In Derek Sivers' latest, he shares a collection of diverse answers to the question of how to live. He describes it as an homage to Sum: Forty Tales from the Afterlives, which takes on the question of "What happens when you die?"

Personally, I really enjoyed How to Live. The ideas are concise and easy to digest, but provocative enough to keep you thinking for some time afterward. These are the quotes and ideas that stood out the most to me:

Author's note: I recommend checking out How to Live for yourself, as the quotations I have picked out act as a personality test of sorts. Basically, I've knowingly over-indexed on the ideas that resonate with me the most. That might look very different for you. Enjoy.

Be Independent

  • All misery comes from dependency. 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.
  • Do what you’d do if you were the only person on Earth.
  • Your past indulgences and habits might be addictions. Quit a harmless habit for a month, just to prove you can.
  • 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. Change yourself and you change the world.
  • When you have no home, the whole world is your home. Be a nomadic minimalist to break dependencies on stuff. Our hunter gatherer ancestors thrived by carrying nothing, then finding or making what they needed.
  • Be a perpetual traveler, living out of a suitcase. Move to a new country every few months, never a registered resident of anywhere.
  • Then you can appreciate everything from a healthy distance. You can appreciate your country from abroad, once it’s not your only option. You can appreciate family, once they’re not forced upon you


  • You’ve been looking for the best person, place, or career. But seeking the best is the problem. 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.
  • You can stop seeking the best option. Pick one and irreversibly commit. Then it becomes the best choice for you. Voilà. dfWhen a decision is irreversible, you feel better about it.
  • Commitment gives you peace of mind. When you commit to one thing, and let go of the rest, you feel free. Once you decide something, never change your mind. It’s so much easier to decide just once.

Fill Your Senses

  • See it all. Touch it all. Hear it all. Taste it all. Do it all. Appreciate this wonderful physical world.
  • If you knew you’d go blind tomorrow, how intensely would you look at the world today? If you knew you’d go deaf tomorrow, how intensely would you listen? Fill your senses as if this was your last day on Earth. One day that will be true.
  • Life is short. How to experience it all? Here’s the key: Nothing twice.
  • Find places that bombard your senses. India. Burning Man. Festivals. Museums. Celebrations. Funerals. Skydive. Scuba dive. Run with bulls. Swim with sharks. Float in space.
  • Simple systems help force change. Every month, get rid of your existing clothes. Get new clothes in a new style. Do this while traveling, so one month your clothes are from Morocco, next month from Italy, next month from Japan.
  • But after decades of this, you’ll need something radically new. Stay in one place. Be with one person. Buy a home. Raise a baby. It’s terrifying, but if you don’t, it will be the one experience you never had.

Do Nothing

  • Your whole experience of life is in your mind. Focus on your internal world, not external world.
  • Let go of feeling needed. Let go too soon instead of too late. The world doesn’t need you. You’re relieved of your duty because soon you won’t exist. Do nothing now to show that life goes on without you. Be selfless. Be free.

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.
  • The actions are obvious. Put money in an investment account and never withdraw. Eat mostly vegetables. Exercise always. Get preventative health checkups. Make time for your relationships. Do these, yes, but let’s look at less-obvious ones.
  • Your future self is depending on you. Your descendants are depending on you. Our future generations are depending on us. Use the compounding amplifier of time.

Intertwine with the World

  • We’re all cousins. Everybody on Earth, no matter how far apart, has a surprisingly recent common ancestor. Go meet your family in the Middle East, in Asia, in Africa, in the Americas, and in Europe. Understand that there is no “them”. It’s just “us”. Feel those connections.
  • 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.
  • Move somewhere far away. Plan to stay. Bring no baggage. Leave your expectations and certainties behind.
  • This new strange place will feel wrong. You’ll find fault in most of its ways. The clothes you arrive in are not suited for its climate. The beliefs you arrive with are not suited for its culture. Replace both with locally-made clothes and beliefs. Eventually, they’ll fit you well.
  • Don’t ask how “they” do things. Ask how “we” do things. That small difference is important. This is your new home.
  • 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.

Make Memories

  • What if, when you’re older, you can’t recall entire years? 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. What a horrible way to live.
  • 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.
  • Go make memories. Do memorable things. Experience the unusual. Pursue novelty. Replace your routines. Live in different places. Change your career every few years. These unique events will become anchors for your memories.
  • 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.

Master Something

  • 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.
  • 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 need ritual, not inspiration. Every day, no matter what, you must practice. Your practice ritual is your highest priority — an unbreakable commitment. Stubbornly protect this time against the demands of the world.
  • Once you get momentum, never stop. It’s easy to continue, but if you stop, it’s hard to start again. Never miss a day.
  • You don’t get extreme results without extreme actions. If you do what most people do, you get what most people get. Don’t be normal. Society’s guidelines are for the lost - not for you.

