A Modern Dose of Timeless Perspective: “How to Live” by Derek Sivers (Book Summary)

This post is a detailed book summary of How to Live: 27 Conflicting Answers and One Weird Conclusion by Derek Sivers.

🔒 Premium members have access to the companion post: How to Design a Life & Live It with “How to Live” by Derek Sivers (+ Infographic)

Wow! I loved How to Live so much more than I expected I would. I highly recommend reading it in full because it’s a short and easy read—and one of those books where a summary doesn’t really do it justice. If you want to buy it, it’s only available directly from Derek Sivers’ website:

Here’s how Derek Sivers describes the book:

After being inspired by the book Sum: Forty Tales from the Afterlives by David Eagleman (Amazon), Sivers decided to write the book How to Live in the same format. Each chapter gives a different answer to the question of how to live your life:

“Each chapter disagrees with the rest. But in this case, they’re all true, so how can you reconcile it? You’ll see.” — Derek Sivers

Sivers says he wrote 16 hours/day for the last 4 years to compile a first draft of the book that was 1300+ pages. Then he spent 2 years editing the book down to 8% of its original size—only 112 pages remain.

Quick Housekeeping:

• All quotes and photos are from the author unless otherwise stated.
• I’ve limited this summary to 5 quotes per chapter.

Book Summary Contents: Click a link here to jump to a section below

1. Be independent
2. Commit
3. Fill your senses
4. Do nothing
5. Think super-long-term
6. Intertwine with the world
7. Make memories
8. Master something
9. Let randomness rule
10. Pursue pain
11. Do whatever you want now
12. Be a famous pioneer
13. Chase the future
14. Value only what has endured
15. Learn
16. Follow the great book
17. Laugh at life
18. Prepare for the worst
19. Live for others
20. Get rich
21. Reinvent yourself regularly
22. Love
23. Create
24. Don’t die
25. Make a million mistakes
26. Make change
27. Balance everything
28. Conclusion

A Modern Dose of Timeless Perspective: How to Live by Derek Sivers (Book Summary)

1. Be independent

Being fully independent is how to live.

• “If you weren’t dependent on income, people, or technology, you would be truly free. The only way to be deeply happy is to break all dependencies.”
• “Most problems are interpersonal. To be part of society is to lose a part of yourself … Do what you’d do if you were the only person on Earth.”
• “Don’t let ideas into your head or heart without your permission.”
• “You can’t be free without self-mastery … When you say you want more freedom from the world, you may just need freedom from your past self. You don’t see things as they are. You see them as you are.”
• “Learn the skills you need to be self-reliant.”

2. Commit

Committing is how to live.

• “No choice is inherently the best. What makes something the best choice? You. You make it the best through your commitment to it. Your dedication and actions make any choice great.”
• “When you commit to one outcome, you’re united and sharply focused. When you sacrifice your alternate selves, your remaining self has amazing power.”
• “The more social ties we have, the happier we are. The bond of friendship is one of the deepest joys in life. Notice those words: ties, bond. These are words of commitment. We say we want freedom, in theory. But we actually prefer this warm embrace.”
• “Commit to your habits to make them rituals. If it’s not important, never do it. If it’s important, do it every day.”
• “Commitment gives you peace of mind. When you commit to one thing, and let go of the rest, you feel free.”

3. Fill your senses

Filling your senses is how to live.

• “See it all. Touch it all. Hear it all. Taste it all. Do it all. Appreciate this wonderful physical world.”
• “Life is short. How to experience it all? Here’s the key: Here’s your mission: Nothing twice.”
• “This is good for you. The variation in diet is good for your health. The new situations are great for your brain.”
• “Have no expectation of how something should be, or you won’t see how it really is.”
• “How amazing that everything you’re doing is both the first and last time. The thrill of the first. The sentimentality of the last.”

4. Do nothing

Doing nothing is how to live.

