
Derek Sivers on How to Negotiate Anything, The Joys of Parenthood & Why Nothing You Believe is True
08/23/23 • 109 min
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: [email protected]
📚 Derek's Book Reviews
🙋♂️ Derek's /now page
📖 Buy his masterpiece How to Live (don't buy on Amazon!)
Connect + Follow Jonny:
🐦 Follow on Twitter @jonnym1ller
💌 Subscribe to the Curious Humans Newsletter
🫁 Learn more about Nervous System Mastery
🙋♂️ Join Five to Thrive — a zero-cost educational email series.
Episode Sponsors
🩸 Inside Tracker — One of the things I've changed my mind on in the past year is the value of getting blood panels taken prophylactically (ideally every six months, according to Dr. Peter Attia) rather than waiting until you have a health issue. Inside Tracker recently added hormone testing alongside a bunch of other important biomarkers that aren't included in traditional blood panels (ApoB, for example). Despite generally feeling great, my most recent set of results showed that I have some work to do to reduce levels of inflammation, and I'll be following some of their dietary + supplement recommendations to address this asap. So I highly recommend making this something you make time for at least once or twice yearly. Save 20% here
🥶 The Cold Plunge — I reached out to the founder of the plunge, Ryan after hearing his powerful story on the Danny Miranda podcast. I've shared how getting in icy cold water every day helped me to move through intense grief, and taught me what it meant to surrender. These days I use their plunge every, single, day. It's like a high-stakes meditation—a mirror into my own internal state. The Plunge team have done a phenomenal job architecting what I consider as the world's best cold plunge (it doesn't get grimy like the conve...
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: [email protected]
📚 Derek's Book Reviews
🙋♂️ Derek's /now page
📖 Buy his masterpiece How to Live (don't buy on Amazon!)
Connect + Follow Jonny:
🐦 Follow on Twitter @jonnym1ller
💌 Subscribe to the Curious Humans Newsletter
🫁 Learn more about Nervous System Mastery
🙋♂️ Join Five to Thrive — a zero-cost educational email series.
Episode Sponsors
🩸 Inside Tracker — One of the things I've changed my mind on in the past year is the value of getting blood panels taken prophylactically (ideally every six months, according to Dr. Peter Attia) rather than waiting until you have a health issue. Inside Tracker recently added hormone testing alongside a bunch of other important biomarkers that aren't included in traditional blood panels (ApoB, for example). Despite generally feeling great, my most recent set of results showed that I have some work to do to reduce levels of inflammation, and I'll be following some of their dietary + supplement recommendations to address this asap. So I highly recommend making this something you make time for at least once or twice yearly. Save 20% here
🥶 The Cold Plunge — I reached out to the founder of the plunge, Ryan after hearing his powerful story on the Danny Miranda podcast. I've shared how getting in icy cold water every day helped me to move through intense grief, and taught me what it meant to surrender. These days I use their plunge every, single, day. It's like a high-stakes meditation—a mirror into my own internal state. The Plunge team have done a phenomenal job architecting what I consider as the world's best cold plunge (it doesn't get grimy like the conve...
Previous Episode

Becoming Fully Yourself, What AI Wants, Family Rituals & Rites of Passage with Kevin Kelly
Show Notes
A large part of my personal motivation for creating this podcast — is the privilege of speaking with those who I consider to be elders, those who have lived their lives to the absolute fullest and have stories and insights to share with younger generations about what it means to truly live well.
And this conversation with Kevin Kelly turned out to be exactly that. You'll probably want to have a pen and paper handy to take notes, and it was so rich with practical wisdom — in part because that was the subject of Kevin's new book — called 'Excellent Advice for Living'
Some of the pieces that resonated most with me were:
- How his curiosity and obsession with tinkering & making things paved the way for his later career
- Why giving your time away is by far that's the most valuable thing that you can offer
- The immense value in designing family rituals and rites of passage
- Why he believes that AI will eventually want to have an identity and a name and will act as a forcing function to propel us forward — like children do, to be better than we would have been
- Finally, why we should attend as many funerals as possible — and endeavor to become fully ourselves
⏳ Timestamps
[00:05:07] Thoreau and the Whole Earth catalog were influential in shaping the interviewee's passion for inventing their own life and stripping down to the minimum to achieve contentment. Thoreau was a mentor and hero while Stuart Brand was a greater influence.
[00:09:15] Deep listening means trying to hear what's unsaid, not just focusing on responding. It involves being affected by what's being said, not just hearing it like a recorder. Many people don't truly listen and miss out on understanding.
[00:13:08] The worthiest projects take five years to complete, but prototyping is important too, and only one five-year project should be focused on at a time. Anything worthwhile should be accounted for as a five-year project.