Let Randomness Rule

  • We think we see patterns and causes. Really there are none.
  • Let the random generator decide what you do, where you go, and who you meet. It’ll scramble your habits. It’ll break the myth of causality. It’ll guide you to see places you’d never ordinarily see, and do what you never would have done.
  • Randomness keeps your mind open and observant. You can’t predict, so you see clearly. You can’t use old solutions and rules-of-thumb. You can’t blame karma, astrology, demons, saints, anyone or anything else.
  • When ordering in a restaurant, ask them to surprise you. When doing creative work, let the random generator make your artistic decisions, shaking up your usual style. Let your random generator decide where you live every year. That increases the randomness of everything else.
  • Randomness helps you learn acceptance. You can’t take the blame for failures. You can’t take credit for successes.

Pursue Pain

  • Everything good comes from some kind of pain. You avoid pain, you avoid improvement.
  • The goal of life is not comfort. Pursuing comfort is both pathetic and bad for you. Comfort makes you weak and unprepared
  • People say they’re not doing the work because it’s hard. But it’s hard because they’re not doing the work.
  • Comfort is a silent killer. Comfort is quicksand. The softer the chair, the harder it is to get out of it.
  • Put yourself into stressful situations. Eventually, almost nothing will seem stressful.
  • Socially, try to get rejected. Learn about “rejection therapy”. Make audacious requests that you think will be denied. This removes the pain of rejection. And you’ll be surprised how often they say yes.

Do Whatever You Want Now

  • The past? That’s what we call our memories. The future? That’s what we call our imagination. Neither exists outside of your mind. The only real time is this moment.
  • 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.
  • Live like a frog sitting on a lily-pad. When it feels like it, it jumps to a different one, and stays until it feels like jumping again.
  • Your feelings are wise. Bad feelings mean you need to take action. Good feelings mean you took the right action. Following your feelings is the most natural and rewarding thing to do.
  • 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.

Be a Famous Pioneer

  • 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. 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.

Chase the Future

  • 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.
  • Give away everything you haven’t used in a week. Ownership binds you to the past. Don’t get invested in any one thing. Stay immersed only in what’s coming next.

Value Only What Has Endured

  • The longer something lasts, the longer it will probably last. Something that’s been around for a year will probably be around for another year.
  • Master the fundamentals, not new tricks. Learn the timeless aspects of your craft. This knowledge will never lose its value. In any given field, learn the oldest thing still around, since it’s the one most likely to last.


  • The biggest obstacle to learning is assuming you already know. Confidence is usually ignorance. Never consider yourself an expert.
  • Don’t believe what you think. Have questions, not answers. Doubt everything. The easiest person to fool is yourself.
  • Don’t answer a hard question too quickly. Don’t stop at the first answer. In mystery stories, the first suspect is not the culprit.
  • Get out of your room and try out a new skill in the real world. Go to the physical place where it’s happening, and put your ass on the line with something to lose. A vivid, visceral feeling of danger will teach you better than words.
  • 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.
  • Communicate knowledge to others to make sure you understand. Don’t quote. Put it in your own words without looking up or referencing what others said. If you can’t explain it yourself, you don’t know it.

Follow the Great Book

  • First, make a “born again” split. Let go of your old identity. Let your new self be incongruent with your old self. Let your friends and family know that you’ve changed.
  • Self-control is always rewarding. Self-control is always the right thing to do. This is a universal law. Your self-control is highest in the morning and diminishes during the day, so review your book’s rules every afternoon.

Laugh at Life

  • Humor means using your mind beyond necessity, beyond reality, for both noticing and imagining. That’s why we admire a quick wit. It shows you quickly looked at something from many angles, found the one that amused you the most, and considerately expressed it to someone else.
  • 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. When kids play make-believe, anything goes. To play is to be free from constraints.
  • Comedy doesn’t care what’s true, and neither should you. Whatever makes you happy is what works. Humor transcends reason. Life is meaningless. That’s what’s funny.

Prepare for the Worst

  • Things are going to get harder. The future will test your strength.  So far, you’ve lived in a time of prosperity. You haven’t experienced massive devastation, but you probably will. It’ll be harder to make money. It’ll be harder to be happy. Much of what you love now will be gone. You’ll look back at this year as one of the easiest you ever had.
  • 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.
  • Comfort reduces your future happiness. You get upset that your meal doesn’t come as ordered, or angry at your phone for having an imperfect connection. You lose appreciation. You forget the perspective of how bad things could be.
  • Practice being uncomfortable, even in small ways. Take the stairs instead of the elevator. Skip eating for a day, or sugar for a month. Go light-weight camping for a week. Befriend discomfort so that you’ll never fear it.
  • Distinguish between what’s in your control and what isn’t. If it’s not in your control, put it out of your head. Trying to control outcomes makes you disappointed and resentful. Focus only on your thoughts and actions.
  • Emotions can be tamed. You are in control. The problem comes from going easy on yourself. Instead, train your emotions like you would a dog. 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.
  • Visit your favorite places. Listen to your favorite music. Taste your favorite food. Touch your favorite people. This might be the last time you do all these things, so appreciate each moment fully.

