Derek Sivers — The Joys of an Un-Optimized Life, Discovering Paths Much less Traveled, Creating Tech Independence (and Dangers of the Cloud), Taking Big Leaps, and Choosing the Proper “Sport of Life” (#668)

Derek Sivers — The Joys of an Un-Optimized Life, Discovering Paths Much less Traveled, Creating Tech Independence (and Dangers of the Cloud), Taking Big Leaps, and Choosing the Proper “Sport of Life” (#668)


Illustration through 99designs

“I feel that saying ‘ok’ is a superpower.”

— Derek Sivers

Derek Sivers (@sivers) is an creator of philosophy and entrepreneurship, recognized for his stunning, quotable insights and pithy, succinct writing type. He’s a former musician, programmer, TED speaker, and circus clown, who offered his first firm, CDBaby, for $22 million and gave all the cash to charity.

Derek’s books (Learn how to Reside, Hell Yeah or No, Your Music and Individuals, Something You Need) and latest initiatives are at his web site: His upcoming ebook is Helpful Not True.

Please get pleasure from!

P.S. To comply with the precise step-by-step “Tech Independence” directions from Derek, please go to

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

Dropped at you by Allbirds extremely comfy sneakers, Wealthfront high-yield financial savings account, and Shopify world commerce platform offering instruments to begin, develop, market, and handle a retail enterprise. 

The transcript of this episode may be discovered right here. Transcripts of all episodes may be discovered right here.

#668: Derek Sivers — The Joys of an Un-Optimized Life, Discovering Paths Much less Traveled, Creating Tech Independence (and Dangers of the Cloud), Taking Big Leaps, and Choosing the Proper Sport of Life

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Wish to hear the primary time Derek was on the present? Hearken to our dialog right here, by which we mentioned growing confidence, discovering happiness, saying ‘no’ to thousands and thousands, Derek’s favourite books, and a lot, rather more.

#125: Derek Sivers on Growing Confidence, Discovering Happiness, and Saying No to Tens of millions

What was your favourite quote or lesson from this episode? Please let me know within the feedback.



  • Join with Derek Sivers:

Web site | Podcast | Twitter | YouTube


  • [06:16] The Derek Sivers Faculty of Sufficient.
  • [11:24] Scuba diving and empathy classes in Iceland.
  • [16:13] Classes we apply to ourselves and others.
  • [22:46] Derek’s folks compass.
  • [28:14] Learn how to safe your tech independence.
  • [1:05:19] The unoptimized life.
  • [1:16:37] The that means of Derek’s upcoming ebook, Helpful Not True.
  • [1:32:55] The issue with ethical relativism and different -isms.
  • [1:51:24] Big leaps.
  • [2:00:10] Discovering and asking mentors for assist.
  • [2:08:18] Video games.
  • [2:12:26] The knowledge of quitting once you’re forward.
  • [2:17:13] Why would Derek — by no means in want of exterior validation — search fame?
  • [2:20:45] What makes Derek so darned fascinating?
  • [2:23:18] Has Derek all the time been a satisficer?
  • [2:31:43] Residing on the sting case.
  • [2:35:33] The actual query behind “What would you inform your youthful self?”
  • [2:40:29] Giving instructions in Antarctica.
  • [2:41:46] How do you educate an 11-year-old to behave like a 16-year-old?
  • [2:45:45] Parting ideas.


“When you marvel why I’m so comfortable, why I’m thriving, why I appear to be doing properly, plenty of my happiness comes from this worldview that’s radical doubt. It’s skepticism. I’m going to provide this the shorthand of calling it ‘Helpful Not True.’”
— Derek Sivers

“When you arrange your enterprise to serve the folks that you just love being round, even when it makes much less cash, you’re going to be a lot happier.”
— Derek Sivers

“I feel that saying ‘ok’ is a superpower.”
— Derek Sivers

“We spend the primary half of our life deferring to authority and considering that authority has energy over us. And at a sure level, you notice that you just’re free. You’re liberated from that so long as you don’t break the regulation.”
— Derek Sivers

“The temptation to maintain enjoying, regardless that the rewards are performed, isn’t that the definition of dependancy? Persevering with a conduct regardless that it’s not rewarding you anymore?”
— Derek Sivers


The Tim Ferriss Present is one of the most well-liked podcasts on the earth with greater than 900 million downloads. It has been chosen for “Better of Apple Podcasts” thrice, it’s typically the #1 interview podcast throughout all of Apple Podcasts, and it has been ranked #1 out of 400,000+ podcasts on many events. To hearken to any of the previous episodes totally free, try this web page.


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