The Tim Ferriss Show Transcripts: Ryan Holiday — Turning the Tables (#410)

Please enjoy this transcript of a “turning the tables” episode in which I will be the one being interviewed by my friend, Ryan Holiday.

Ryan (TW/IG: @RyanHoliday) is one of the world’s foremost thinkers and writers on ancient philosophy and its place in modern life. He is a sought-after speaker and strategist and the author of many bestselling books, including The Obstacle Is the Way, Ego Is the Enemy, and The Daily Stoic. His books have been translated into more than 30 languages and have sold more than two million copies worldwide. He lives with his family outside of Austin, Texas.

You can subscribe to receive his writing at RyanHoliday.net and DailyStoic.com. Ryan was also the fourth-ever guest on the podcast in the very beginning, and he has written multiple popular guest posts for my blog, which you can find at tim.blog.

His latest book is Stillness Is the Key, which was an instant #1 New York Times bestseller and Wall Street Journal bestseller.

Transcripts may contain a few typos—with some episodes lasting 2+ hours, it’s difficult to catch some minor errors. Enjoy!

Listen to the episode on Apple Podcasts, Spotify, Overcast, Stitcher, Castbox, Google Podcasts, or on your favorite podcast platform. You can also watch the conversation on YouTube

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Ryan Holiday: I’ve known you for a long time, and I was thinking one of the biggest changes that I’ve seen in you as a person came when you got your dog. I remember you approached it in very Tim Ferriss fashion, you didn’t just like—hey, like me, like I got a goat one day, because we saw it on Craigslist, and we just went and got it. That’s not really the Tim Ferriss way.

Tim Ferriss: Yeah.

Ryan Holiday: You talked to a bunch of people, you read a bunch of books but you also really end up—was it 10 years ago you had a dog?

Tim Ferriss: Four and a half years ago, maybe five.

Ryan Holiday: But it’s been an interesting pivot in your life. Why do you think it impacted you so much?

Tim Ferriss: I think that there are a few aspects to it. Number one is caring for a puppy, at least if you do it well, takes your attention outside of any type of self-indulgent reflection/ obsessive-compulsive rumination.

Ryan Holiday: Sure.

Tim Ferriss: And as someone who’s had a history of depression, which is being stuck in the past and I think being highly self-referential—I mean, depression is, I think, as someone who’s experienced it a lot in life, very self-obsessive.

Ryan Holiday: Yeah.

Tim Ferriss: And so when you have something in front of you that requires and demands care, or it’s going to pee in your carpet every two and a half hours, like Molly, my dog, it’s incredibly antidepressive in that sense because it forces a complete refocus.

I also, I think, realized very quickly how absurd some of my reactions are to things or have been historically in the sense that if you have a problem at work, you have a problem with your partner, your spouse, your girlfriend, boyfriend, you can get upset and sort of create an imaginary agenda that they have where they deliberately did A, B, or C to upset you.

Ryan Holiday: Sure, sure.

Tim Ferriss: But with a dog, that’s completely absurd, at face value, it’s completely absurd. Right?

Ryan Holiday: Part of the problem’s is that it’s your fault with your dog.

Tim Ferriss: It’s your fault, right, so if your dog chews on your shoes, that’s your fault. It’s a dog, and you left your shoes out.

Ryan Holiday: Right.

Tim Ferriss: So a big part of, I think raising a puppy well is making it extremely difficult to make mistakes that then become habits. Right? That’s an approach or at lens through which you can look at raising a puppy, and if you don’t want your dog to develop a taste for chewing on shoes, don’t leave your shoes out.

Ryan Holiday: Right.

Tim Ferriss: Put them on something or in something that makes that impossible. And similarly, peeing in the house. To avoid that, use something like crate training. So I think that when I became, particularly in the early periods of training Molly, upset because she wouldn’t follow my instructions.

Ryan Holiday: Yeah.

Tim Ferriss: After an initial period of just getting upset, which I think was my default and has been my default for a long time, anger has been a go-to emotion which I think is—I think Krista Tippett once said it’s fear shown in public or something like that, which I tend to agree with on some level.

Ryan Holiday: Getting upset is fear shown in public?

Tim Ferriss: Getting angry.

Ryan Holiday: Yeah.

Tim Ferriss: Yeah, and it’s a coping mechanism. Some people shut down.

Ryan Holiday: Right.

Tim Ferriss: Some people learn to angry, I learned to get angry when I was little. So doing that though, with this dog who does not speak English, was so ridiculous and ineffective that I had to resort to doing other things that lo and behold, translate to other people and even to yourself, like positive reinforcement.

Ryan Holiday: Yeah.

Tim Ferriss: Right? I didn’t—through sports and coaching, and teaching or receiving teaching, had a little bit of positive reinforcement, not a whole lot.

Ryan Holiday: Yeah.

Tim Ferriss: And so I’ve learned to go without it, even though that is unhealthy.

Ryan Holiday: Sure.

Tim Ferriss: And reading about animal training, if you really want to take it seriously, if you look at say, training marine mammals, like dolphins, you can’t get pissed and hit it with a rolled up newspaper. Doesn’t work underwater, and they’re faster than you are, so you have to figure out how to use like, whistles and different clickers and means of marking the desired behavior and then rewarding.

Ryan Holiday: Sure.

Tim Ferriss: And getting into the habit of providing positive reinforcement I think led to me doing that more, I could still do it more with other people, and how you treat other people, I think impacts how you treat yourself and relate to yourself. So I think that those are all pieces of the puzzle.

And then last but not least, feeling unconditional love, although granted—

Ryan Holiday: It’s very conditional.

Tim Ferriss: Giving your dog food and treats helps a lot, but feeling this love from an animal and experiencing that in the absence of language I think is really powerful.

Ryan Holiday: Yeah.

Tim Ferriss: As someone who tends to get tangled in their own inner voice in the form of language to experience that type of deep positive emotion and connection without language to trip over, has been really impactful for me.

