“Whatever you feel yourself leaning away from, try leaning into. If you hate opera, then go learn more about opera. And if you hate sports, well, then go learn more about sports. It’s usually just learning about something gives you an appreciation for this thing that you used to just dismiss.”
— Derek Sivers
Derek Sivers is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. Derek’s books (How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: sive.rs. His new book is Useful Not True.
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Listen onOvercast#777: Derek Sivers, Philosopher-Entrepreneur — The Greatest Year of His Life
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Want to hear the last time Derek was on the show? Listen to our conversation here, in which we discuss the benefits of an unoptimized life, finding and asking mentors for help, the wisdom of quitting when you’re ahead, how to teach an 11-year-old to act like a 16-year-old, the problem with moral relativism and other -isms, securing tech independence, and much more.
What was your favorite quote or lesson from this episode? Please let me know in the comments.
SELECTED LINKS FROM THE EPISODE
- Connect with Derek Sivers:
Website | Podcast | Twitter | YouTube
- Useful Not True: Whatever Works for You by Derek Sivers
- How to Live: 27 Conflicting Answers and One Weird Conclusion by Derek Sivers
- Hell Yeah or No: What’s Worth Doing by Derek Sivers
- Your Music and People: Creative and Considerate Fame by Derek Sivers
- Anything You Want: 40 Lessons for a New Kind of Entrepreneur by Derek Sivers
- Derek Sivers — The Joys of an Un-Optimized Life, Finding Paths Less Traveled, Creating Tech Independence (and Risks of the Cloud), Taking Giant Leaps, and Picking the Right “Game of Life” | The Tim Ferriss Show #668
- Derek Sivers: Weird, or Just Different? | TED Talk
- Gahwa: A Quintessential Symbol of Emirati Hospitality | National Geographic
- Gourmet Arabian Hospitality | Café Bateel
- Ruby vs. Python: What’s the Difference and How to Choose? | Learn Enough
- Work Quickly and Integrate Systems More Effectively | Python
- Is a Rat the Right Pet for You? | The Humane Society of the United States
- Woman Brings Home a Rat and Discovers He’s Just like a Puppy | GeoBeats Animals
- 26 Years of Growth: Shanghai Then and Now | The Atlantic
- For Global Business | Alipay
- Connecting a Billion People | WeChat
- Things to Do in Taipei | The Complete Guide
- How Did Taipei Change in the Last Decade? | Quora
- China’s World View: Demystifying China to Prevent Global Conflict by David Daokui Li | Derek Sivers
- Blade Runner | Prime Video
- Japan Was the Future but It’s Stuck in the Past | BBC
- Shenzhen, China: All You Must Know Before You Go | Tripadvisor
- Chengdu, China: All You Must Know Before You Go | Tripadvisor
- Visit Dubai | Official Tourism Board in Dubai
- City of Gold: Dubai and the Dream of Capitalism by Jim Krane | Derek Sivers
- Arabian Sands by Wilfred Thesiger | Derek Sivers
- The Bedouin — Desert Nomads | Bedouin Experience
- How Lee Kuan Yew Engineered Singapore’s Economic Miracle | BBC News
- Muscat, Oman: All You Must Know Before You Go | Tripadvisor
- Keeping Our Culture Alive Through Footwear | Tamashee
- Tamashee Steps Up Khaleeji | Gulf News
- Independent Adventuring Supply Shops | 826 Valencia
- The Birth of Islam | The Metropolitan Museum of Art | Heilbrunn Timeline of Art History
- Cormac McCarthy Writes to the Editor of the Santa Fe New Mexican | McSweeney’s Internet Tendency
- The Road by Cormac McCarthy | Amazon
- Blood Meridian: Or the Evening Redness in the West by Cormac McCarthy | Amazon
- Seven Types of Hammered Dulcimers Around the World | Songbird Dulcimers
- The 4-Hour Workweek: Escape 9-5, Live Anywhere, and Join the New Rich by Tim Ferriss | Derek Sivers
- The 4-Hour Body: An Uncommon Guide to Rapid Fat Loss, Incredible Sex, and Becoming Superhuman by Timothy Ferriss | Derek Sivers
- How Groupthink Impacts Our Behavior | Verywell Mind
- What Is Asset Allocation and Why Is It Important? | Investopedia
- Varadaraja V. Raman — The Heart’s Reason: Hinduism and Science | The On Being Project
- System 1 and System 2 Thinking | The Decision Lab
- Thinking, Fast and Slow by Daniel Kahneman | Derek Sivers
- The Gift of Fear: Survival Signals That Protect Us from Violence by Gavin de Becker | Amazon
- The Work | Byron Katie
- Oblique Strategies: Over One Hundred Worthwhile Dilemmas by Brian Eno | Amazon
- A Quiet Place to Think About Music | MusicThoughts
- Brian Eno: Interview with the Producer of U2’s No Line on the Horizon | The Telegraph
- Nam June Paik: Moon Is the Oldest TV | Prime Video
- John Cage Performs “Water Walk” | I’ve Got a Secret
- Seesaws Built On US Border Wall Win Prestigious Design Prize | NPR
- The Story Of ‘4’33″‘ | NPR
- A 639-Year-Long John Cage Organ Performance Strikes a New Chord in Germany | NPR
- How Buildings Learn: What Happens After They’re Built by Stewart Brand | Derek Sivers
- Stewart Brand – The Polymath of Polymaths | The Tim Ferriss Show #281