• “Stop all the thinking and doing. Be still and silent. No actions and no reactions. No judgments and no conclusions. No craving and no fixing.”
• “Change your need to change things. In your most peaceful moments, your mind is quiet. You’re not thinking you should be doing anything else. When everything feels perfect, you say, ‘I wouldn’t change a thing.’ So, live your whole life in this mindset.”
• “Shallow rivers are noisy. Deep lakes are silent.”
• “Most actions are a pursuit of emotions. You think you want to take action or own a thing. But what you really want is the emotion you think it’ll bring.”
• “Your whole experience of life is in your mind. Focus on your internal world, not external world.”

5. Think super-long-term

Thinking super-long-term is how to live.

• “Serve the future. Do small things now with huge benefits for your older self, your descendants, and future generations.”
• “Only spend money on things that do long-term good, like education. In other words, never spend, only invest.”
• “Many huge achievements are just the result of little actions done persistently over time.”
• “When you choose a behavior, you choose its future consequences.”
• “Short-term thinking is the root of most of our problems, from pollution to debt, both personal and global.”

6. Intertwine with the world

The way to live is to spread your seeds widely before you die.

• “We’re all cousins. Everybody on Earth, no matter how far apart, has a surprisingly recent common ancestor.”
• “If you want a successful network of connections, what matters is not how many people you know but how many different kinds of people you know. Building relationships worldwide brings more opportunity, more variety, and more chance for circumstance.”
• “You can’t see your own culture while you’re inside of it. Once you get out and look back, you can see which parts of your personality actually come from your environment.”
• “Raise your kids with many influences, many parents, and many families. Help raise other people’s kids for the same reason.”
• “Some say ‘blood is thicker than water,’ as if only your immediate relatives have blood. But everyone has blood, and you’re related to all of them.”

7. Make memories

Making memories is how to live.

• “If you can’t remember something, it’s like it never happened. You could have a long healthy life, but if you can’t remember it, it’s like you had a short life.”
• “To enjoy your past is to live twice. Nostalgia links your past and present.”
• “Your memories are a mix of fact and fiction. Your story about an experience overwrites your memory of the actual experience.”
• “The more something means to you, the more you’ll remember it. Give moments meaning to remember them. Take away meaning to forget.”
• “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.”

8. Master something

Pursuing mastery is how to live.

• “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.”
• “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.”
• “If you haven’t decided what to master, pick anything that scares you, fascinates you, or infuriates you.”
• “Mastery is not about doing many things. It’s doing one thing insanely well. The more you take on, the less you’ll achieve. Say no to everything but your mission. This is your one contribution to the world.”

9. Let randomness rule

Letting randomness rule is how to live.

• “Choose a life where you choose nothing. Let the random generator decide what you do, where you go, and who you meet.”
• “Eventually, you’ll look, act, and socialize very differently than your previous self. You won’t define yourself by these things anymore, since you didn’t choose them.”
• “Randomness helps you learn acceptance. You can’t take the blame for failures. You can’t take credit for successes. You can’t regret what you didn’t cause.”
• “How liberating to not decide and not predict anything. Stoics and Buddhists work hard to feel indifferent to outcomes. But you’ll feel detachment as a natural side effect of every day being random. Since nothing has consequences, you’ll greet everything with healthy indifference.”
• “You’ll be living a lesson that everyone should learn. Random stuff happens. All you can control is your response.”

10. Pursue pain

Steering towards the pain is how to live.

• “Everything good comes from some kind of pain. Muscle fatigue makes you healthy and strong. The pain of practice leads to mastery. Difficult conversations save your relationships.”
• “Remember the classic story arc of the hero’s journey. The crisis — the most painful moment — defines the hero.”
• “Choosing pain makes it bearable. It loses its power to hurt you. You become its master, not victim.”
• “Since you can’t avoid problems, just find good problems. Happiness isn’t everlasting tranquility. Happiness is solving good problems.”
• “The English word ‘passion’ comes from the Latin word ‘pati’, meaning ‘to suffer or endure’. To be passionate about something is to be willing to suffer for it — to endure the pain it’ll bring.”

