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November 13, 2024 • 2hr 3min
#777: Derek Sivers, Philosopher-Entrepreneur — The Greatest Year of His Life
The Tim Ferriss Show
Derek Sivers returns to The Tim Ferriss Show to discuss things he's changed his mind about, people he's studying, and his latest philosophical explorations. Derek is an entrepreneur, programmer, musician, and author known for founding CD Baby and writing several books including his latest "Useful Not True."
#777: Derek Sivers, Philosopher-Entrepreneur — The Greatest Year of His Life
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Key Takeaways
- Challenging your prejudices and preconceptions can lead to profound personal growth and happiness
- Simple vs Easy: Simple things stand alone while complex things are intertwined with dependencies - aim for simplicity even if it's harder initially
- Travel to inhabit philosophies - don't just visit places, but try to embody and understand different ways of living
- Question your default responses and be willing to go against your initial reactions to discover new perspectives
- Cultivate friendships with people you disagree with to expand your thinking and develop conflict resolution skills
Introduction
Derek Sivers returns to The Tim Ferriss Show to discuss things he's changed his mind about, people he's studying, and his latest philosophical explorations. Derek is an entrepreneur, programmer, musician, and author known for founding CD Baby and writing several books including his latest "Useful Not True."
Topics Discussed
Things Derek Has Changed His Mind About (9:51)
Derek shares five major perspective shifts that contributed to making the past year one of his happiest:
- Coffee - After disliking coffee his whole life, he discovered he enjoys Emirati coffee in Dubai
- Python Programming Language - Overcame 20 years of prejudice against Python to discover its beauty
- Pet Rats - Went from killing rats to loving them as pets after his son's suggestion
- China - Found modern China vastly different and more advanced than his 2010 impressions
- Dubai - Transformed from "would never visit" to considering it as a potential home
The Value of Changing Your Mind (32:49)
Derek emphasizes the joy and growth that comes from overcoming prejudices and preconceptions:
- Personal growth comes from leaning into what you initially resist
- "If you feel completely averse to something, get to know it better. Whatever you feel yourself leaning away from, try leaning into."
- The greatest joy can come from loving what you previously hated
- This approach leads to a more diverse and enriching life experience
Simple vs Complex - Rich Hickey's Philosophy (1:04:07)
Derek discusses programmer Rich Hickey's insights about simplicity versus complexity:
- Simple means standing alone (from simplex)
- Complex means braided together with dependencies (from complex)
- Easy means near at hand or familiar
- "It can be very easy to make something very complex, and very hard to make something simple"
- Applications beyond programming to life choices and decision-making
The George Costanza Principle (1:19:50)
Derek shares his experience of deliberately doing the opposite of his instincts:
- Used this principle after selling CD Baby to change his life trajectory
- Led to some mistakes but also valuable growth experiences
- "I deliberately fucked up my life and made a bunch of crazy decisions. Some worked out great and some didn't."
- Should be used selectively as a tool, not as a constant approach
Travel and Cultural Philosophy (1:46:35)
Derek introduces his concept of traveling to inhabit philosophies:
- Travel purpose: To experience and embody different ways of living
- Cultural immersion: Learning language and living as locally as possible
- "I travel to inhabit philosophies, not to look at things or take pictures"
- Example: Understanding Arab culture's emphasis on generosity and hospitality
Dubai and Multicultural Experience (1:51:32)
Derek shares his discoveries about Dubai as a global crossroads:
- 90%+ foreign-born population compared to 35% in other multicultural cities
- Opportunities for cultural learning and exchange
- Example of taxi driver learning 8 languages in 18 months
- "It's like the cantina in Star Wars - everybody comes from all over the world to this spot"
Translation Project - Incword.com (1:36:07)
Derek discusses his innovative approach to improving book translations:
- Goal: Create continuously improving translations through incentivized collaboration
- Process: Multiple translators building on each other's work
- Quality control: Reader voting system to verify improvements
- Addressing misaligned incentives in traditional translation process
Conclusion
The conversation demonstrates the value of questioning assumptions, embracing change, and seeking out diverse perspectives. Derek's experiences highlight how deliberately challenging our preconceptions can lead to personal growth and unexpected joy. His approach to travel, technology, and life choices emphasizes the importance of simplicity while remaining open to new experiences and ways of thinking.