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” (#668)

Illustration via 99designs

“I think that saying ‘good enough’ is a superpower.”

— Derek Sivers

Derek Sivers (@sivers) is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. He is a former musician, programmer, TED speaker, and circus clown, who sold his first company, CDBaby, for $22 million and gave all the money to charity.

Derek’s books (How to Live, Hell Yeah or No, Your Music and People, Anything You Want) and newest projects are at his website: His upcoming book is Useful Not True.

Please enjoy!

P.S. To follow the exact step-by-step “Tech Independence” instructions from Derek, please visit

Listen to the episode on Apple Podcasts, Spotify, Overcast, Podcast Addict, Pocket Casts, Castbox, Google Podcasts, Stitcher, Amazon Musicor on your favorite podcast platform. You can watch the interview on YouTube here.

Brought to you by Allbirds incredibly comfortable shoes, Wealthfront high-yield savings account, and Shopify global commerce platform providing tools to start, grow, market, and manage a retail business. 

The transcript of this episode can be found here. Transcripts of all episodes can be found here.

#668: 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

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Want to hear the first time Derek was on the show? Listen to our conversation here, in which we discussed developing confidence, finding happiness, saying ‘no’ to millions, Derek’s favorite books, and much, much more.

#125: Derek Sivers on Developing Confidence, Finding Happiness, and Saying No to Millions

What was your favorite quote or lesson from this episode? Please let me know in the comments.



  • Connect with Derek Sivers:

Website | Podcast | Twitter | YouTube


  • [06:16] The Derek Sivers School of Enough.
  • [11:24] Scuba diving and empathy lessons in Iceland.
  • [16:13] Categories we apply to ourselves and others.
  • [22:46] Derek’s people compass.
  • [28:14] How to secure your tech independence.
  • [1:05:19] The unoptimized life.
  • [1:16:37] The meaning of Derek’s upcoming book, Useful Not True.
  • [1:32:55] The problem with moral relativism and other -isms.
  • [1:51:24] Giant leaps.
  • [2:00:10] Finding and asking mentors for help.
  • [2:08:18] Games.
  • [2:12:26] The wisdom of quitting when you’re ahead.
  • [2:17:13] Why would Derek — never in need of external validation — seek fame?
  • [2:20:45] What makes Derek so darned interesting?
  • [2:23:18] Has Derek always been a satisficer?
  • [2:31:43] Living on the edge case.
  • [2:35:33] The real question behind “What would you tell your younger self?”
  • [2:40:29] Giving directions in Antarctica.
  • [2:41:46] How do you teach an 11-year-old to act like a 16-year-old?
  • [2:45:45] Parting thoughts.


“If you wonder why I’m so happy, why I’m thriving, why I seem to be doing well, a lot of my happiness comes from this worldview that is radical doubt. It’s skepticism. I’m going to give this the shorthand of calling it ‘Useful Not True.'”
— Derek Sivers

“If you set up your business to serve the people that you love being around, even if it makes less money, you’re going to be much happier.”
— Derek Sivers

“I think that saying ‘good enough’ is a superpower.”
— Derek Sivers

“We spend the first half of our life deferring to authority and thinking that authority has power over us. And at a certain point, you realize that you’re free. You’re liberated from that as long as you don’t break the law.”
— Derek Sivers

“The temptation to keep playing, even though the rewards are done, isn’t that the definition of addiction? Continuing a behavior even though it’s not rewarding you anymore?”
— Derek Sivers


The Tim Ferriss Show is one of the most popular podcasts in the world with more than 900 million downloads. It has been selected for "Best of Apple Podcasts" three times, it is often the #1 interview podcast across all of Apple Podcasts, and it's been ranked #1 out of 400,000+ podcasts on many occasions. To listen to any of the past episodes for free, check out this page.

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18 Replies to “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” (#668)”

  1. So many useful tools in this one, but my favorite is the way Derek tells stories. I could listen to him tell the scuba diving story and about London and the cardboard box quite a few more times.

  2. Fantastic! I’ve been a big fan of Tim Ferriss and Derek Siver for nearly a decade. God bless anyone who’s been following them. Pray for you from Vietnam!

  3. Greetings from Strasbourg, France
    Fantastic podcast with Derek Sivers, loved the first one, and this second one was even better.
    You looked really supportive, present and focus when things got emotional
    Was a privilège to listen and watch. Thank you! CRIS

  4. Always a pleasure to listen to Derek Sivers. Choked me up when he started talking about his kid. That kind of love is huge.

    On radical skepticism, “Only thing that’s true is what an alien, a cat and an octopus can agree on.” Haha. Moral relativism discussions aside, that little convo helped me to ground myself.

  5. Hi, Derek,
    you don’t need to run rsync manually.
    Yes, you can schedule it (and you probably know it) but syncthing (you mentioned) has a great option to not delete the file on other side when deleted on primary location.
    I’m using it to backup photos (besides any other backups) from phone of my wife – even she (or our daughter) deletes any photos they remain on backup side. And you can cascade syncthing replications as well.
    And as prevention against replication of damaged file, yes, you can schedule running syncthing in intervals you wish (and catch damage before sync starts)
    The advantage of syncthing is it works even behind home router.
    On the other side, advantage of rsync is simplicity…

    Anyway, great episode. It’s a pleasure to listen friendly chat of you, guys.

