Turning the Tables: Ryan Holiday Interviews Tim Ferriss on The Tim Ferriss Show

Check out The Tim Ferriss Show Episode Page & Show Notes

Key Takeaways 

  • “It’s easy for life to become an arms race, but when you live in a place with more diversity, when you live where there’s not one industry or one scene that dominates all the others, you become more inwardly focused on what’s important to you.” Ryan Holiday
  • Treat seemingly absurd ideas as reversible experiments
    • Whether it’s dropping out of college to pursue a dream or quitting your job to launch a startup, you can almost ALWAYS go back (especially if you’re good at your craft)
  • When assessing huge life moves, don’t just examine the upsides and downsides of the new option, also consider the disadvantages of maintaining the status quo. Just as there are costs of action, there are costs of inaction.
  • Avoid sacrificing your short-term quality of life for a potential long-term reward 
  • Remember these two things:
    • You’re going to die
    • We’re just a bunch of monkeys on a spinning rock
  • Studying investors helps improve your understanding of probabilistic thinking 
  • You don’t have to finish every book you start. If you’re not enjoying something, put it down. Life’s far too short for bad books. 

Books Mentioned

  • If you’re new to Ryan’s books, he recommends you start with The Obstacle is the Way, Ego is the Enemy or his latest, Stillness is the Key
  • After experiencing burn out from writing The 4-Hour Chef, Tim launched his podcast as a short experiment
  • Muneeb Ali, as discussed in Tim’s book, Tribe of Mentors, to better appreciate life’s small moments, likes to frequently ask himself, “How much would I pay to relive this experience 40 years from now?”
  • If you’re world-class as your craft, it’s relatively easy to take some time off and come back years later
  • Want to learn more about the idea of not sacrificing your short-term quality of life for a potential long-term reward? Give Tim’s book, The 4-Hour Workweek, a read.
  • A few recommendations from Tim to better your understating of statistical thinking:
  • We Feel Fine by Sep Kamvar and Jonathan Harris discusses how, as humans age, they tend to find more happiness through connection, rather than achievement 
  • When looking to learn more about the contemporary art world, many people recommended Tim read The $12 Million Stuffed Shark by Don Thompson
  • Tim highly recommends Essentialism by Greg McKeown

Intro

How Taking Care of His Dog, Molly, Changed Tim’s Life for the Better

  • ~5 years ago, Tim adopted his dog, Molly
  • “Caring for a puppy, at least if you do it well, takes your attention outside of any type of self-indulgent reflection or obsessive-compulsive rumination”Tim Ferriss
    • Having a history of depression, this is a massive benefit for Tim; in a sense, caring for Molly is anti-depressive
  • Another advantage of having a puppy: With people, it’s easy to convince yourself that someone deliberately did something to upset you. Having a dog pulls you more towards the opposite end of the spectrum—do you think your dog deliberately sh*t on the rug to piss you off? No!
    • (In other words, taking care of Molly has allowed Tim to better put himself in other people’s shoes)
    • Similarly, caring for a dog makes it easier to see things as a fault of your own, not others’. Dog chew your shoes? Your fault—you left them out. 

Tim’s Advice: Don’t Get a Dog if You Can’t Prioritize Its Care

  • Don’t get a dog if you plan to wedge caring for him/her into the few open slots in your schedule. It should, instead, be the other way around—caring for your dog should come before anything else.
    • Tim adds: “When I ended up getting Molly, I reversed that. I prioritized taking excellent care of her, and fitting everything else in my life around her.”
  • Just like having a kid, getting a dog pivots your reality; they decide your schedule, not you—prepare yourself for this

Just Had Your First Kid? Welcome to the Human Race

  • There’s a certain self-absorption that’s encouraged and fostered in modern life; having a kid shifts you out of this and drastically increases your empathy

Living in Austin, Tim is Avoiding Mono Conversations (and Mono Thinking)

  • Tim left the Bay Area ~4 years ago
  • “Living in Austin has been very refreshing and rejuvenating in part because there’s no one mono conservation” – Tim Ferriss
    • NYC attracts people who are highly driven; Silicon Valley lives and breathes startups; Los Angeles lives and breathes entertainment; in Austin, however, things are much more diverse
  • “The main downside of mono conversation is mono thinking” – Tim Ferriss
    • AKA group think—an echo chamber that pushes you towards the status quo (and when you’re pushed towards the status quo, it becomes increasingly difficult to test your—often faulty—assumptions)

Living in a Diverse City Makes Avoiding Life’s Arms Race Much Easier

  • “It’s easy for life to become an arms race, but when you live in a place with more diversity, when you live where there’s not one industry or one scene that dominates all the others, you become more inwardly focused on what’s important to you.”Ryan Holiday

Competition is for Losers

  • “I remember having Peter Theil on the podcast … One of the questions he asks himself is, ‘In what areas of my life can I be less competitive?‘… If your default is competition, I think it pays enormous dividends to be aware of that and to ask those types of questions.” – Tim Ferriss

Why Tim Stopped Angel Investing & Why He Tends to “Walk Away at the Top”

