Title: Hell Yeah or No what’s worth doing

Author: Derek Sivers

Completed: November 2025 (Full list of books)

Overview: For many years, I’ve been interested in the writings of Derek Sivers. It goes back far enough I don’t have any idea where I first heard about him, but the idea of sharing all my book notes came from him. I’ve had several of his books on my to read list for a while and when he announced they were free for a week on his website I decided now was the time. (I was going to get it from the library for free already but this was just the prompt I needed to get to it).

Reading through this book, there were many ideas that I completely agreed with and several that I disagreed with, but each idea was conveyed clearly and succinctly which encouraged me deeply think about my views and understand why I felt that way. Knowing what I do about Derek, I suspect he would be much happier knowing that he made me consider my own views far more than he would be if I just accepted his which is somewhat uncommon these days. Either way, this was a quick read and I’d recommend reading it when you have time to ponder.

Highlights:

• And then if you stopped doing all these things you’re doing just for the money or the attention, what would be left? Who would you be if you didn’t do these things? If you were completely satiated, then what? After an understandable period of relaxing, what would you pursue? Don’t say “sit around and do nothing,” because that’s still just relaxing. I mean after that, when you’re ready to be useful to others again.
• No matter what you tell the world or tell yourself, your actions reveal your real values. Your actions show you what you actually want. There are two smart reactions to this: Stop lying to yourself, and admit your real priorities. Start doing what you say you want to do, and see if it’s really true.
• Stop fooling yourself. Be honest about what’s past and what’s present. Retiring outdated titles lets you admit what you’re really doing now. And if you don’t like the idea of losing your title, then do something about it! This goes for titles like “leader,” “risk-taker,” and “good friend,” too.
• If you’re not feeling “hell yeah!” then say no. Most of us have lives filled with mediocrity. We said yes to things that we felt half-hearted about.
• Though it’s good to say yes when you’re starting out, wanting any opportunity, or needing variety, it’s bad to say yes when you’re overwhelmed, over-committed, or need to focus.
• I rebel against anything that feels like addiction. When I hear myself saying “I need this,” I want to challenge that dependency and prove my independence.
• Kimo’s high expectations set a new pace for me. He taught me that “the standard pace is for chumps” — that the system is designed so anyone can keep up. If you’re more driven than most people, you can do way more than anyone expects. And this principle applies to all of life, not just school.
• During my last unmotivated funk, I realized that because nothing is exciting me, that means nothing is exciting me more than this boring necessary stuff. And since I don’t want to waste my inspired times on brainless work, this is a perfect time to do those dull tasks.
• Imagine what it’s like to be the silver medalist. If you’d been just one second faster, you could have won the gold! Damn! So close! Damn damn damn! Full of envy, you’d keep comparing yourself to the gold winner. Now imagine what it’s like to be the bronze medalist. If you’d been just one second slower, you wouldn’t have won anything! Awesome! You’d be thrilled that you’re officially an Olympic medalist and get to stand on the winner’s podium. Comparing up versus comparing down: Your happiness depends on where you’re focusing.
• The problem is taking any one person’s advice too seriously. Ideally, asking advice should be like echolocation. Bounce ideas off of all of your surroundings, and listen to all the echoes to get the whole picture.
• Don’t be a donkey. You can do everything you want to do. You just need foresight and patience. If you’re thirty now and have six different directions you want to pursue, then you can do each one for ten years, and have done all of them by the time you’re ninety. It seems ridiculous to plan to age ninety when you’re thirty, right? But it’s probably coming, so you might as well take advantage of it.
• Ninety-three percent of drivers say they are safer-than-average drivers. When I learned this, it shook my soul. At first, like almost everybody, I thought, “Yes, but I really am above average!” Then I realized I was doing it again. So I decided to gamble on the opposite. Now I just assume I’m below average. It serves me well. I listen more. I ask a lot of questions. I’ve stopped thinking others are stupid. I assume most people are smarter than me. To assume you’re below average is to admit you’re still learning.
• I had collected 232 unbroken sand dollar shells. I put them all out in the sun to dry, amazed at my good luck. I bragged to my family. I tried to think of all the things I could do with 232 sand dollars. After two days the excitement wore off. I realized I was never going to do anything with them. Now it was just stupid for me to keep all of these sand dollars sitting there doing nothing. The excitement was in finding them, not keeping them.
• 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? Answers to this double-negative question seem to be better indicators of what’s really worth doing.
• I felt ready to do something new, so I started to learn. But the more I learned, the more I realized how little I knew and how dumb-lucky I had been. I continued learning until I felt like an absolute idiot.
• Learning without doing is wasted. If I don’t use what I learn, then it was pointless! How horrible to waste those hundreds of hours I spent learning, and not turn it into action.
• Alvin Toffler said, “The illiterates of the 21st century will not be those who cannot read and write but those who cannot learn, unlearn, and relearn.”
• Many people learn only in their first third of life, so schools don’t teach unlearning.
• the differences among men, and the differences among women, are much bigger than the differences between men and women. So instead, to compensate for your tendency to exaggerate those differences, just assume that men and women are the same. They’re not the same, but if you follow this rule, your thinking will be closer to correct than not.
• You really learn only when you’re surprised. If you’re not surprised, then everything is fitting into your existing thought patterns. So to get smarter, you need to get surprised, think in new ways, and deeply understand different perspectives. With effort, you could do this from the comfort of home. But the most effective way to shake things up is to move across the world. Pick a place that’s most unlike what you know, and go. This keeps you in a learning mindset. Previously mindless habits, like buying groceries, now keep your mind open, alert, and noticing new things.