An Unconventional Path: Derek Sivers on Useful Beliefs, Pragmatic Positivity and Embracing Randomness

Derek sivers

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Here’s how to live: Learn. – Derek Sivers

My guest on this episode is Derek Sivers. Derek is proof that an unconventional background can be the perfect foundation for a wonderfully interesting life and groundbreaking success.

Originally a professional musician and circus clown, Derek founded CD Baby in 1998. It became the largest seller of independent music online, with $100 million in sales for over 150,000 musicians. In 2008, Derek sold CD Baby for $22 million, giving the proceeds to a charitable trust for music education.

His TED talks have garnered over 20 million views, and he has published 34 books, including Hell Yeah or No, Your Music and People, Anything You Want) and his most recent book as it pertains to this conversation is How to Live, 27 Conflicting Answers and One Weird Conclusion – but note we do slightly touch on his current yet-to-be-completed book Useful Not True.

Talking points include …

  • Derek’s transition from a musician to circus performer to entrepreneur and author.
  • The power of books and new ideas.
  • The concept of “useful, not true” and the practicality of a belief.
  • In his book Anything You Want, he revisits “hell yeah or hell no” as a decision heuristic.
  • On creativity and oblique strategies for releasing creative potential
  • Embracing unpredictability and the use of “random generators.”
  • The pragmatic rabbi’s approach to simplifying problems
  • Thoughts on songwriting and book writing.
  • Seeing emotions as ends bypassing things as means.
  • The orchestra-instrument framework.
  • The motivation of being temporarily-abled.
  • The practice of journaling to understand emotions and situations.


There is much more here, as we cover a lot of ground.

Tim Ferris called Derek a philosopher-king programmer, master teacher, and merry prankster and quote (one of my favorite humans), and after chatting with Derek, I understand why.

Please enjoy.

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