a clear way to get out of your head. Even during a pandemic, jumping on a quick FaceTime can be a critical decompressor. Hanging with others forces us to be engaged in the conversation, thus ensuring that we don’t think about the things that are bothering us. While the issues you are dealing with don’t go away, socialization is a necessary reprieve. Getting your mind focused on something else allows you to come back to the problem with fresh eyes.

Distract

We avoid stress, and we do so alone. Grab a book, pick up a controller, swipe on your phone, or go for a workout. Do whatever you need to do to get away from whatever is causing you stress. Taking this traditional decompression break—avoiding whatever is giving you anxiety—is a powerful resource. For me, it means watching go-to sitcoms such as Friends or It’s Always Sunny in Philadelphia. However, too much time in this quadrant isn’t a good thing, either. When you spend too much time here, distraction transforms into procrastination, which becomes a real problem. When you distract for too long, it can cause items to pile up or become more serious than they need to be. Try to keep your time in this quadrant short. Watch an hour of content and then get back to work. If you give yourself a short break to clear out your mind, you will be able refocus with greater processing power and endurance.

Grid Shortcomings

1. The grid falls short of explaining when to avoid or confront an issue. Only you can decide how to handle the challenges in your life. That said, recognize which method you are biased to choose and perhaps try to pick the alternative every now and then.

2. The grid doesn’t specify what stressors correspond to what quadrant. This is by design. Everyone responds differently and it is up to you to know how to relax best given the stressor.

This upcoming week will be a real challenge mentally. Try to carve out space to make sure you are finding time to decompress. That could be anything that reduces your anxiety and relieves the pressure of the moment. It could even mean looking at this adorable picture of Murray wearing a cardigan:

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here or you can check out the podcast.

Despite the 3-hour line, it was fantastic to be out—sprawled across two complete city blocks—feeling the New York City energy. Plus there’s nothing better than wearing your “I Voted” sticker. It’s a fall fashion accessory necessity (say that five times fast)…

Today, I’m excited to be co-writing with Kyla Scanlon—a fellow Compound Writing member and a talented writer. It’s been a few months since my last collab, and today’s grid is a topic I’ve wanted to write about for some time: creativity. Before we jump in, I wanted to give Kyla a chance to introduce herself in her own words:

Hey, I am Kyla! I currently work in asset management, and spend most of my free time reading and running. Most of my work centers around building narratives with data, and I’m especially interested in game theory and behavioral economics. I am from Kentucky, currently based out of Los Angeles, and am so happy to collaborate with Ross on this grid!

Let’s get to it:

Subscribe now

The most annoying work is boring work. There’s nothing worse than staring at the clock and watching time stand still as you do a mind-numbing task. You feel stuck—trapped in some weird time vortex of boredom, destined to be forever lost in the dreariness of the status quo. 

It’s a feeling I experienced at my very first internship. My high school offered the opportunity for seniors to forgo the last month of classes and opt into an internship program. So, I ended up being assigned to work at a hedge fund. My big project for the month was manual data entry—cross-referencing numbers on hundreds of PDFs to ensure they matched in a spreadsheet. The project made me realize that I never, ever wanted to be in a role that didn’t allow me to be creative—to dream of new solutions, innovate off the status quo, and optimize the wildly inefficient.

In John Mulaney’s wonderful stand-up special, New in Town, he goes into a hilarious bit about childhood fears:

He jokes that his biggest fear was quicksand. Even as adults, Kyla and I agree. However, not in the literal sense. While we have never walked into an actual pile of disintegrating mush, operating in the status quo and feeling bored doing repetitive tasks may as well be considered the same thing.

Both Kyla and I think one of the most difficult and dangerous things in life is the existence of a “status quo.” It’s because it entices us into a world of complacency. It encourages us to think, “Oh but it’s always been done this way… if it ain’t broke, why fix it?”

Even worse, it leads to thoughts such as, “How could I be the person who changes such a long-standing process? What makes me special?”

In essence, we deter ourselves from capitalizing on the whitespace in front of us. We turn off our creativity, resign ourselves to boredom, and never get anywhere exciting, challenging, or new.

In the workplace, abiding by the status quo is especially treacherous. A lot of large corporations can get stuck not innovating. In doing so, they leave an opening for startups to take advantage of new market opportunities, optimizing and enhancing the inefficient.

Thinking bigger, it’s also dangerous for us to get stuck in the status quo. We all have a finite amount of time and energy. Why should we spend hours on mindless tasks just because it’s always been done that way? 

So, for today’s grid, Kyla and I are digging into a question that centers around feeding your creativity but is anchored around optimizing your energy. When you use your energy efficiently, there’s nothing you can’t achieve. Mark Twain has a wonderful quote about creativity that’s worth sharing:

“There is no such thing as a new idea. We simply take a lot of old ideas and put them into a sort of mental kaleidoscope.”

If there are no new ideas, then anyone can be creative. It’s about affording yourself the space to learn, grow, and experiment. Today’s grid is about channeling that energy.

On the x-axis, we have how much time you spend on a given task or project. When projects take a long time, for instance, it may be because the status quo has become inefficient or because coming up with creative solutions is time-consuming work. This grid will explore how you can use your energy to make things more efficient and exciting.

On the y-axis, we have how creative you can be. We can’t always opt to pursue creative solutions to tasks. For example, you could be working on a project that depends on the status quo, and thus is heavy with standards. Or, perhaps, you could be working on something that requires exploration, allowing you to tap into your creative side.

Subscribe now

Understanding the Grid

This grid is intended to help you migrate to the top half. When you’re on the bottom half, that means you’re performing inefficient, mind-numbing, and tedious work. While some tasks and projects require this level of painstaking detail and repetition, many don’t. Below, find ways to identify when you’re operating in the (boring) status quo and strategies for how to escape those moments.

Canvas

The project takes a long time, and the work you are doing is exciting and creative. The Canvas quadrant is an ideal place to land. It’s the intersection of processes that take a long time, but you’re able to approach it with a creative flair. Rome wasn’t built in a day. The Sistine Chapel wasn’t painted in an afternoon. When working on a Canvas, you want to be in touch with how you think. You want to understand your own mental models and frameworks. Being creative should afford you the chance to be loose and free, but it’s easiest to be most creative when you have some guardrails. That’s because you need to understand exactly what you’re trying to innovate. If you don’t focus, there will be too many possibilities. Plus, it will be tough to work on a Canvas project without real passion. You have to be willing to put in the time—and sometimes it can be weeks or months—that a Canvas project will require. Creativity demands constant learning, which requires flexibility and adaptability. You have to give yourself a margin of error, and the freedom to tinker with ideas. Use tools like Whimsical, Figma, and Notion to map your ideas on a screen. Of course, scribbling on pen and paper always works great, too. Ultimately, you have to allow yourself to try, fail, learn, and grow multiple times.

Back when I was at LinkedIn, I worked on a Canvas project where I helped our customer success team be more productive. Every month, customer success managers had to make operational reviews for their top clients. To do so, here’s the process they’d follow: they’d navigate to 10-20 different Tableau dashboards, select custom filtering (which could take 30-45 seconds to load for each), take a screenshot of the charts and tables, and paste it into a PowerPoint presentation. Rinse and repeat for every customer. I knew there had to be a better way. So, for the better part of a year, I worked to imagine a simpler solution. I partnered with the team to create a distilled 7-page report that automatically filtered the most critical metrics for their top clients. A process that used to take 10-12 hours a month per customer success manager now took just one hour. A creative solution broke through the status quo.

