Kevin Kelly — Excellent Advice for Living (#669)

Illustration via 99designs | Photo originally by Christopher Michel

“Your goal in life is to be able to say on the day before you die that you have fully become yourself.”

— Kevin Kelly

Kevin Kelly (@kevin2kelly) helped launch and edit Wired magazine. He has written for The New York Times, and The Wall Street Journal, among many other publications.

He is the author of the new book Excellent Advice for Living: Wisdom I Wish I’d Known EarlierOther books by Kevin Kelly include Out of Control, the 1994 classic book on decentralized emergent systems; The Silver Cord, a graphic novel about robots and angels; What Technology Wants, a robust theory of technology; Vanishing Asia, his 50-year project to photograph the disappearing cultures of Asia, and The Inevitable: Understanding the 12 Technological Forces That Will Shape Our Future, a New York Times bestseller.

Kevin is currently co-chair of The Long Now Foundation, which is building a clock in a mountain that will tick for 10,000 years. He also has a daily blog; a weekly podcast about cool tools; and a weekly newsletter, Recomendo, a free, one-page list of six very brief recommendations of cool stuff. He is also a Senior Maverick at Wired. He lives in Pacifica, California.

Please enjoy!

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 LinkedIn Jobs recruitment platform with 900M+ users, Pique premium pu’er tea crystals, and Eight Sleep’s Pod Cover sleeping solution for dynamic cooling and heating.

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

#669: Kevin Kelly — Excellent Advice for Living

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Want to hear one of my favorite conversations with Kevin? Listen to this interview (recorded in three short parts), in which we discussed population implosions, The Long Now Foundation, organizational methods for learning, Amish technology assimilation, why you don’t want to be a billionaire, the greatest gift you can give to your child, and much more!

#25: Interview of Kevin Kelly, Co-Founder of WIRED, Polymath, Most Interesting Man In The World?
#26: Interview of Kevin Kelly, Co-Founder of WIRED, Polymath, Most Interesting Man In The World?
#27: Interview of Kevin Kelly, Co-Founder of WIRED, Polymath, Most Interesting Man In The World?

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

Erratum: In the interview, Nova Scotia was named as the setting for Anne of Green Gables, whereas the setting is Prince Edward Island.



  • Connect with Kevin Kelly:

Website | Twitter | Instagram | YouTube


  • [05:51] Is Kevin Kelly the most interesting man in the world?
  • [08:37] Kevin’s long bet against the human population.
  • [15:00] Out Of Control.
  • [19:34] Why did it take 11 years to complete The Silver Cord?
  • [24:28] 1,000 True Fans.
  • [29:48] Kevin’s failed campaign to discover all the species of life on Earth.
  • [31:31] Stewart Brand.
  • [36:20] Resurrecting extinct species.
  • [39:38] Why Kevin believes optimists shape the future.
  • [42:48] Active optimism vs. passive optimism.
  • [46:39] What constitutes progress?
  • [48:18] Is regression inevitable if we don’t embrace “degrowth?”
  • [52:38] Kevin’s $20 time machine.
  • [55:27] Will AI take our jobs?
  • [1:07:58] The future of AI is dumbsmarten.
  • [1:10:50] What’s currently underhyped?
  • [1:13:20] Posting an AI picture a day keeps Kevin at play.
  • [1:15:29] How Kevin uses AI chatbots to help write first drafts.
  • [1:21:40] Potential scenarios for where AI will be going soon.
  • [1:24:38] What prompted Kevin to write Excellent Advice for Living?
  • [1:28:46] Examples of Kevin’s simple, tweetable advice.
  • [1:32:02] Don’t aim to be the best. Be the only.
  • [1:35:32] Good uses of time spent with one’s children.
  • [1:38:47] Tips for traveling with children.
  • [1:42:22] Being a tourist in your own town and troubleshooting advice.
  • [1:45:06] What Kevin hopes readers will take away from Excellent Advice for Living.
  • [1:46:37] Sabbaticals.
  • [1:52:17] How Kevin uses YouTube.
  • [1:56:03] Why is Kevin huge in China?
  • [1:59:16] Fully becoming yourself and other parting thoughts.


“It isn’t as if these mechanical systems are imitating biology. I’m saying they actually have the same dynamics. The dynamics that are powering biology are powering the technium and the technology. It’s the same.”
— Kevin Kelly

“It’s very hard to make good, complicated things work because generally there’s more ways things can fail than they can succeed, and it’s very unlikely that we’re going to make something really good that’s complicated, inadvertently. They’re hard to do. So we have to see it and believe that it can be done, and that is where the optimism comes in, is envisioning something and then believing that you could make it real.”
— Kevin Kelly

“Exotropy is this idea of this increasing order that comes at the cost of increasing entropy.”
— Kevin Kelly

“Tools will get specialized. They will become so embedded that we will cease to think about them.”
— Kevin Kelly

“There’s something I call thinkism, which is this reliance on trying to solve problems by thinking about them.”
— Kevin Kelly

“You can find no better medicine for your family than regular meals together without screens.”
— Kevin Kelly

