In a conversation like no other, Musician, writer, and entrepreneur, Derek Sivers chats about creating and running CD Baby, reading, mental models, living a meaningful life, and that biggest mistake he’s ever made.
Now available on: YouTube | Apple Podcasts | Spotify | Transcript
Derek is the philosopher-king and so thoughtful about his approach to everything as you’ll hear. We discuss the benefits to being naïve to the ways of the world, how to decide what to work on, who to spend your life with, delegation, the value of execution over ideas, mental models and the biggest mistake he’s ever made.
Here are a few highlights from our conversation:
To me, the world feels unnecessarily ceremonial, like people imitate others without questioning it enough, but I don’t want to learn their ways. I don’t want to be like them. Instead, I just ignore it all and ask myself, what’s the real point? Meaning like, what am I really trying to do here?
I really like deep work and I really love focusing. For work to turn into this constant state of every five minute an interruption just made it unbearable. I stopped going to the office. I started shutting off my phone until I realized that I was running from my problems instead of solving them. I realized this was a do or die moment, like I need to fix this or I’m toast.
You know you’re a true business owner when you could leave your business for a year and come back a year later and find that it’s doing better than when you left. That’s when you’re no longer self-employed, you’re a business owner.
How to Live, the book that I’m writing right now, this is kind of what the book ended up being. It’s grown out of this process of surrounding myself with a bunch of thoughts around one subject, and then writing my own thoughts around that subject as kind of a reaction to the others around me. Metaphorically, it almost feels like if I was a painter and I was allowed to bring a blank canvas into a great museum and I could sit in a room of my favorite paintings ever and paint my own, which is not imitating theirs, but it’s influenced by.
I feel like the reflection time is when you really learn. The moment when you read somebody else’s idea, that’s a wow moment, but you don’t really learn it until you’ve put aside the time to reflect on it.
Whatever makes you take the necessary actions is the perspective that helps you. I’m never aiming for reality. I’m trying to make decisions usually based on finding the perspective that helps me take actions.
I often focus on an aspect of my life that’s lacking, and then I’ll enhance it until maybe it’s almost overflowing. Then I turn my attention to whatever aspect is now lacking after that. I think it’s really interesting that we all have conflicting needs simultaneously. At the same time, we have a need for stability and a need for adventure.
I don’t think life has meaning. I don’t think anything has inherent meaning. I think it’s all just a blank slate that we can project whatever meaning we want onto.
