Hell Yeah or No by Derek Sivers

Dec 4, 2020 16:57 · 891 words · 5 minute read books


This was a good book. It’s a quick read, and I found it very enjoyable. I’m not sure how much of that was because I think it will be a useful book for others to read or if it was simply nice to read about someone that I seem to have so much in common with.

My thoughts

Similarly to Your Music and People, I was surprised to discover how short this book was, but it is concise and so enjoyable.

Derek Sivers has proven to me that it is possible to live life in a way that most other people don’t. Many of the paths that he has followed are paths that I am on, and it is heartening to learn that someone else has been here, and they made it to the other side.


The author has traveled significantly, and I appreciated hearing about a different way to do it. I have been a nomad in the past, and I spent several years basically living nowhere. I would be somewhere for 2-6 weeks, and then I would be somewhere else. So the following bit releived some tension that I still have when thinking about that:

I feel equally connected to many places. Just because I live in one place now, that doesn’t mean I should ignore the others. To me, the emphsis on local stuff never felt right.


The thing I want out of life is freedom. In the book, he provides a suggestion for how to acheive freedom, and his suggestion (become a business owner) is exactly what I’m doing. The validation felt good.


I had heard that America was the land of entrepreneurs and overconfidence, but I couldn’t really see it until I was outside it

I read this book on my way back from Europe, and it is spot on. A lot of other cultures place much more importance in stability and working together. America is all about “rugged individualism”. Or, stated differently: “fuck you, I’m doing it my way, and nothing will stand in my way”


There is a very insightful thought experiment in this book:

Suppose you put up a $100 bill at an auction, but there’s a catch. The person who comes in second has to pay what they bid.

Once they get to $99, the other person offering $98 thinks, “Uh oh. The other person isn’t backing down” They raise their bid to $100 so as not to be the second highest bidder and lose it all

And then the bids keep going.

I had not heard of this thought experiment before, but it is a really good way of explaining lots of bad human behavior.

Working hard

There are two conflicting points brought up in the book. On the one hand, you should work really hard, because:

“the standard pace is for chumps” […] If you’re more driven than most people, you can do way more than anyone expects

But then, he goes on to tell a story of taking a relaxing bike ride and doing almost exactly as well as he had when he was all-out sprinting.

This is something that I have experienced as well. Pushing through things is a recipe for success, but it’s easy to overdo it and end up doing negative work by pushing too hard.

Finding your passion

This book had the best advice I have found for finding your passion:

What do you hate not doing?

What makes you feel depressed, annoyed, or like your life has gone astray if you don’t do it enough?

The future

While reading, I got this idea that the future is a garden that you cultivate. Thinking of all the things that you could do in the future is a fun exercise, and sometimes people will appreciate it for what it is. But it isn’t going to be useful for accomplishing anything else.

Why is your picture in the book?

If, for some reason, Derek reads this, I have a bone to pick with you. In the book, you state:

When I buy a book that has a picture of the author on the cover ,I rip off and trash the cover before I even leave the store. I don’t care who the author is. All that matters are the ideas inside the book and what I do with them.

And yet, this book has a picture of your face on page 2.

UPDATE: I ended up trading emails with Derek Sivvers (he’s a super approachable dude), and I think I misunderstood the quote. I believe what he’s saying is that the author shouldn’t be the one selling the book. The ideas of the book should be doing the selling - more specifically, don’t buy Hell Yeah or No because it was written by Derek Sivers; buy it because it has compelling ideas that are worth reading. Howevver, it’s still interesting to know who the author is, so putting a bio in the book is fine.

Action items

This book provided me with a couple of personal action items including discussing particular topics with some people I am close with and: - Listening to (and judging) Sivers’ music - Creating a “Possible futures” note-set in my collection of notes. - Adding “output” to my daily notes. - I ended up calling this “artifacts”