But on your death bed, you don’t want that horrible regret, feeling like you spent your life pursuing what someone said you should want, instead of what you actually wanted.

If you expect criticism in advance and take pride in your unusual stance, you can bash on with a smile, being who you want to be. Then every time they say you’re wrong, that’s a sign you’re doing it right.

Be careful when you say you like or dislike something, because you could change your mind soon.

I have to smile, thinking about what my former self would say. But the former self is not always right. We shouldn’t preserve our first opinions as if they reflect our pure, untarnished, true nature. They’re often just the result of inexperience or a temporary phase. Old opinions shouldn’t define who we are in the future.

Never forget that the public you is not you.

Fifteen years later, I came back to New York and met with many of the people I hadn’t seen since then. Every single one of them had ended up about where you’d expect, based on their character. The disciplined ones had succeeded. The temperamental ones had flamed out. The ones who’d acted like leaders were now leaders. The ones who’d blamed everyone else for their lack of results were still doing just that.

Character is the result of your little choices and little actions. How you do anything is how you do everything. It all matters.

Fish don’t know they’re in water. If you tried to explain it, they’d say, “Water? What’s water?” They’re so surrounded by it that it’s impossible to see. They can’t see it until they jump outside of it. This is how I feel about culture. We’re so surrounded by it that it’s impossible to see. Many things we think are true are really just our local culture.

My culture isn’t in the center. It’s off on the edge, like one petal in a flower, like they all are. Not right or wrong — just one of many options. So I’m just a fish who didn’t know he was in water. And in some aspect of your life, you probably are, too.

Both mindsets are necessary. You need a present-focus to enjoy life. But too much present-focus can prevent the deeper happiness of achievement. (I call this “shallow happy” versus “deep happy”.)

The world treats you as you treat yourself. Your actions show the world who you are.

It’s an easier decision. Say no to almost everything. This starts to free your time and mind. Then, when you find something you’re actually excited about, you’ll have the space in your life to give it your full attention. You’ll be able to take massive action, in a way that most people can’t, because you cleared away your clutter in advance. Saying no makes your yes more powerful. Though it’s good to say yes when you’re starting out, wanting any opportunity, or needing variety, it’s bad to say yes when you’re overwhelmed, over-committed, or need to focus. Refuse almost everything. Do almost nothing. But the things you do, do them all the way.

When someone asks me a deep question, I say, “Hmm. I don’t know.” The next day, I have an answer. I’m a disappointing person to try to debate or attack. I just have nothing to say in the moment, except maybe, “Good point.” Then a few days later, after thinking about it a lot, I have a response. This probably makes me look stupid in the moment, but I don’t mind. I’m not trying to win any debates.

People say that your first reaction is the most honest, but I disagree. Your first reaction is usually outdated. Either it’s an answer you came up with long ago and now use instead of thinking, or it’s a knee-jerk emotional response to something in your past.

Personal change needs some space to happen. To bring something new into your life, you need somewhere to put it. If your current habits are filling your day, where are these new habits supposed to go? The English word “quit” comes from old French, meaning “to free” or “to release”. We know about quitting something that’s bad for you, or something you hate. But what about quitting something you love? I rebel against anything that feels like addiction. When I hear myself saying “I need this,” I want to challenge that dependency and prove my independence.

Ten years ago, I felt addicted to America. It was my comfort zone. I loved it too much. I couldn’t imagine living anywhere else. So I made myself quit. I haven’t lived there in ten years, and probably never will again. People often ask if I miss it. Any regrets? Not at all. I still love everything I quit. But not as much as I love all this room for change.

But now the person offering $99 raises their bid to $101. Better to lose only $1 than $99, right? Soon they’re offering me well over $100 to buy a $100 bill, just hoping the other person quits first. The real problem was not thinking it through in advance. When the game starts, it’s easy to think short-term and say, “Ooh! Good deal!” Then when it’s too late, you slowly realize, “Uh-oh. What have I done?” A lot of people get into bad life situations this way. A homeowner buys a house at the top end of their budget. A romantic falls for someone who’s already in a relationship. Later they complain about how they’re so in debt, or their sweetheart is cheating. Before you start something, think of the ways it could end. Sometimes the smart choice is to say no to the whole game.

Then when friends want to hang out with me, I say I need some me-time first. They wonder why, since I’ve been alone all day, so I explain how I’ve actually been very social and connected with so many people.

It’s unusual to be physically alone, but extremely social. A solitary socialite. At first I thought this was a new internet thing. But for decades, there have been people who talk on the phone all day. Before that, there were people who just answered paper mail all day. It works for me. I love people one-on-one. When I’m not answering emails, I’m often talking on the phone with one of my dear friends across the world, getting into great conversations for hours. But it’s a strange life. The solitary socialite.

When I’m feeling cloudy, my decisions and actions will be cloudy too. So I wait a few days before acting on anything. I watch the emotions pass by like a thunderstorm. And the longer I wait, the smarter I get.

Going through the motions, even though I don’t feel like it, is peaceful. I think and process in the background as going about real life.

Kimo’s high expectations set a new pace for me. He taught me that “the standard pace is for chumps” — that the system is designed so anyone can keep up. If you’re more driven than most people, you can do way more than anyone expects. And this principle applies to all of life, not just school.

All the best, happiest, and most creatively productive times in my life have something in common: being disconnected. No internet. No TV. No phone. No people. Long uninterrupted solitude.