Mud

The project takes a long time, and the work you are doing is boring and abides by the status quo. The Mud quadrant is a tough place to be, but it is also ripe with opportunity. It’s as if you go off-roading in a Jeep and you get stuck in the mud. You start spinning your tires, dirt spraying everywhere, the car exerting force... but you’re not getting anywhere. That said, you have the chance to be a hero—the person who figures out the solution to get back on the road. Being in the Mud happens with assigned work or with projects you’ve inherited. The work is usually redundant and makes you want to pull your hair out. Not only are you bored, but you’re “busy”—all you can do is listen to podcasts while you input numbers into an Excel spreadsheet. You’re stuck.

For example, in the first few months at Kyla’s job, she was tasked with building her team’s external communication experience. Her team was deep in the Mud. Emails were piling up and meetings needed to be scheduled across numerous time-sensitive projects. The team responded to ad-hoc requests and repeated similar tasks to each other because there was no unifying information to organize everyone. It was overwhelming. So, Kyla drafted an internal website that would serve as a website for requests, responses, and all other forms of communication between her team and relevant stakeholders. It took time to get people on board with the concept, but once they were (and understood the value it added) the website made a huge difference in boosting team productivity and happiness.

So, to get out of this quadrant, let your mind wander. Ask yourself an important question: If you could redesign the process for how you are doing what you are doing, what would you create? Let that question fill your mind as you trudge through the Mud work. Share your ideas with others. Do they get excited about your solution? When you carve out the time to calculate what needs to be changed, you can communicate the impact of what getting out of the Mud would mean to relevant stakeholders.

Light Bulb

The project takes a little time, and the work you are doing is exciting and creative. While it may feel as easy as flipping a switch, light bulbs don’t just “turn on.” Said simply, the electricity flows into the bulb through a thin wire, a bunch of science happens, and then the wire heats up and glows. (Disclaimer: We aren’t scientists.) That said, the bulb only glows because of friction created between the wire and the electricity.

When applied to energy optimization, Light Bulb moments feel like a blip of serendipity, a big bang, a “Eureka!” While moments like these can seem and feel random, they occur more frequently when you take the time to learn, reflect, and practice. Light Bulb moments are the result of figuring out a thousand ways something won’t work (à la Edison). Once you find the solution that does work, it doesn’t take long to implement.

When you are focusing on putting yourself in a position to grow—that means reading, having interesting conversations, listening to podcasts, or watching meaningful films—your brain will connect dots in ways that others can’t. We are a reflection of what we read and listen to. When you engage with personal and interesting content, it empowers you to be creative in ways that only you can be.

Band-Aids

The project takes a little time, and the work you are doing is boring and abides by the status quo. Band-Aids are patches for small yet annoying wounds. Let’s say you have a blister. Typically, the first thing you’d do is peel off a Band-Aid and stick it on for some relief. However, this treatment rarely cures the problem. Over time, the Band-Aid becomes a nuisance. It gets caught on things, peels off, gets dirty, and ultimately the pain returns. A Band-Aid is a system patch… but system patches aren’t effective forever. Eventually, there needs to be an overhaul. It’s like having an iPhone 5 and trying to run iOS 14… your phone simply can’t handle the new operating system. You’d need to buy a new one. (Pro Tip: The iPhone 12 Pro is awesome.) When Band-Aids pile up or go unchanged for extended periods, they transform into Mud quadrant projects.

Generally, to escape the Band-Aid quadrant, you need to dedicate time for healing. Running with our blister analogy (pun intended), it doesn’t make much sense to participate in a marathon if your feet are covered in blisters. By taking time to heal, you’ll run much faster and with less pain. When it comes to your work, healing means taking time to pause and brainstorm a better way. Sometimes, you may need to explain to others that short-term solutions are never the correct solutions for long-term problems. Live in the Light Bulb and Canvas quadrants for ideas as to how you can channel your inner creativity to solve Band-Aid challenges.

Grid Shortcomings

1. This grid doesn’t account for everyone’s tolerance for boredom and the status quo. For some, settling into redundant work is a nice way to relax while also being productive. For others, it’s soul-crushing. Some people enjoy doing “status quo” jobs such as accounting or legal work. That’s fine (and necessary for a functioning society). This grid is more geared to those who seek out variety in their day to day lives.

2. This grid assumes we always will have the opportunity to flex our creativity. Sometimes, we can’t be creative when we want to be. It’s hard to shift entire organizations in one direction without overhauling tasks that have been stuck in Mud for a long time. Some work needs to be completed in a certain way.

3. This grid assumes you have an easy time channeling your creativity. Where does creativity come from? Finding sources of inspiration is a challenge for many. This grid doesn’t solve the inspiration problem, but hopefully, we’ve provided relevant examples as to how you can get your creative juices flowing.

Energy optimization comes from allowing yourself to be creative in situations where innovation is needed. We all have been covered in Mud or have needed a Band-Aid. Typically, those aren’t fun experiences. They’re annoying and cumbersome and drain our energy. When we have the chance to operate like a Light Bulb or paint on a Canvas, the options are limitless. Opportunities start to present themselves. Excitement builds. When you have chances to innovate off the status quo, don’t shy away from them… lean in and grab a paintbrush.

Life’s only as confusing as you let it be,
Ross & Kyla

Subscribe now

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here or you can check out the podcast. If you want more from Kyla, check out her blog, and follow her on Twitter!

If engines power cars, then mentors power careers. They are the lifeblood of the professional world, transforming rookies into athletes and athletes into superstars. I would not be where I am today, professionally or personally, without mentors.

My mentors have coached me through promotion negotiations, next play conversations, and challenging workplace interactions. They’re simultaneously a sounding board and a north star.

Without mentors, it’s impossible to know where I’d be. A great mentor has the ability to not only know the road you’re traveling on, but also the skillset needed to help you tackle the terrain. The best mentors are teammates: Your success is their success. However, success doesn’t mean just getting the job done. It means getting the job done in a way that forces you to learn, improve, and grow.

Mentors don’t open doors for you. They teach you how to open doors for yourself.

When imposter syndrome creeps in, a mentor is invaluable. When the way forward is daunting, a mentor is invaluable. When the decision needing to be made is a challenging one, a mentor is invaluable. Mentors are often the difference between giving up and going forward.

Oprah says it best:

“A mentor is someone who allows you to see the hope inside yourself.”

Not everyone is lucky enough to already have a mentor. Finding a great mentor is a bit like trying to find a romantic partner or a best friend—it requires trial and error, loads of patience, and a keen eye.

Today, I want to share a framework we all can use when searching for new mentors who have the power to change your life.

On the x-axis, we have where the individual focuses attention. Often we think of mentorship within the confines of thriving in an organization. The best mentors, however, transcend the office and make you not just a better professional, but a better person altogether.

On the y-axis, we have the individual’s approach. Mentors aren’t there to remove obstacles that are in your way. That would be a waste. The best mentors choose to collaborate on solutions, providing frameworks and tools to help you come up with answers for yourself.

