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How to Live: 27 conflicting answers and one weird conclusion

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Not quite non-fiction, not quite self-help. It’s a work of art about conflicting philosophies.




Many books believe they know how you should live.
But each book disagrees with the next.
In “How to Live”, each chapter believes it knows how you should live.
And each chapter disagrees with the next.


One chapter makes a compelling argument for why you should be completely independent, keeping all options open. The next chapter argues why you should commit to one career, one place, and one person.


One chapter persuades you to be fully present, and experience each moment. The next, to delay gratification and invest for the future.


Which one is right? Which does the author believe? All of them. It's a philosophy of conflicting philosophies.


A very unique and thought-provoking book.
Meant for reflection as much as instruction.


113 incredibly succinct pages of profound insights.
No philosophers are quoted.
No -isms are named.
Only actionable directives.
The end result feels more like poetry than prose.

115 pages, Hardcover

First published August 1, 2021

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About the author

Derek Sivers

60 books1,148 followers
Derek Sivers is an author of philosophy and entrepreneurship, known for his surprising quotable insights and pithy succinct writing style.

Formerly a musician, programmer, TED speaker, and circus clown, he sold his first company for $22 million and gave all the money to charity.

Sivers’ books (How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: https://sive.rs/

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Displaying 1 - 30 of 235 reviews
Profile Image for Andrej Karpathy.
110 reviews3,480 followers
September 1, 2022
I love this book and I've recommended it a number of times because it charts its way through the space of self-consistent philosophies for life, none of them strictly right or wrong. I love the idea that, as miraculously conscious entities that we are, we experience a kind of awareness and are empowered to adopt a philosophy and a system for life. This book is an enumeration of ways of being, view on life and its purpose and morality. For me the enumeration in this book is only a step 1, and has given me a lot of food for a more fundemantal theory. E.g. a slider that controls how much you care about people at a different radius away from you (you alone, family, community, all people alive, people alive in the future), how you measure the distance function (e.g. proximity/genetics), and over what time (e.g. right now or in the future and how far). Or how much you value hedonism vs. meaning. Or whether your sense of worth/meaning is more internally or externally driven. Etc. But the 27 answers are then the narrative that emerges out of a certain setting of these more fundamental variables in some interesting high-dimensional space of personal philosophy.
Profile Image for Martin Brochhaus.
145 reviews138 followers
June 21, 2021
It is really good.

But: I'm a Sivers fan. 10 years ago I sent him an email out of the blue because I knew that he had moved to Singapore and I wanted to do the same. Lo and behold, in good old Sivers fashion he replied and introduced me to a young accountant who would eventually help me to set foot into the country and start a business and quite quickly get my PR status. 10 years later, this very accountant is still working with me, I made a fortune in Singapore, married the love of my life and somehow I feel forever a little bit indebted to Derek because he sent me, a complete stranger, that one contact.

So I am biased.

Being an expat and traveller, an entrepreneur, a musician, a designer, a creator, a rebel, a humanitarian and a husband myself, I found myself nodding along. "Yeah, I get it. I did that. I'd totally do that".

There are a lot of chapters about having many women and at first it bothered me a little, but I *think* I understand that each chapter is an exaggeration, not to be taken quite literally, more like an extreme, a thought experiment, what if you walked the talk all the way to the end?

It also needs to be read slowly, as warned in the introduction. Actually, I think the first read should be fast, so you get the whole picture. But that will leave you wanting and unimpressed. Now that I'm through it once, it is time for my second read.

My second read will probably take me a few years.

Another reviewer said it's a "modern day "Meditations"" and I think that nails it. There's a lot of Stoicism buried in this book, albeit far more accessible than any of the stoic source materials.
Profile Image for Stephen Heiner.
Author 2 books46 followers
July 14, 2021
Derek says that this is his best book ever, and I fully understand that an author is always going to have his/her own perspective on a book, not just because of the experience of bringing it into being, but because of what he/she hopes the book might achieve. It is that latter reason, I think, that inspired Derek to say this was his best book ever. He is truly trying to challenge existing paradigms for "how to live" in a world with so many conflicting messages.

Like me, you may find yourself deeply underlining the sections you agree with and almost speed-reading the sections you don't. But that's the point: you need to be willing to immerse yourself in the "alternative" world view of every chapter in order to get the overarching message: there is no one way to live your life. There are many - find elements that appeal to you and your personality and lean into them. But also be open to retooling and reorienting today, tomorrow, next year, or next decade.