It’s not that I hate people. The other best times in my life were with people. But it’s interesting how many highlights were just sitting in a room in that wonderful creative flow, free from the chatter of the world. No updates. No news. No pings. No chats. No surfing. Silence is a great canvas for your thoughts. That vacuum helps turn all of your inputs into output. That lack of interruption helps you flow.

Every business wants to get you addicted to their infinite updates, pings, chats, messages, and news. But if what you want out of life is to create, then those are your obstacles.

I once went without food for ten days, and that was fine. But the two things I can’t do without for long are solitude and silence. (Freedom from people and their noises.)

It’s so important to separate the real goal from the old mental associations. We have old dreams. We have images we want to re-create. They’re hard to untangle from the result we really want. They become excuses, and reasons to procrastinate.

Comparing up versus comparing down: Your happiness depends on where you’re focusing. The metaphor is easy to understand, but hard to remember in regular life. If you catch yourself burning with envy or resentment, think like the bronze medalist, not the silver. Change your focus. Instead of comparing up to the next-higher situation, compare down to the next-lower one.

On the other hand, when you’re being ambitious, trying to be the best at a specific skill, it’s good to be dissatisfied, like that silver medalist focusing on the gold. You can use that drive to practice and improve. But most of the time, you need to be more grateful for what you’ve got, for how much worse it could have been, and how nice it is to have anything at all. Ambition versus gratitude. Comparing up versus comparing down.

When people say they have only two options, it means they got stuck. Once people get two options, they start comparing the pros and cons of those two, and forget to think of more.

Great insight comes only from opening your mind to many options. Brainstorm them all, from the hybrids to the ridiculous. It takes under an hour, but has always helped my friends feel less stressed, think clearly, and get excited about decisions that used to feel like dilemmas.

The problem is taking any one person’s advice too seriously. Ideally, asking advice should be like echolocation. Bounce ideas off of all of your surroundings, and listen to all the echoes to get the whole picture.

Most people overestimate what they can do in one year, and underestimate what they can do in ten years.

I decided to gamble on the opposite. Now I just assume I’m below average. It serves me well. I listen more. I ask a lot of questions. I’ve stopped thinking others are stupid. I assume most people are smarter than me.

What power! Now you’re the person who made things happen, made a mistake, and can learn from it. Now you’re in control and there’s nothing to complain about.

Whenever something has gone wrong in my life, I’ve asked myself, “What’s great about this?"

Eventually, I had an epiphany. I actually love being wrong, even though it cracks my confidence, because that’s the only time I learn. I actually love being lost, even though it fuels fears, because that’s when I go somewhere unexpected.

After two days the excitement wore off. I realized I was never going to do anything with them. Now it was just stupid for me to keep all of these sand dollars sitting there doing nothing. The excitement was in finding them, not keeping them.

But afterwards, I realized something surprisingly profound: Everybody’s ideas seem obvious to them. I’ll bet even John Coltrane or Richard Feynman felt that everything they were playing or saying was pretty obvious. So maybe what’s obvious to me is amazing to someone else.

Eventually, some new thoughts helped: Learning without doing is wasted. If I don’t use what I learn, then it was pointless! How horrible to waste those hundreds of hours I spent learning, and not turn it into action. Like throwing good food in the trash, it’s morally wrong.

At the end of the year, look where the grass has worn away. That shows where the students are walking. Then just pave those paths.

So when should you make decisions? When you have the most information, when you’re at your smartest: as late as possible.

My friend was a brilliant conversationalist, one of the brightest minds I’ve met, but he never put his thoughts into writing. It’s extra-sad that his thoughts are gone, too. So this lesson is dedicated to you, Milt Olin. I’m going to start writing again.

John Cage said, “I can’t understand why people are frightened of new ideas. I’m frightened of the old ones.” Alvin Toffler said, “The illiterates of the 21st century will not be those who cannot read and write but those who cannot learn, unlearn, and relearn."

The adding mindset is deeply ingrained. It’s easy to think I need something else. It’s hard to look instead at what to remove.

The most successful people I know have a narrow focus, protect themselves against time-wasters, say no to almost everything, and have let go of old limiting beliefs.

But if you keep experiencing the same things, your mind keeps its same patterns. Same inputs, same responses. Your brain, which was once curious and growing, gets fixed into deep habits. Your values and opinions harden and resist change. If you don’t flex, you lose your flexibility. You really learn only when you’re surprised. If you’re not surprised, then everything is fitting into your existing thought patterns. So to get smarter, you need to get surprised, think in new ways, and deeply understand different perspectives.

This keeps you in a learning mindset. Previously mindless habits, like buying groceries, now keep your mind open, alert, and noticing new things. New arrivals in a culture often notice what the locals don’t. (Fish don’t know they’re in water.)

To make a change, you have to be extreme. Go all the way the other way. It will feel like overcompensating, but you have to stack a huge pile of bricks on the other side.

Nothing at all. Nothing has inherent meaning. It is what it is and that’s it. We just choose to project meaning onto things. It feels good to make stories.

A bad goal makes you say, “I want to do that some day.” A great goal makes you take action immediately. A bad goal is foggy, vague, and distant. A great goal is so clear, specific, and close you can almost touch it.

Then I made a little change that made a big difference: on my computer, I made a folder called “Possible Futures.” For each big plan, I make a new file in that folder and put all of my ideas and research into it.

You grow by doing what excites you and what scares you.

Legendary psychologist Abraham Maslow said it well: “Life is an ongoing process of choosing between safety (out of fear and need for defense) and risk (for the sake of progress and growth). Make the growth choice a dozen times a day."