For Others

  • Focusing on yourself seems smarter and easier, but it’s short-sighted. It’s ignoring the huge benefit of cooperation.
  • You can’t actually pull yourself up by your bootstraps. Ultimately you are lifted by those around you.
  • Helping others is a better path to happiness than helping only yourself. Giving makes you happier than receiving. People with strong social ties live longer, healthier, happier lives. The most miserable people are self-absorbed. So aim to be the opposite.
  • 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.
  • Ask open-ended questions, asking people’s thoughts. Ask them to elaborate on whatever they’ve said. Show that you’re interested. Allow silence. Don’t fill it. Silence gives space to think, and an invitation to contribute without pressure.
  • Assume everyone is just as smart and deep as you. Assume their temperament is just their nature, and not their fault. Don’t be mad at them for being that way, for the same reason you can’t be mad at someone for being tall.
  • Whenever you’re thinking something nice about someone, tell them. A sincere compliment can put a lot of fuel in someone’s tank. People don’t hear enough compliments.
  • Be consistent. People can only depend on you if you’re consistent. Meet up regularly to maintain each friendship, so the connections grow stronger. Be patient with your friends, even for years at a time.

Get Rich

  • 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. But if you truly feel you deserve it, you’ll do whatever it takes. So adjust your self-image first.
  • The world needs more boldness. Refuse the comfortable addiction of a steady paycheck. Boldly jump on opportunities. Take risky action.
  • Use other people’s ideas. Ideas are worth almost nothing. Execution is everything. The world is filled with ideas, yet so few take action and make them happen. Better to be filled with action than ideas. Best of all to be the owner. Own and control 100% of whatever you create.
  • Money is your servant, not your master. Don’t act rich. Don’t lose touch with regular people. Stay frugal. Reducing your expenses is so much easier than increasing your income.
  • You don’t need to tell anyone you have money. You don’t even need to spend it. Don’t buy too many things, too big of a house, or hire too many people. Rich people who do this feel trapped and miserable. The less you buy, the more you’re in control. Forget lifestyle. Forget yourself. Stay 100% focused on creating value. Everything else is a corrupting distraction.

Reinvent Yourself Regularly

  • Something happened. Something else happened. People love stories, so they connect two events, calling them cause and effect. But the connection is fiction
  • 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. What you call your personality is just a past tendency. New situations need a new response.
  • Your identity. Your meanings. Your trauma. They’re all based on the core idea that you’re in a continuum, living a story. But there is no line between moments in time. There is no story. There is no plot.
  • Doing what you’ve always done is bad for your brain. If you don’t change, you’ll age faster and get stuck. The way to live is to regularly reinvent yourself. 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.


  • Not love, the feeling, but love the active verb. It’s not something that happens to you. It’s something you do. You choose to love something or someone. You can love anything or anyone you decide to love.
  • To love something, first you have to connect with it. Give it your full attention. Deliberately appreciate it. Try this with places, art, and sounds. Try this with activities and ideas. Try this with yourself.
  • Many times a day, you have the opportunity to connect. You can dash through a place, or stop to appreciate it. You can do an activity absent-mindedly, or pay full attention to every detail of it. (Work is love in action.) You can make shallow small-talk, or really get to know someone. Choose to connect every time.
  • 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.
  • 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.
  • When someone tells you what’s broken, they want you to love the brokenness, not try to eliminate it.
  • Break down the walls that separate you from others and prevent real connections. Take off your sunglasses. Don’t text when you should talk. Avoid habitual comebacks and clichés. Admit what you’re really feeling, even when it’s uncomfortable. Keep communicating instead of shutting down. We think walls protect us from enemies, but walls are what create enemies in the first place.
  • 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. When you’re going through an unstable time in your life, you latch on to whatever makes you feel stable.
  • Projecting perfection onto someone is not love. You say “I love you” but really mean “I love this”.
  • Be together by choice, not necessity or dependence. Love your partner, but don’t need your partner. Need is insatiable. Need destroys love.


  • Don’t wait for inspiration. Inspiration will never make the first move. She comes only when you’ve shown you don’t need her. Do your work every day, no matter what.
  • 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.
  • Don’t alter your state with alcohol or drugs. They make the mundane more interesting to you, which then makes you less interesting to others. They make you think you’re creative when you’re actually boring. Only creating makes you creative.
  • Creating is a higher form of communicating. You join the elite conversation by contributing
  • When your creation is good enough, let it go. Release it, so it can go out into the world, without you. It can join the conversation.

Don't Die

  • 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.

Make a Million Mistakes

  • Try 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.
  • Writers say you should quickly finish a bad first draft, because it gets the idea out of your head and into reality, where it can then be improved.
  • See, 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.

Make Change

  • 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.
  • Work is whatever you want to change.

Balance Everything

  • When we lack balance, we’re upset.
  • When you’re balanced, you’re unlikely to get stressed. You’ve got a stronger foundation and a resilient structure. You can handle surprises, and make time for what’s needed.
  • 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.
  • Schedule everything to ensure balance of your time and effort. Scheduling prevents procrastination, distraction, and obsession. A schedule makes you act according to the goals of your highest self, not your passing mood.
  • Schedule quality time with dear friends. Schedule preventative health checkups. Schedule focused time to learn. Schedule each aspect of your life, ignoring none. List what makes you happy and fulfilled, then schedule those things into your year.

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