"When you're indifferent to people's words and actions, nobody can affect you." (loc 41)

"Being fully independent is how to live." (loc 76)

"So why not act that way and live that day every day? Commit to your habits to make them rituals. If it's not important, never do it. If it's important, do it ever 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. New habits are what you're trying. Old habits are who you are." (loc 115)

"Let go of feeling needed." (loc 220)

"Choose a culture that values what you value." (loc 304)

"To enjoy your past is to live twice." (loc 322)

"When you make a big mistake and want to learn its lesson, deliberately amplify the pain, the deep regret, and the consequences. Keep the bad feelings vivid and visceral. Make the lesson memorable, so you won't do it again." (loc 339)

"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." (loc 347)

"When you're not practicing, remember: someone somewhere is practicing. When you meet them, they will win." (loc 374)

"Don't live somewhere pleasant surrounded by normal people. Live among your fellow freaks, where obsession is normal and ambition is rewarded." (loc 382)

"You don't need to hang out, make small talk, or join in common rituals. You don't need to sleep at normal hours, keep a tidy home, or even relax. Be sharply focused, not well-rounded." (loc 391)

"Keep the rest of your life boring. Drama is a distraction. Your personal life and other concerns can shrink to almost nothing. Focus everything on your work." (loc 391)

"The goal of life is not comfort. Pursuing comfort is both pathetic and bad for you." (loc 441)

"Pain is coming anyway. Don't get a shield. Get a saddle." (loc 451)

"Never consider yourself an expert. It's the strong swimmers who drown. 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. If you're not embarrassed by what you thought last year, you need to learn more and faster." (loc 638)

"When you're really learning, you'll feel stupid and vulnerable - like a hermit crab between shells." (loc 647)

"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." (loc 665)

"Great public speaking comes from great private thinking." (loc 665)

"Learning is a pursuit you can't lose." (loc 665)

"An undisciplined moment seems harmless, but they add up to disaster. Without discipline, the tiny things in life will be your downfall." (loc 700)

"Someone says life is hard. The comedian says, 'Compared to what?' Comedians are philosophers." (loc 737)

"Then imagine the relief of finding shelter, the joy of controlled fire on command, and the satisfaction of hot water." (loc 765)

"Want nothing, and nothing will disappoint you. Want nothing, an nothing is outside your control. Want nothing, and fate can't hurt you." (loc 774)

"Shallow happy is pursuing pleasure. Deep happy is pursuing fulfillment. Fulfillment is more fun than fun." (loc 799)

"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." (loc 839)

"The world is full of money. There's no shortage. So capture the value you create. Charge for what you do. It's unsustainable to create value without asking anything in return. Remember that many people like to pay." (loc 869)

"Sell your business before you have to. Sell before it peaks. The fun is in creating a business, not maintaining it." (loc 895)

"Avoid exciting investments." (loc 904)

"Money makes problems go away, but amplifies your personality traits. Money won't change you, but it will amplify who you are." (loc 921)

"Something happened. Something else happened. People love stories, so they connect two events, calling them cause and effect. But the connection is fiction." (loc 928)

"'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." (loc 928)

"Putting a label on a person is like putting a label on the water in a river. It's ignoring the flow of time." (loc 937)

"You built that boat to cross that river, so leave it there. Don't drag it along with you." (loc 954)

"Avoid habitual comebacks and cliches." (loc 967)

"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." (loc 984)

"If you choose not to love someone, break up with one last boost of love, empathy, and kindness, instead of showing your lack of love." (loc 1002)

"Most people die with everything still inside them." (loc 1015)

"Someone who hasn't created anything in years because you're so busy consuming?" (loc 1015)

"Distribute your work as widely as you can. Do whatever it takes to call attention to it. Art needs an audience. There are no unknown geniuses. Charge money to make sure your creations are going to people who really want them. People don't value what's free. Charge for their sake as much as yours. Charge even if you don't need the money." (loc 1051)

"To have good people in your life, just cut out the bad ones." (loc 1072)

"A mistake only counts as experience if you learn from it." (loc 1093)

"The world's greatest achievements were squeezed into existence by deadlines." (loc 1184)
17 reviews
May 31, 2021
Initially I found it confusing and contradictory, but the intention became clear as I read through the book.
43 reviews
June 1, 2021
It reads like the highlights of a great book. If you want to extract the essential you will highlight 80%. That’s why I think I will come back to it time and time again.

Profile Image for Adam.
413 reviews28 followers
May 23, 2022
A book that spins you around so that you take a 360 view.
Profile Image for Tim Niehenke.
18 reviews1 follower
July 28, 2022
27 short chapters going in all kinds of directions on how to live your live and what to focus on. Super interesting and thought provoking book, which is all over the place but at the same time preaches one simple thing: balance.
December 2, 2021
No matter what one does, it's always the best decision ever. Color me a sucker but I love it.