Ryan Holiday: You think it was sort of giving you something to care about, like to be responsible for that wasn’t—there’s no reason to have the dog, you have the dog because you love the dog.

Tim Ferriss: Right.

Ryan Holiday: You know what I mean?

Tim Ferriss: Yeah.

Ryan Holiday: You’re not getting anything out of it in the sense of, sure if you have a nice car, you have to take care of the nice car, but you know what I mean?

Tim Ferriss: I think so. I mean, you get a dog because you want a dog. It’s in a sense a very selfish act.

Ryan Holiday: Yeah.

Tim Ferriss: Even though you can adopt and do all these other things, as I did with Molly, that, well, I would hope have some positive karmic impact—

Ryan Holiday: Sure.

Tim Ferriss: But ultimately, you are choosing to have a dog.

Ryan Holiday: Right.

Tim Ferriss: Similarly, I think having kids is—and this isn’t a bad thing, it’s not a value judgment, but it is a selfish decision. You have kids because you want to have kids. Right?

Ryan Holiday: Yeah.

Tim Ferriss: I remember Mike Maples, who’s this very well-known investor and friend of mine, he said to me, “Rule number one with kids, is they owe you nothing. Their job is to receive love, not to give you love.”

Ryan Holiday: Yeah.

Tim Ferriss: Because you decided to have the kids.

Ryan Holiday: Right.

Tim Ferriss: And I think that’s true to dogs as well, or any type of pet. And for that reason, I do not recommend that everybody get dogs. Right? Because I think that for a lot of folks, as I felt for a really long time, I was too self-focused/obsessed, and the only way I could see having a dog was to kind of wedge it into the open spaces that were left over once I had already executed on everything else I wanted to execute on, or fixate on.

And when I ended up getting Molly, I made the decision that I was going to actually reverse that and get Molly prioritized, really taking good care of her, and then fit everything else around the dog. And those are two fundamentally different ways to look at it.

I think if you look at the realm of behavior in humans and dogs, like most animals, including humans, are poorly trained. And to do it well takes a lot of effort and consistency, so if someone’s ready for that, then I suggest adopting, ideally. But otherwise, I’ve seen people who get dogs and then just neglect them.

Ryan Holiday: Sure.

Tim Ferriss: I’m conflicted as to how to feel about that, because on the one hand if they’re rescuing a dog from a kill shelter—

Ryan Holiday: It’s probably better.

Tim Ferriss: Probably better. One could argue that’s better, but I don’t know. I’m not—yeah, I’m no professional ethicist, so—

Ryan Holiday: There’s a thing David Brooks talks about when his son was born, someone sent him an email and said, this was his first kid, he said, “Welcome to unavoidable reality.” And the idea being that up until then, sure, you have responsibilities. There’s work and life, but pretty much anything you don’t want to have to put up with, you don’t have to put up with.

Tim Ferriss: Right, yeah.

Ryan Holiday: But as soon as you take on something like that, with a kid it’s like you think, “Okay, I’m going to go to this thing at one o’clock.” But if your kid falls asleep at 12:59, you’re going to the thing when your kid wakes up.

Tim Ferriss: Yep.

Ryan Holiday: And I think dogs have an element of that too, because suddenly you’re responsible for this thing that is totally dependent on you.

Tim Ferriss: Yeah.

Ryan Holiday: And the dog decides what the schedule is, not you, which if you’re successful or self-absorbed, and they’re kind of the same thing in different ways, it forces you to pivot your reality in a way that makes you a better person, I think.

Tim Ferriss: I think so. And you develop, I don’t want to—I don’t really want to use the word patience, I think it’s something else, maybe greater self-awareness and resilience in the face of the unpredictable, so—

Ryan Holiday: Equanimity is what I think it is.

Tim Ferriss: Equanimity, yeah, equanimity we could use because it’s like, all right, Molly gets sick. I’ll give you an example, I remember one morning I woke up to the most awful stench imaginable at like four in the morning.

Ryan Holiday: Right.

Tim Ferriss: And I’m very protective of my sleep. Historically, one of the best ways to get me really spun up and upset is to negatively affect my sleep.

Ryan Holiday: Okay.

Tim Ferriss: And it’s like four in the morning, went to bed at 1:00.

Ryan Holiday: Yeah.

Tim Ferriss: And it’s the most horrible stench you can imagine. I wake up, I turn on the light, and Molly has shit everywhere in the bedroom, including on the wall, which I thought was very impressive. I’m like—

Ryan Holiday: Of course.

Tim Ferriss: What possesses a dog to shit against the wall? I don’t know. Nonetheless, all right, this is what you’re dealing with for the next—

Ryan Holiday: It’s unavoidable reality.

Tim Ferriss:—hour, two hours.

Ryan Holiday: Right.

Tim Ferriss: It’s putting on your Hazmat gear and dealing with this. I think you develop, or I have developed, to some extent, I don’t think I’m the best at this. But the ability to put my better, put myself in other people’s shoes.

Ryan Holiday: Sure.

Tim Ferriss: Because in a situation like that, it’s clear to me Molly doesn’t want to do what she’s doing.

Ryan Holiday: Right, right.

Tim Ferriss: There’s something that’s—

Ryan Holiday: She did not do this to ruin your sleep.

Tim Ferriss: She did not do it to ruin my sleep, and it’s not just unhelpful, but it’s damaging to lose your—I was going to say lose your shit, but to get really upset in a situation like that. It actually makes it harder to train your dog effectively, so the unavoidable reality piece I think is a big part of it.

And I think there’s something to be said for—a phrase I heard recently and this scientist I’ve come to know really well, when he had his first kid and he had his first kid pretty late. By his standards—

Ryan Holiday: Yeah.

Tim Ferriss: He’s a lot older than I am, so I think I’m like an 80-year-old when it comes to possible procreation these days, but he said his brother, who had a few kids at that time said, “Oh, welcome to the human race.”

