How To Live by Derek Sivers

Date read: 2021-09-01

How strongly I recommend it: 8/10

High-level thoughts

A delightful, wide-ranging book with a really cool promise: there are 27 chapters, each presenting a way to live - and each contradicting each other. Some chapters consolidated things I’d already thought about - others opened my eyes to completely new perspectives on life. Feels like a collection of the world’s best maxims and quotes on different areas of life. My favourite chapters were 12, 13, 19 and 21. (Note: I remixed the highlights, so they appear in a different order to the original book)


On commitment, discipline and defining your own rules

When you can’t change your situation, you change your attitude towards it. So remove the option to change your mind.

Choose your home. Stay there for good. Get to know everything about it. Even if you’ve lived there for years, hire a local expert and learn even more about the history, architecture, and areas you haven’t explored.

Commit to your habits to make them rituals. If it’s not important, never do it. If it’s important, do it every day.

Rockets use most of their fuel in the first minute of flight, to escape the pull of gravity. Once they get outside that pull, it’s effortless. Same with your habits. Starting is hard. The rest is easy.

Marriage is for getting through the times when you’re not in love. Expect things to get bad. Your mutual commitment gives you the security to weather the storms, knowing they won’t destroy the relationship. Be loving even when you’re not feeling loving.

Once you decide something, never change your mind. It’s so much easier to decide just once.

Rules must be absolutely unbreakable. If you try to decide, each time, whether it’s OK to break the rule or not, then you’ve missed the whole point of rules. Rules are to save you from deciding. That’s why hard rules are easier to keep.

Discipline turns intentions into action. Discipline means no procrastination. Discipline means now. Choose the pain of discipline, not the pain of regret.

An undisciplined moment seems harmless, but they add up to disaster. Without discipline, the tiny things in life will be your downfall.

Self-control is always rewarding. Self-control is always the right thing to do. This is a universal law.

Define a good life as more than shallow pleasure. A good life is contribution. A good life is resisting temptation. A good life is being the best you can be. A good life is diligently following your rules.

Think super-long-term

Small actions now have a massive impact on the future. Let this fact guide your life. Use a time machine in your mind, constantly picturing your future self, and your great-grandchildren’s world. Act now to influence that time.

We overestimate what we can do in one year. We underestimate what we can do in ten years. If you take up a new hobby at the age of forty, or whatever age you think is too late, you’ll be an expert by the age of sixty.

Be extra-careful of habits that seem harmless. Imagine each choice continuing forever. Eat a cookie, and eventually you’re obese. Shop for fun, and eventually you’re deep in debt. When you choose a behavior, you choose its future consequences.

If an action feels necessary, and you can’t let it go, just write it down for later. Everything seems more important while you’re thinking of it. Later, you’ll realize it’s not. But if it still feels necessary, adjust your time frame. A year from now, will it be important? Ten years from now? Zoom out as far as you need to make it unimportant. Then you’re free of it.

Make and treasure memories

The more memories you create, the longer and richer your life feels.

When you’re young, time goes slowly because everything is new. When you get older, time flies by, forgotten, because you’re not having as many new experiences. You need to prevent this. Monotony is the enemy. Novelty is the solution.

Replace your routines. Live in different places. Change your career every few years. These unique events will become anchors for your memories.

Without memories, you have no sense of self. You have to remember your past to see your trajectory. You use your past to make your future.

Turn your experiences into stories. A story is the remains of an experience. Make your stories entertaining, so people like to hear them. By telling good stories, your memories can last longer, because people will echo them back to you occasionally, or ask you to tell them again.

Develop mastery

Mastery is the best goal because the rich can’t buy it, the impatient can’t rush it, the privileged can’t inherit it, and nobody can steal it. You can only earn it through hard work. Mastery is the ultimate status.

Striving makes you happy. Pursuit is the opposite of depression. People at the end of their life, who said they were the happiest with their life, were the ones who had spent the most time in the flow of fascinating work.

The more you learn about something, the more there is to learn. You see what normal people don’t see. The path gets more and more interesting as you go.

Decisions are easy when you have only one priority. Your destination is a huge mountain peak on the horizon. You can see it from everywhere. Yes to that mountain, and no to everything else. You’ll always know where you’re going, and what you’re doing next. All paths go either towards that mountain or away from it.

If you haven’t decided what to master, pick anything that scares you, fascinates you, or infuriates you. Don’t ask, “Is this the real me?” or “Is this my passion?” Those questions lead to endless searching and disappointment. People don’t fail by choosing the wrong path — they fail by not choosing. Make your choice, then make a lifetime commitment to constant improvement. The passion comes after you start getting good.

You don’t get extreme results without extreme actions. If you do what most people do, you’ll get what most people get. Don’t be normal. Society’s guidelines are for the lost - not for you.

When you live, dream, and work with one single mission, you will achieve that mission.

How long will it take you to become a master? It doesn’t matter. Imagine getting to a mountaintop after a long hike through a gorgeous forest. Achieving your goal would feel like taking off your backpack. That’s all. You do it for the journey, not the destination.