“What you do on your bad days matters more than what you do on your good days.”
— Kevin Kelly

“Greatness is incompatible with optimizing in the short term.”
— Kevin Kelly

“You don’t marry a person, you marry a family.”
— Kevin Kelly

“If you can’t tell what you desperately need, it’s probably sleep.”
— Kevin Kelly

“Don’t aim to have others like you, aim to have them respect you.”
— Kevin Kelly

“A balcony or porch needs to be at least six feet deep or it won’t be used.”
— Kevin Kelly

“Learn to tie a bowline knot. Practice in the dark with one hand for the rest of your life. You’ll use this knot more times than you could ever believe.”
— Kevin Kelly

“When you feel pressure to pick a choice, don’t forget the choice of not choosing any.”
— Kevin Kelly

“When you’re in your twenties, you should spend a little bit of time doing something that’s sort of crazy, insane, unprofitable, unorthodox, orthogonal, because that’s going to be your touchstone and the foundation of your success later on.”
— Kevin Kelly

“Don’t aim to be the best. Be the only.”
— Kevin Kelly

“You want to be doing something where it’s hard to explain to your mother what it is that you do.”
— Kevin Kelly

“Your enjoyment of travel is inversely proportional to the size of your luggage.”
— Kevin Kelly

“For the best results with your children, spend only half the money you think you should but double the time with them.”
— Kevin Kelly

“A vacation plus a disaster equals an adventure.”
— Kevin Kelly

“If an elementary school student is struggling, first thing, check their eyesight.”
— Kevin Kelly

“Purchase the most recent tourist guidebook to your hometown or region. You’ll learn a lot by playing the tourist once a year.”
— Kevin Kelly

“To signal an emergency, use the rule of three: Three shouts, three horn blasts, or three whistles.”
— Kevin Kelly

“When you’re stuck, explain your problem to others. Often simply laying out a problem will present a solution. Make ‘explaining the problem’ part of your troubleshooting process.”
— Kevin Kelly

“Your goal in life is to be able to say on the day before you die that you have fully become yourself.”
— Kevin Kelly


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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6 Replies to “Kevin Kelly — Excellent Advice for Living (#669)”

  1. Hi Tim,
    Fantastic interview with Kevin Kelly. What a brilliant mind. I’ve been a follower of yours and of a Kevin Kelly. Just a correction about the famous”Anne of Green Gables” books, the author and subject are from Prince Edward Island in Canada, not Nova Scotia . A big difference and as married to an Islander, quite an insult to Lucy Maude Montgomery the author. In Japan, the book is revered and throngs of Japanese tourist visit PEI to get the”real” Anne’s land experience.. thank you for the deep dive into important and critical topics.

    1. Hey CM, I was going to write exactly the same thing, however in light of the conversation I had my AI intern do it for me.

      I was thoroughly impressed by the fascinating interview with Kevin Kelly and his exceptional intellect. I’ve been an admirer of both Kevin Kelly and yourself for some time. I’d like to bring to your attention a small correction regarding the renowned “Anne of Green Gables” books. The author and subject of the books are from Prince Edward Island in Canada, not Nova Scotia. This distinction is significant, it may be an affront to Lucy Maude Montgomery’s more than 1000 real fans. In Japan, the book is highly respected, and numerous Japanese tourists flock to PEI to experience the authentic “Anne’s Land” experience. Thank you for delving into important and critical topics.

  2. Tim & Kevin, I lost my job to AI!! I’m a marketing content writer and my former boss (NOT a trained writer/editor) apparently felt so emboldened by using Jasper AI that he and leadership felt fine about laying me off. I was the only writer in the IT consulting company!
    There are those in leadership with less understanding of marketing, writing, and AI who actually think they’re fine without trained writers.

    Thanks for a great episode!

    And if you know anyone hiring an excellent content writer, contact me at [Moderator: contact information removed.] 😊👍

    Take care!

  3. I have mixed feelings about Kevin Kelly’s point on the power of goofing off.

    On one hand, I totally get his point. Young people should take advantage of their youth, energy, and flexibility to take some time off to travel, work interesting jobs, make art, start a business, make a product, learn to cook/dance, or volunteer—you name it. Taking some time to dabble in different things is not only super fun but also a great way to learn about the world and oneself. Jumping right from college or grad school straight into the grind of a career track has the risk of working hard on the wrong career (i.e., hill climbing) or simply burning out (because you’ve been grinding for so long).

    But there are a lot of challenges around Kevin Kelly’s recommendation to goof off more. First off is that housing, healthcare, food, etc., are much more expensive than they were for the baby boomers. Baby boomers helped put people like Bush Jr. and Reagan into office, who drastically reduced taxes on the wealthy. And we’ve seen just how much of the wealth is now concentrated in the hands of the super wealthy. The website covers this topic really well. Those previously high/progressive taxes were funding a lot of things like low-cost college education. I’m oversimplifying a bit, of course. Baby Boomers also helped to vote in more restrictive zoning laws, thus making it harder to add housing supply and driving up the price of housing. In California, Baby boomers (and other voters, of course) put in Prop 13, so that property taxes don’t go up over time. Prop 13 is great if you own a home but kind of sucks for everyone else who relies on things that property taxes help fund. There are many other examples where Baby Boomers pulled up the ladder behind them. They were given tons of opportunities but didn’t want to pay it forward.