Ryan Holiday: Yes.

Tim Ferriss: When his first kid was born.

Ryan Holiday: Sure.

Tim Ferriss: And I do think that there’s no need to apply it to everybody, but there is a certain self-absorption that is encouraged and fostered in modern life that I think is relatively new.

Ryan Holiday: Yeah.

Tim Ferriss: Does that make sense?

Ryan Holiday: Mm-hmm (affirmative).

Tim Ferriss: Because we’re, even in a densely populated city, you can be very physically isolated and you don’t have responsibilities or things to care for that for the vast majority of our evolution would’ve been commonplace.

Ryan Holiday: Totally.

Tim Ferriss: You’re not having kids at 19 or 18—

Ryan Holiday: You don’t live with your grandparents.

Tim Ferriss: Right. You don’t live with your grandparents, you’re not—

Ryan Holiday: You’re not hunting together.

Tim Ferriss:—hunting and gathering.

Ryan Holiday: Yeah.

Tim Ferriss: Where dogs have certainly, have played a role and did play a role. So I think that in some way, having a dog or having a garden or having kids, these are all things we’ve evolved, sort of co-evolved with.

Ryan Holiday: Totally.

Tim Ferriss: And in the absence of that, you develop a lot of neuroses, which I was sort of the poster child for, for a really long time, and probably still am on some level, but less so.

Ryan Holiday: I think that’s totally interesting, the idea of sort of consciously developing empathy is—and how almost you could argue that the way society is set up now consciously stunts the development of empathy. The famous one, you’re like, “Oh,” you hear someone who’s like, “How was your flight?” And they’re like, “Oh, it was terrible. I sat next to this crying baby the whole time.”

Then you have kids, and you’re like, you get on a plane you hear a crying baby, you don’t go, “Oh, there’s a crying baby, this is bad for me.” You go, “That baby is upset.” It literally never occurred to you that the baby was crying because there’s something wrong with the baby, and that this isn’t fun for the baby. Right? Or—

And it’s definitely not fun for the parent, like they don’t want—so it’s like, I think with dogs too, you’re like you hear a dog barking—you hear about those, you’re like, “Oh, I’ve been through that,” or, “Oh, that’s not fun for you.”

Tim Ferriss: Yeah.

Ryan Holiday: It sort of forces you, I think that’s what they mean by that idea of, “Welcome to the human race.” Not, “Welcome to the human race, you now have made—you’re reproducing.” It’s, “Welcome to the human race, you’re no longer a lone wolf. You understand how—you understand what everyone else has been dealing with while you’ve been self-absorbed this entire time.”

Tim Ferriss: Yeah. It’s sort of like, “Welcome to the human/hominid condition that was the norm for millennia.”

Ryan Holiday: Yes.

Tim Ferriss: Has been the norm, and thank God you’ve snapped out of your aberrant strange behavior that is really kind of a new luxury.

Ryan Holiday: Yeah, that’s right. Have you felt like moving to Austin has had an impact on you in a similar way? I feel like there is also something selfish and strange about the New York life or the San Francisco life or the L.A. life that I’ve just experienced the South and Texas and being a little bit different.

Tim Ferriss: Yeah, well, Texas, the South, and Austin are all—

Ryan Holiday: A little different but—

Tim Ferriss: A little different, but I understand what you mean. I think that Austin has been so far, let’s call it three years in. Three, four years in, however long it is, has been very refreshing and rejuvenating, and part—this is coming back to your point about, or observation of New York and L.A. and so on.

In part, because there is no one mono conversation. And that can be seen as symptomatic of a huge benefit of living here, or a huge drawback.

Ryan Holiday: Right.

Tim Ferriss: Meaning, there’s certain locations in the world, like New York for finance. In New York, you have finance.

Ryan Holiday: Yeah.

Tim Ferriss: True in other places too, say in London. If you want to be in the NBA All-Star game of finance, it behooves you to go to one of those places.

Ryan Holiday: Sure.

Tim Ferriss: And as a result, it attracts people who are highly driven in certain fields, whether that’s fashion, finance, and so on. And as you’ve mentioned to me before, I think it’s—there’s a high correlation between self-absorption and professional success, on some level.

Ryan Holiday: Yeah, has to be.

Tim Ferriss: And if you look at Los Angeles, even though Los Angeles is a huge, in reality, combination of different cities, entertainment is the predominant mono conversation. Whereas here in Austin, you have more of a medley.

Ryan Holiday: Yeah.

Tim Ferriss: And for that reason, I find it—I find that I don’t overtax a single conversational track or part of my brain, like you can quite easily hop from lily pad to lily pad and maintain some degree of mental dexterity, emotional dexterity. There’s just more to easily dip your toe into here.

Ryan Holiday: Yeah.

Tim Ferriss: And it does exist in a place like San Francisco, but it takes more effort to avoid the mono conversations.

Ryan Holiday: And don’t you think one of the downsides of the mono conversation is also let’s call it mono thinking? Right, so I think we’ve tended these days to define diversity as merely a function of race or gender, but I think diversity as far as lifestyles, thinking, careers, interests, is also super important.

Tim Ferriss: The main downside of the mono conversation is mono thinking and a group think that produces an echo chamber that, at least in my experience, doesn’t stress test a lot of your own beliefs because you end up succumbing to this preaching to the choir.

Ryan Holiday: Yeah.

Tim Ferriss: And that, I think, is—I think it’s very dangerous.

Ryan Holiday: Yeah.

Tim Ferriss: I think it’s very dangerous. I think at Silicon Valley, where you have so much capital and so much power and so much culture-shaping technology, that you really want to have, not necessarily a court jester, but someone who can poke fun at the status quo and challenge deeply held beliefs.

Or I should say, better yet, deeply assumed beliefs. And that is very, increasingly difficult to do in the Bay Area, and in much of certainly culture in the United States. And we’re in Austin, which is jokingly referred to as “the blueberry in the tomato soup.”