- The Latest in Technology, Science, Culture, and Business | Wired
- Interview of Kevin Kelly, Co-Founder of WIRED, Polymath, Most Interesting Man In The World? | The Tim Ferriss Show #25, #26, & #27
- How to Do a Turkish Get-Up | Furthermore from Equinox
- Robust, Practical, and Fast | Clojure
- Simplicity Matters by Rich Hickey | Rails Conf 2012 Keynote
- Etymology of Complex | Online Etymology Dictionary
- Six Reasons the Puerto Rico Tax Incentives Aren’t All They’re Cracked Up to Be | US Tax Services
- Money — Master the Game: 7 Simple Steps to Financial Freedom by Tony Robbins | Derek Sivers
- Emergency: This Book Will Save Your Life by Neil Strauss | Amazon
- Tools of Titans: The Tactics, Routines, and Habits of Billionaires, Icons, and World-Class Performers by Tim Ferriss | Amazon
- George Does the Opposite | Seinfeld
- No Yes. Either HELL YEAH! or No. | Derek Sivers
- The Billionaire’s Guide to Doing Taxes | Vox
- Release Your Music Everywhere | CD Baby
- Who Was Bitcoin’s Satoshi? I Need to Know and So Do You. by Tyler Cowen | Bloomberg
- Betteridge’s Law of Headlines | Wikipedia
- E-Gold | Stanford University
- Tyler Cowen on Rationality, COVID-19, Talismans, and Life on the Margins | The Tim Ferriss Show ##413
- All Food Is Ethnic Food. | Tyler Cowen’s Ethnic Dining Guide
- After National Acclaim over the past Decade, Where Is Pittsburgh’s Food Scene Headed? | Trib Live
- Translation Tools to Help People Translate Books | Inchword
- Japanese vs. Korean: Which is Easier to Learn? | Busuu
- Your Fast Track to Speaking a New Language | Fluent in 3 Months
- A Beginners Guide to Esperanto | The Guardian
- Universala Esperanto-Asocio
- Language Crash Course: Klingon | PGO 2020
- Pimsleur Spanish Level 1 Lessons 1-5 | Amazon
- Learn to Read Korean in 15 Minutes | Ryan Estrada
- How to Do Basic Pen Tricks | Tim Ferriss
- Traditional Welcoming | Bedouin Experience
- Burj Khalifa: Unpacking the World’s Tallest Building | Architectural Digest
- UAE’s Diversity and Multiculturalism, Discussed By Those Who Live it Every Day | Vogue Arabia
- Mos Eisley Cantina Scene | Star Wars: Episode IV A New Hope
SHOW NOTES
- [00:07:18] Derek Sivers: A Man who brings his own introduction.
- [00:09:25] First mind change: Emirati coffee.
- [00:12:34] Second mind change: Ruby to Python.
- [00:13:54] Third mind change: Rats.
- [00:17:23] Fourth mind change: China.
- [00:23:24] Fifth mind change: Dubai.
- [00:26:48] Tamashee: Come for the sandals, stay for the culture.
- [00:30:52] Cormac McCarthy Writes to the Editor of The Santa Fe New Mexican.
- [00:31:47] Shifting perspectives and the value of questioning preconceptions.
- [00:51:23] Brian Eno and MusicThoughts.
- [00:53:57] John Cage.
- [00:56:34] Three glasses.
- [00:57:08] Derek’s experimental housing project.
- [01:03:51] Rich Hickey and practical applications of simplicity.
- [01:29:20] Tyler Cowen.
- [01:35:57] Inchword and language learning.
- [01:46:35] Traveling to inhabit philosophies.
- [01:54:14] Parting thoughts.
MORE DEREK SIVERS QUOTES FROM THE INTERVIEW
“Whatever you feel yourself leaning away from, try leaning into. If you hate opera, then go learn more about opera. And if you hate sports, well, then go learn more about sports. It’s usually just learning about something gives you an appreciation for this thing that you used to just dismiss.”
— Derek Sivers
“I travel to inhabit philosophies.”
— Derek Sivers
“Don’t jump through hoops to save taxes, jump through a hoop to go make more money. That’s the growth choice anyway. That’s the thought process that leads you to make growing decisions, not shrinking decisions.”
— Derek Sivers
“I’m willing to throw myself in and feel the pain to see if I’ve done it wrong.”
— Derek Sivers
“When I’m around people who I know agree with me, my inherent curiosity level drops a bit. And when I’m around people who I know don’t think like me, my curiosity piques.”
— Derek Sivers
“I deliberately fucked up my life and made a bunch of crazy fucking decisions, and some of them worked out great, and some of them didn’t. And I’m so happy that I did that.”
— Derek Sivers
“So often, the difference between success and failure is the mindset that leads you to take different actions. But if you just look at a situation, and you say, “That’s it. That’s what the situation is,” I’m not talking about physical things. I mean declaring something to be a dead end, declaring something to suck, these are all things of the mind, and nothing of the mind is necessarily true. Everything that’s just in the mind is just one perspective.”
— Derek Sivers
“It can be much harder to do something that is objectively simple, that stands alone, that isn’t dependent on other things. It can be harder to make that, but it’s ultimately usually a better choice because it’s more maintainable, it’s easier to change, it’s easier to stop and start. It’s simpler even if it’s harder to make.”
— Derek Sivers
“Esperanto is hippie Klingon.”
— Derek Sivers
PEOPLE MENTIONED
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