11. Do whatever you want now

Doing whatever you want, at every moment, is how to live.

• “The only real time is this moment. So live accordingly. Whatever benefits you right now is the right choice.”
• “When people ask the meaning of life, they’re looking for a story. But there is no story. Life is a billion little moments. They’re not a part of anything.”
• “If you want to do something, do it now. If you don’t want to do it now, then you don’t want to do it at all, so let it go.”
• “Most problems are not about the real present moment. They’re anxiety, worried that something bad might happen in the future. They’re trauma, remembering something bad in the past. But none of them are real.”
• “Happiness is something to do, someone to love, and something to desire. Heaven is not what’s at the end of the path. Heaven is the path itself.”

12. Be a famous pioneer

Being a famous pioneer is how to live.

• “This is the power of the pioneer: To enable the impossible. To open a new world of possibility. To show others that they can do it too, and take it even further.”
• “Modern explorers like Tim Ferriss, Neil Strauss, and A.J. Jacobs, instead of finding unknown lands, are finding unknown lifestyles. Each of them shows new possibilities for the rest of us.”
• “Pioneers have a massive impact on the world because their stories help people do things they wouldn’t have dreamed of otherwise. A famous pioneer does more for human progress than a billion others who live a normal life.”
• “If you want to help humanity while having the most exciting life, then the way to live is to be a famous pioneer.”
• “Your job is not just to act, but to tell a fascinating story of how you did so, and inspire others to do it. Make great adventures, but tell greater stories. Pursue massive media attention, not for vanity or ego, but so your stories can open minds, spark imaginations, and lead to further explorations.”

13. Chase the future

Chasing the future is how to live.

• “Live in the world of tomorrow. Surround yourself only with what’s brand new and upcoming. That’s where life is made. It’s the most optimistic environment, full of hope and promises.”
• “Since everything will always be new, you won’t rely on assumptions or habits. You’ll pay full attention and keep learning every day.”
• “Ownership binds you to the past. Don’t get invested in any one thing. Stay immersed only in what’s coming next.”
• “Spend your social time meeting new people. You’re not the same person you were last year or even last week.”
• “The best benefit of living this way is how you cut all ties and never look back. Every day will be like amnesia. Whatever traumatic thing might have happened in your past, it no longer defines you. In your world, the past has no power at all.”

14. Value only what has endured

The way to live is to ignore everything new.

• “The pleasure of buying a new thing disappears in days, even hours. So much misery comes from indulgences in current junk.”
• “Ignore all marketing and advertising. Nobody is pushing what really matters. Friendships, nature, family, learning, community. The best things in life aren’t things.”
• “Watch the greatest movies of all time. Read the classics. Listen to the legends. These things have lasted because they work so well. Time is the best filter.”
• “Technology advances faster than wisdom. It’s smarter to move at wisdom’s pace.”
• “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.”

15. Learn

Learning is how to live.

• “Learning is underrated. People wonder why they’re not living their ideal life. Maybe they never learned how.”
• “If you’re not embarrassed by what you thought last year, you need to learn more and faster.”
• “Be surprised by something every day. Find that exciting moment when you get a completely new perspective … If you’re not having these moments often, find new inputs.”
• “Knowledge is often described simply — ‘in a nutshell’. But the inside of a nutshell is complex. So crack open nutshells to understand them better. Put concepts in a nutshell to keep them in your pocket and pass them around.”
• “Learning makes you a better person and makes the world a better place. Learning is a pursuit you can’t lose. As you age, you’ll lose muscle and beauty, but you won’t lose your wisdom.”

16. Follow the great book

Following your book is how to live.