Ryan Holiday: Yeah.

Tim Ferriss: Right?

Ryan Holiday: Yeah, the “blue dot in the red ocean.”

Tim Ferriss: Yeah.

Ryan Holiday: Yes.

Tim Ferriss: And so it is a—one might think that Austin is just a smaller version of San Francisco, but it’s not. You do have a co-mingling of political, artistic, and financial interests that I deeply enjoy. And the ability to easily, for instance—

I mean, we’re sitting here right above a restaurant called Jeffrey’s, and next door is Josephine House, and I had dinner at Josephine House with someone who I won’t mention by name, most people wouldn’t recognize them, but an extremely successful investor or financier who came in from out of town, came in from elsewhere in Texas.

Very well educated, extremely smart, and also a sort of staunch Republican on many levels, not all levels. Right? It’s easy to paint with that brush. And when you have the ability to sit down with someone like that easily here, it becomes harder to do what is so frequently done in San Francisco, as a place where I spent a lot of time, almost two decades in the Bay Area, to say, “Oh, right-wingers are all knuckle-dragging idiots.”

Ryan Holiday: Yeah.

Tim Ferriss: It becomes much more difficult to paint—

Ryan Holiday: Because you know by direct, first-hand experience that that’s not true.

Tim Ferriss: It’s not true in many cases, and it’s just not that simple.

Ryan Holiday: Right.

Tim Ferriss: Right? It’s just not that simple, and it forces you to contend with I think a messy reality that it behooves all of us to recognize as messy.

Ryan Holiday: Yeah.

Tim Ferriss: It just requires more thought, but I like the fact that it’s not as easy to kind of divide this country into a left-right civil war of smart versus dumb, rich versus poor, this versus that. It’s not as easy to do here, and I like that.

Ryan Holiday: Yeah.

Tim Ferriss: I also think that it would be difficult for me to live in many places outside of Austin in Texas.

Ryan Holiday: Sure.

Tim Ferriss: Right? Which is not a slight against Texas, it just means that Austin has a combination of factors, it’s the combination of factors that makes it interesting to me, and the fact that it has some of the ingredients, and we’ll see if this backfires over time, it might, but that made Silicon Valley Silicon Valley.

You have large, famous research universities with world-class talent from dozens of countries around the world, and it attracts a very intellectual crowd. And as you and I know, there is an incredible writing scene here, there’s some fantastic writers.

Ryan Holiday: Mm-hmm (affirmative).

Tim Ferriss: It has a lot of the ingredients I like about Silicon Valley without the sort of smug self-satisfaction that I find so unappetizing.

Ryan Holiday: You know what I think is important when I was thinking about places to live, is you’re naturally a competitive person, this sort of “keeping up with the Joneses” part of it, like it’s very easy for life to become an arms race. Right? And when you live in a place with more diversity where you live, where there’s not sort of one industry or one scene that dominates all the others, you become more inwardly focused on what you want to do, and what’s important to you, rather than going, “Oh, did you hear what so-and-so just got?”

Tim Ferriss: Yeah.

Ryan Holiday: And I think that’s a healthier way to live, also.

Tim Ferriss: Yeah. I think that’s a very good observation. There’s no one lead dog to follow.

Ryan Holiday: Yes.

Tim Ferriss: Right? And as a result, you have to make more conscious decisions about who you might want to emulate. It’s not an immediate default.

Ryan Holiday: Yeah.

Tim Ferriss: And I like that. I also don’t know if Austin would be the right place to live—it probably wouldn’t for many industries—if you are in your 20s and looking to cut your teeth and make your mark and kind of summit the mountain. 

Ryan Holiday: Sometimes you need that to drive you forward, but that maybe isn’t how you want to spend your whole life.

Tim Ferriss: Yeah. I think that there’s a point, at least there was for me, where you’ve basically alternated between park and sixth gear, and you’re like, “Oh, wait. There are five other gears. I don’t actually need to have this binary lifestyle that is either like rest and recover or full-out sprint for the Olympic gold medal.”

There are actually all these gears in between that allow you to experience and enrich life in a myriad of other ways that, were I geographically located in one of these no-holds-barred, type A cities, I probably wouldn’t give myself the slack and the system to discover.

I would like to think it doesn’t matter where I am, I can cultivate all these amazing habits and types of awareness that will allow me to blah, blah, blah. But the reality is I’m highly flawed with all sorts of predispositions, and I am, to my benefit and often to my detriment, highly, highly competitive.

Ryan Holiday: Yeah.

Tim Ferriss: So if I’m thrown into any game, even if it’s a stupid game that I shouldn’t participate in—

Ryan Holiday: You want to win.

Tim Ferriss: I’m going to win. I’m going to want to win. And recognizing that is important. I remember having Peter Thiel on the podcast long ago.

Ryan Holiday: Yeah.

Tim Ferriss: And I believe, I don’t remember the context exactly, but one of the questions, and I’m paraphrasing here, I believe one of the questions he asked himself is, “In what areas of my life can I be less competitive to be more satisfied or more content?”

Ryan Holiday: Yeah.

Tim Ferriss: And if your default is competition, I think it pays huge dividends to be aware of that, and to ask those types of questions.

Ryan Holiday: My favorite line from him is that “competition is for losers.”

Tim Ferriss: Competition is for losers.

Ryan Holiday: No, but I think what is interesting about you though is you are a very competitive person, and yet, and this is something I wrote down to ask you about, you have a habit of walking away from things that you’re at the top of. Right?

Correct me if I’m wrong, but I think your decision to sort of stop angel investing or stop actively to angel invest coincides with your decision to move to Austin, or overlaps?

Tim Ferriss: Yeah, very, very much an overlap. Yeah, 2015 and then shortly thereafter.

