Tim Ferriss

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)

Artist's rendering of Derek Sivers in profile in a gray turtleneck and black blazer, hand on his chin, eyes wide with possibilities.
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: sive.rs. 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 sive.rs/ti.

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

This episode is brought to you by Allbirds! Allbirds are incredibly comfortable shoes, sustainably made, with design rooted in simplicity. Find your perfect pair at Allbirds.com today and use code TIM for free socks with a purchase of $48 or more. Just add a pair of socks to your shopping cart and apply code TIM to make the pair free.


This episode is brought to you by Wealthfront! Wealthfront is a financial services platform that offers services to help you save and invest your money. Right now, your cash can earn 3.30% APY—that’s the Annual Percentage Yield—with the Wealthfront Cash Account from its network of program banks. That’s 8 times more interest than a typical savings account at a bank, according to FDIC.gov as of 05/18/2026 (Wealthfront’s 3.30% APY vs. 0.38% average savings rate). Right now, for a limited time, Wealthfront is offering new clients that use my sign-up link an additional 0.75% boost over the base rate for three months, meaning you can get up to 4.05% APY, limited to a $150,000 balance. Terms & Conditions apply. Visit Wealthfront.com/Tim to get started. 

The Cash Account, which is not a deposit account, is offered by Wealthfront Brokerage LLC (“Wealthfront Brokerage”), member FINRA/SIPC. Wealthfront Brokerage is not a bank. The 3.30% Base APY on cash deposits is as of January 30, 2026, is representative, subject to change, and requires no minimum balance. Wealthfront Brokerage sweeps cash balances to Program Banks, where it earns the variable base APY. The Direct Deposit Plus Investing Program from Wealthfront Advisers LLC and Wealthfront Brokerage LLC provides eligible clients a 0.25% APY increase above the base APY on eligible Cash Account balances (up to an overall boosted rate of 4.30% for a limited time when including the three month 0.75% APY boost for new Cash Account clients) when you direct deposit $1,000/month plus maintain a funded investing account. Wealthfront may change or end the program at any time and determine eligibility at its discretion. Terms and conditions apply. Full details for both promotions at wealthfront.com/promo-terms.

Tim Ferriss, who is not a client, receives cash compensation from Wealthfront Brokerage LLC for advertising and holds a non-controlling equity interest in the corporate parent of Wealthfront Brokerage LLC, which creates an incentive that results in a conflict of interest. Tim expresses his own opinions and Wealthfront does not endorse, sponsor, or promote them. This ad may not reflect the experience of other Cash Account clients, and similar outcomes are not guaranteed. Investment advisory services are provided by Wealthfront Advisers LLC, an SEC-registered investment adviser. Securities investments: not bank deposits, not bank-guaranteed or FDIC-insured, and may lose value. See full disclosures here


This episode is brought to you by ShopifyShopify is one of my favorite platforms and one of my favorite companies. Shopify is designed for anyone to sell anywhere, giving entrepreneurs the resources once reserved for big business. In no time flat, you can have a great-looking online store that brings your ideas to life, and you can have the tools to manage your day-to-day and drive sales. Go to Shopify.com/Tim to sign up for a one-dollar-per-month trial period. It’s a great deal for a great service, so I encourage you to check it out. Take your business to the next level today by visiting Shopify.com/Tim.


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.

SCROLL BELOW FOR LINKS AND SHOW NOTES…

SELECTED LINKS FROM THE EPISODE

  • Connect with Derek Sivers:

Website | Podcast | Twitter | YouTube

SHOW NOTES

  • [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.

MORE DEREK SIVERS QUOTES FROM THE INTERVIEW

“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

PEOPLE MENTIONED

Subscribe
Notify of
guest

Comment Rules: Remember what Fonzie was like? Cool. That's how we're gonna be — cool. Critical is fine, but if you're rude, we'll delete your stuff. Please do not put your URL in the comment text and please use your PERSONAL name or initials and not your business name, as the latter comes off like spam. Have fun and thanks for adding to the conversation! (Thanks to Brian Oberkirch for the inspiration.)

19 Comments
Oldest
Newest Most Voted