Understanding the Grid

While finding someone who lands in the top right quadrant would be the ideal combination to seek out in a mentor, each quadrant in this grid valuable.

Mentor

The individual is focused on what’s best for you as a person and does so in a collaborative way. Great mentors will rarely tell you the correct path to pursue. The best ones treat mentoring conversations like Socratic seminars—they ask the perfect follow-up questions to ensure you considering every possible angle before making a decision. Back in November 2019, mentors played a critical role in helping me choose the next best step in my career. There were three paths ahead of me: going to business school, starting a new job at a new company, and starting a new role within LinkedIn. My mentors helped me think through the relevant professional questions, yes, but they also helped me frame the personal ones, too. Often, when making big career decisions, we believe that one choice is “correct” and all other alternatives are wrong. My mentors shifted this thinking. In reality, any of these three choices could be “correct.” It was about committing 100% to whichever option I chose.

Friend

The individual is focused on what’s best for you as a person and does so in a prescriptive way. When you confide in a friend, the initial reaction is for them to be prescriptive. After all, they want to help. If you’re struggling, they want the struggle to end. They fling tips, advice, and guidance your way. Of course, not every friend is like this, but many strive to be helpful through idea generation. Friends are difference makers. Without them, it’s hard to fathom how to get started tackling some of the most confusing challenges and difficult tasks when they’re thrown our way. When it comes to career challenges, friends always see the personal side of the issue. If you’re unhappy with your job, a friend can help brainstorm ways to make it better or find a new one.

Advocate

The individual is focused on what’s best for you as a professional and does so in a collaborative way. Advocates are only found in corporate environments. These are people who admire your work and ability. Because they appreciate your work, they help you thrive. Advocates tend to lobby for promotions and pay raises on your behalf. They help you negotiate big career moves. However, all of this help is provided when thinking about you as a professional, not as a person—meaning they’re optimizing for your career success rather than your personal success. That doesn’t mean they don’t care about you. It means they are more concerned about your professional success than whatever side effects that success could have on your personal life. Regardless, advocates are critically important. There are several jobs I would have never had if it were not for advocates speaking up on my behalf. A great advocate can help you hop to the next level of your career at lightning speed. Be mindful that their help and advice do not consider every aspect of your life.

Resource

The individual is focused on what’s best for you as a professional and does so in a prescriptive way. Resources are sounding boards. You come to them with professional problems and roadblocks. They provide answers. It’s a transactional relationship. That said, it doesn’t mean that these relationships aren’t valuable. When you have resources in your life, they are typically experts who are busy but want to help. So, engaging with them at career inflection points allows them to provide meaningful input with maximum impact. When you engage a resource for professional help, these individuals usually share advice based on their own professional experience. They preach taking the path they chose given they know that path already leads to success (it did for them, after all). However, because this advice is prescriptive, it’s up to you to figure out how it fits into your life. Asking several resources for guidance requires analysis afterward. Once you learn about all of the potential solutions, it’s up to you to negotiate which path to choose. Here, a mentor would be helpful. A mentor would ask additional questions to help you begin whittling down the list until you get to the best option.

Grid Shortcomings

1. The grid ignores that your mentors can change over time. A mentor you had in high school may not be the mentor you have in college or beyond. As you grow, so do your mentors.

2. The grid ignores how to actually find a mentor. For me, my mentors are usually previous managers who meet two criteria: I loved their management style and I’m encouraged to stay in touch with them after being on their team. Over time, as we continue to stay in touch, these ex-managers become mentors.

While mentors may have all the answers, they protect the answer as something that the person they are advising (you!) needs to figure out for him or herself. Mentors provide guidance, frameworks, and questions that narrow optionality. With increased focus, you can expect outsized professional and personal returns.

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here or you can check out the podcast.

Listen to episode 1

The show is hosted by Sounder, but you can also find it on Spotify, Apple, TuneIn, and Stitcher. Have a different listening platform of choice? Give me a shout, so I can add it there. Please subscribe so that you can listen to new episodes when they’re released. As always, your feedback is very much appreciated.

Now on to today’s post:

Subscribe now

If you’ve been reading Gridology since the beginning, this question may sound familiar. It’s because I answered “How do I reflect on life?” on April 26. However, the post didn’t tell the full story. When I hit publish, I realized I had much more to share on the topic of reflection. As an introspective person, I often find myself looking back on projects, relationships, and interactions with a (sometimes overly) discerning eye.

At times, it can feel like being trapped inside of a detective movie—a dimly lit room, a single flickering light overhead, a metal table bolted to the ground so it can’t be flipped for dramatic effect. However, it’s not a normal investigation. I’m both the interrogator and suspect.

This scene can play out in many formats and mediums. Ultimately, what matters most, is that I’m asking myself the tough and necessary questions required for reflection and growth.

Reflection is an essential part of the learning and development process. We all fail. What’s the point of trying and messing up if you’re not going to take the time to reflect so you can get better?

Reflection is a way to add fuel to fire. Yes, reflection is critical for diagnosing what went wrong, but it is arguably even more powerful for highlighting what went well. As we reflect, we are able to double down on the actions and habits that work in our favor while cutting out those that don’t.

Reflection is our mind’s way of self-optimizing. It allows us to strive for higher-level problems—each time we try, fail, and reflect, we level up. As we respond to simple mistakes, it allows us to tackle harder challenges and more nuanced situations. As we tackle those, reflection again allows us to master these obstacles and move on to even meatier ones. It’s all about working to maximize our potentials over time—compounding on honest feedback from yourself.

That’s the focus of today’s grid. I’m sharing a framework for self-optimization through reflection—how to take planned and unplanned moments to reflect, refine, and rebound.

On the x-axis, we have how the reflection is scheduled. Do you have an annual review at work or is there something ad-hoc that requires analysis? Both pre-planned and spontaneous reflections are essential. A pre-planned reflection is like scheduling time to clean out your entire closet—figuring out which items don’t fit, are out of fashion, or ready for donation. It’s laboring, time-intensive, and important to do every now and then. A spontaneous reflection is like tidying up your closet when laundry piles up. You aren’t going to wait until your next big cleanout to address these smaller disorganized moments.

On the y-axis, we have the reflection topic. Are you analyzing something specific, such as your job performance, a relationship, or your health? Or, are you dissecting something vaguer, such as how your life is going or what you want to achieve next year? Both types of reflection are essential for charting out pivots both big and small.

Understanding the Grid

This framework is most effective when you spend time in each quadrant. Each serves its own purpose in trying to help you understand your strengths, weaknesses, goals, and opportunities.

Adjust

You reflect in real-time, and you have a specific topic to dissect. When I adjust, it’s because one of two triggers typically happened. The first trigger is when I receive a targeted piece of feedback. Remember, with all feedback, you must first assess whether it’s coming from someone with the authority to cause you to make a change to your life. Since great feedback is specific, there should now be a topic that warrants your attention and introspection. The second trigger is when I’ve completed a big project or attended a large event. After these milestones are perfect times to reflect on what went well and what went not so well. When you adjust after either trigger, it’s like treating yourself like a Formula 1 racecar—recognizing that you require frequent tune-ups or you run the risk of veering off course. These moments of maintenance keep us honest and self-aware. They allow us to respond to new information in real-time.