Ryan Holiday: I’m curious about your decision to sort of—you’re not putting out a book a year, even though you could make a lot of money and sell a lot of copies, you sort of have been disciplined about what you don’t do. But how much of that is also related to designing a life or a day-to-day reality? How much are they connected?

Tim Ferriss: I think they’re all really interrelated and I’m not going to try to fabricate some grand master plan because I don’t have one. But I do think that I tend to pause and 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 or scarcity or fear-based decision-making.

Not perfect, but in the case of angel investing and the reason I stopped effectively all of it in 2015 or so is that I realized the conditions were becoming more difficult to place effective bets, especially as an individual using their own capital versus a fund with a nice like two percent management fee and 20 percent carry when you’re using other limited partner money, which is a fine model.

Ryan Holiday: Sure.

Tim Ferriss: I don’t have an ethical issue with it, but I realized that to do a good job with an increasingly high number of decks in the blackjack game in the form of bloated terms, higher prices, foreign capital flight, and places like China coming into the US and affecting terms, I would either—I could no longer do an effective job part-time, and that if I wanted to continue to compete in that game, I would need to create a fund, do it semi full-time, and in that world, I would be effectively replaceable.

I would be in a long line of people trying to do the same thing and that my drive to do that would be predominantly driven by fear of missing out, and I think a sort of cortisol-driven scarcity mentality that has really fostered in the world of startups.

Ryan Holiday: Sure.

Tim Ferriss: And even if I were to win that game, I felt like the toll it would take would not be worth those—sort of Faustian bargain, in other words. So from a mental health perspective, from a physical health perspective, from an emotional health perspective, that it would end poorly.

And I tried to make a realistic assessment of my track record in angel investing, which has been very good to date, but a lot of it’s on paper, and I began investing around 2008, 2009. I was like, okay. So if we flash-forward, that’s about six years, many of these bets and the jury’s not out until the final outcome—

Ryan Holiday: Till the wire transfer comes in.

Tim Ferriss: Until the wire transfer comes in, and that final outcome, for many of the startups that you bet on, will take seven to 12 years.

Ryan Holiday: Yeah.

Tim Ferriss: So looking at that timeline, I thought to myself, “Well, I’ve placed between 50 and 70 bets, I’m not yet convinced that I’m good at this, so why would I commit to doing this full-time if I’m not yet fully satisfied that I am good at this?”

Ryan Holiday: Right.

Tim Ferriss: Or that things are sufficiently influenced by elements under my control that I can help steer outcomes.

Ryan Holiday: Yeah.

Tim Ferriss: Right? You could be the best at picking the initial horses, but by the end of the race, if they’re falling apart, it doesn’t make a difference. So these are all questions I thought about and that, in addition to many other things, a very close friend of mine asking me to please not stop writing—

Ryan Holiday: This is Kamal, right?

Tim Ferriss: Kamal Ravikant, great guy. Given the feedback that he’d seen at events with readers of mine, he said, “You’ll never have that impact investing.”

Ryan Holiday: Right.

Tim Ferriss: “So please, don’t stop writing.” And those all then coincided, when I asked many of these questions, which were uncomfortable because I’ve done very well financially in investing. I’ve done better in investing, by far, than I have in writing. And that was very—

Ryan Holiday: Well, certain fields are more lucrative than other fields. Right?

Tim Ferriss: Yep, certain fields—

Ryan Holiday: Not all success is created equal.

Tim Ferriss: Yeah, for sure. And if you’re trying to get rich, when people are like, “I’m just going to sell a few million copies of books.” I’m like, “God bless you, good luck,” because that is a really—it’s difficult to make that math work.

Ryan Holiday: Yeah.

Tim Ferriss: There are far easier ways to make money. When I began to ask these questions, I realized that much of my being in the Bay Area was predicated on maintaining and building a competitive advantage in investing.

Ryan Holiday: Right.

Tim Ferriss: So if you remove the investing—

Ryan Holiday: Why am I here?

Tim Ferriss: And you look at your surroundings with fresh eyes, you’re like, “Well, wait a second. A lot of my best friends have left, so my social reasons for being here are few to none.”

Ryan Holiday: Yeah.

Tim Ferriss: Not none, but few. If I remove the investing, my professional need to be here is nonexistent.

Ryan Holiday: Sure.

Tim Ferriss: So why am I here?

Ryan Holiday: Yeah.

Tim Ferriss: What do I like? What do I dislike? And a lot went into the decision, but led me to consider a lot of different places, but predominantly Austin, which I wanted to move to right after college, just didn’t get the job at Trilogy Software. And if you look at some of these decisions, they’re almost all catalyzed by a breakdown of some type.

Ryan Holiday: Yeah.

Tim Ferriss: Wearing out, some type of burnout.

Ryan Holiday: Yeah.

Tim Ferriss: That happened with The 4-Hour Chef leading to podcasting.

Ryan Holiday: Yeah.

Tim Ferriss: It was flamed out, because I tried to do what should’ve been a three or four-year project in a year or a year and a half, which was a suicide mission. And that extreme pain and burnout then led to test-driving the podcast.

Ryan Holiday: Right.

Tim Ferriss: All right, so a lot of my walking away at the top, so to speak, I would like to say is this sort of grand philosophical insight and balls of steel and—

Ryan Holiday: You’re not looking at the pile of chips and going, “I have enough, let’s walk away.” You’re actually going, “This is awful. I’m miserable.”

Tim Ferriss: It’s often both.

Ryan Holiday: Yes, right.

Tim Ferriss: But it starts with, “This is awful and miserable.”

Ryan Holiday: Right.

Tim Ferriss: So it’s sort of the breakdown equals breakthrough—I’m borrowing that from someone—that is catalyzed by wearing out.

Ryan Holiday: Yeah.

Tim Ferriss: And I suppose where I’ve been fortunate or made some good decisions is instead of just plowing through that, sometimes it’s physically impossible. I will say, I have enough chips where I don’t need to race into the next decisions, let me take some time to journal. Journal, journal, journal, and I do a lot of journaling asking questions. I don’t find my thinking to be clear at all unless I’m writing.

