Episode 334: Endless Curiosity with Derek Sivers

After decades of following his own interests, today’s guest Derek Sivers has gone down many interesting rabbit holes. With an ambitious title for his new book, ‘How To Live’, we explore what makes a good life.

Derek Sivers is best known as a writer, musician, programmer and the founder of CD Baby, an online CD store for independent musicians. For the past 12 years he’s been living a nomadic lifestyle and pondered a lot about what makes a good life. 

In this episode we explore his new book he’s currently writing ‘How To Live’ – and how there is no one ‘right’ way to live. Derek’s life philosophy of being curious is infectious, and I enjoy going down a few rabbit holes with him in this interview. Join us as we explore how time is personal, setting creative constraints, and the surprising conclusion from his book. Get ready for a few Star Wars references too.

Talking Points

  • The reason why he wrote his new book ‘How To Live’
  • The role curiosity plays in his life
  • How setting constraints gives your freedom
  • Thinking beyond New Year’s Eve: how time is personal
  • The big phases throughout Derek’s life
  • Is Derek always having fun?
  • His relationship with email

“Constraints free you from the daunting prospect of infinite possibility”

– Derek Sivers


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