Avoid comfort and learn from pain

Comfort is a silent killer. Comfort is quicksand. The softer the chair, the harder it is to get out of it.

The right thing to do is never comfortable. How you face pain determines who you are. Therefore, the way to live is to steer towards the pain. Use it as your compass. Always take the harder option. Always push into discomfort. Ignore your instincts.

Good luck makes you complacent. Practice thriving with bad luck. Bad luck makes you resourceful and strong. No matter what the world throws your way, you can stand worse.

Be absolutely honest with everyone. Stop lying, completely. You lie when you’re afraid. You lie to avoid consequences. Always say the truth. Take the painful consequences.

Facing pain helps you relate to others. Your problems are never unique. Whatever problems you’ve had, many other people have had the same problem. We empathise with someone who’s struggling. It opens our hearts more than seeing someone win.

The value of fame

A famous pioneer does more for human progress than a billion others who live a normal life.

If someone else innovated in obscurity, they didn’t make an impact. Marco Polo wasn’t the first European to reach China, but he was the first to write a book about it. Then his book inspired Christopher Colombus, and so on.

So if you want to help humanity while having the most exciting life, then the way to live is to be a famous pioneer. Go to new extremes. Try new ideas. Visit undiscovered cultures. Show what can be done. Your job is not just to act, but to tell a fascinating story of how you did so, and inspire others to do it.

The most extreme version of living for others is becoming famous. Do everything in public, for the public. Share everything you do, even though it’s extra work. It’s giving yourself to the world. But being famous means you’ll never be able to reciprocate enough.

Value only what has endured

Ignore all news. If it’s important, there will eventually be a good book about it. When people ask you about current news, proudly have no opinion. Admit you’ve given it no thought at all — and don’t plan to — because it’s not important. Indulging is common. Refraining is rare.

The world of news is noisy, because they have to hype it. They try to get you to pay attention to something that’s not actually important. They create a false sense of urgency, social status, fear, shock, or any tricks possible to manipulate your psychological triggers, and ultimately help them profit. By contrast, the truly important things are quiet. Life is incredibly peaceful when you shut out the noise.

Before trying to improve something old, find out why it is the way it is. Never assume people in the past were ignorant. They did it that way for good reasons. Study the past — understand Chesterton’s fence — before thinking you know better.

Learn time-tested skills that were just as useful in your grandparents’ time as they are today. Speaking, writing, gardening, accounting, persuasion, and survival skills. These skills have hardly changed in a century. They’re unlikely to change in your lifetime.

And so, by ignoring the new, you will improve your life in every way. Better investment of your time. Better peace of mind. Better quality items and entertainment. Better skill set. Better perspective. Better everything.

Value relationships

After age twenty, you need deliberate effort to make new friends. Friends are made, not found. If you sincerely appreciate someone, and really engage with their interests, you will become friends.

Meet up regularly to maintain each friendship, so the connections grow stronger. Be patient with your friends, even for years at a time. Real friendship doesn’t end.

Imagine if you found out someone was going to die tomorrow. Imagine how much attention, compassion, and generosity you’d give them. Imagine how you’d forgive their faults. Imagine what you’d do to make their last day on Earth the best it could be.

You could prepare for disaster by stocking food and ammunition in a bunker by yourself. But what if, instead: You made yourself an integral member of your community. You built a reputation of being helpful and generous. And many people around you cared for your well-being. Obviously, this is a better strategy.

Even if you prefer solitude, you have to admit that being a valuable member of a group is smarter. The best way to be safe is to help others be safe. The best way to be connected is to help others be connected. People look out for each other. But nobody helps the unhelpful. You can’t actually pull yourself up by your bootstraps. Ultimately you are lifted by those around you.

To appreciate something fully, picture losing it. Imagine losing your freedom, reputation, money, and home. Imagine losing your ability to see, hear, walk, or talk. Imagine the people you love dying tomorrow. Never take them for granted.

Develop empathy

Talk with people you usually avoid. Pursue subjects you know nothing about, and experiences unlike anything you’ve done before. If you’re not surprised — if you didn’t feel your brain changing — then you didn’t really learn.

Actively listen to people. When they’re succinct, ask them to elaborate. People aren’t used to someone being sincerely interested, so they’ll need some coaxing to continue. But never try to fix them. When someone tells you what’s broken, they want you to love the brokenness, not try to eliminate it.

Learning is loving. The more you learn about something, the more you can love it. Learn about a place to appreciate it. Learn about people to empathize with them. Not just individuals, but cultures, mindsets, and worldviews. If you are apathetic about or against something, learn more about it.

You don’t love someone to shape their future. You don’t judge your friendships by how successful your friend becomes. So don’t love and judge your children that way. Don’t try to change them. Just give them a great environment where they can thrive. Give them the safety to experiment, make mistakes, and fail up.

Once a place really feels like home, move somewhere new. Pick a confusing or scary place that you don’t understand. Repeat the process. Make it your home. Try to make the connection official by getting visas, residency, and citizenship. Do this until no part of the world feels foreign.