Q:
Crowds are hysterical, and inbreed opinions. Don’t be a part of any group. Don’t take sides on any fight.
Instead of standing out from the crowd, just avoid and ignore the crowd. Avoid social media and the zeitgeist. Its stupidity will infect you. (c)
Q:
Don’t align with any religion, philosophy, or political stance. Stay unlabeled and unbound. (c)
Q:
Dogs bark.
People speak.
It doesn’t mean a thing. (c)
Q:
What they say and do has nothing to do with you, even if it seems directed your way.
The only opinion that matters is your own. (c)
Q:
When you know what you’re doing, you won’t care what anyone else is doing. (c)
Q:
Never agree with anything the same day you hear it, because some ideas are persuasively hypnotic. (c)
Q:
Never agree with anything the same day you hear it, because some ideas are persuasively hypnotic. (c)
Q:
When you say you want more freedom from the world, you may just need freedom from your past self.
...
Change yourself and you change the world. (c)
Q:
You don’t see things as they are.
You see them as you are. (c)
Q:
Move symbolically far away from where you grew up. (c)
Q:
If a country enters into war or makes your life hard, just leave. (c)
Q:
Make friends wherever you go, so that no one place has all of your friends. (c)
Q:
You can laugh at the hysteria of the crowd, and learn from it too.
You can take sides in a fight, with a smirk.
You can even take responsibility for someone else.
Being fully independent is how to live (c)
Q:
To go one direction means you’re not going other directions. When you commit to one outcome, you’re united and sharply focused. When you sacrifice your alternate selves, your remaining self has amazing power. (c)
Q:
Falling in love is easy. Staying in love is harder. Enthusiasm is common. Endurance is rare. (c)
Q:
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.
Commitment gives you integrity and social bonds.
Commitment gives you expertise and power.
Commitment gives you love and happiness.
Committing is how to live. (c)
Q:
Things are neither good nor bad — they’re as neutral as a rock.
When people give opinions, add a question mark.
If they say, “Immigration is bad,” change it to, “Immigration is bad?”
Let the questions drift away, unanswered.. (c)
Q:
Your own mind is the best laboratory. It’s also the most private and peaceful place to work. (c)
Q:
We treat the future like a garbage dump.
We dump our debts, pollution, junk, and responsibilities on the future, as if it’s a problem solved.
It’s the most psychopathically inconsiderate thing we do to our children, since it’s their world, not ours. (c)
Q:
If you eventually need a permanent home, choose the place you’d want to be if everything goes wrong. (c)
Q:
Make a story for the things you want to remember. Never make a story for the things you want to forget. Let those disappear with time.
Your memories are a mix of fact and fiction. Your story about an experience overwrites your memory of the actual experience. So use this in your favor. Re-write your past. (c)
Q:
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. (c)
Q:
The path gets more and more interesting as you go. (c)
Q:
All paths go either towards that mountain or away from it.
Because of this perspective, problems won’t deter you.
Most people look down at the ground, upset by every obstacle.
With your eyes on the horizon, you’ll step over obstacles, undeterred.
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. (c)
Q:
Don’t do well what you shouldn’t do at all. (c)
Q:
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.
Pursuing mastery is how to live. (c)
Q:
Random stuff happens. All you can control is your response. Every day, you’ll practice how to react to chaos: with dignity, poise, and grace. (c)
Q:
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.
The best way to learn a foreign language is to stop speaking your mother tongue. No matter how embarrassing or frustrating, communicate only in your new language. Necessity is the best teacher. But it hurts. (с)
Q:
Since you can’t avoid problems, just find good problems. Happiness isn’t everlasting tranquility. Happiness is solving good problems. (c)
Q:
When talking with people, ask deep open-ended questions — like “What’s your biggest regret?” — that will lead to unexpected stories. (c)
Profile Image for Paul Sochiera.
64 reviews4 followers
April 18, 2022
Very stimulating and thought-out book about how to live your life.

It presents 27 conflicting answers that overexaggerate purposely but always present many good points. Besides having many very good points and wise thoughts, I like how it is provokative and consciously shows the negative aspects of any one lifestyle taken to the extreme.

