"In practice, “stay upwind” reduces to “work on hard problems.” And you can start today. I wish I’d grasped that in high school."
"Most people like to be good at what they do. In the so-called real world this need is a powerful force. But high school students rarely benefit from it, because they’re given a fake thing to do. When I was in high school, I let myself believe that my job was to be a high school student. And so I let my need to be good at what I did be satisfied by merely doing well in school."
"If you’d asked me in high school what the difference was between high school kids and adults, I’d have said it was that adults had to earn a living. Wrong. It’s that adults take responsibility for themselves. Making a living is only a small part of it. Far more important is to take intellectual responsibility for oneself."
"If I had to go through high school again, I’d treat it like a day job. I don’t mean that I’d slack in school. Working at something as a day job doesn’t mean doing it badly. It means not being defined by it. I mean I wouldn’t think of myself as a high school student, just as a musician with a day job as a waiter doesn’t think of himself as a waiter.  And when I wasn’t working at my day job I’d start trying to do real work."
"When I ask people what they regret most about high school, they nearly all say the same thing: that they wasted so much time. If you’re wondering what you’re doing now that you’ll regret most later, that’s probably it. "
"You may be thinking, we have to do more than get good grades. We have to have extracurricular activities. But you know perfectly well how bogus most of these are."
"It’s dangerous to design your life around getting into college, because the people you have to impress to get into college are not a very discerning audience. At most colleges, it’s not the professors who decide whether you get in, but admissions officers, and they are nowhere near as smart. They’re the NCOs of the intellectual world. They can’t tell how smart you are. The mere existence of prep schools is proof of that."
"Right now most of you feel your job in life is to be a promising college applicant. But that means you’re designing your life to satisfy a process so mindless that there’s a whole industry devoted to subverting it. No wonder you become cynical."
"By putting you in this situation, society has fouled you. Yes, as you suspect, a lot of the stuff you learn in your classes is crap. And yes, as you suspect, the college admissions process is largely a charade."
"One of the most dangerous illusions you get from school is the idea that doing great things requires a lot of discipline. Most subjects are taught in such a boring way that it’s only by discipline that you can flog yourself through them."
"A key ingredient in many projects, almost a project on its own, is to find good books. Most books are bad. Nearly all textbooks are bad.  So don’t assume a subject is to be learned from whatever book on it happens to be closest. You have to search actively for the tiny number of good books."
"The important thing is to get out there and do stuff. Instead of waiting to be taught, go out and learn."
"You start being an adult when you decide to take responsibility for your life. You can do that at any age."