Rehash

You reflect in real-time, but you don’t have a specific topic to dissect. Rehashing is often used in an unhealthy manner in the form of instant replay. It’s like your life is a televised NFL game—most plays are replayed and dissected by the guys in the booth. Life is lived in hindsight. You tend to judge yourself back then with what you know now. It’s irrational and unfair, but you do it anyway. Rehashing, however, doesn’t need to be unhealthy. I find rehashing can be beneficial when used during meditation (that could be on a run, during yoga, or with a cup of coffee). I typically spend a few moments as I lay in bed with my eyes closed rehashing key moments of the day. I ask important questions such as:

• What things energized me?

• What things would I undo if I could?

• If I could undo those things what would I do instead?

These questions are targeted about the day’s events. They afford me the opportunity to surface important inflection points during the day. Where did I thrive? Where did I falter? Healthy rehashing is a powerful tool to drive daily improvement. Remember, when you get 1% better every day for a year, it leads to a 37x increase in performance.

Discuss

You reflect at a planned time, and you have a specific topic to dissect. These moments of reflection are typically mapped out at the beginning of the year. These are mine: the time around New Year’s, mid-year / annual reviews at work, and Thanksgiving. Starting around December 15, I spend time reflecting on what I achieved last year and what I want to achieve for the upcoming one. During reviews at work, I dissect where I thrived and where I need to improve. During Thanksgiving, I focus on all of my relationships, thinking through which ones serve me and which ones require more attention. While reflection in this quadrant typically starts with writing (more on that below), the real work commences when you share your reflection with others. This solidifies your thinking and brings it to life. Recently, for example, at Thanksgiving, we go around the dinner table and ask what everyone was most thankful for this year. Saying these things out loud gives them more gravitas. It makes the takeaways of your reflection manifest into reality.

Write

You reflect at a planned time, but you don’t have a specific topic to dissect. Like the discuss quadrant, these moments are also mapped moments of the year. These are mine: my birthday, Labor Day, and Yom Kippur. I use each of these days similarly—reflecting generally on what is working and not working about my life in general. Am I happy? If I’m sad, why? How can I make improvements to change my mood or confidence? These thoughts are jumbled and confusing. Writing is a way of untangling the knots of my thoughts. Tom White recently published a post in his newsletter, White Noise, that captured this exactly:

“To write is to wade, alone, into the vast, murky ocean of thought and idea. It is equal parts treading water and drowning, a haphazard stumbling toward insight and inspiration. It is plumbing into the depths of your soul, groping around to grab hold of something true and real and unique and you. It is casting and reeling, changing the tackle and hoping that the Big One doesn’t just nibble at your hook, but firmly latches on. And that you can successfully reel it in.”

Sometimes I write prose, but often I write lists—outlining my top moments or achievements of the year, writing out all that’s bothering me, or creating a detailed gameplan for the next week or month. The words don’t have to be perfect. I’m not being graded on sentence structure. Just getting thoughts on paper causes them to make more sense then they do just floating in my skull. As I write, my disparate ideas begin to converge. I realize there’s a specific topic to my reflection. Specificity then allows me to share my insight with others, manifesting it to reality.

Grid Shortcomings

1. This grid ignores the importance of triggers for kicking off moments of reflection. Reflection is hard work. People can shy away from reflecting just as they would shy away from ordering a salad for dinner when pasta is on the menu. It’s a more difficult option (and the less tasty one). Setting up a habit of reflection requires a powerful trigger.

2. This grid doesn’t underscore the importance of associating an action with reflection. A reflection is only as good as the action-oriented takeaways it generates. If your reflection doesn’t adjust your next move, your reflection wasn’t thorough enough.

Reflection drives improvement. When you ponder your actions, it allows you to become more self-aware—an important skill for anyone looking to become more self-compassionate. When you play the role of investigator and suspect, I hope it brings you moments of enlightenment you can celebrate like this:

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate. Want more from Gridology? You can always access the entire archive here.

Now, for a topic that has captured a lot of my mindshare recently.

Here we go:

Subscribe now

Three months ago I joined an online writing group called Compound Writing. It’s a collection of writers—ranging from hobbyists to journalists—who are looking to hone their crafts, be held accountable, and meet others in the online writing community. So far, I’ve made real online relationships with about a dozen people. These are people I’ve never met in person. Who knows if I ever will. (The internet, guys, amirite?!)

In the group, I’ve edited others’ work, publicly brainstormed Gridology content, and attended fireside chats with up-and-coming online writers. Without Compound Writing, these two Gridology posts would not have been what they were. The point is this: the organization captures and applies a concept that is essential to finance, health, personal development, building relationships, careers, and learning.

That lesson is compounding.

Compound Writing anchors itself in the idea that a little progress made every day towards being a better writer can exponentially change your ability to create better content and grow your audience.

The creator community on Twitter loves to talk about compounding. Taking a page out of Albert Einstein’s playbook, Jack Butcher visualized the concept of compounding being the eighth wonder of the world (click to read the full thread):

Given its magic, you’d expect everyone in the world to compound something—whether it be their finances, a skill they’re trying to master, or a career goal. The tricky part about compounding is that it’s extraordinarily difficult. It requires patience, dedication, and mastery… and a long (and sometimes unknown) time horizon.

Regardless of how challenging compounding is, the gains are very, very real. James Clear, author Atomic Habits, says:

…[I]mproving by 1 percent isn’t particularly notable—sometimes it isn’t even noticeable—but it can be far more meaningful, especially in the long run. The difference a tiny improvement can make over time is astounding. Here’s how the math works out: if you can get 1 percent better each day for one year, you’ll end up thirty-seven times better by the time you’re done. Conversely, if you get 1 percent worse each day for one year, you’ll decline nearly down to zero. What starts as a small win or a minor setback accumulates into something much more.

Here’s how James Clear visualized this concept:

Source: JamesClear.com/marginal-gains

The math checks out. Compounding every day is a superpower.

If you need more proof: Let’s say you’re half as consistent—meaning you improve 1% every other day for a year—by the end of the year you’d only be six times better (not 37 times better) than where you began. Going further, if you focus your improvement just on the weekends for an entire year, you’d only become 2.8 times better.

Warren Buffett, the godfather of compound interest, thinks about exponential growth in very real terms. For every transaction, he considers how much it could cost him in future wealth:

“His friends and family regularly heard the young Mr. Buffett mutter things like “Do I really want to spend $300,000 for this haircut?” or “I’m not sure I want to blow $500,000 that way” when pondering whether to spend a few bucks. To him, a few dollars spent that day were hundreds of thousands of dollars forgone in the future because they couldn’t compound.”

So for today’s grid, I’ll be breaking down what it takes to compound—your time or your money—successfully.

On the x-axis, we have the size of the task you’re trying to complete. Compounding is easiest when the task is as simple as possible. I wrote about this concept back in August when talking about how to build habits. The most successful way to start compounding is with small tasks. It’s much easier to commit to writing for 5 minutes every day rather than to write for two hours every day.

On the y-axis, we have your level of consistency. As mentioned, how consistent you are dictates how much better you get over time. Carving out time every single day to do whatever it is you want to do will have incredible, eye-popping returns years later.

Understanding the Grid

This grid’s intention is to help you migrate important initiatives to the top right quadrant—that’s where you’ll find exponential growth. However, not everything you do in life needs to accomplished by compounding over time.

