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July 10, 2024 • 2hr 32min
#753: Derek Sivers and Kevin Kelly
The Tim Ferriss Show
This episode features segments from interviews with Derek Sivers and Kevin Kelly. Derek Sivers is a former musician, programmer, TED speaker, and entrepreneur who founded CD Baby. Kevin Kelly is the founding executive editor of Wired magazine and bestselling author on technology and culture. Both guests share unconventional wisdom and insights on success, meaning, and navigating life and work.
#753: Derek Sivers and Kevin Kelly
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Key Takeaways
- Say yes to opportunities early in your career - Derek Sivers got his start in the circus by saying yes to a small gig playing music at a pig show, which led to a 10-year career
- Develop confidence by focusing on giving the audience what they want, not worrying about how you're being judged
- "The standard pace is for chumps" - You can often achieve things much faster than the typical timeline by being strategic and putting in focused effort
- Use the "H**l Yeah or No" philosophy to avoid mediocre commitments and free up time for truly exciting opportunities
- Automate and systematize your business to free up your time for creative work and new projects
- Don't be a "donkey" trying to pursue many directions at once - Focus on one thing at a time over longer periods
- Money is overrated - experiences, time, and relationships are often more valuable than accumulating wealth
- Practice "voluntary simplicity" to realize how little you truly need to be content
- Take technology sabbaticals to gain perspective and appreciation
- Think long-term on a civilizational timescale to work on truly meaningful projects
- Build your own house/shelter as an empowering life experience
- Discovery and invention are the same in high-dimensional spaces - finding yourself and creating yourself are intertwined
Introduction
This episode features segments from interviews with Derek Sivers and Kevin Kelly. Derek Sivers is a former musician, programmer, TED speaker, and entrepreneur who founded CD Baby. Kevin Kelly is the founding executive editor of Wired magazine and bestselling author on technology and culture. Both guests share unconventional wisdom and insights on success, meaning, and navigating life and work.
Topics Discussed
Derek Sivers' Unconventional Career Path (6:50)
Derek shares how he got his start in the entertainment industry by saying yes to a small gig playing music at a pig show in Vermont for $75. This led to more gigs and eventually a 10-year career performing with a circus.
"I said h**l yeah. I'm a professional musician now. This is amazing. So I said yes to everything, which is going to come up later, you know, with the h**l yeah or no thing that I think it's really smart to switch strategies, but when you're earlier in your career, I think the best strategy is you just say yes to everything."
- Saying yes to small opportunities can lead to big breaks
- Early in your career, be open to any experience to discover what you enjoy
- Derek went from musician to circus performer to ringleader over 10 years
Developing Confidence as a Performer (10:42)
Derek explains how he overcame self-consciousness on stage by realizing it wasn't about him being judged, but about giving the audience the experience they came for.
- Focus on serving the audience, not yourself
- Over-the-top energy and enthusiasm is often what people want from a performance
- Confidence comes from shifting perspective away from self-consciousness
Accelerated Learning - "The Standard Pace is for Chumps" (13:05)
Derek shares how a music teacher helped him graduate Berklee College of Music in 2 years instead of 4 by teaching him intensively and showing him how to test out of classes.
"The standard pace is for chumps. That's the school has to organize its curricula around the lowest common denominator so that almost nobody is left out, so they have to slow down so that everybody can catch up. And he said, you're smarter than that, or anybody can be smarter than that if they want to be. So you can go as fast as you want."
- Look for ways to accelerate learning beyond standard timelines
- Intensive, focused study can compress years of material into months
- Test out of requirements when possible to avoid redundant coursework
Relaxing for the Same Result (18:51)
Derek describes an epiphany he had while cycling - that pushing himself to exhaustion only saved 2 minutes compared to a relaxed ride. This taught him to stop stressing unnecessarily in life.
- Extreme effort often yields diminishing returns
- A relaxed approach can often achieve nearly the same results with less stress
- Focus on being effective rather than just working harder
The "H**l Yeah or No" Philosophy (24:01)
Derek explains his approach of only saying yes to things he's truly excited about, and declining everything else.