    It’s also worth pointing out how much baby boomers (and Gen X) over-protected and sheltered their kids. Tim has a great interview with Jon Haidt about the coddling of the American mind – Haidt argues that parenting really changed in the 1990s and kids were overparented/overscheduled/sheltered, etc. Kids weren’t allowed to roam free, have unstructured play, and gain confidence in the world. As a result, more young people are now struggling to put themselves out there in the world and suffering from more mental health challenges (search Jon Haidt on YouTube to learn more about this). This generation of young people is simply not raised in such a way that would allow them to ‘goof off.’ They need the structure they’ve had their whole lives.

    Finally, I would point out just how competitive the world has become. I definitely goofed off plenty in my 20s and early 30s (traveling, freelancing, and doing random projects). I work in the tech space now as a sales engineer and got laid off last year. Never once have I met a boss or manager who valued my travel or diverse array of experiences. Instead, they judge me as a generalist and perhaps as a dilettante. Most jobs I’ve interviewed for simply want the most specialized and experienced person for the role that they can find. These managers are time-strapped and risk-averse and just want to make the surest bet. They don’t know what to do with a scrappy, smart generalist who has goofed off and explored a bit. I think a lot of these managers might actually resent people who have goofed off because so many of them have been on the stressful grind for so long. Or maybe this is just the type of people that I meet in the sales engineering world.

    Zooming out a bit more, I’ve become more skeptical of advice by people like Kevin Kelly and Derek Sivers. These are truly exceptional people—like far to the right of the bell curve in terms of smarts, motivation, and work ethic. Not everyone can move in the world like they can, and we should be cautious about taking their advice if we aren’t like them. In Tim’s recent interview with Derek Sivers (, he talks about how maniacal he was at practicing music at a young age. His friends gave him a hard time because all he wanted to do was practice scales over and over. The dude was exceptionally motivated from a very early age. If you’re not naturally highly motivated as a teenager, maybe you should be cautious about taking his advice.

    In Sivers’ blog post ‘There’s no speed limit’ (, he talks about how the average pace is for chumps and that he was able to finish Berklee School of Music in much less time than the average person takes, thanks to studying ahead of time with a mentor and reading the books and testing out. He wasn’t a ‘chump,’ and the lesson is that you shouldn’t be either. His advice is great if you are already highly intelligent and motivated. But the rest of us chumps (i.e., average and ordinary people), we might have to play by different rules.

    Even though it’s made for a lot of difficult job hunts so far in my life, I still don’t regret my ‘goof-off’ time. I’ll get to where I need to go in my career; it’s simply going to take me longer than if I had specialized in something ten years ago. I’ve accepted feeling ‘behind’ as a price I have to pay. I felt like pointing out the variety of issues with ‘goofing off’ as a blanket recommendation. There are a lot of things that work against goofing off. I still absolutely recommend it, but with more caveats than Kevin Kelly gives.

  4. Kevin Kelly really is the most interesting man in the world. I’ve heard of the 1,000 true fans concept but didn’t know he originated it until this episode! I’ve noticed the interest in parenting come up in your interview questions in the past few years and as a mom I love it so much!! I daydream that one day you might interview your mom on an episode. Then I wondered who would be “world class” in the realm of parenting and immediately thought of Janet Lansbury. She has a podcast called Respectful Parenting, is an author, and has changed my life. She taught me that good parenting is more than raising a child. It’s also re-parenting yourself. Parents and non-parents should hear her wisdom. I hope hope hope you see this comment and reach out to her! Cheers!

  5. Thanks for the amazing episode, I’m not yet done with it but I’ve already decided to bookmark it and revisit it often…
    I’ve just realised around 1:16:00 that one of, if not the, first episode I’v ever heard of this podcast was when Tim and Kevin were discussing travel tools. I had come to it through a 4-hour work week recommendation, and I very vividly remember picturing those two guys sitting at the back of a car in the middle of nowhere… That’s probably how I got hooked to this podcast actually, even though I soon realized how peculiar this particular episode was. But the energy I felt, a mix of lightness fun and serious deep thinking about life, I found it again here… Great feeling, very inspiring!

    Anyways, more than six years later, I’m no longer catching all of the podcasts, I reserve my time for those rare ones that I like to revisit several times, just to let the ideas and concepts sink it deeper. Thank you very much for sharing that conversation, it’s inspiring me to be more daring, live more fully, have fun and seek what makes life just a little more interesting each day, pursuing passion…

    Favourite quotes, paraphrased: “Have people respect you rather than like you”, “Be not the best but the only one” and finally “if you don’t know what you need, it’s probably sleep”… I’ll try to remember those!!

    ps: Sorry if I posted twice, I tried first on my old phone and I’m not sure it worked…