Ryan Holiday: Yeah.

Tim Ferriss: And I think Kevin Kelly was the one who said this to me, amazing guy, that he doesn’t write to put his ideas down, he writes to think. He writes as a means of thinking. And in doing that, I then have looked at options like stopping all angel investing. I like to ask these absurd questions. “What if I left the Bay Area entirely and moved to Austin, Texas?”

And I think that another reason I’ve been comfortable pulling the trigger on a lot of these things—trying the podcast—is that I view them all as—I don’t know why I find this so easy, but a lot of people find it hard, I’m not sure why that is. I think it’s practice, predominantly.

What would a meaningful but reversible experiment look like? That’s it. Okay, with the podcast I committed to, I think it was six episodes, then if I don’t like it, I can walk. That’s it. And with Austin, it’s like you can always—I can always move back to the Bay Area if my realization is, “Oh, my God, I didn’t realize how much I loved these things I now miss.”

Ryan Holiday: Sure.

Tim Ferriss: I can always move back; it’s completely reversible.

Ryan Holiday: I think that’s a great—because I remember I was asking you recently for some advice, it was sort of a big purchase, it would be a big lifestyle transition. And you were like, “How else are you going to find out if you want to do it or not?” And you said, “Wait. Why don’t you just commit to doing it for two years?”

Tim Ferriss: Yeah.

Ryan Holiday: And that’s totally right, because I remember when I dropped out of college, I was just like, “I’m dropping out of college. This is the biggest decision I’ve ever made in my life.”

Tim Ferriss: Yeah.

Ryan Holiday: I remember I went to someone, they were like, “You know you can go back, right?” It didn’t even occur—even when I went to drop out, I was like, “I’m here to drop out.” They were like, “There’s not a form for that. There’s a take-a-semester-out form.” But we think these lifestyle decisions are irrevocable and life-altering, and really, they can start very small.

Tim Ferriss: They can start really small, and I want to just highlight something you just said, which I think it’s missed oftentimes in the romanticizing about dropping out of college, that for many of the folks who are the name-brand titans, who have adopted dropping out of college as one of their favorite stories and drums to beat.

If you have the Zuckerbergs, the Thiels, or whoever it might be—although Thiel is not a great example of dropping out himself—but you talk about these incredible icons of entrepreneurship who dropped out of school, it’s really important to realize that when you drop out of Harvard or Stanford—

Ryan Holiday: It’s different.

Tim Ferriss: Those administrations effectively say, “Come back anytime you want.”

Ryan Holiday: Yeah.

Tim Ferriss: And that is really important, it’s a footnote that people need to be—

Ryan Holiday: Yeah, although what I would add to that is actually think the Zuckerbergs and the Gates are proof of the experimenting thing. Right? Because I hear from people wanting to drop out of college all the time, they’re like, “I’d like to be an entrepreneur. I want to drop out of college.” Mark Zuckerberg left college because Facebook was successful.

Tim Ferriss: Right.

Ryan Holiday: Right? He wasn’t dropping out of college to then go start The Facebook.

Tim Ferriss: Yep.

Ryan Holiday: And so you can do the thing now, and then if it’s working, you can transition away from it. 

Tim Ferriss: Right.

Ryan Holiday: You can decide to go, “Hey, what would it look like if I committed full-time to this for six months? What would come of that?” And I think it’s not like you’d never been to Austin before and you sold everything you own—

Tim Ferriss: Yeah, no.

Ryan Holiday: And you were like, “I’m going to see if I like it.” You can experiment, you dip your toe in these things in a bunch of different ways. And then, yeah, you are jumping off a cliff, but there’s also an exit strategy.

Tim Ferriss: Yeah. I almost never burn the ships.

Ryan Holiday: Yeah.

Tim Ferriss: I can’t think of, off-hand, a single example of me burning the ships and throwing caution to the wind and just leaping into the unknown. That’s just not how I do things. And—

Ryan Holiday: It’s also because you don’t need to do them. I think you don’t need to do that, and—

Tim Ferriss: And by “you,” I think that means most people. Most people should not jump head-first into the shallow end and hope that they figure it out. I think that’s a terrible idea. And if you look at some of the entrepreneurs who are thought of as these swashbuckling risk-takers, Richard Branson—Sir Richard Branson—I’ve had on the podcast as one example.

They’re actually, when you peek under the hood and start looking at the details, they are better called experts in risk mitigation and capping the downside. He figured out how to lease planes, I think from Boeing, might have been Airbus, for Virgin Atlantic.

Ryan Holiday: Yeah.

Tim Ferriss: And set up a structure such that the financial risks usually associated with airlines were dramatically mitigated.

Ryan Holiday: Yes.

Tim Ferriss: He made a lot of exciting unusual bets, most of which were survivable bets. Right?

Ryan Holiday: Jeff Bezos says, “I don’t believe in bet-the-company bets.”

Tim Ferriss: Yeah.

Ryan Holiday: He’s like, “I want to be constantly taking risks, small risks, that are survivable. I don’t want the if-this-doesn’t-work-we-go-out-of-business risk.” He’s like, “You’ve waited too long if you have to take those risks.”

Tim Ferriss: Yeah. And as you mentioned with Austin, I mean, I’d been in Austin 15 times?

Ryan Holiday: Yeah.

Tim Ferriss: I spent increasingly long periods of time here each trip to South by Southwest, so I had already done more than dip my toe in the water, and it was really a question of whether I would enjoy living here. I knew I enjoyed being here for short periods of time. Would I enjoy living here? Which is a whole separate question.

Tim Ferriss: And there are ways to test. So I think my comfort with walking away at the top is a result of a high degree of comfort with—and a large amount of practice in thinking about—my life as a series of experiments.

Ryan Holiday: Yeah.

