How To Live – Derek Sivers

Being on the private email list of Derek Sivers has some advantages (anyone can be on the list, it is not something elitist, just go here: One advantage is getting early access to Derek’s new work. How To Live is Derek’s new book, he pointed me to through the email list. I bought it and read it.

book cover

The book is a great guidance to life, as the title suggests. It is packed with great advice, categorized into 27 topics. The advice is sometimes contradictory, and Derek does not hide that: he gave the book the subtitle: “27 conflicting answers and one weird conclusion”. And I don’t care either; life is contradictory.

Much of the advice Derek has thought up or gathered in this book may have its origins in Buddhism and Stoicism, and I think it also build on folks like Nassim Taleb (Antifragile), Kevin Kelly and Seth Godin.

The book is way too dense to summarize in anyway. Just some parts by topic that I found useful for myself.

Be independent.

Instead, do what you’d do if you were the only person on Earth.


You and your best friends don’t decide anew each day whether you’re friends or not. You are friends, without question. You’re committed to each other, even if you’ve never said so. That’s what’s wonderful about it. Commit to your habits to make them rituals.

Fill your senses.

Never have the same thought twice.

Do nothing.

Expressing your anger doesn’t relieve it. It makes you angrier. Actions often have the opposite of the intended result. People who try too hard to be liked are annoying.

The stock market takes money from the active traders and gives it to the patient.

Think super-long-term.

Imagine your future self judging your current life choices. When making a decision, ask yourself how you’ll feel about it when you’re old.

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

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.

Make 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.

Turn your experiences into stories. A story is the remains of an experience.

Master something.

Pick one thing and spend the rest of your life getting deeper into it. 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.

Concentrating all of your life’s force on one thing gives you incredible power. Sunlight won’t catch a stick on fire. But if you use a magnifying glass to focus the sunlight on one spot, it will. Mastery needs your full focused attention.

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

You need to understand something very counter-intuitive about goals. Goals don’t improve your future. Goals only improve your present actions. A good goal makes you take action immediately.

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.

Take tiny breaks when working, to go longer than most.

Pursue your mission at the expense of everything else.

You do it for the journey, not the destination.

Let randomness rule.

Let the random generator decide what you do, where you go, and who you meet. When doing creative work, let the random generator make your artistic decisions, shaking up your usual style.

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.

Pursue pain.

Comfort is a silent killer. Comfort is quicksand. The softer the chair, the harder it is to get out of it. The right thing to do is never comfortable. How you face pain determines who you are. Be a famous pioneer.

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.

Chase the future.

Work as a futurist and technology journalist. Stay on the cutting edge of things so new they barely exist.

Old friends and family see you as you used to be, and unintentionally discourage your growth.

Value only what has endured.

Be aware if the Lindy effect I mentioned in a previous post – and Grandmother’s wisdom of Nassim Taleb.

The longer something lasts, the longer it will probably last.

The world of news is noisy, because they have to hype it.


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.

Follow the great book.

Rules must be absolutely unbreakable. If you try to decide, each time, whether it’s OK to break the rule or not, then you’ve missed the whole point of rules.

Discipline turns intentions into action. Discipline means no procrastination. Discipline means now.

Choose the pain of discipline, not the pain of regret. Self-control is always rewarding.

Laugh at life.

They win by being playful, creative, adaptive, irreverent, and unbound by norms.

Comedy is tragedy plus time. Time belittles anything by showing it’s not as bad as it seemed. Humor does that instantly.

Prepare for the worst.

Vividly imagine the worst scenarios until they feel real (Seneca of course). Accepting them is the ultimate happiness and security. Realize that the worst is not that bad.

Live for others.

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.

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.

Get rich.

Money is nothing more than a neutral exchange of value. Making money is proof you’re adding value to people’s lives.

Create your own business. Come up with a brand name that can be attached to any business. (Perhaps it’s your name.) Use it for the rest of your life on everything of quality. A recognized brand can charge a premium price, earning more than unrecognized names.

Use other people’s ideas. Ideas are worth almost nothing. Execution is everything.

Be separate—in a category of your own.

Nothing destroys money faster than seeking status. Don’t show off.

I meet this young salesman he had a good year. From the bonus he bought his wife a Landrover for shopping. The car cost him more than 2000 euro per month. Quickly he realized his mistake and sold the car, 10000 down.

You only need to get rich once. When you win a game, you stop playing. Don’t be the dragon in the mountain, just sitting on your gold. Don’t lose momentum in life. Once you’ve done it, take it with you and do something else.

Reinvent yourself regularly.

Your past is not your future. Whatever happened before has nothing at all to do with what happens next. There is no consistency. Nothing is congruent. Never believe a story.

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.

In other words – be Antifragile.


Break down the walls that separate you from others and prevent real connections. Take off your sunglasses. Don’t text when you should talk.

The hardest part of connecting with someone is being honest.

Notice how you feel around people. Notice who brings out the best in you. Notice who makes you feel more connected with yourself—more open and more honest.


Calling yourself creative doesn’t make it true. All that matters is what you’ve launched. Make finishing your top priority.
Suspend all judgment when creating the first draft. Just get to the end.

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.

Stay in situations where you’re forced to show your work to others.

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.

Let the deadline of death drive you. Create until your last breath.

Don’t die.

Avoiding failure leads to success. The winner is usually the one who makes the least mistakes. This is true in investing, extreme skiing, business, flying, and many other fields. Win by not losing.

Most of eating healthy is just avoiding bad food. Most of being right is just not being wrong. To have good people in your life, just cut out the bad ones.

Make a million mistakes.

People who avoid mistakes are fragile, like the robot that only walks. Your million mistakes will make you someone that can’t be knocked down.

Make change.

Don’t accept anything as-is. Everything you encounter must change. Preservation is your enemy. Only dead fish go with the flow.
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 worship your heroes. Surpass them.

Balance everything.

All bad things in life come from extremes. Too much of this. Too little of that.

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.

Schedule everything to ensure balance of your time and effort. Scheduling prevents procrastination, distraction, and obsession.
Even creative work needs scheduling. The greatest writers and artists didn’t wait for inspiration. They kept a strict daily schedule for creating their art.

As said, this is the things I found important. The book is fully packed with things for you. Get the book through Derek’s site:

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