How can I be more self-compassionate?

We should treat ourselves like we treat our friends

Week 26. Half a year. Thank you all. I’ve absolutely loved writing Gridology—it’s been a way for me to get thoughts out of my mind and onto paper. While this newsletter first and foremost is for me, it makes writing each week much easier when I know others are finding value from it, too. I couldn’t have a better group of readers. Thank you.

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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.


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.


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.


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.


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.


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.


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,

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