Exponential

You focus on small wins consistently. The beauty of compounding is consistency is king, not the level of effort. Just look at 1% daily improvements can do when considered over just on year. It’s wild to think you could be lightyears ahead of where you are today when you added simple and consistent activities to your life. I saw exponential growth when I focused and developed an accidental system of compounding to learn Python. Every day at the office, I carved out a little bit of time to learn Python for a team project. Often, this focus would carry over into the weekend—I’d read through tutorials and watch videos so I could start the week off ready to work. At the end of each month, I’d reflect back to where I was at the start of the month in complete shock. Knowledge was building in a way that allowed me to learn more, faster. Learning certain concepts allowed me to master new ones faster than the old ones. Time spent learning in the past unlocked increased learning potential for the future.

Scattered

You focus on small wins inconsistently. Hobbies, unprioritized ideas, and experimentation fits in this quadrant. Not everything in life needs to be looked at through the lens of compounding. I have a scattered approach when it comes to crossword puzzles. Once or twice a month I get laser focused on doing crosswords. I find them to be a relaxing and fun way to unwind before bed (when I’m not frantically refreshing Twitter, of course). However, I don’t complete puzzles consistently enough to get better, meaning I’m permanently in a loop where I can only answer the Monday puzzle in the New York Times without asking for hints. With a more consistent focus, perhaps I could make more progress improving from Monday all the way to Sunday (where the crossword experts spend their time). While crosswords are just an occasional and fun activity for me right now, if I ever got serious about expanding outside of Mondays I’d figure out a way to embed 20 minutes for a puzzle every single day. With that consistent time commitment, I’m sure I’d see quick progress to more challenging levels after a year or two of dedicated effort.

Bursts

You focus on big wins consistently. These goals take time to accomplish, but once completed, you check them off your list and move onto the next thing. It’s buying a few stocks, doubling your money, and immediately selling to hold cash. It’s training for a marathon and then giving up running. It’s buying a guitar, learning how to play a Wonderwall by Oasis, and then calling it quits. With bursts, there’s a set goal at hand. This is where I had focused much of my time until recently. I was dead set on finding large, meaty objectives to sink my teeth. In doing so, I would achieve the given objective but fail to dream bigger—forgetting to think how this objective could be just a stepping stone for something bigger down the road. Now, I’m more determined to pick skills that I’m interested in pursuing for years at a time. That way, I can start to see compounding at work. Whether it is Gridology or not, I’m making an investment that my writing can improve by compounding my online writing practice.

Aspirational

You focus on big wins inconsistently. When you set big goals without a real plan for achieving them, you’re doing the opposite of compounding. You’re hoping you strike gold. Want to write a world-class fiction novel? That doesn’t mean writing for eight hours a day a few times a year. It should mean writing a little bit every day for years. It should mean writing a bunch of books before ultimately writing the book. When you land in this quadrant, it’s because success looks so distant that spending time feels like it could be a waste. Why do so many children say they want to be an astronaut, an actor, or a professional athlete when they grow up but few rarely realize that dream? It’s because the road to success is winding, difficult, and long. It’s not easy to become the next Buzz Aldrin, Brad Pitt, or LeBron James. It requires years of practice, studying, and experience. The lessons compound. The skills improve faster and faster. Take Pablo Picasso, for example (story originally comes from What They Don’t Teach You at Harvard Business School by Mark H. McCormack):

It always reminds me of the story about the woman who approached Picasso in a restaurant, asked him to scribble something on a napkin, and said she would be happy to pay whatever he felt it was worth. Picasso complied and then said, “That will be $10,000.”

“But you did that in thirty seconds,” the astonished woman replied.

“No,” Picasso said. “It has taken me forty years to do that.”

Grid Shortcomings

1. This grid doesn’t explain how long a long time horizon actually is. This is done purposefully. There’s no way to calculate how long certain things take to accrue compounding gains. Others, such as money, can be tracked with a bit more finesse (i.e. if you assume 10% gains per year you can model out how much money will be in your account 40 years from now).

2. This grid doesn’t take fun into account. In my Python example, if I wasn’t having fun learning, then what was the real point of compounding? Why should I dedicate lots of time to something that doesn’t satisfy me? Always be sure that you’re compounding things that matter and bring you joy.

Compounding, when executed correctly, is magic. It can transport your money and abilities from ordinary to spectacular gains. What is that big, lofty goal you’re trying to achieve? How can you break it up into daily opportunities for growth every single day? If you can figure it out, you may have tapped into a superpower hidden within us all.

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s Gridology post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate.

That’s it. Go vote. Our nation depends on it.

Let’s jump in:

Subscribe now

Hater culture is everywhere. It’s in the real world. It’s online. It’s at work. It’s at school. It can even be within your family. There’s no escaping harmful comments, hypercritical remarks, and external judgments about your personality, passions, and projects—that’s a certainty life will always offer. So, if we can’t change the world, how do we change ourselves? What does it take to build a more discerning eye and filter negativity directed thrown our way?

Generally speaking, it’s a great feeling when society likes and approves of you. This dates back to our origins. Humans are tribal animals—our survival is contingent on our ability to get along and work together. When we aren’t liked it threatens our survival. Our primal instincts kick in. We could be outcasted… thrown out of the village! Fear starts to settle.

With this in mind, it makes sense why you would inflate the magnitude of every negative comment directed your way—I know I do this often. Simply put, not every comment deserves the same level of consideration, attention, and respect. It’s a strange concept. It’s natural to want to listen to others and pay close attention to what someone is saying. I’m trying to practice and master discernment now, and I can already see how it will have incredible long-term positive implications.

The power of this skill is best understood through an extreme example. Let’s say you are writing a book. You share your first chapter on Twitter to get some feedback. One comment, magically, comes from a published author you admire. She says it’s a wonderful start to your book. Another comment comes from a colleague who notoriously hates to read. He says it’s crap and suggests you hire a ghostwriter. How do you feel? In this example, you may feel ecstatic the author provided positive feedback while simultaneously being a bit bummed that someone told you to turn off the computer and give up. In reality, both should motivate you to continue writing your book. Here’s why:

Praise from someone you admire should motivate you.

Admonishment from someone you contempt should motivate you. Wait… what?

Yes, this is so important let me say it again: admonishment from someone you contempt should motivate you. Think about it. If you are angering people you disagree with or who don’t have the authority to provide meaningful feedback, then you are doing something right. I often forget this. It’s not a good thing to be liked by everyone. There are plenty of people out there who don’t align with your core values, understand your passions, and appreciate your personality. Why on Earth would you try and adjust your actions to please these people?

Simple answer: you wouldn’t and shouldn’t.

So, for today’s grid, we are going to walk through a framework I’ve started to use to help me discern when a comment is or is not worth my time.

On the x-axis, we have how you interpret negative or hypercritical comments. Do you accept what others say immediately? Do you pause and assess their motives? This axis centers on your ability to play poker, so to speak. There’s a poker adage that says, “play the man, not the cards.” This wisdom should be applied across life. Seeking to understand the motivations and the psychology of the person spewing negativity is a surefire way to immediately become more discerning. Understanding the person enables you to better handle the comments.

On the y-axis, we have how you respond to negative or hypercritical comments. Once you have chosen to either accept or assess the judgment, what’s your next move? Do you engage or ignore the person who slighted you? Part of the assessment needs to be deducing whether or not responding is even worth your time.

