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 you cannot skip to the punchline of the cosmic joke. If you’re ambitious, it will be hard to believe that achievement won’t make you completely happy until you accumulate some achievements, and notice the gaps in your happiness. Legend has it that the Buddha woke up at 35, and this seems about right — by your mid-thirties, you have... See more

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 silence is an underused conversational tactic. It makes people more interesting and builds intimacy.

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 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 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. One might call this a balance between dignity and humility. Pro tip: people who always cling to high status aren’t confident... See more

I know that almost nobody hears too many sincere compliments. Compliment them to their face. Then, compliment them behind their back. Practice naming pleasant feelings you have about people, as soon as they bubble up, in the moment: “It’s always fun to see you.” Lower the resistance around this to zero.

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.