I have credited the people who gave me this advice, but this is worded in the way I would say it, and the precise examples are mine. If any of this sounds stupid, I am to blame.

Remember What Used to Work, Then Do It Again

The current composition of your behaviors is probably not strictly rational. Some behaviors, you do because they’re adaptive. Some behaviors are just random accretions of actions that seemed like a good idea at the time, that you then repeated, because repetition is the rule. Some things you do are just bad, and you know they’re bad, but you still do them. It is probably the case that, somewhere in the past, you did something that made you more happy/productive/fulfilled, but you don’t do it anymore, for no good reason. Think about that, and do it again, preferably instead of one of your less desirable behaviors. (I got this from Chris Sparks.)

When Choosing a Life Path, Think About What Contexts It’ll Place You In

When you select a profession, you are choosing the scenes that will compose your life. You should think pretty hard about those scenes. If you start a plumbing company with more than one employee, you will be telling plumbers what to do. You’d better enjoy hanging out with plumbers, and telling them what to do. And when you ask yourself whether you’ll enjoy a given context, don’t just say yes or no to a quickly-sketched abstraction. Really imagine the textures of the experiences you’re likely to have. It’s surprisingly easy to make a decision about the future based on a very crude hypothetical measurement of some objective you’re aiming for, totally excluding any reasoning about what your future might feel like. (I got this from Devon Zuegel.)

Minor Barriers Aren’t Minor

When I have a to-do list, I follow it more reliably if it’s on a sheet of paper, rather than in a notebook with a cover. The minor barrier of a cover between me and the words “SEND BEN AN EMAIL ABOUT THE MEMO” can be the difference between me being effective and ineffective. Having a kettlebell within sight of my window, on the porch, makes it easier for me to exercise than it would be if I had to open a closet to get out my equipment. To some extent, this is probably true of you too, unless you’re abnormally conscientious. Make it incredibly easy to do whatever you want to do. You want to design your life for the least effective, least intelligent, least conscientious version of yourself. That person is probably an idiot. (I also got this from Chris Sparks.)

If You Put Behavior Into the World, You Get Behavior Out

If you’re bored with your life in whatever way, it’s hard to plan for an exciting life. Whatever pre-existing image of an exciting life you have might not map onto your resources, or the actual opportunities in the world, and it might not actually be exciting. However, it is absolutely certain that if you bump into the world in some way, it will bump back, often unpredictably and to a greater extent than you think. Just do anything that’s even slightly interesting to you, without paying too much attention to what you’re trying to achieve. You will find that the world will throw behavior at you, and, at some point, you can curate the behavior you receive into a life you find entertaining. (I got this from Naomi Skwarna.)

Don’t Blunder

Beginning chess players often focus on studying the great games of chess, learning fancy openings, and so on, when they should actually just focus on not blundering. If you make twenty random moves, and then your opponent, after playing nineteen good moves, gives you their queen, you will win the game. Chess is a context that punishes blunders to an unusually great extent, but the lesson does generalize. Avoiding obvious catastrophic failure modes is often more important than improving procedure in minor ways. Slightly upgrading your wardrobe is less important than getting a decent haircut, if your haircut sucks. Improving your knowledge of options trading is less important than not doing leveraged crypto day trading when you’re emotional. If you survive in some field of endeavor long enough, you’ll improve, but survival is the pre-requisite, and that’s what you should attend to first. (I got this from Ben Finegold and Charlie Songhurst.)

It’s Unlikely for People to Be Extreme on Many Dimensions

When we’re impressed by someone, the halo effect often leads us to think they’ll be impressive in every way. But this is not what we should expect. There’s no good reason to believe that someone extremely attractive would be a great conversationalist, or that someone extremely intelligent would be emotionally intelligent, etcetera. In fact, people with extreme traits can often structure their lives in such a way that they can trade on the ways they’re exceptional, leaving no persistent reason to address some particular deficit they have. And, generally, people are savvy enough to hide their dysfunction. People will disappoint you, eventually, and it’s your fault if you take this personally. (This came from Milan Cvitkovic.)

Listening Is in Your Interest, Even If You’re Totally Selfish

Listening empathetically is nice to do because it makes people feel good, and it deepens relationships. But listening is good for you anyway, even if you don’t care about niceness or feeling good. If you want to get your way, you’ll have to bring people over to your side, unless you have enough power to stably coerce them. Doing that requires coming up with a plan that those people will agree to. Doing this effectively requires understanding the full breadth of their experience, opinions, emotions, etc. If you’re not listening to people, but you think you’re persuading them and getting your way, probably what’s actually going on is that you’ve achieved some limited victory at a significant cost that may or may not be initially visible—and you could be missing information that would allow you to better pursue your interests. (This came from Misha Glouberman.)

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