Understanding the Grid

For this framework, the goal is to work your way to always be on the right half of the grid—to assess before you accept. Depending on the person and the comment, engaging may or may not be in your best interest. What is for sure, however, is that blindly accepting all negative feedback as the truth gets you nowhere.

Debater

You assess comments before accepting them, and you engage in a response. In this quadrant, your discernment is high. You’ve made the internal calculations necessary to understand the motivations behind both the person before dealing with the comment. The result is that you believe the best response is engaging, debating, and making your case. Landing in this quadrant is common when having a civil discussion about politics—difficult these days (especially online). However, when you’re able to have a cordial conversation about politics, it requires having a strong understanding of the other people involved. Your assessment leads you into the conversation. You deduce that there is something to gain (maybe respect or knowledge) through participation.

In one of my group threads, my friends and I lob politically commentary at each other almost daily. The eight of us run the political spectrum: from progressive to moderate to conservative. Often comments can be hypercritical of someone else’s views. Rather than immediately accepting and digesting that opposing viewpoint, we all engage in debate. We defend, grow, and learn. In the background, silently, we all understand everyone’s intentions. These comments aren’t meant to denigrate anyone in the group. They’re designed to lead to a greater collective understanding and well-roundedness of the issues. Our discernment allows us to play a game we can win: enlightenment.

Pragmatic

You assess comments before accepting them, but you end up ignoring them. This is the quadrant we should strive to land in when disparaging or hateful comments are thrown our way. Being pragmatic means trusting our discernment to protect our mood and self-esteem. Said differently, being able to assess someone else’s motivations, recognize them as ill-intended, and quickly move on to more important topics allows us to better self-regulate our emotions. Often, when we assess why others put down our personality, projects, or passions it comes from a place of jealousy, envy, and frustration.

This happened to me recently. While I often receive replies praising Gridology, sometimes I hear negativity and trolling, too. My initial reaction is to internalize, accept their words as truth, and lament about it to myself and my loved ones. I start to question if these people are actually right. Rather than going down the internalizer path, I now strive to be a pragmatist. I seek to understand the person behind the comment. Why are they saying what they are saying? Does their opinion matter? Do they have clout or expertise that compels me to listen? After a quick analysis, I realize that the person behind the comments is just a balloon—easy to deflate or, even better, let go of and watch fly away. There’s no need to respond, the comments just aren’t worth my time.

Apologetic

You immediately accept comments without assessment, and you engage in a response. In this quadrant, what you hear—negative or hypercritical—immediately is accepted as truth. There is no outer layer of discernment to protect your emotional well-being. Once the comment is accepted, you feel compelled to respond to save face. Whether you can win the game at hand (convincing the other person that their comment is wrong and unjustified) doesn’t matter. You have to at least try. The notion that someone could negatively think about you deeply bothers you. The need to be well-liked consumes your thoughts and actions. Since you’re accepting their words as truth, you look to apologize rather than fight back. It can be easy to land in this quadrant at the office (er, video chat). We all have a strong desire to keep peace with our colleagues. Whether right or wrong, social norms and unwritten workplace rules tell us that we should look to extend olive branches rather than throw gasoline on fires. Whether you believe you’re in the right or the wrong, office culture tells us we’re better off being the one to extinguish fires than to be the one to make them bigger.

Internalizer

You immediately accept comments without assessment, but you end up ignoring them. In this quadrant, you are kept up at night from negative and hypercritical comments. You may as well be a contestant on Naked and Afraid—out in the open and ready to be eaten alive by bugs and pummeled by the rain. You’re totally unprotected. When negativity is tossed your way, you gobble it up and blame yourself. Above all, you’ve forgotten the golden rule of today’s grid (it’s so essential I’ll say it for a third and final time): admonishment from someone you contempt should motivate you. Not all negativity should be treated equally. Do not let unjustified negativity slow you down rather than speed you up. Ideally, internalizers can begin the process of becoming pragmatists. It starts with asking two important questions when someone flings hate your way:

1. Do I admire or respect this person?

2. Is this someone I’d come to for advice on this topic?

These questions can help you perform a rudimentary assessment if the comments that are currently weighing you down are coming from a credible and worthy source. Sometimes we just need to put on the noise-canceling headphones so we can do our thing.

Grid Shortcomings

1. This grid assumes you aren’t an externalizer. An externalizer is someone who looks to blame others rather than ever blaming him or herself. If you are an externalizer, this framework can be useful to help understand how internalizers can receive your comments. When you externalize, negative comments bounce off of you like rain on a raincoat. Discernment, most likely, is not top of mind as its already hard-wired into your system—it never can be you because it’s always someone else’s fault.

2. The negative and hateful comments in this grid are understood not as valuable feedback. I’ve spoken at length about the importance of feedback and how to give great feedback to others. This grid is not about feedback. It’s about comments that come unsolicited, are meant to bring your mood down, or meant to make you see one point of view as better than another.

Discernment is an underrated and crucial social skill. Without it, we are left unprotected from everyone else’s personal baggage and negativity. It would be like playing an NFL game without pads on—you simply wouldn’t do it. I hope this framework helps you begin mastering how to be more discerning of other’s intentions before accepting their comments as fact.

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s Gridology post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate.

This year will go down as the worst year in a long, long time. It’s been one filled with loss, hardship, and pain. On top of the nearly 200k lives lost from COVID-19, we’ve also lost so many inspirational societal changemakers. Every time another one passes away it sucks the hope out of the room. Kobe Bryant. John Lewis. Regis Philbin. Chadwick Boseman. And now, Justice Ruth Bader Ginsberg.

With so much bad news to bear this year, it’s essential we talk about it and—more importantly—figure out ways to move past it.

Let’s get to it:

Subscribe now

My fiancé and I started rewatching the Harry Potter movies this week. They’re a great (and much needed) escape. Entering the wizarding world, watching some quidditch, and seeing the good guys win is a real mood booster. That said, the series gets dark and has me flashing back to tough moments this year. This scene from the third movie, especially:

Every time Twitter or a push notification delivers yet another piece of bad news, it feels like an encounter with a dementor. The room grows cold. Light becomes darkness. My mood sours. My energy dips. To fight a dementor requires the Patronus Charm—a defensive spell that produces a bright guardian angel. Successfully conjuring the charm requires “happiness and hope.”

In the wizarding world, using the Patronus to fight dementors is a sign of elite ability and strength. It’s actually the same in the muggle world too. The better you can recover from bad news, the stronger you become.

I’ve previously written about how I overcome adversity, but dealing with bad news is a bit different. Adversity is a personal struggle. Bad news can happen at a macro (city, state, country, global) level. More specifically, adversity often is just a personal type of bad news.

Dealing with bad news requires your own type of Patronus Charm—a way to confront misfortune with happiness and hope. Today, I’ll break down how you can cast your own Patronus Charm to defend against bad news.

On the x-axis, we have your response to receiving bad news. When you’re hit with something terrible, there are usually two ways to handle it: you can ignore it or you can confront it.

