How can I use self-reflection to improve?

Be both the detective and the suspect

In case you missed it, earlier this week I published the first episode of the Gridology podcast (it’s the audio version of this post). Special, special thank you to Nathan Frazer for the original theme music. Fun fact: Nathan was the very first person to sign up for Gridology, so it’s only fitting to have him help get the podcast off the ground. More episodes are coming as soon as I’m able to record them.

Listen to episode 1

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Now on to today’s post:

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.


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.


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.


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.


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,

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.