[00:17:14] Textual content is created as reminders of timeless wisdom from past philosophers and religions. Advice includes putting things back where they were found and deciding not to be outraged for a day. These reminders are short and condensed, meant to be easily remembered and applied.
[00:20:50] Invest in a donor appointed fund that grows and can be given to high leverage charities, which teach people to fish rather than just giving a fish. Volunteering and donating time is the most precious thing to give.
[00:25:19] Parents celebrate their kids' coming-of-age at 21 with a small ceremony where they cut a symbolic cord, give them their last check, and allow them to drink legally. The event sometimes includes wagers or promises, and kids add their own innovative participation. One child ate paper with advice written on it.
[00:30:30] Create family rituals to provide stability, consistency, and a sense of anticipation for children, which will become part of the family identity and provide comfort in adulthood.
[00:34:21] The author believes that technology has tendencies that are independent of humans, and that consciousness, sentience, and identity may be inevitable for technology. He thinks that technology may want a name.
[00:40:36] The goal is to fully become yourself with the help of others, it's a long process involving constant self-challenge and it's the key to accomplishments. Attend funerals to hear about character over achievements. The question to ask is "who do I want to become?".
[00:47:02] AI development will force us to question what we want the AI to be like, as they will carry biases and issues of average humans. It will lead to a discussion of how we can make ourselves better as well.
Official Links
📚 Order Kevin's book 'Excellent Advice for Living'👋 Follow Kevin on Twitter @kevin2kelly
🖥️ See Kevin's homepage and extensive bio — kk.org
Connect + Follow Jonny:
🐦 Follow on Twitter @jonnym1ller
💌 Subscribe to the Curious Humans Newsletter
🫁 Learn more about Nervous System Mastery
Episode Sponsors
🌬️ Othership Breathwork App — I've written at length about why breathwork is like the operating manual for your nervous system, and I have been highly impressed by the app that the Othership team has created. You can choose between guided daily practices that will up or downshift your state, as well as breathwor...
Next Episode

A Radical Playbook for Full Aliveness with Jim Dethmer
Jim Dethmer is co-author of the bestselling book 'The 15 Commitments of Conscious Leadership' and is one of the most sought-after executive coaches in the world. It was an honor to speak with Jim, and I had the sense that I was sitting in the presence of someone who really had spent a lifetime embodying and living what he teaches.
In this wide-ranging conversation, you can expect to learn:
🙋♂️ How to use the Sedona method for yourself
👐 What it means to live an undefended life
👊 How to take radical responsibility for your emotions
💚 What it means to 'SAFE' yourself rather than be at the mercy of the external situation
🗣️ Why leaning into difficult conversations and revealing your experience is key to aliveness
🧰 Practical strategies for having clearing conversations and practicing radical honesty
Official Links
🔨 Free resources on The Four Pillars of Integrity, Emotional Intelligence,
📚 The 15 Commitments of Conscious Leadership: A New Paradigm for Sustainable Success
Connect + Follow Jonny:
🐦 Follow on Twitter @jonnym1ller
💌 Subscribe to the Curious Humans Newsletter
🫁 Learn more about Nervous System Mastery
🙋♂️ Join Five to Thrive — a zero-cost educational email series.
Episode Sponsors
🩸 Inside Tracker — One of the things I've changed my mind on in the past year is the value of getting blood panels taken prophylactically (ideally every six months, according to Dr. Peter Attia) rather than waiting until you have a health issue. Inside Tracker recently added hormone testing alongside a bunch of other important biomarkers that aren't included in traditional blood panels (ApoB, for example). Despite generally feeling great, my most recent set of results showed that I have some work to do to reduce levels of inflammation, and I'll be following some of their dietary + supplement recommendations to address this asap. So I highly recommend making this something you make time for at least once or twice yearly. Save 20% here
🥶 The Cold Plunge — I reached out to the founder of the plunge, Ryan after hearing his powerful story on the Danny Miranda podcast. I've shared how getting in icy cold water every day helped me to move through intense grief, and taught me what it meant to surrender. These days I use their plunge every, single, day. It's like a high-stakes meditation—a mirror into my own internal state. The Plunge team have done a phenomenal job architecting what I consider as the world's best cold plunge (it doesn't get grimy like the converted chest freezers that I used to use). For optimal health benefits, I recommend deliberate cold exposure for 11 minutes per week total. Save $150 with the code CURIOUS. Learn more.
🫁 Nervous System Mastery — this is my flagship 5-week boot camp designed to equip you with evidence-backed protocols to cultivate calm and emotional regulation. Our fourth cohort will be running in September 2023 ~ 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 that I've learned in recent years about how to create 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 not only improved their sleep and quality of relationships but also tapped into deeper states of joy, clarity, and confidence in their lives. We've had over 500 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
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