There is an analogy my therapist tells me to consider when dealing with bad news: Imagine you’re a cow grazing in a large pasture. In the distance, you see a horrible thunderstorm coming. You’re left with two choices:

1. Run away from the thunderstorm.

2. Run towards the thunderstorm.

Often, we (myself especially) may find ourselves taking option one. When bad things happen, we want to avoid thinking about them and enduring the pain they cause. Instead, we let the bad news loom—allowing it to permeate our brains with stress, frustration, and apprehension without ever dealing with the issue. Eventually, however, the storm catches up to us, and when it does it actually takes longer to pass.

The better response is to run towards the thunderstorm. When you run through it, you can get through the pain faster, get to the other side, and start grazing again. This requires mental fortitude, though. You need to want to embrace hardship.

On the y-axis, we have how you tap into support resources. When you try to handle bad news alone, it is significantly harder than when you tap into resources, talk to your friends and family, and engage with commentary on the matter. We don’t have all of the answers. Engaging with content and people who can help makes bad news easier to digest. That said, there are times when dealing with bad news by yourself can be a fruitful and meaningful experience.

Understanding the Grid

To deal with bad news, I recommend landing in the top right quadrant. Landing here allows you to handle bad news more effectively and efficiently than you would otherwise. You confront the issue head-on while also tapping into an important web of resources. Landing in other quadrants, from experience, just makes the process of dealing with bad news tougher than it needs to be. While it is still possible to deal with bad news from other quadrants, the result is more challenging and often more grueling.

Recover

You confront bad news and you engage with support resources. I landed here when Kobe Bryant died suddenly earlier this year (which also happened to be my birthday). Kobe was an icon and inspiration. Watching someone who appeared larger than life die so tragically was tough to process. To work through the pain, I confronted it directly. I shared what his life meant to me with friends and in therapy. I wrote down valuable traits from his life I wanted to incorporate into my own. I spent a week or so processing the news and letting it consume me. I ran into the thunderstorm and felt freer on the other side. When I think of Kobe now, I think of all the aspects of his life worth emulating and less about the tragedy of his untimely death. Recovery from bad news is not easy. What makes this quadrant so essential are the long-term benefits that only healthy closure can provide. The hard work is complete. Emotions shouldn’t sneak up on you in the future.

Struggle

You confront bad news but you don’t engage with support resources. Sometimes bad news needs to be handled alone. This is commonly found when you see people writing, journaling, meditating, or exercising when misfortune strikes. For example, you could create a “bad news response habit”—a process designed to help you overcome frustration, grief, and anxiety. For example, when Chadwick Boseman died, I wrote this Gridology post. It helped me organize my thoughts, transfering them from my brain to a physical space. It allowed me to stop thinking about the news and process what had happened. I did the writing all by myself and often struggled through it—taking at least two breaks to let out the raw emotion of what I was feeling.

Sometimes, though, you don’t engage with resources, not by design but because you don’t know where to turn. In these cases, try opening up to a friend or family member. Ask for help. Here’s the worst that can happen: that person can’t help you but offers other resources that could help.

Stress

You ignore dealing with bad news but you engage with support resources. This is the most dangerous quadrant to land. Here you ignore the issue, but still are engaging with resources that you think can help. Another name for this quadrant could be mainstream news syndrome. When bad news happens—especially at the national or global level—you turn on the news and forget to turn it off. You get lost in a cacophony of hot takes, dire warnings, and alarmist undertones. What’s disguised as informing yourself to make you feel better actually makes you feel worse. Although you are engaging with lots of resources to process the news, you haven’t taken the time to confront the issue for yourself. Rather than mindlessly tuning in to cable news this weekend to process the passing of RBG, can you perhaps pause and think about why you’re upset, what actions you will take to process, and how you recover. In this quadrant, you conflate engaging with the issues as dealing with them. They are starkly different.

Deflect

You ignore dealing with bad news and you don’t engage with support resources. This quadrant is the “pretend it never happened” strategy in action. You take option one in the cow analogy above. When you deflect dealing with bad news, you extend the amount of time the news can have control over your mind. Unprocessed bad news accumulates. My dad always says the only thing you can count on with bad news is that it’s not the last piece you’ll ever hear. So, deflecting it only adds to your hardship. It allows anxiety to brew. While the short-term gains are extraordinary (out of sight, out of mind), the long-term implications are devastating. If you have a leak in your house, the last thing you’d want to do is put duct tape over it. With that strategy, you are almost ensuring a bigger and more dangerous problem for yourself down the road.

Grid Shortcomings

1. This grid ignores time. Some bad news takes a long time to move beyond. It hits home in a way that really lingers, no matter how much you try to confront the issue and use resources that help. Sometimes, even when you move past an issue, it can rear its head months or years later. Just because you are dealing with bad news in the right manner, that doesn’t mean the process is quick.

I hope this framework helps you triage whatever the rest of 2020 (and beyond) brings. While I’m not perfect in always responding to bad news in the ways I prefer, I do strive to confront things that bother me directly rather than letting them fester. Plus, the more that I can ask for help when I need it helps ensure I can begin the healing process sooner rather than later.

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s Gridology post, please consider forwarding it to your friends, family, or colleagues. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate.

Given Gridology is a serious weekly time investment, I’d appreciate it if you can help share this newsletter. Can you have one friend, colleague, or family member who you know would enjoy this newsletter subscribe by this time next week? If so, I’d be so, so grateful.

Subscribe now

Let’s jump in:

Jeff Weiner, the former CEO of LinkedIn and its current Executive Chairman, defined compassion in his 2018 Wharton undergraduate graduation speech like this (full text):

“When I was 30 years old I came across a book called The Art of Happiness. It’s about the teachings of the Dalai Lama. That’s how I first learned the difference between empathy and compassion. Empathy is feeling what another living thing feels. Compassion is putting yourself in the shoes of another person and seeing the world through their lens for the sake of alleviating their suffering.

“Though most people in western society typically use the two words interchangeably, there’s a fundamental difference. The Dalai Lama explains it this way: Picture yourself walking along a mountainous trail. You come across a person being crushed by a boulder on their chest. The empathetic response would be to feel the same sense of crushing suffocation, thus rendering you helpless. The compassionate response would be to recognize that that person is in pain and doing everything within your power to remove the boulder and alleviate their suffering. Put another way, compassion is empathy plus action.”

Side note: I highly recommend watching the entire speech.

COMPASSION = EMPATHY + ACTION

Jeff’s definition of compassion is one I love and use daily. It forces you to be a great listener while also being a great problem solver. Plus, it’s fun. It’s also healthy:

“Several studies suggest that supporting others helps buffer our bodies against the detrimental effects of stress. A five-year study of 846 people in Detroit found that stressful life events appeared to take a greater toll on people who were less helpful to others, while helping others seemed to erase the detrimental physical effects of stressful experiences.”

However, it’s a completely different story when we try to be self-compassionate. That’s hard work. It’s something I’ve struggled with for a long time. I hold myself to a high standard, and when I feel as if that high standard isn’t met, I judge and ridicule myself. Once I get going, it’s hard to snap out of that line of thinking. I don’t do this all the time, but growing up this was my default response to failure.

It takes a lot of work to be self-compassionate. I try to get better at it every day, but I still have a ways to go. Sometimes my fiancé catches me disparaging myself and she shouts out, “Hey! Stop that! That’s my fiancé you’re talking about!” It’s always a funny moment, but it helps snap me out of a downward and harmful spiral. She wouldn’t let someone else talk about me the way I was talking about me… so why should she tolerate it from me?