  • Ryan notes that Tim “has a habit of walking away from things he’s at the top of”
    • One example: despite experiencing success, Tim stopped all angel investing in 2015 (read more about his decision here)
  • “I tend to pause, try to reflect, and ask a lot of questions when I feel that my decisions in any area of my life begin to bleed into fear of missing out, scarcity, or fear-based decision making.” – Tim Ferriss
  • In the case of angel investing, Tim realized that the conditions were becoming more difficult, and to do a good job, he’d have to create a fund and start investing full-time
    • “In that world, I’d be effectively replaceable. I’d be in a long line of people trying to do the same thing, and my drive to do that would be predominantly driven by a fear of missing out and a cortisol-driven scarcity mentality … Even if I were to win that game, I felt like the toll it would take wouldn’t be worth it from an emotional, mental, and physical health perspective.” Tim Ferriss

View Seemingly Absurd Ideas as Reversible Experiments

  • Tim’s question-based journaling practice has helped facilitate several big career moves. A few examples of questions he’s pondered in the past:
    • “What if I stopped all angel investing?
    • “What if I left the Bay Area and moved to Austin, Texas?”
    • “What if I started a podcast?”
      • (After experiencing burn out from writing The 4-Hour Chef, this question led Tim to launch his podcast as a short, six-episode experiment)
  • Further, through journaling on the above, combined with a bit of pondering the worst-case scenario, it becomes much easier to view these seemingly humongous life moves as reversible experiments 
    • Whether it’s dropping out of college to pursue a dream or quitting your job to launch a startup, you can almost ALWAYS go back (especially if you’re good at your craft)
      • “People who focus on being good at their craft can almost always come back … If Will Smith doesn’t do a movie for two years, people won’t be asking, ‘Whatever happened to Will Smith?’ Will Smith can take all the time he wants.” – Tim Ferriss

Tim is Extremely Risk-Averse & Always Tries to Cap the Downside (Good Risk vs. Bad Risk)

  • When assessing risk, it’s essential to consider both good and bad risk:
    • Good risk characteristics include something having a high likelihood of leading you to develop:
      • Skills that transfer to other areas
      • Relationships that transcend any given project
      • Attributes of emotional resilience (i.e., trying something scary to you that, once completed, allows you to demystify it for others)
        • For example, before launching a podcast, the process of doing so seemed incredibly daunting to Tim. But, after releasing a few episodes, he realized that all you need is a few hundred-dollar mics and a computer—recording and releasing a podcast doesn’t need to be a big production.
    • An essential characteristic of bad risk: allowing unknowns that don’t need to be unknowns be unknowns
      • For instance, before moving to Austin Tim did a TON of research to learn everything he could about the city
  • When assessing huge life moves, don’t just examine the upsides and downsides of the new option, also consider the disadvantages of maintaining the status quo—what’s the opportunity cost of staying put?
    • Just as there are costs of action, there are costs of inaction. Telescoping out two years into the future, what effect does maintaining the status quo have on you and your loved ones from an emotional, physical, and financial perspective?

Tim Cultivates Walkaway Power with His Projects Through Regular Fear-Setting

  • Tim expands: Cultivating walkaway, for him, is a function of:
    • Frequently revisiting how little he actually needs to survive
      • For instance, to help internalize this, Tim will regularly practice brief “periods of poverty,” in which he only eats oatmeal or beans/rice
    • Frequent fear-setting (pondering the worst-case scenarios)
      • By meditating or journaling on everything you think might go wrong, it becomes much easier to see that, often, the imagined worst-case scenarios aren’t as bad as you think
  • “Making good decisions is often negotiating with yourself, and the person you want to have win that negotiation is the person who cares the least.” – Tim Ferriss
    • Further, when two people are negotiating, very often, he/she who cares the least wins. The above practices help pull Tim towards the side of the spectrum.

Is This Necessary?

  • Marcus Aurelius has famously said: “Ask yourself at every moment, ‘Is this necessary?’ What you’re thinking, what you’re doing, what you’re desiring—is it necessary?”

When Weighing Potential New Projects, Energy Management is Critical for Tim

  • “When I’m considering doing a project, partnering with someone, or embarking on some type of creative endeavor, the question that I’m trying to ask myself now is, ‘Over the intermediate or long-term, will this give me more energy or deplete me of energy?'” – Tim Ferriss

Avoid Sacrificing Short-Term Quality of Life for Potential Long-Term Reward

  • This idea is discussed in much more detail in Tim’s groundbreaking bestseller, The 4-Hour Workweek
  • Often, we have the tendency to do something in the short-term only for the long-term reward of fame, success, money—whatever it be
    • Often, though, the desired outcome is quite far in the future and very much not guaranteed
  • “Don’t work a crappy job that you hate, so, in 50 years, you can retire and go to the beach. Think about what decisions you can make now that give you access to the beach in the intermediate or short-term.” – Ryan Holiday

