I know how to spot real confidence. Look for people who are fluid with status—who allow themselves to be the butt of a joke, or accept criticism, but also avoid false modesty, and inhabit the spotlight when it falls on them.

I know that it feels horrible to create from a place of defense. For example: you will find it exceedingly difficult to write if your motive is trying to convince people that you are not dumb, or not boring, or if you’re hoping that you will not offend anybody.

I know how to spot real confidence. Look for people who are fluid with status—who allow themselves to be the butt of a joke, or accept criticism, but also avoid false modesty, and inhabit the spotlight when it falls on them.

I know that freedom is earned by confronting things that embarrass and trigger you, over and over again, until you are cringe-proof in your desired environment.

I know what makes people grow more reliably than anything else. It is: taking on a difficult project with some amount of public accountability. This can be large or small: a lecture series, a business, a blog, a house, a child, etc.

I know that travel is valuable because most knowledge can’t be written down. The most crucial info about a society is how it feels to be there—the rhythms of street life, where and when people eat meals, how gender works. You can read a million things about Japan without knowing the bodily experience of walking around in a truly high-trust society,... See more

I know that freedom is earned by confronting things that embarrass and trigger you, over and over again, until you are cringe-proof in your desired environment.

I know that talent doesn’t feel like you’re amazing. It feels like the difficulties that trouble others are mysteriously absent in your case. Don’t ask yourself where your true gifts lie. Ask what other people seem weirdly bad at.

I know that talent doesn’t feel like you’re amazing. It feels like the difficulties that trouble others are mysteriously absent in your case. Don’t ask yourself where your true gifts lie. Ask what other people seem weirdly bad at.