• “You know what your great book is. Whether the Bible, Tanakh, Upanishads, Quran, Think and Grow Rich, Seven Habits of Highly Effective People, or another, follow it diligently.”
• “Your book is the expert on how to live. It’s helped millions of people. Defer to its wisdom.”
• “The human condition remains the same. Your book has all the wisdom you need. Read metaphorically, and apply it to your modern life.”
• “Bring your book with you everywhere as a constant reminder and reference. Refer to its rules in every situation, every day.”
• “Rules give you freedom from your desires. When you rise above your instincts, you still feel them but no longer do what they say.”

17. Laugh at life

Laughing at life is how to live.

• “Humor means using your mind beyond necessity, beyond reality, for both noticing and imagining.”
• “To laugh at something is to be superior to it. Humor shows internal control.”
• “No matter what you need to do, there’s a playful, creative way to do it. Playing gives you personal autonomy and power.”
• “You can make light of anything. Respond to life’s events however you want. Nothing has to get you down.”
• “Humor helps you see the familiar from a surprising new perspective. It reminds you that there is no grand truth.”

18. Prepare for the worst

Preparing for the worst is how to live.

• “How can you thrive in an unknowable future? Prepare for the worst. Train your mind to be ready for whatever may come.”
• “Your biggest enemy is insatiability. Recognize your desire to be entertained by life, and break the habit. Practice being happy with what you have.”
• “Your circumstances in life don’t actually change your happiness. People who become paralyzed or win the lottery go back to being as happy as they were before. So don’t depend on circumstances. Everything that happens is neutral. Your beliefs label it as good or bad.”
• “When something happens, don’t interpret. No story, no ‘should have’, no judgment, not even an opinion. This is seeing clearly.”
• “Shallow happy is having a donut. Deep happy is having a fit body. Shallow happy is what you want now. Deep happy is what you want most. Shallow happy serves the present. Deep happy serves the future. Shallow happy is trying to conquer the world. Deep happy is conquering yourself. Shallow happy is pursuing pleasure. Deep happy is pursuing fulfillment. Fulfillment is more fun than fun.”

19. Live for others

Living for others is how to live.

• “What’s good for your community is good for you. Whatever affects others affects you. The quality of your life is tied to the quality of your community, neighborhood, and country. You can’t be healthy in a sick society.”
• “Psychologists, philosophers, and religions all agree on one thing. Helping others is a better path to happiness than helping only yourself.”
• “Success in business comes from helping people — bringing the most happiness to the most people. The best marketing is being considerate. The best sales approach is listening. Serve your clients’ needs, not your own. Business, when done right, is generous and focused on others. It draws you out of yourself, and puts you in service of humanity.”
• “Share everything you do, even though it’s extra work. It’s giving yourself to the world.”
• “Your caring should grow until it reaches past your community, past your country, past your generation, and past your species.”

20. Get rich

Getting rich is how to live.

• “Money is nothing more than a neutral exchange of value. Making money is proof you’re adding value to people’s lives. Aiming to get rich is aiming to be useful to the world. It’s striving to do more for others. Serving more. Sharing more. Contributing more. The world rewards you for creating value.”
• “Money is social. It was invented to transfer value between people.”
• “Charge for what you do. It’s unsustainable to create value without asking anything in return. Remember that many people like to pay.”
• “The more something costs, the more people value it. By charging more, you’re actually helping them use it and appreciate it. Charge more than is comfortable to your current self-image. Value yourself higher, then rise to fit this valuation.”
• “Stay frugal. Reducing your expenses is so much easier than increasing your income.”

21. Reinvent yourself regularly

The way to live is to regularly reinvent yourself.

• “What you call your personality is just a past tendency. New situations need a new response.”
• “Putting a label on a person is like putting a label on the water in a river. It’s ignoring the flow of time.”
• “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.”
• “Nature changes seasons at regular intervals. So should you. We can’t prolong one season. Never stay too long.”
• “Every reinvention is the beginning, which is the most exciting time.”

22. Love

Loving is how to live.

