Tim Ferriss

November 14, 2024

Derek Sivers, Philosopher-Entrepreneur — The Greatest Year of His Life (#777)

“Whatever you feel yourself leaning away from, try leaning into. If you hate opera, then go learn more about opera. And if you hate sports, well, then go learn more about sports. It’s usually just learning about something gives you an appreciation for this thing that you used to just dismiss.”
— Derek Sivers

Derek Sivers is an author of philosophy and entrepreneurship, known for his surprising, quotable insights and pithy, succinct writing style. 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 new book is Useful Not True.

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#777: Derek Sivers, Philosopher-Entrepreneur — The Greatest Year of His Life

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Want to hear the last time Derek was on the show? Listen to our conversation here, in which we discuss the benefits of an unoptimized life, finding and asking mentors for help, the wisdom of quitting when you’re ahead, how to teach an 11-year-old to act like a 16-year-old, the problem with moral relativism and other -isms, securing tech independence, and much more.

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

SELECTED LINKS FROM THE EPISODE

Connect with Derek Sivers:

Website | Podcast | Twitter | YouTube

SHOW NOTES

[00:07:18] Derek Sivers: A Man who brings his own introduction.
[00:09:25] First mind change: Emirati coffee.
[00:12:34] Second mind change: Ruby to Python.
[00:13:54] Third mind change: Rats.
[00:17:23] Fourth mind change: China.
[00:23:24] Fifth mind change: Dubai.
[00:26:48] Tamashee: Come for the sandals, stay for the culture.
[00:30:52] Cormac McCarthy Writes to the Editor of The Santa Fe New Mexican.
[00:31:47] Shifting perspectives and the value of questioning preconceptions.
[00:51:23] Brian Eno and MusicThoughts.
[00:53:57] John Cage.
[00:56:34] Three glasses.
[00:57:08] Derek’s experimental housing project.
[01:03:51] Rich Hickey and practical applications of simplicity.
[01:29:20] Tyler Cowen.
[01:35:57] Inchword and language learning.
[01:46:35] Traveling to inhabit philosophies.
[01:54:14] Parting thoughts.

MORE DEREK SIVERS QUOTES FROM THE INTERVIEW

“Whatever you feel yourself leaning away from, try leaning into. If you hate opera, then go learn more about opera. And if you hate sports, well, then go learn more about sports. It’s usually just learning about something gives you an appreciation for this thing that you used to just dismiss.”
— Derek Sivers

“I travel to inhabit philosophies.”
— Derek Sivers

“Don’t jump through hoops to save taxes, jump through a hoop to go make more money. That’s the growth choice anyway. That’s the thought process that leads you to make growing decisions, not shrinking decisions.”
— Derek Sivers

“I’m willing to throw myself in and feel the pain to see if I’ve done it wrong.”
— Derek Sivers

“When I’m around people who I know agree with me, my inherent curiosity level drops a bit. And when I’m around people who I know don’t think like me, my curiosity piques.”
— Derek Sivers

“I deliberately fucked up my life and made a bunch of crazy fucking decisions, and some of them worked out great, and some of them didn’t. And I’m so happy that I did that.”
— Derek Sivers

“So often, the difference between success and failure is the mindset that leads you to take different actions. But if you just look at a situation, and you say, “That’s it. That’s what the situation is,” I’m not talking about physical things. I mean declaring something to be a dead end, declaring something to suck, these are all things of the mind, and nothing of the mind is necessarily true. Everything that’s just in the mind is just one perspective.”
— Derek Sivers

“It can be much harder to do something that is objectively simple, that stands alone, that isn’t dependent on other things. It can be harder to make that, but it’s ultimately usually a better choice because it’s more maintainable, it’s easier to change, it’s easier to stop and start. It’s simpler even if it’s harder to make.”
— Derek Sivers

“Esperanto is hippie Klingon.”
— Derek Sivers

PEOPLE MENTIONED

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Joseph

1 year ago

Hey Tim how do I get in contact with you about an interesting guest for the show?

Aurelia

1 year ago

Book rec for Tim ref living in the woods – ‘The Consolations of the Forest’ by Sylvia Tesson. I just finished it. Superb read.

Tadeusz

1 year ago

Easily the most hilarious moment for me in the entire history of your podcasts, Tim, I was rolling on the floor and couldn’t stop laughing for a few minutes:

Derek Sivers: Please stay at my home.” I want to return that generosity.
Tim Ferriss: It’s going to be a six-by-eight-foot cube.
Derek Sivers: Touché. “Come, my home.”
Tim Ferriss: “Everything I have is yours.” “Wait, Derek…”
Derek Sivers: “There’s nothing here.”
Tim Ferriss: Quick text, “Where’s the bathroom?” “Oh, no, there’s no bathroom.”
Derek Sivers: “Oh, no, my friend. Question whether you truly need it or not. You will find out.”
Tim Ferriss: “Let me know where you think the sink should be.”
Derek Sivers: I’ll be a bad Emirati. I’ll be fired.

And great job Tim and containing your amusment.

J A

11 months ago

Re the comment about living in a Frank Lloyd Wright house and not being able to change anything during the “Derek’s experimental housing project” discussion: Before Derek made this comment, I was thinking “oh, this is how Frank Lloyd Wright did things at Taliesin.” Taliesin is Wright’s personal home and estate in Wisconsin.

When Wright himself was the owner, he changed things constantly. There are no floor plans. It’s been a many-decades long mystery to figure out what he built when and what changes he instituted. Because, exactly as Derek was describing, he’d understand a new need or desire and immediately change Taliesin. Or more accurately, he’d direct his apprentices to make the change. Taliesin is largely constructed of inexpensive materials. So while current owners of his houses may be trapped in a landmark they can’t change (which might be true for some but not all), Wright himself was a lot more like Derek!

Further, in Wright’s Autobiography, he explicitly directs clients to first spend time living on the land where they want to build their house. See where the sun rises and sets etc. I don’t have time to find the exact quote but he wasn’t even having them start with a rectangle! Just a tent at most!

While Wright certainly practiced prediction for his clients, he did advise experience driving design. And most certainly he lived that himself at his own homes. Ironic Derek used his designs in current state as an example of the opposite.

I’ve always thought Wright wanted his ideas to be his legacy. It’s a shame his ideas have been overshadowed by watered-down cliche notions about his legacy such as extended eaves called “Wright-style.” If his ideas were practiced instead, we’d be living way more in tune with nature and our own patterns and needs.

PS Yes, I know he has feet of clay and many of his ideas and life choices are not admirable. There’s some good stuff if you look past the stories about his relationships and business dealings.