Within maybe 10 minutes of meeting, he showed me this terrifying — to him it was probably wonderful — spreadsheet of how he accounted for every hour of the day for the last couple of years. That’s probably not even as unusual as we might think, but there was a score at the end of the thing based on whether he had spent enough hours doing the different categories of things he wanted to be doing. I don’t know if he secretly feels punished by his own system or if he feels empowered by it. There’s not really any way for me to know. My skepticism is more about that rhetoric and way of thinking of time as being offered as a solution to someone who doesn’t have control of their time — that if they controlled their time in this gridlike way, they could succeed in life. I think that person has the potential to use that way of thinking very self-punitively.

Since you mentioned kids: A couple of weeks ago, I was hanging out with a friend who has a 3-year-old, and it took us half an hour to walk two blocks. There is a way in which, as you were saying, you could view that experience as potentially boring, but you could also see that the reason we were walking slowly is that kids are looking at stuff in a weird way! It’s a way I appreciate trying to imagine. For time spent like that, the whole question of “What are you getting out of this?” would be absurd.

A life of total efficiency and convenience? Well, why? What is left if you were to make everything superconvenient? It is helpful to make certain things more efficient, but that can tip over into becoming its own end, which moves the focus away from that larger question of why.

I want to be in contact with things, people, contexts that make me feel alive. I have a specific definition of alive, which is I want to feel like I am being changed. Someone who’s completely habitual, is set in their ways of thinking and doing, that type of person is liable to see days in a calendar as being pieces of material that you use to achieve your goals. There’s all kinds of degrees between that and someone who’s so completely open to every moment that they’re dysfunctional or something, but I want to live closer to that second pole.

What is our purpose on this planet? Do we have a responsibility to one another? Who even are we?Answering those questions alone is asking a lot of a person. The easier option is to choose from the platter of social-strata-acceptable possibilities we’re presented with for education, occupation, geographical location, personality, etc, and call it a day.

if you spend all your time constantly sketching (probably quickly outdated) pictures of your thinking on the bigger questions we’ve all been tasked with answering, you neglect the actual doing that would reveal answers with richer hues

incredible opportunities are unlocked by constructing a digitally consumable caricature of yourself that makes you legible to literally anyone in the world. It’s probably the most far-ranging bat signal possible to find people who think and feel similarly to you.

There’s simply so much friction in the process of turning belief into action online — meaning that most of the time all you actually get from internet attention is internalized impossible-to-attain expectations for yourself and an extremely confused ego.

If you care about personally choosing the shape, scale, and direction of your impact on the world, you might find that playing off-the-shelf games turns out to be a remarkably risky bet. There’s just no money/time-back guarantee that any of the off-the-shelf options will continue to fit you as your desires evolve. And maybe that’s ok — but continually reinventing yourself is a tiring and time-consuming task that too often leads you away from the real “calling”-finding-and-defining work.

In my book, big things are only worth committing to if the answer to the question “would you do this thing even if no one was watching?” is an immediate and unequivocal yes