Very nice and enlightening read.
Profile Image for Peter Sanchez.
25 reviews1 follower
June 15, 2021
What a whirlwind. A great read and the idea is to toy with the reader to show that you can learn from all sides of life. Contradicting advice and points of view that will help you realize that you truly do need a balance in your life. Take a step back and view situations from different eyes.
Profile Image for Tobias Weghorn.
38 reviews
December 24, 2021
I'm a huge fan of Derek Sivers and everything he wrote - so I started recommending this book even before reading myself. When I finally started reading the first chapter I actually was a bit shocked and thought "Wow, that's quite an extreme view, maybe I should have been more careful with my recommendations."

A few chapters further, I found that this is the point of the book: 27 short chapters, each stripped to its minimum, with super short paragraphs and sentences, providing different perspectives on life and often contradicting the previous one.

Often his points seem Buddhist and Stoic advice, spiced with his entrepreneurial pragmatism and irony. So now, after being over the 27 chapters and the weird conclusion, I would like to recommend this book - again and wholeheartedly. :)


Some of my highlighted quotes:

From "Do nothing": There’s no deeper happiness than wanting nothing. Desire is the opposite of peace.

From "Master something": The most rewarding things in life take years. Only bad things happen quickly. (...) Goals don’t improve your future. Goals only improve your present actions. A good goal makes you take action immediately.

From: "Let randomness rule": 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. (...) Random stuff happens. All you can control is your response.

From "Pursue pain": Since you can’t avoid problems, just find good problems. Happiness isn’t everlasting tranquility. Happiness is solving good problems.

From "Do whatever you want now": 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. If you stop and look around the room, and ask yourself if you have any actual problems right now, the answer is probably no. Unless you’re in physical pain or danger, the problems were all in your head. Memories and imagined futures are not real. The present moment is real and safe.

From "Prepare for the worst": Vividly imagine the worst scenarios until they feel real. Accepting them is the ultimate happiness and security. Realize that the worst is not that bad. People talk about pessimism and optimism by saying, “Glass half-empty or glass half-full?” But a caveman would say, “Oh my god! A glass! What a great invention! I can see what I’m about to drink! This is amazing!

From "Laugh at life": To laugh at something is to be superior to it. Humor shows internal control. (...) A bad situation can feel all-consuming. A laugh shows you’ve escaped. Humor puts distance between an event and yourself.

From "Live for others": 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. Now treat everyone like that, every day.

From "Get rich": Making money isn’t evil, greedy, shallow, or vain. Money isn’t your worth as a human being, or a substitute for love. But don’t pretend it doesn’t matter. 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.

From "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. 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. What you call your personality is just a past tendency. New situations need a new response. Are you more emotional or intellectual? Early bird or night owl? Liberal or conservative? No. Disagree with the question. You aren’t supposed to be easy to explain. Putting a label on a person is like putting a label on the water in a river. It’s ignoring the flow of time.

From "Love": You choose to love something or someone. You can love anything or anyone you decide to love. Love is a combination of attention, appreciation, and empathy. (...) 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.

From "Create": 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. Suspend all judgment when creating the first draft. Just get to the end. It’s better to create something bad than nothing at all. You can improve something bad. You can’t improve nothing.
26 reviews3 followers
February 17, 2023
4.5/5 - 'How to Live' by Derek Sivers is an incredibly dense and thought-provoking read. With a multitude of perspectives and concepts, it provides readers with the opportunity to create their own unique interpretation and experience. The author offers extreme examples of each lifestyle, helping readers identify where they may align or where they may need to make changes.

The book has a "Bible"-like quality, in that it encourages readers to revisit it periodically to reassess their priorities and values. However, it's important to note that not all world-views are represented in the book, as it has a heavy bias towards Western and American perspectives. While the author acknowledged this blind spot in the past, it is still a significant limitation in the book.

I personally recommend reading only one or two chapters at a time, as the content is so dense and requires time for reflection. It's evident that the book has been meticulously revised and condensed to distill an essential message into each sentence, making it a challenging but rewarding read.

One common critique of the book is that it presents conflicting stances, where you can't possibly follow all of the advice simultaneously. However, that is the point - it encourages readers to pick and choose what works best for them and not try to follow everything simultaneously. It's an essential reminder that there is no one-size-fits-all solution to living a fulfilling life.

Despite some limitations, 'How to Live' is a thought-provoking and challenging book that will help readers identify their values and priorities.
Profile Image for Chris Bracco.
52 reviews1 follower
December 11, 2021
A collection of cliche, quippy, and contradictory statements about how to live life, presented in a tongue-in-cheek sequential summary format. It’s like reading the last page of twenty seven different self-help books all at once.

