How to find your blind spots

Anyone who knows me can vouch for my tendency to frenetically pick up and drop hobbies. I’ve found two benefits of this:

• No one’s ever intimidated by you because your next embarrassment is right around the corner
• By starting out mediocre at so many things, you notice similarities in how to improve – at least up until somewhere in the middle of the bell curve

One striking similarity is how many skills have a saying among the experts akin to “the key to drawing well is learning to see well.” I’ve heard variations of this phrase used for chess, cooking, and programming.

The root of these sayings is that humans are just awful at debugging why things really go wrong. Unfortunately, this ability is absolutely crucial to improving at things. In my experience, the most pernicious bias at play is the tendency to immediately blame failures on the most proximal (closest) cause of a problem rather than searching harder for the most important cause. For example, a chess player may blame a blunder on a careless tactical mistake when in reality their poor opening led them into a situation in which some mistake was inevitable. I’ve written about my own experience with this phenomenon in Rocket League and Root Cause Misattribution.

To get better at debugging failures, you need to develop a better understanding of what’s happening under the scenes, thereby separating the inputs of the activity from the outputs - a win or a loss, a good painting or a bad one. Without this understanding, your only validation that you performed well is success, which is a regrettably noisy and lagging indicator. It’s entirely possible to play a good game of chess that you lose. It’s also possible to play a bad game of chess that you win. Success is an even worse measure for endeavors like engineering, where a result may arrive only after months, years, or decades of work. To improve rapidly, you need to consciously seek out shorter feedback cycles.

Across domains, I’ve found that experts almost always find these shorter feedback cycles by breaking the larger skill down into “minigames” with clearer objectives. This is what I call “vision”: being able to peek under the surface of an activity to recognize the minigames being played and when each is applicable. Improving your vision allows you to identify which minigame your ultimate failure can be attributed to and focus your improvement efforts.

A decent start to a list of “minigames” for an amateur sketcher might be:

• Do I have the right shapes for the items in the scene?
• Are these items positioned correctly relative to another?
• Are the items’ relative sizes correct?

In my experience, “reaching the next level” in a skill usually means adding one or two new minigames to your arsenal while making only modest improvements in minigames that you’re already aware of. In contrast, I find that most people think that the path to improvement lies solely in building upon minigames they know. This difference can lead to significant frustration because “what got you here won’t get you there”.

I regularly see junior software engineers make this mistake: after landing their first “real” job, they’ll seek to reach the next level by trying to learn how to solve trivial Leetcode problems faster. They’d almost always be better served by “going deep” and closing some foundational gap they see between themselves and the more effective senior engineers. The number of those gaps may seem daunting, but the gains compound. Leetcode may have gotten you the job, but it almost certainly won’t help you make more of an impact in your role.

In my opinion, identifying which minigames you should be focusing on at which skill level is the most important value a good coach can provide. Whenever you fail, you almost certainly could have done something better along some axis that you already know about: you could have worked another hour per day or been more (or less) responsive to email. You could have played a better chess opening or seen some tactic. You’re human. Furthermore, if you were failing, chances are you were under some amount of pressure that caused you to make tradeoffs.

A good coach or mentor can provide the superior vision to help you find the ultimate cause of your failure rather than just the most proximal one. Furthermore, that coach can help you identify which minigame you need to improve at and find good resources to do so.

When seeking out a good coach, it’s not sufficient to find someone that’s an expert at the activity. In the chess world, Magnus Carlsen may be the world chess champion but he seems like he’d be a pretty miserable chess coach: he’s notoriously unenthused about explaining his reasoning to others. John Bartholomew, on the other hand, is a very-good-but-not-great chess streamer who’s gifted at explaining how he makes decisions each step along the way. Given the choice between each player as a coach, I’d choose John every time.

Recently, many of the best “coaches” I’ve found are actually content creators: listening to them is like eavesdropping on a conversation between people far, far smarter than I am. The Acquired podcast has taught me more about “big tech strategy” and venture capital than working in big tech ever did. Rob Walling’s Startups Like the Rest of Us has proven similarly useful for learning how to launch bootstrapped businesses. John Bartholomew was a wonderful chess coach even though I just watched his YouTube channel. This is a huge benefit to the information age: you can get access to some of the best coaches in the world without changing out of your sweatpants.

Given the number of successful professionals that credit a mentor they actually talk to for their success, I wish I had better advice about how to find one. I’ve struggled with this myself, but I suspect the right person would be invaluable. Until that time, I’ll just remain thankful that we live in the age of YouTube and podcasts.