Contemplating Life’s Finiteness Helps Tim Keep Perspective

  • This relates to a famous Stoic saying: “Momento Mori,” which translates to, “Remember you must die”
  • “I think about death all the time, and it becomes easier the older you get because friends start dying, family members die, and you realize life isn’t an indefinite lease … I find that having an awareness of that impermanence greatly encouraging because it drives a sense of urgency.” – Tim Ferriss
  • “It doesn’t matter how much money you’re willing to pay on your deathbed, you’re not going to be able to buy back more time.” Tim Ferriss

“We’re Just a Bunch of Monkeys on a Spinning Rock”

  • (The above quote comes from Naval Ravikant)
  • Remembering the above, in addition to pondering the mystery of the cosmos with stargazing, for instance, helps keep your daily, minute problems in perspective
    • It’s all dust—you’re but a blip in the history of the universe. In all honesty, nothing you do matters, and nothing you do will be remembered. Everything you’re worried about will, one day, be completely irrelevant.

How to Better Appreciate Life’s Small Moments

  • As you go about life, in even the smallest of moments, ask yourself, “How much would I pay to relive this experience 40 years from now?”
    • (This question originates from Muneeb Ali, as discussed in Tim’s book, Tribe of Mentors)
    • Just think: When you’re 80 after your wife’s died, how much would you pay to rewind to the present, waking up with her on a beautiful sunny day?

Studying Investors Improves Your Understanding of Expected Value & Probability

  • “Even if you keep all your money in a mattress, studying good investors is worth a lot, not necessarily in terms of financial return, but in temporal return—how you think about time.” – Tim Ferriss
  • EVERYTHING in life comes down to probability/expected value, and probabilistic thinking isn’t a strong suit for humans by any means
  • A few recommendations from Tim to better your understating of statistical thinking:
  • In summary: “It changes how you relate to the world, decisions, opportunities, and risks when you start thinking in terms of probabilities.” – Tim Ferriss

Something to Think On

  • “When young people say, ‘I feel happy,’ it tends to be followed with statements about accomplishments or activity. As you get older, the statements drift steadily towards feelings of contentment or connectedness.” Ryan Holiday
    • (This finding originates from We Feel Fine by Sep Kamvar and Jonathan Harris)

Test Your Assumptions

  • “I think it’s safe to assume that at almost any given point in time, almost everybody is getting it wrong with many, many, many many, many things.” Tim Ferriss
    • A few examples:
      • For the longest time, no one realized we could put wheels on a suitcase
      • TONS of investors passed on Uber because of faulty pricing and market size assumptions 
    • Frequently ask yourself: “What am I completely taking for granted because this is the way it’s always been?

How does Tim choose which books to read?

  • Firstly: “I very rarely read anything that isn’t recommended to me by someone who I know is very selective and snobby about book choice.” Tim Ferriss
  • Secondly, Tim will often poll his audience for recommendations—once a book gets recommended several times, he’ll head to Amazon to read the reviews
    • For example, when looking to learn more about the contemporary art world, many people recommended he read The $12 Million Stuffed Shark by Don Thompson
    • Tim NEVER reads the one or five-star star Amazon reviews—he prefers to read the in-depth three and four-star reviews
      • One related point: once a book has more than a few hundred reviews, the book’s rating is probably reasonably accurate (Amazon reviews can be gamed on a smaller level, but most authors won’t be motivated to do so over the long-term)
  • Third: “I like looking at Goodreads for quotes from given books. If you don’t love some of the quotes from the book, that’s like hating the movie trailer and then going to see a three-hour movie.”Tim Ferriss
  • A final note, Tim prefers to do all of his reading on a Kindle

Tim’s Quick to Put Down a Book He’s Not Enjoying (Life’s Too Short for Shitty Books)

  • “I’ll read two or three chapters of a new book, and if I don’t want to take a photograph of some of the highlights and send it to a friend, I’ll consider putting the book down … Life’s too f**king short.” Tim Ferriss
  • Ryan has a similar rule: After you’ve read 100 pages minus your age, it’s okay to put down a book you’re not enjoying

Read More of What’s Stood the Test of Time

  • At the start of 2020, Tim publically committed to not reading any new books for the following year—he’s instead focusing on reading more books that have stood the test of time
    • Why? – This decision gets rid of the FOMO that comes up every time a new book is released (and having to decide whether or not to read it)
  • Another reason not to prioritize new books: “I don’t want to read things that are going to be quickly proven, irrelevant, incorrect, or out of fashion” – Ryan Holiday
    • “Looking at the half-life of information, and deciding to consume information that’s likely to remain true overtime, forces you to be more general, but also more timeless.”

Additional Notes

  • “Getting angry is fear shown in public” – Krista Tippett
  • Mike Maples once said, “Rule number one with kids is that they owe you nothing. Their job is to receive love, not to give you love. YOU decided to bring them into this world. Not you.
  • Kevin Kelly once told Tim: “Don’t write to put your ideas down; write to think”
  • “Just because you’re good at something doesn’t mean you have to keep doing it for the rest of your life” – Ryan Holiday
  • “Any fool can learn by experience; I prefer to learn by the experience of others.” – Otto Von Bizmark
  • “People can be really precious with information when actually, you’re almost always better sharing information.” – Ryan Holiday

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