It’s a fun little book to read through once, collect your favorite quips, and revisit them periodically.
Profile Image for Matthias.
198 reviews60 followers
April 8, 2023
This seems to be a sort of deadpan "gentle" satire of self-help books, and especially of the self-help content that comes out of Silicon Valley. It's a collection of recommendations on how to live life, all delivered in a bold, overconfident tone; each one of them represents a certain angle (appealing to a certain personality trait or moral value), and they often end up contradicting one another. I guess the final goal is highlighting how unrealistic and meaningless these type of advices are, and that ultimately the question itself can be answered in any way one prefers. Ok, nice "intellectual" exercise. But what's the value of it, really? The reader has to go through a bunch of low quality material just to get to the final punchline "Do you see how pointless all of this is? Hehe". It's almost like a joke on the reader, more than anything else.
Profile Image for Harsha.
28 reviews8 followers
June 10, 2021
Sivers has reached an epitome of clarity in his latest masterpiece that would make Hemingway want to come out of his grave. It’s full of contradictions by design (almost bringing clarity through confusion) and there is not one unnecessary word or article. It’s Sivers reaching his purest form in writing, with lessons that bewilder and make you think more.
Profile Image for Cristiana.
4 reviews1 follower
May 27, 2023
I never read self-help books and did not pick up this one for self-help purposes, so I can't really compare. Nonetheless, I hope all self-help books convey at least a few of the fundamental truths I found in this one.

I did not agree with everything, no one will. It is in that that lies the power of Derek Sievers' portrait of one's existence - that the right messages will resonate with you when it's the right time for you. I also found flaws in it, especially when it lacks to acknowledge that which economic situation one is born in will prevent some people to follow some (not all) of the advice on how to live.

Nonetheless, this book made me analyse, cherish, challenge or judge how I navigate the world. I'm incredibly grateful to my sister who recommended it.

I listened to this book on a Sunday afternoon during a session of meal-prepping for the week and finished it with barely no breaks. If you can, listen to the audiobook as it is read by Derek himself and his persona really shines through.
Profile Image for Willian Molinari.
Author 2 books118 followers
November 24, 2021
I'm posting the full review with my notes on my blog. You can read it here: https://pothix.com/howtolivebook

Another great book. I really like the content Derek produces on his blog and books. It's usually dense and full of meaning, there are almost no fillers.

The proposal here is cool: there are many ways to live, you don't have to choose one, you can pick many! All of them are valid ways to live a meaningful life. I can already see many people quoting small pieces of this book and saying things on the internet because they disagree. 😅

I'm wondering if Derek agrees with everything he wrote here, I believe he doesn't, but it still doesn't change the fact that it is how to live.

Recommended as usual!
111 reviews52 followers
April 16, 2022
The writing style is wacky yet hard hitting with occasional contradictions (for eg. there are 2 contradictory principles - "Chase the future i.e. chase the new stuff" versus "value what has endured" (Lindy effect).
Thus, the best way to gain insights from this book is to "interpret objectively and adopt subjectively"

Key takeaways:
1. Be independent.
a. All misery comes from dependency. If you weren’t dependent on income, people, or technology, you would be truly free.
Avoid social media and the zeitgeist. Its stupidity will infect you.
Don’t align with any religion, philosophy, or political stance.

Don’t believe anything anyone says.
Listen if you want, but always decide for yourself.
Never agree with anything the same day you hear it, because some ideas
are persuasively hypnotic.
Wait a few days to decide what you really think.

Being independent means you can’t blame others.
Decide everything is your fault.
Whoever you blame has power over you, so blame only yourself.
Everyone has their own lives to manage.
Nobody is responsible for you, and you aren’t responsible for anybody.
You don’t owe anyone anything.
Learn the skills you need to be self-reliant.
Learn to drive, fly, sail, garden, fish, and camp.
Learn emergency medical and disaster preparedness.
Assume nobody will help you.
Don’t depend on any company, especially not the big tech giants.
Use only open-source software and open communication protocols.
Keep your own backups.
Get your own domain.
Run your own server.

Be a perpetual traveler, living out of a suitcase.
Move to a new country every few months, never a registered resident of
anywhere.
Spread the different aspects of your life across different countries to
avoid depending on any one country.
Earn multiple passports.
If a country enters into war or makes your life hard, just leave

2. Commit.

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

This even goes for technical choices, whether hardware or software.
Pick one.
Commit to it.
Learn it deeply.
This is much more rewarding than always switching and searching for
the best.

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.
Commitment gives you integrity and social bonds.
Commitment gives you expertise and power.
Commitment gives you love and happiness.
Committing is how to live.

3. Fill your senses.

See it all.
Touch it all.
Hear it all.
Taste it all.
Do it all.
Appreciate this wonderful physical world.