Tim Ferriss: It’s also just being a student of recent history, right? Look at Dave Chappelle. “He’s crazy, he walked away from 50 million,” or whatever. And then he comes back and he does, I don’t know what the numbers are exactly, what, $100 million with Netflix?

Ryan Holiday: Yeah.

Tim Ferriss: Dave Chappelle is fine.

Ryan Holiday: Yeah, sure.

Tim Ferriss: And people who really focus at being good at their craft can almost always come back, and no one—I can’t remember who said this, this was in Tribe of Mentors, but someone said if Will Smith doesn’t do a movie for two years, people aren’t like, “Whatever happened to Will Smith?” Will Smith can take all the time he wants.

Ryan Holiday: Yeah.

Tim Ferriss: And I think that underscores the importance of just focusing on being as good as possible at your craft.

Ryan Holiday: Yeah. That’s the Cal Newport thing. Like, if you’re So Good They Can’t Ignore You, you get to dictate your terms.

Tim Ferriss: Yeah. Yeah, and I am extremely risk-averse. Risk defined as something with a high likelihood of an irreversible outcome.

Ryan Holiday: Yeah.

Tim Ferriss: The bet the farm type of—

Ryan Holiday: Do you have any strategies for mitigating—if you’re thinking about doing something, what do you look at to sort of separate good risk and bad risk?

Tim Ferriss: Good risk, for me, has a few characteristics. Two of the key characteristics would be high, high, 90-plus-percent likelihood of developing or deepening skills that will transfer to other things —

Ryan Holiday: Okay.

Tim Ferriss:—whether now or in the future, even if this project fails. Another characteristic of good risk would be developing relationships that can transcend this project, even if it fails, and this is borrowing from Scott Adams quite a bit, the creator of Dilbert, who talks a lot about this type of thing, how to win even if a project fails.

Another characteristic of good stress would be something that will help me to develop attributes or emotional resilience or to take things less seriously, which I think often go together.

Ryan Holiday: Yeah.

Tim Ferriss: To try something that is scary to me or to most people that I can demystify in such a way that it’s less intimidating. Right? The podcasting and doing six episodes is a great example. Because in the beginning, the idea of podcasting in my head was having this big studio and all this equipment, and it’s This American Life with a staff of 40 people.

And no, it’s not. After doing six episodes I was like, “Oh, all right, actually I’m not scared by audio at all,” because these mics, these cables, and the recorder that’s on this chair are like 500 bucks, and you’re locked and loaded. And the editing’s actually pretty straightforward.

So those are three characteristics of good risk, and then a bad risk I think is largely a function of allowing unknowns that don’t need to be unknowns. And so I do a lot of homework for many of my bets. If I’m looking at say, Austin, all right, I want to understand what the landscape, political, legal, and so on looks like in Austin.

I want to look at population growth, I want to look at employment growth, I want to look at median home costs and how prices are moving, not just in Austin but compared to my other options on the table.

Ryan Holiday: So the opportunity cost of the decision?

Tim Ferriss: It’s a relative decision, it’s not an absolute decision.

Ryan Holiday: Yeah.

Tim Ferriss: And I’m also going to look at, let’s say if I stay in San Francisco, what are the risks of the status quo? What are the knowns that I dislike, and then what are the possible changes that I might dislike? So not just looking at the potential upside and downside and pros and cons of the new option, but comparing it to the current option.

That sounds so self-evident, but it is not common practice. Right? Most people just assume, “All right. This is my known, and I’m going to look at the risks and pros and cons of this new option.” I’m always looking at relative. I’m looking at not just opportunity cost, but the sort of relative attractiveness. Right? And that can apply to just about anything. I mean, it can apply to startups, certainly. In terms of bad risk, I do look at financial risk.

I look at reputational risk, I look at legal liability risk and I do more comprehensive risk assessment than I do opportunity assessment. In part, because I want to look for asymmetric bets, in the sense that if I know I can cap my downside, that there is little—or I can manage or completely eliminate reputational and legal risk by asking for, let’s say, an indemnity clause and having a written record of what we agree my responsibilities will or will not be, and I’m putting in $50,000.

Ryan Holiday: Yeah.

Tim Ferriss: In a sense, if I can control my time that is allocated to this, my max downside risk is 50 percent.

Ryan Holiday: Right.

Tim Ferriss: But if I’m investing in software as a service company—

Ryan Holiday: It’s $50,000, you mean?

Tim Ferriss: Sorry, $50,000. If, though, I’m investing in a sector in a vertical—in a type of company like software as a service or whatever—that has comparables which show 100x returns, 1000x returns, I’ll take that bet all day long.

Ryan Holiday: Yeah.

Tim Ferriss: Right, if the team and so on give it a reasonable likelihood of success, that is a great asymmetric bet. And I think you can do that outside of investing and startups. I think investing helps to hone the questions you ask and the types of lens through which you look at things, and how you might consider arbitrage and so on. But Austin, for me, is a very—it’s a very simple bet where it’s easy to cap the downside.

Ryan Holiday: It seems to me that’s the main strategy in your life, is capping downside, so it’s like, okay, you put $50,000 in this startup, the most you can lose is 50,000. You spend $500,000 on real estate investment, you’re responsible for the cost of maintaining the property, like—

Tim Ferriss: Yep.

Ryan Holiday: It’s a totally different—and I think that explains your experiment thing. So it’s not, “I’m starting a podcast. Now I have to have a podcast forever.” You’re thinking, “I’m committed to six, so the most—if I don’t like it, the most I have to do is six episodes of something I don’t like.”

Tim Ferriss: Yeah.

Ryan Holiday: Do you know what I mean? You’re capping—so it’s not endless amounts of losses, whether that’s time, resources, happiness, money.

Tim Ferriss: Yeah. And I always try to cultivate walkaway power with my own projects.

Ryan Holiday: How do you do that?

Tim Ferriss: I’ll explain or try to explain why I think it’s important first. If I feel like I have to do something, you lose your optionality.