People, generally, know what is and isn’t good for them. Choosing to act in a way that serves us repeatedly over time is the real challenge. Simply put, it’s much easier to don out advice than redirect that advice and apply it to yourself. That’s why this tweet resonates:

I replied back to Jeff and said this:

When you give advice, you’re being compassionate towards your colleagues or friends. You’re listening and problem-solving in real-time. Applying that advice to yourself is tougher. It first requires us to act as a bystander to our own actions—to get outside of our own minds and treat ourselves as we would treat a friend. Then, it requires us to actually act on the advice we’d typically just share and forget about.

It’s part of the reason why I created Gridology. I thought that if I codified advice I’d often share with others, it could help me use it myself. I’m happy to report that 26 weeks in, that hypothesis is true. I find myself listening to my own advice more. I’m less stressed. I’m less anxious. When I’m regressing into old patterns, I read old posts and snap out of it faster than I would have otherwise.

That brings us to today’s grid. When I break down what’s worked for me as I continue improving my ability to be self-compassionate, it comes down to being both forgiving and positive.

Self-compassion is really about training yourself to see yourself as a friend. That’s it. When we believe we are above the advice we’d share with others, we lose. A simple, yet challenging game.

So, on the x-axis, we have how you speak to yourself. When you stumble or fall short, are you judgmental or do you forgive yourself? Do you try to change the past or do you look for ways in which you can improve going forward? Comforting and forgiving yourself cannot be overlooked. We can’t always depend on others to tell us “everything is going to be okay.” We need to develop those muscles and mantras for ourselves. However, being forgiving doesn’t mean to forgive and forget. It means to accept defeat, roll back the mental tape, learn from mistakes, and fix them going forward. Forgiveness without reflection is a superficial endeavor.

On the y-axis, we have your outlook on the future. Do you assume the worst in your actions? Do you see the new opportunities that failure can create? Pessimism kills compassion. Going back to Jeff Weiner’s boulder example, a pessimist looks at the situation and says, “Wow that rock looks way too heavy to move… I’m just one person… there’s nothing I can do to help.” An optimist looks at the same situation and says, “I need to find something to give me better leverage so I can lift this darn thing.” Optimists seek to help no matter what. Pessimists tend to give up fast.

Share

Understanding the Grid

To be self-compassionate, the goal is to land in the top right quadrant. This is where I have had the most success. You should strive to be optimistic and forgiving towards your actions and behaviors. When your inner thoughts gravitate towards ridicule, frustration, and anger, try to flip the script. Pretend you’d say these things out loud to your best friend. If you wouldn’t do it, then you shouldn’t be telling those things to yourself.

Compassionate

You are forgiving and optimistic. When you fall short you recognize that you are human, you’re born to make mistakes, learn from them, and get back up stronger than ever. The optimist in you kicks in. You realize that despite this setback, there are so many wonderful opportunities and new things ahead of you. When you start to criticize yourself for past mistakes, you cut yourself short. You stop rewinding the past and become relentless in optimizing the future. I’ve done a better landing in this quadrant when it comes to my diet. I typically get hypercritical of myself when I eat something unhealthy. Rather than getting down on myself, I’m doing a better job of setting myself up for success at the next meal and getting to the gym more regularly. One error shouldn’t ruin my entire day.

Lackadaisical

You are forgiving but pessimistic. In this quadrant, your thinking allows you to move on from your shortcomings, but not in a way that provides any real value. Imagine this: you take a math test and receive a very bad score. You instantly forgive yourself—telling yourself that it’s okay. However, you aren’t optimistic. Perhaps you start to believe that math just isn’t your thing. Maybe you emptily tell yourself that you’ll do better on the next test. This isn’t being an optimist. Real optimists do not rest until they create positive outcomes in the future. In this scenario, you’re being lackadaisical. You haven’t achieved the high bar you set for yourself and you haven’t created the correct mindset to improve so you can do better in the future. When you’re lackadaisical, you’re able to quiet your inner critic, but you have a growth mindset. Mistakes don’t cripple you, but they also don’t lead to improvement.

Hypercritical

You are judgmental but optimistic. In this quadrant, there is often a lot of frustration and not a lot of celebration. You tend to get angry and disappointed at yourself over things—both big and small—that you deem to be shortcomings. However, you tend to still be positive about the final outcome. This was my experience running the NYC Marathon. When I crossed the finish line, I was ecstatic. I had just completed something I thought I never would be able to do. The experience was incredible and unforgettable. However, when I looked down at my phone and saw that it had taken a second short of four hours and eight minutes, a cloud of frustration hazed my brain. “Just eight minutes short of my goal of breaking the four-hour mark,” I thought. It was like I had forgotten that I crossed the finish line just moments ago for my very first marathon. While I was still hyped on what I just completed, I couldn’t help but feel slightly frustrated too—that things hadn’t gone as I had hoped. I questioned if I should have trained harder or started sooner. That said, I was still optimistic. I didn’t consider the race an utter failure. I believed that if I were to run another marathon, I’d break the four-hour mark then. I’d adjust my training regiment to do so. Ultimately, hypercriticism isn’t crippling, but it sours great moments from being worthy of celebration.

Shameful

You are judgmental and pessimistic. In the wake of failure or hardship, you shut down. It’s hard for you to be kind to yourself when you feel you’re at fault or have done something wrong. The narrative running through your mind is one of judgment and gloom. You can’t find the positive in the situation and nothing you tell yourself makes you feel good. You aren’t treating yourself like you would a friend. Your inner dialogue makes you spiral downward. Each comment makes you feel worse, more remorseful, and less hopeful about the events that transpired. Basically, you’re an Eeyore. There is no positive spin going through your mind to build your self-esteem. To fight this line of thinking, seek the counsel of others. While self-compassion should be the goal, there is no point in needlessly suffering if you aren’t in a place to be self-compassionate. Find someone who can be compassionate to you so you can teach yourself how to play that role in the future.

Grid Shortcomings

1. This grid ignores how important others are in helping you become self-compassionate. Self-compassion is something that is difficult to master yourself. Oftentimes, I need someone to tell me when my internal dialogue sounds nuts. I need a voice of reason when I don’t have one myself. These are critical learning and calibration moments. Eventually, across different domains of my life, I’m able to take the wisdom shared by others and start leveraging it myself. Self-compassion, again, is about being gentle with yourself such that you can work to solve your own challenges.

2. This grid ignores how resilient you are. Resilience and self-compassion are linked. The more resilient you are, the more self-compassionate you tend to be. That’s because, as I wrote with Guillermo Echarte, resilience “…is a mindset. It empowers you to believe you can enter the arena and that you have what it takes to build a successful plan.” That mindset fuels self-compassion.

We deserve the chance to forgive, learn, and grow from our shortcomings. Self-compassion powers this internal chain of events. Without it, we get caught in a cycle of negative thinking, detrimental self-talk, and frustration. We should all strive to look at our own struggles and think to ourselves, “What can I do or say to alleviate my own suffering?”

Life’s only as confusing as you let it be,
Ross

Subscribe now

If you enjoyed today’s Gridology post, please consider forwarding it to your friends, family, or colleagues or checking out the entire archive. As always, please reply to this note or find me on Twitter if you have any feedback, have ideas for a post, or want to collaborate.