Here’s the key:
Here’s your mission:
Nothing twice.
Never eat the same food twice.
Never go to the same place twice.
Never hear the same thing twice.
Everything only once.
Be systematic.
Follow guides.
“Top Places You Must Visit”
“Greatest Movies of All Time”
“Best Restaurants in Town”

Go through them all.
That’s the optimized way to experience the most, without repetition.
4. Do nothing.

You don’t need recognition to feel pride.
Recognition doesn’t give you pride.
You don’t need a beach to feel tranquility.
Places don’t make emotions.
You do.

Junk may reach your senses, but don’t let it reach your mind.
Don’t accept the false stories people tell.
Things are neither good nor bad — they’re as neutral as a rock.
When people give opinions, add a question mark.
If they say, “Immigration is bad,” change it to, “Immigration is bad?”
Let the questions drift away, unanswered.


5. Think super-long-term.

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.


You owe your quality of life to people in past generations.
We say someone is lucky if they are born into a rich family, in a stable
country, full of opportunity.
But that luck was created by the grandparents that moved to that
promising place, then worked hard and saved money for the next
generation instead of spending it themselves.
Make your grandchildren lucky like this.
Move to a place with good values that’s headed in the right direction.
Climate change might make everything between 40° and -40° latitude
quite unlivable, so start getting legal resident status in a country outside
of that, like Canada, New Zealand, or the Nordics.
These might be the last livable places on Earth.
Make sure your grandchildren will have citizenship.
Be a great ancestor.


6. Intertwine with the world.

part of the world feels foreign.
From Brazil, learn to live in the present, and embrace every stranger as a
friend.
Leave before you forget about the future.
From Germany, learn rationality and directly honest communication.
Leave before you start scolding strangers.
From Japan, learn deep consideration for others, social harmony, and
intrinsic perfection.
Leave before you get so considerate that you can’t express yourself or
take action.
From China, learn pragmatism and the multi-generational mindset.
Leave before you get superstitious or prioritize social status.
From France, learn idealism and resistance.
Leave before you oppose everything in theory.
From America, learn expressive rebellious individualism.
Leave before thinking you’re the center of the world.
From India, learn to improvise and thrive in complexity.
Leave before feeling a divide between what’s inside versus outside your
circle.
In all cultures, avoid the madness of the crowd.


7. Make memories.

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.
Remember them all.
Document everything, or you’ll eventually forget it.
Nobody can erase your memories, but don’t lose them through neglect.
Journal every day.
Write down your activities, thoughts, and feelings for future reference.
Video everything.
Compile and edit them, so they’re appealing to watch.

To enjoy your past is to live twice.
Nostalgia links your past and present.
Nostalgia protects against stress and boredom, and improves your mood.
Nostalgia makes you more optimistic, more generous, more creative, and
more empathetic.
Nostalgia is memories minus the pain.
Being nostalgic makes you less afraid to die.


8. Master something.

Define “success” for yourself.
Describe the outcome you want.
You can’t hit a target you can’t see.

9. Let randomness rule.

Life is determined not by causes, but by randomness and odds.
By taking a minute to do the math, you’ll have a clearer understanding of
why things are the way they are.

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

10. Pursue pain.

Practice taking on the various kinds of pain.
Attempt something that seems impossible — something that terrifies
you.
Give a speech.
Do a ten-day silent meditation.
Quit a habit.
Apologize to someone you wronged.
Don’t congratulate yourself if your attempt avoids failure.
Remember: you want the pain.
The sooner you pay a price, the less it costs.
You weren’t meant to be idle.
You weren’t built for sitting and staring at screens.
You live to push, pull, climb, and grow.
11. 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.
So live accordingly.


12. 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.
Here’s the best way to do it:
First, make a stage name.
Create a company with the same name, and have it own all the rights to
everything you do.
Never reveal your real name.
This is to manage the trappings of your upcoming fame.
Find a writer and a publicist to create your first pioneering adventure.
Collaborate with the writer to make a great story arc before you begin.
So, for example, it’s not just a story of how you escaped a cult, but how
you joined the cult, uncovered a surprising history, fell in love, were
almost discovered and captured, then escaped by changing the mind of
your captor, and finally learned some interesting counter-intuitive
lessons along the way.
Consult with the publicist to make sure it’s interesting to the media.
Then begin.
Record everything on video.
Find ways to make the story arc happen in real life.
When you’re done, have your writer make it a fascinating story of
various lengths for various outlets — making it a great article, book,
video, screenplay, stage talk, and more.
Have the publicist get it everywhere — on every popular platform of the
day.

13. 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.