Learn the local mindset. Don’t ask how “they” do things. Ask how “we” do things. That small difference is important. This is your new home.

Be honest, vulnerable and fun

Be warm, open, and fully present with everyone you encounter. Confidence attracts. Vulnerability endears.

Manners are shallow. Honesty is deep. Always tell the real truth, or they’ll never know the real you, so you’ll never really feel loved.

To love something, first you have to connect with it. Give it your full attention. Deliberately appreciate it. Try this with people. Try this with places, art, and sounds. Try this with activities and ideas. Try this with yourself.

Honesty is an ideal that’s always a little further away. It has no finish line. No matter how honest you are, there’s always more honest.

Humor helps you see the familiar from a surprising new perspective. It reminds you that there is no grand truth. Any belief can be up-ended. Every belief can be mocked. Nobody knows anything. See? Laughing is subversive.

Everyone wants to be with someone who’s having more fun. At every moment in life, choose whatever action or angle amuses you.

Get rich

Money can represent freedom, safety, experience, generosity, attractiveness, power, or whatever you want. But really, money is as neutral as math. Because it’s neutral, people have projected all kinds of meaning onto it.

Your biggest obstacle to getting rich is the harmful meaning you’ve attached to it. Your biggest advantage can be projecting a helpful meaning onto it. Make it mean you’re on the right path. Make it a game. Make it mean you’re free.

Study profitable companies the way an artist studies great art. Apply their best techniques to your own pursuit. Doing the math helps you think critically, be realistic, and make better decisions.

You have to be fully committed to getting rich, or it won’t happen. Adjust your self-image so that you congruently feel that you should and will be rich. If you subconsciously don’t feel you deserve it, you’ll sabotage your pursuit.

Don’t aim to just be comfortable. You don’t make the world a better place by just getting by. If you aim to be comfortable, you won’t get rich. But if you aim to be rich, you’ll also be comfortable. Aiming to be rich makes you think bigger, which is more exciting, more fun, and less conventional since most people don’t think big.

Own and control 100% of whatever you create.

Avoid difficult business problems. Your time is more profitably spent doing what comes easily to you.

Follow the rising tides of where profits are going. Get in early on an industry that’s developing quickly. More risk, more opportunity, more investors, more rewards.

Once your business is successful, stay paranoid. Technology is improving faster, so a successful business model doesn’t last as long as it used to. You’ll be disrupted by others if you don’t keep improving or disrupting yourself.

Investing is easy unless you try to beat the market. Settle for average. Don’t over-think it.

Stay frugal. Reducing your expenses is so much easier than increasing your income

Then you’ll get philosophical, since you’ll have all the options in the world. You’ll find your riches are worthless, and maybe even an obstacle, when it comes to friendship and love. Money makes problems go away, but amplifies personality traits. Money won’t change you, but it will amplify who you are.

Reinvent yourself regularly.

What you call your personality is just a past tendency. New situations need a new response.

People love stories, so they connect two events, calling them cause and effect. But the connection is fiction. It’s a hard fiction to escape. “My parents did that, so that’s why I did this.” No. Those two events are not connected. There is no line between moments in time. Same with definitions. “I’m an introvert, so that’s why I can’t.” No. Definitions are not reasons. Definitions are just your old responses to past situations.

Should you try to be consistent with your past self? Should a newspaper try to be consistent with past news? You’re an ongoing event — a daily improvisation — responding to the situation of the moment.

Every year or two, change your job and move somewhere new. Change the way you eat, look, and talk. Change your preferences, opinions, and usual responses. Try the opposite of before.

At every little decision, ten times a day, choose the thing you haven’t tried. Act out of character. It’s liberating. Get your security not from being an anchor, but from being able to ride the waves of change.

Create more than you consume

Most people die with everything still inside of them. The way to live is to create. Die empty. Get every idea out of your head and into reality.

When most people see modern art, they think, “I could do that!” But they didn’t. That is the difference between consumer and creator.

Which would you rather be? Someone who hasn’t created anything in years because you’re so busy consuming? Or someone who hasn’t consumed anything in years because you’re so busy creating?

Most of what you make will be fertilizer for the few that turn out great. But you won’t know which is which until afterward. Keep creating as much as you can.

Separate creation and release. When you’ve finished a work, wait a while before you release it to the world. By then, you’re on to something new. The public comments won’t affect you, since they will be about your past work.

When you’re gone, your work shows who you were. Not your intentions. Not what you took in. Only what you put out.

Change the world

Change the world as much as you can. All your learning and thinking is wasted if you don’t take action. People try to explain the world, but the real point is to change the world.

If you go through life without changing anything, what have you done? Just observed?! The world doesn’t need more audience.

Think of the scientific method. Someone proposes an idea, then others skeptically and rigorously try to disprove it. Use this approach on the world. Assume everything is wrong the way it is. Doubt it and attempt to change it, to prove it’s not correct.

Make it how it should be. Don’t complain. Just make the change.