"If you're feeling anything less than, like, oh, h**l yeah, I would love to do that. Oh, my God, that would be amazing. If you're feeling anything less than that, then just say no. Because most of us say yes to too much stuff, and then we let these little mediocre things fill our lives."
- Only commit to things you're genuinely enthusiastic about
- Saying no to mediocre opportunities frees up time for great ones
- Helps avoid overcommitment and maintain control of your time
Automating CD Baby (28:03)
Derek shares how he systematized CD Baby to run without his constant involvement by documenting processes and training employees thoroughly.
- Document your decision-making process and philosophy to empower others
- Train multiple people on each role for redundancy
- Automate and delegate to free up time for creative/strategic work
Kevin Kelly's Unconventional Path (40:24)
Kevin discusses dropping out of college after one year to travel Asia, which he considers his "PhD in East Asian studies." He emphasizes the value of unstructured exploration when young.
- Formal education isn't always necessary - self-directed learning can be powerful
- Travel and diverse experiences provide invaluable life education
- Youth is a time for exploration before optimizing for productivity
Practicing Voluntary Simplicity (43:13)
Kevin advocates experimenting with minimalism and simple living to overcome fears about survival and contentment with less.
"I think one of the many kind of life skills that you want to actually learn at a fairly young age is the skill of being like ultra thrifty, minimal, kind of this little wisp that is traveling through time in the sense of learning how little you actually need to live."
- Practice living on very little to build confidence and overcome financial anxiety
- Realizing you can be content with less is empowering and liberating
- Voluntary simplicity provides perspective on what's truly necessary
Developing as a Writer and Thinker (50:33)
Kevin explains how he developed his writing skills later in life through travel experiences, letter writing, and online communication.
- Having experiences worth writing about is key to developing as a writer
- Writing helps clarify thinking - write to figure out what you think
- Direct, concrete communication (like emails) often produces better writing than formal essays
The Overrated Nature of Money and Success (1:06:50)
Kevin argues that beyond a certain point, more money doesn't significantly improve quality of life. He emphasizes experiences and relationships over wealth accumulation.
"There's nothing that you can really do with [a billion dollars], that you can't do with a lot of less money. It was a set then aside. But even just wealth itself, in this world, where there is more and more abundance, even the money for, say, middle class is less significant in a certain sense."
- Experiences and relationships are often more valuable than money
- True success is about creating your own unique "slot" in life
- Focus on meaning and impact rather than traditional markers of success
Optimizing in Middle Age (1:11:05)
Tim and Kevin discuss the challenges of continuing to explore and take risks in middle age versus optimizing existing skills and businesses.
- The "creator's dilemma" - balancing optimization with exploration of new areas
- Success can make it harder to take risks and try new things
- Consider incremental experiments rather than completely abandoning existing work
Living as if You Only Had 6 Months Left (1:15:28)
Kevin shares an experience of living for 6 months as if he was going to die, which helped clarify his priorities.
- Regularly consider what you'd do if you only had limited time left
- Use a sense of mortality to focus on what's truly important
- Balance long-term thinking with an appreciation for limited time
The Long Now Foundation (1:48:53)
Kevin explains the mission of the Long Now Foundation, which aims to foster long-term thinking on a civilizational timescale.
- Encourages thinking in terms of decades, centuries, or millennia
- Balances short-term needs with very long-term projects and goals
- Provides perspective on humanity's place in time
Building Your Own House (2:17:14)
Kevin advocates for the transformative experience of building your own shelter or house.
"You need to build your own house, shelter. And it's not that hard to do, believe me. I actually. I built my own house."
- Empowering to know you can create your own shelter
- Designing and building a home helps you understand yourself
- The process of creating a personal space is both practical and philosophical
Conclusion
This episode provides a wealth of unconventional wisdom from two innovative thinkers. Key themes include the value of saying yes to opportunities early in your career, the power of focused learning, the importance of long-term thinking balanced with an appreciation for limited time, and the benefits of simplicity and direct experience. Both Derek Sivers and Kevin Kelly emphasize creating your own unique path rather than following conventional notions of success, and using constraints and challenges as opportunities for growth and self-discovery.