
Title: How to Live
Author: Derek Sivers
Completed: May 2026 (Full list of books)
Overview: A quick read that explores many different (often contradictory) philosophies of life. I read the first one or two and disagreed with them so much, I started to wonder if I had misunderstood the messages I’d heard from Derek before. I decided to read a few more and saw these more as thought experiments he wrote down to better understand his own thinking. Don’t read this expecting to agree with everything. Instead read this to have it push your thinking about how to live.
Highlights:
- You think you want more choice and more options. But when you have unlimited choice, you feel worse. When you keep all options open, you’re conflicted and miserable.
- If you need money, be an investor. It’s the only career where you profit the most by doing the least. It should take no more than an hour per month. The stock market takes money from the active traders and gives it to the patient.
- 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.
- 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.
- In Icelandic, the word for “idiot” means “one who has never left home to journey abroad”. Only idiots think they’re always right.
- Ignore all marketing and advertising. Nobody is pushing what really matters. Friendships, nature, family, learning, community. The best things in life aren’t things.
- To communicate clearly, you have to think clearly. Writing is refined thinking. Public speaking tests your writing on a real audience. Great public speaking comes from great private thinking.
- 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. Rules are to save you from deciding. That’s why hard rules are easier to keep.
- 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. Observation, creativity, and empathy, all in an instant. What could be a better sign of a healthy mind?
- No matter what you need to do, there’s a playful, creative way to do it. Playing gives you personal autonomy and power.
- 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.
- 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.
- Don’t convince yourself your home is an asset. Your home is an expense, not an investment, because it doesn’t put money in your pocket each month.
- Imitate your heroes. It’s not copying because it won’t be the same. Your imitation of anything will be unrecognizably warped by your own twisted perspective. Most creations are new combinations of existing ideas. Originality just means hiding your sources.
- Learn by hands-on experience. The more mistakes you make, the faster you learn. Once you’ve made all the mistakes in a field, you’re considered an expert.









