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

I know that, if you can pull it off, you should continuously have mentors, and be offering mentorship. This can be as formal or informal as you want.

I know how to handle a day when you feel extremely lazy. Decide that, given that you’re a lazy person, you will work diligently for only 30 entirely focused minutes on the most important thing, and then take the rest of the day off. You will do your best work on these days.

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 am not the funniest person, but I am funny enough, and I know how to become funnier if you’re not naturally gifted at comedy. Simply say the stupidest things that enter your head, in a normal tone of voice.

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