Work as a futurist and technology journalist.
Stay on the cutting edge of things so new they barely exist.
Every new invention will come to you first, before the world has heard
of it.
Learn the basics of every field, so you can understand new innovations
in logistics or chemistry or anything else.

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.

future.
Avoid Europe and anywhere that lives in the past.
Places that resist change have no vision, only memories.
Yesterday is gone for good.
The past is dead.
Resurrecting it makes ghosts and zombies.
Avoid religion because faith is not meant to be questioned.
Tradition is the opposite of what you want.
Nothing worshipped will change.
Oppose convention because that’s how things were.
Slavery was a convention.
Human sacrifice was a convention.


14. Value only what has endured.
Time is the greatest filter
So the way to live is to ignore everything new.
All of it.
Let the test of time filter everything.
Value only what has endured.
The modern life is shallow and distracted.
The timeless life is deep and focused.
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

15. Learn.

Never consider yourself an expert.
It’s the strong swimmers who drown.
Don’t believe what you think.
Have questions, not answers.
Doubt everything.
The easiest person to fool is yourself.
Take notes.
Review them often.
Make flash cards to remind your future self what you learned today.
Quiz yourself with spaced repetition.
Knowledge fades and eventually disappears unless you keep it refreshed.

16. Follow the great book.

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 wiser than you.
It’s describing natural law — the way our world works.
17. Laugh at life.

Humor is the spirit of life — a sign of a healthy, vibrant mind and soul.
Life is meaningless. That’s what’s funny
Besides, it makes you very appealing.
Everyone wants to be with someone who’s having more fun.
18. Prepare for the worst.

How can you thrive in an unknowable future?
Prepare for the worst.
Train your mind to be ready for whatever may come.
This is how to live.
The future is unpredictable and uncontrollable.
Picture all the things that could go wrong.
Prepare for each, so they won’t surprise or hurt you.
Never worry.
This isn’t emotional.
Just anticipate and prepare.
Remember the fable of the ant and the grasshopper?
The grasshopper was just enjoying the summer, teasing the ant for
working instead of relaxing.
Then winter came, and the grasshopper starved, but the ant was ready.
Expecting life to be wonderful is disappointing.
Expecting life to be disappointing is wonderful.
If you expect to be disappointed, you won’t be.
19. Live for others.

Never say, “Not my problem.”
We’re all in this together.
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.

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.
20. Get rich.

Suspend judgment.
Making money isn’t evil, greedy, shallow, or vain.
Money isn’t your worth as a human being, or a substitute for love.
But don’t pretend it doesn’t matter.
Money can represent freedom, safety, experience, generosity,
attractiveness, power, or whatever you want.
But really, money is as neutral as math.

Or consider this:
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.
Pursue wealth because it’s moral, good, and unlimited.
Money is social.
It was invented to transfer value between people.
One job pays way more than another because it has more social value.
To get rich, don’t think about what’s valuable to you.
Think about what’s valuable to others.
To do the opposite is the cliché of the starving artist: creating something
that’s valuable to you, but not to others.

21. Reinvent yourself regularly.

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.
Disconnect from your past.
Cut all common threads.
Keep nothing permanent
22. Love.

Love is a combination of attention, appreciation, and empathy.
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.
23. Create.

Live in a city.
Cities are more conducive to creativity.
Geniuses come from cities.
It reminds you of your audience.
Ultimately, you need to connect with people, not trees.
Stay in situations where you’re forced to show your work to others.
Collect ideas in a crowd.
Create in silence and solitude.
Like your bedroom, your work space needs to be private.
This is where you dream and get naked.
Keep a counterweight job.
Something effortless that covers your bills.
Something you can do a few hours per day, but otherwise not think
about.
It gives discipline and regularity to your life.
It gives deadlines and freedom to your art.

24. Don’t die.
25. Make a million mistakes.
26. Make change.
27. Balance everything.

Notice the similarities in the physical and emotional definitions.
Physical upset: to knock something over.
Emotional upset: to be disturbed.
Physically unstable: likely to fall.
Emotionally unstable: prone to dangerous, impulsive behavior.
All related to a lack of balance.

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.
Profile Image for Mikhail Kalashnikov.
86 reviews27 followers
January 6, 2023
Здесь классное описание на Goodreads, не буду его повторять. Действительно, это книга про 27 способов жить, где каждая глава спорит с предыдущей.

