Over the years, as I’ve gradually grown dumber relative to my peers through a combination of aging and making smarter friends,

What I discovered by casting a wide net was that I have very little ability to predict how useful a call will be in advance. Relevance is easier to predict, but it’s not a very good proxy for usefulness, which is a product of lots of other things including the other person’s enthusiasm and the breadth of their interests. To some extent, the more... See more

radical agency is about finding real edges: things you are willing to do that others aren’t, often because they’re annoying or unpleasant. These don’t always surface in awareness to the point one is actually choosing -- often they live in a cloud of aversion that strategically obscures the tradeoff.

In my way of thinking, radical agency is about finding real edges: things you are willing to do that others aren’t, often because they’re annoying or unpleasant. These don’t always surface in awareness to the point one is actually choosing -- often they live in a cloud of aversion that strategically obscures the tradeoff.

If you aren’t trying to get real feedback from people who know you, you’re cooking without tasting.

I sent an email recently that I wouldn’t have dared try a few years ago, something along the lines of “I’m planning to start an organization similar to yours; would you consider letting me run yours instead?” The response? Crickets. Maybe that person thinks I overstepped. But it doesn’t matter, because a similar pitch delivered to someone else put... See more

My rule is never to take instructions on how hard I should work from someone who hasn’t burned out before. Very few people take this seriously enough.

The idea is that making changes in your life, especially when learning new skill sets, requires you to cross a moat of low status, a period of time where you are actually bad at the thing or fail to know things that are obvious to other people.

It’s called a moat both because you can’t just leap to the other side and because it gives anyone who can... See more

Burnout is the ultimate agency-killer. This is so true that I’ve learned to identify a reduction in agency as one of the first signs of burnout, one that shows up even before I consciously realize what’s happening