Things I Learned from Derek Sivers

January 31, 2021

Derek Sivers has been writing his articles for the past twenty years. Here is a distilled summary of all the ones that resonated with me.

How to write?

  • Write all your thoughts. Argue against them.
  • Get rid of all except essential. Post the outline.

Benefits of a daily diary.

  • Write what you did, how you are feeling, even if it seems boring. Include the daily facts of life.
  • Do this for your future you. Years from now he will look back, wondering if you were as happy or as sad as you remember during this time.
  • Tag your articles with various relevant topics.

Don’t be a Donkey.

  • Don’t pursue too many directions all at once.
  • Think long term. Do just one thing for a few years, then another for a few years, then another.
  • You can do everything you want to do. You just need foresight and patience.
  • Focus on few things at a time, without feeling conflicted or distracted.
  • We overestimate what we can do in few months, and underestimate what we can do in few years.

How to deal with uncertainty.

Copy others. Shamelessly.

  • Your imitation will turn out much different from the original, anyway. Maybe even better.
  • Nobody usually notices the similarity. People don’t make connection unless you tell the the source of its inspiration.

Let go of outdated dreams that keep you from noticing what’s here now.

  • If you have a too specific goal, you are blind to other new means.
  • Reevaluate your old goals to see if new means have come along.
  • Ask yourself what the real point it. Then look for a better way to get to that point.

Avoid being rigid.

  • If you keep experiencing the same things, your mind keeps its same patterns. Same inputs, same responses.
  • Your brain, which was curious and growing, gets fixed into deep habits. Your values and opinions harden and resist change.
  • To get smarter, you need to get surprised, think in new ways, and understand different perspectives.

Money is nothing more than a neutral exchange of value.

  • If people give you money, it’s a proof that you’re giving them something valuable in return.

Why am I here?

  • Look around. It’s a useful question to ask occasionally.
  • Either it will re-focus your reasons for being where you are, or it will make you realize your reasons have expired and you should be somewhere else.
  • Many times, you are where you are is because of decisions you made years ago. But are they valid today?

Don’t try to sound Big.

  • Don’t appear flawless. Show a charming flaw. Vulnerability endears.
  • Be small and independent instead of big and corporate.

Think slowly.

  • Don’t have an immediate reaction, or don’t come to conclusion immediately.
  • You don’t need to answer. Take your time. Have an answer next day. Sleep on it.

Share whatever you’ve got

  • It might be a skill you have, something you own, resources, experience, etc.
  • If it takes some effort for you to share it, charge a little something, so you can continue.

To be happy, think like a bronze medalist, not silver

  • Your happiness depends on who you are comparing yourself against.
  • For ambition and getting better, use the reverse strategy.
  • Most of the time, be grateful for what you’ve got, for how much worse it could have been, and how nice it is to have anything at all.

Success comes from persistently improving and inventing, not from persistently promoting what’s not working.

  • Don’t waste years fighting uphill battles against locked doors.
  • Improve and invent until you get that huge response.


  • Discard old ideas which are not serving you.
  • Doubt what you know. Stop thinking what you knew or believed is true.
  • Require current proof that it’s still valid. Otherwise, let it go. Subtract.

This is only a test. See what happens.

  • It’s impossible to fail if your only goal was to see what happens!

Get Specific

  • Get specific about what’s needed. Write down every detail you know.
  • Create milestones, and concrete action steps you can take next.
  • Research what you don’t know.

Focus. Do not be distracted.

  • Next few years are your training sequence. Ignore everything else.
  • Your enemy is distraction. Getting distracted by the noise in the world.

There are no speed limits.

  • The standard pace is to accommodate everyone.
  • The system is designed so anyone can keep up.
  • If you are more driven than most, you can do way more than anyone expects.

We’ll see.

  • Events are just that. Just events. We assign meaning to them.

Show success before asking for help

  • You have to make your own success first, before you ask the industry for help.
  • Show that you’re going to be successful without their help. Show that you have momentum.

Don’t talk about your plans

  • Keep your goals private. Don’t share them until they are achieved.
  • People who expect to receive a reward do not perform as well as those who expect nothing.


  • Hide conscious effort and appear to accomplish difficult actions with casual nonchalance.
  • Practice and prepare so well that you can put on an effortless performance.

Do what you want to do.

  • If you want to read, read a lot.
  • If you want to write, write a lot.
  • If you want to program, program a lot.

Not happy with existing venues? Make a new one.

  • Don’t complain. Go make things how they should be.

Make decisions as late as possible

  • When you have the best information.
  • Resist the urge to figure it all out in advance.

How will this game end?

  • The real problem is not thinking it through in advance.
  • When the game starts, it’s easy to think short-term and get seduced. When it’s too late, you realize what you have done.
  • Before you start something, think of the ways it could end. Sometimes the smart choice is to say no to the whole game.