  6. When “The Power of Now” came up in this Episode, Tim correctly named Eckhart Tolle and then proceeded to say he’s never read the book, but has heard it’s good. I learned of that book from Tim’s podcast (3 years ago?), when in fact he claimed that he tries to read it once per year. Someone please tell me I’m not crazy.

    1. Hi, Matthew –

      We just went through a bunch of transcripts of interviews in which “The Power of Now” gets mentioned. We’re not seeing it brought up by Tim, and, usually, when a guest brings up a book Tim has read, Tim comments on the book and says he’s read it. There are definitely a number of guests who have brought it up as a favorite or very impactful book. There are also similar books that Tim reads often, such as Anthony De Mello’s “Awareness.” But if you happen to remember the podcast on which you heard Tim say he’s read it, do let us know, and we’ll take a look. Thanks!


      Team Tim Ferriss

  7. Hey Tim and Team! Awesome to hear that you’re currently in New Zealand. I’ve been listening to you for ages and have gotten so much out of you and your guests.
    Let me know if you’re planning to visit Auckland as well and I’ll by you coffee or lunch to say thanks!

  8. Wow Tim!! I haven’t commented here in a while but dang this was an beautiful and interesting conversation. Derek shared a lot of thought provoking ideas – that concept of “enough” is such contrast with a lot of other “high performers” you may have had on the podcast. More Derek & Josh & Matt! 😉
    Keep it up!!

  9. Hi Tim,
    You’re on a roll ! Like Pierre pointed out the last few episodes have been some of the best ever recorded in my opinion ! I’ve been a follower for a while now, on and off depending on my interest in the topics mentioned.
    It sounds like they were all recorded shortly after your breakup, sorry to hear about it, no matter what happens it’s always tough to go through, but the business silver lining is that you’ve been producing amazing podcasts since 😉
    The Peter Attia podcast made me preorder the book and enroll into private training (can’t wait for the French version of the book though to give it to my trainer). Andrew Huberman made me get more into the sun and made me focus on the essential things for living healthy. Kelly Starrett was super interesting and reinforced my motivation to get back into exercise and focus on mobility (also subscribed to yoga lessons). Matt walker : well having a newborn doesn’t help (such a shame this topic wasn’t covered but I understand why) although I bought the book and gifted it even before reading it to people who could benefit. And Derek Sivers, just a delight to listen to from beginning to end, the friendship shows, the conversation is reallly genuine, honest and endearing. Plus he was very prepared for this and seriously delivered to the audience. Thanks for that ! A lot of the show notes are of interest (I wish they were more visual and not so much text to go through but that’s another battle – which I’d love to dig into), and particularly interesting and unprecedented is tech independance, I love the step by step process and I’ve put it into the to-do list.

    Thanks for such interesting, honest conversation, both to you Tim and the interviewees !

  10. Hi Tim,
    I’ve been listening to your podcast for a couple of years (love it!), and have a question stemming from your recent interview with Derek Sivers.
    At approximately the 2:28:30 mark in the podcast, Derek observed, “I just noticed from our walking down the street, or walking through the forest and talking, you would pick up on a few words that I said in passing. Two days later, you were like, ‘Let me ask you some more questions about that.’ I was like, ‘What, how the fuck did you remember that?’”
    To which you responded, “Yeah, totally trained.” Prior to his comment you’d said you “can rewind – which, by the way, is totally a developed skill.”
    This is a skill that is seriously lacking in my life. I typically struggle with doing exactly the opposite of what you described – forgetting conversations that are important, rather than remembering comments someone else expected to be forgotten.
    When I heard you say that, I just about jumped out of my chair – if this is a skill that can be developed, how might I go about that? Is this something you’ve addressed in any of your books? (I haven’t read them, only listened to your podcast.) Or are there other resources you’d recommend that could help me with this?
    Thank you for any help you can offer.

  11. Great podcast! You mentioned John Wick 4! You actually met the fight choreographer of that movie years ago at an airport. He’s a friend of mine and actually sent me a photo of you two. Him, Keanu or the director Chad would prob make great future guest.

  12. Thanks for a great episode. Loved the part about becoming great and then quitting at the top of your game to do something else. Tim mentioned that he loved these stories. One of greatest of those stories is Nils van der Poel, two-time Olympic champion in speed skating who did it his entirely own way and then at the age of 25 quit to pursue other things in life. Just wanted to give you the tip.

    Best Emil

  13. Does anybody know the name of the industrial-design documentary that Tim refers to with the garden shear example and the “extremes inform the mean” concept? The show notes only have a link to the Frog Design front page.

  14. Tim, you have to read “A New Earth.” That’s all.

    I just open it to random pages now and it always when I need to step back and it always delivers.

    Always enjoying your podcast and email.


  15. Decentralized blockchain baby seal clubbing expeditions run by AI!!!
    I just had to stop my car and laugh it out.