When I first started this podcast, I had Derek Sivers in mind as the archetypal curious human — and to this day, I think of him as one of the most interesting and provocative philosophers of life. His career path involved joining the circus as a ringleader, then becoming a professional musician and touring, building a company and selling it for $22 million dollars, then giving most of the money away to charity, then becoming a TED speaker and author... to now where he's a minimalist living in New Zealand as a full-time dad.

In this conversation, you can expect to learn the following:

🏙️ His unexpected love affair with Dubai
🤔 Why nothing you believe is actually true
📝 How he journals to find sanity for himself
🤝 What he's learned about negotiation skills
🛠️ Why he created a 'Making Room' in his house
🗺️ How it's possible to have too much freedom in your life
👨‍👦 Why he feels that his son is his best friend and soulmate

Timestamps

[00:08:56] Derek didn't have much curiosity until later in life.

[00:12:20] Rebellious streak seeks balance in all situations.

[00:18:55] Having total freedom can feel disorienting.

[00:25:17] Choose independence, then commit for best results.

[00:29:14] We don't really know why we do things.

[00:35:00] Journaling: Derek's way to process thoughts and find clarity.

[00:43:32] Brain awake, busy day of writing.

[00:49:48] Sister's chaotic household convinced me: no kids.

[00:54:45] Choosing mice for breeding: defying expectations.

[00:57:08] Teach kids to talk confidently and be makers.

[01:05:56] Money obsession feels like a mental disorder.

[01:10:52] The Red Cross can't do much, donate wisely.

[01:17:38] Negotiate Anything by Herb Cohen is a book full of relatable stories that emphasize the idea that everything is negotiable. The author, a professional negotiator, shares his experiences and challenges the notion of non-negotiable things. It's a thought-provoking read that sticks with you.

[01:21:05] Book: "You Can Negotiate Anything" - rating: 10/10. Talks about realizing power in any situation. Prisoner example shows hidden power. Violence comes from feeling powerless. Realize your power in any situation. Must-read.

[01:27:15] Movies portrayed sex as something men want, women don't.

[01:32:45] Dubai is a fascinating, diverse and foreigner-filled place.

[01:38:45] Python: a newfound love, Dubai.

[01:44:21] Aspiration: be read even after death.

Official Links

✉️ Email Derek personally here: derek@sivers.org
📚 Derek's Book Reviews
🙋‍♂️ Derek's /now page
📖 Buy his masterpiece How to Live (don't buy on Amazon!)

Connect + Explore More from Jonny

🐦 Follow on Twitter/X @jonnym1ller
🫁 Learn more about Nervous System Mastery
🪷 Order our deck of Calm Cards (these make great gifts)
📱 Check out Stateshift — our brand new iOS + Android app
📝 Take the Nervous System Quotient (NSQ) Self-Assessment (totally free)
💌 Sign up to The Inner Frontier Newsletter

Episode Sponsors

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🫁 Nervous System Mastery

This is my flagship 5-week bootcamp designed to equip you with evidence-backed protocols to cultivate calm and emotional regulation. Our 8th cohort will run in Fall 2025 ~ and applications are currently open. My sense is that if this conversation resonates with you, then you'd likely be a great fit for our upcoming cohort. This curriculum represents my attempt to distill everything I've learned in recent years about creating the conditions for our nervous system's flourishing. It's run in an intensive cohort-based way since this is, in my experience, the most efficient way to embody and practice the protocols.

Previous students have shared how partaking improved their sleep and quality of relationships and tapped into deeper states of joy, clarity, and confidence in their lives. We've had over 1000 students have completed this training, and many have said that it has been the most impactful thing they've ever done for their personal growth — so if you're intrigued at all, you can find more details and apply to join this year's cohort over at nsmastery.com

Further Ways to Support the Podcast:

🎙️ I use Riverside to record all of my podcast conversations (it's so much better than zoom for podcasting!)
🎧 I also use Transistor to host this podcast, it's fricking awesome, and I would highly recommend.
😎 RaOptics make the world's best Blue Blockers – I wear these anytime I'm out of the house after dark, and it makes a huge difference!
🤖 I use AI wizardry from Castmagic to help with each episode show-notes + timestamps
📹 Want to create a Hollywood-quality home studio? Get in touch with Kevin Shen here & save $500 with code JONNYSENT500OFF

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