Дерек Сиверс – технологический предприниматель (CDBaby), а теперь в первую очередь писатель, я читал все его книжки и все очень понравились. У него классный минималистичный блог, тоже советую: sive.rs

Цитаты сложно приводить, потому что книга по формату вся состоит из цитат (не чьих-то, тут вообще нет ни одного имени собственного, просто так текст устроен). Я выписал себе где-то двести штук по разным темам. Одна из глав посвящена тому, что жизнь случайна и можно жить, принимая решения случайным образом, поэтому выбрал несколько цитат зажмурившись и ткнув пальцем в экран:

«Be surprised by something every day. Find that exciting moment when you get a completely new perspective. Like a movie that reveals something at the end which changes the way you think of everything you’ve seen before. If you’re not having these moments often, find some new inputs.»

«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.»

«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»

«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. Otherwise, aim lower until you find something you can do now. Make it how it should be. Don’t complain. Just make the change.»

«Delay gratification. Today’s discomfort brings future rewards. When you have a clear view of the future, you won’t mind the small sacrifice. You never regret not indulging. Only spend money on things that do long-term good, like education. In other words, never spend, only invest.»

«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.»
Profile Image for Sean Currie.
19 reviews4 followers
January 27, 2023
Timeless. Insightful. Hypnotic. Deranged.

I've often thought that great philosophy is impossible without grand sweeping statements. In this book, every chapter is a series of connected sweeping statement with one overriding point, which is then contradicted in the next chapter.

Sivers is endlessly provocative; In equal measure, he made me laugh out loud, sigh in frustration, and stroke my chin thoughtfully. Above all, the book helped me to zoom out and see my life for what it is. My health, my relationships, and my work; my past, my future, and my present.

Regardless of who you are - read this book. Take everything seriously but nothing literally - except for the last line of the second last chapter:
"Balancing everything is how to live."
63 reviews2 followers
May 17, 2023
A very chaotic book (in a good way) where different answers (conflicting answers, as Derek Sivers says in the titles) will apply to different people.

It's a lovely short book filled with different points of view that will apply to whoever the hat fits.

The world isn't just black and white, right and wrong; this book shows exactly that. There are many ways to live your life, you just need to choose one (or a couple) and go through it.

Not my favorite book from Derek Sivers, but still a worthy read!
Profile Image for Suzette.
33 reviews2 followers
October 5, 2021
I have just finished this book, but feel that it will become one of my all-time favorites to delve into repeatedly. It takes more time to digest and fully appreciate than it takes to read. Short and to the point. Each chapter just a few paragraphs, of which each a few sentences.

It is an unusual book, but it feels open and honest, and as some of the best books do, it leaves you reflecting on your life and how to live a better one. Perfect title then!
January 29, 2022
The book essentially paints 27 extreme scenarios to prosper in life.
I found at-least one point in each “way” relatable.
I absolutely love how contrasting some of the chapters are which each other, it helps you visualise them quite easily,

Definitely a must read by anyone who feels “stagnant” right now.

I’d recommend taking your own sweet time in reading it, invest time in thinking and overthinking what’s written, relate it to an event and it’d make so much more sense.
Profile Image for Peter Knox.
595 reviews73 followers
May 25, 2022
Perfect for reading over a plane ride as I did (or individually, daily as mediations/reminders), this book gives you a lot to mull over and will stay with you a long time.

Framed as something to read one line at a time (which is why I'd recommend the short print paperback) it offers practically every perspective on approaching the big questions in life.

And right after one opinion (Go travel everywhere, own nothing, owe no one anything) he'll reverse course 180 to tell you to do the opposite (Stay put, put down roots, grow a community).

Rare is the book that leads you to think the author knows everything and convinces you that you know nothing, and then do the opposite. It's a real experience.

Would encourage everyone to take this short journey, to inspire and push and question yourself, because you'll emerge more open to possibility.
1 review
October 5, 2022
Might just be the most important self help book I've read- and I've read a lot of them.

It's an Ikea Catalogue of Self Help philosophy-showcasing almost every major great philosophy of what it means to live a good life. From following the Bible to following the Naval. From Buddhism to Nassim Taleb to Robert Greeene.

It's a birds eye view of most every self help life wisdom that exists on the planet, which leads to one freeing conclusion.

That there is no one 'best way to live'. Everything is a value system, that has no more objective merit than the other. Truly freeing and one of the most important books I've read.

Thanks Derek.
Profile Image for peetzweg.
14 reviews
January 11, 2023
My second book by Derek. Not sure if you could call these proper books. They are written a bit different. But thats great for what they try to deliver.
Most of the advices of how to live described in this book were already known to me. However the overall collection, short-form back to back, confident introduction of each makes a special experience.
It‘s not complete by any means but these 27 already probably broadens the readers mind on how to live and let live.
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