• “Not love, the feeling, but love the active verb. It’s not something that happens to you. It’s something you do.”
• “Work is love in action.”
• “The more you really connect with people, the more you learn about yourself: what excites you, what drains you, what attracts you, and what intimidates you.”
• “Beware of the feeling that someone completes you or will save you. You have wounds in your past. You have needs that were ignored. You seek someone to fill these gaps — someone that has traits you crave. But nobody will save you. You have to fill those gaps yourself.”
• “Unless you are drops of liquid, one plus one never equals one. You must both be free and able to live without each other. Be together by choice, not necessity or dependence. Love your partner, but don’t need your partner.”

23. Create

Creating is how to live.

• “The most valuable real estate in the world is the graveyard. There lie millions of half-written books, ideas never launched, and talents never developed. 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.”
• “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.”
• “Most creations are new combinations of existing ideas. Originality just means hiding your sources.”

24. Don’t die

Not dying is how to live.

• “There’s only one law of nature: if you survive, you win.”
• “Avoiding failure leads to success. The winner is usually the one who makes the least mistakes.”
• “People focus on having the upsides in life. Instead, focus on avoiding the downsides.”
• “Don’t waste a single minute. Life can be long if you use time wisely. But wasting time brings death quicker. Time is the only thing that can’t be replaced.”
• “Death reminds us that time is limited and precious. Without death, there would be no motivation. Death gives value to life — gives us something to lose.”

25. Make a million mistakes

Making a million mistakes is how to live.

• “Try absolutely everything, all the time, expecting everything to fail. Just make sure that you capture the lessons from each experience. And never make the same mistake twice.”
• “The more mistakes you make, the faster you learn. Once you’ve made all the mistakes in a field, you’re considered an expert.”
• “You only really learn when you’re surprised — when your previous idea of something was wrong. If you’re not surprised, it means the new information fits in with what you already know. So try to be wrong. Try to disprove your beliefs.”
• “There’s only one difference between a successful person and a failure. A failure quits, which concludes the story, and earns the title.”
• “Your growth zone is your failure zone. Both are at the edge of your limits. That’s where you find a suitable challenge. Aim for what will probably fail. If you aim for what you know you can do, you’re aiming too low.”

26. Make change

Making change is how to live.

• “All progress comes from those who ignore the boundaries, break the rules, or make a whole new game.”
• “Begin by righting what’s wrong. Look for what’s ugly: ugly systems, ugly rules, ugly traditions. Look for what bothers you. If you can fix it, do it now.”
• “Rearrange and remix. That’s how nature grows. A cow is rearranged grass. All the atoms get reused.”
• “Changing the world includes changing yourself. Change your beliefs, preferences, acquaintances, hobbies, location, and lifestyle.”
• “Change others. Changing minds and hearts can have more impact than physical change. A great speech can do the work of a thousand soldiers.”

27. Balance everything

The way to live is to balance everything.

• “Even positive traits, when taken too far, become negative.”
• “Virtue is in the balance between extremes.”
• “Imagine the different aspects of your life as the spokes in a wheel: health, wealth, intellectual, emotional, spiritual, or however you divide it. If any of these are lacking, it makes a lopsided, wobbly wheel, causing you to crash. But if you keep the parts of your life balanced, your wheel is round, and you can roll easily.”
• “Balance input and output, consumption and creation, stability and adventure, body and spirit.”
• “By balancing everything in your life, you postpone nothing. You won’t postpone happiness, dreams, love, or expression. You could die happy at any time.”

28. Conclusion

Derek Sivers ends the book with perhaps the shortest conclusion you’ll ever read in any book. Get the book to find out! Hint: polarity thinking.

You May Also Enjoy:

• See all book summaries

• See all book recommendations and reading list

• 🔒 How to Design a Life & Live It with “How to Live” by Derek Sivers (+ Infographic)

• The Blind Men and The Elephant: A Short Story about Perspective

• Systems Thinking & Understanding how Everything Connects: “Thinking in Systems” by Donella Meadows (Book Summary)