Ryan Holiday: Right.

Tim Ferriss: And furthermore, you begin to make decisions out of fear or guilt, which in my experience turn out, almost always, turn out poorly.

Ryan Holiday: Yeah.

Tim Ferriss: Similar, if you’re making decisions out of prestige, can turn out very poorly. And I think I borrowed that from Maria Popova and what she said once on the podcast, but cultivating walkaway power is a function for me of a) revisiting how little you actually need frequently.

Ryan Holiday: Yeah. This is Seneca.

Tim Ferriss: Yeah, Seneca, not Timon’s paupers’ huts, but you know, I always set aside a certain number of days each month or whatever it is to get by with the scantest, scantest or scantiest? I always mess that up, a fair—but practicing periods of poverty or—

Ryan Holiday: Being okay with the rock-bottom.

Tim Ferriss: I just did this last week. I’m making do for a while with just like instant coffee and oatmeal in a bag that you cook with boiling water, and everything’s great. And granted, it’s different when you do it for an extended period of time; it’s different if that’s your only option.

Ryan Holiday: Sure.

Tim Ferriss: But nonetheless, constantly revisiting and confirming how little is actually needed is number one. Number two is doing fear-setting, is an exercise that I talk quite a lot about, which of course borrowed directly from Stoicism and cognitive behavioral therapy, which is also largely based on Stoic philosophy, of—what is the term in Latin? It’s—

Ryan Holiday: Premeditatio Malorum.

Tim Ferriss: Yeah. Premeditatio Malorum—meditating on the possible evils or risks. so I have a written format of fear-setting. People can check it out at tim.blog/ted, if you want to see what that looks like. It’s all free. I do that routinely, so we’re recording this in January 2020, and I did a lot of fear-setting around—

Ryan Holiday: Us talking, how poorly it was going to go?

Tim Ferriss: How poorly this conversation’s rank could go and how I would possibly repair the incredible reputational damage. Around stopping just about everything. So even though I’m not seriously considering nor do I feel compelled to say, “Stop.” Stopping the podcast.

Ryan Holiday: Yeah.

Tim Ferriss: I would write down like, “Stop the podcast? What if I stopped this? What if I stopped all involvement with real estate? What if I stopped all travel?”

Ryan Holiday: Sure.

Tim Ferriss: “What if I stopped?” And now, I will go through the thought experiment of, “What if I completely stop these various things categorically?” And when you run through the kind of “So what? So what? So what? So what?” For each of those, ultimately you realize you’re going to be fucking fine, with all of them.

Ryan Holiday: Sure.

Tim Ferriss: And to that extent, I think that making good decisions is often negotiating with yourself, and that the person you want to have win that negotiation—and this is advice I got a long time ago—is the person who cares the least. And that’s not a value judgment, but if you have two people negotiating against each other and one feels like they have to do the deal, and the other person has 20 different BATNAs, right, best alternative to negotiate an agreement, and they don’t give two shits whether the deal happens or not, or at the very least, they’re very comfortable walking away.

Ryan Holiday: Yeah.

Tim Ferriss: He or she who cares the least, wins.

Ryan Holiday: Yeah.

Tim Ferriss: And I like to cultivate the side of me that can see how little a lot of the glossy veneer aspects of life add at the end of the day to the core of what you need to feel content on a regular basis. So that might be a lot of word salad at once, but those are at least some of the ways that I think about it.

Ryan Holiday: No, I think that ties into—we were just talking about the Stoics, Marcus really says this thing, says like, “Ask yourself at every moment, ‘Is this necessary?’”

Tim Ferriss: Yeah.

Ryan Holiday: What you’re thinking, what you’re doing, what you’re desiring, is this necessary? And that seems—you used to have a sign in your house that said “Simplify.”

Tim Ferriss: Still have it, yeah.

Ryan Holiday: Yeah, that seems like you guys are in alignment, that you’re like, “Do I need this? Do I want this? What would happen if I didn’t have it? Why does everyone else want it?” It seems like you’re constantly questioning that.

Tim Ferriss: I am, or I try to do it at regular intervals, and I get caught up in the slipstream and start swimming against the riptide all the time.

Ryan Holiday: Sure.

Tim Ferriss: Right? I mean, I get sucked into stuff all the time, but I do very frequently take plane rides and so on to journal, and to also try to identify, this is relatively new, I mean in the last few years, but especially crossing 2020 and looking at not just 2019 but the last decade.

Ryan Holiday: Yeah.

Tim Ferriss: And the better decisions that I had made, and the poor decisions that I’d made, which are different from good and bad outcomes.

Ryan Holiday: Right.

Tim Ferriss: But just the—so where I made mistakes in decision-making, and some of the catastrophes and things that really caused me a lot of angst and upset. One of the corollaries is I, to the bad decisions, is that—or correlations, rather—is that I wasn’t paying attention to energetic management or like energy management. And I’ll explain what I mean by that.

Ryan Holiday: Yeah.

Tim Ferriss: So it’s—

Ryan Holiday: Managing your own energy?

Tim Ferriss: Yeah, it’s pretty simple. As I get older, I still feel like I’m in good shape, but if I don’t sleep well for two or three nights, life is not good, generally.

Ryan Holiday: Right.

Tim Ferriss: And that’s a really simple example, but the point being when I’m considering doing a project, partnering with someone, embarking on some type of creative endeavor, the question that I’m trying to ask myself now is: Over the intermediate or long term—which to me could be three months—will this give me more energy or take away or deplete me of more energy?

Ryan Holiday: Sure.

Tim Ferriss: And—

Ryan Holiday: So it’s not like the “Hell, yes,” or “Hell, no,” it’s like, “What does this do to my energy levels?”

Tim Ferriss: Yeah, which are closely related but it’s—some of the things that give me a lot of energy are not necessarily a “Hell, yes.”

Ryan Holiday: Right.

Tim Ferriss: They’re a “Yes,” like swimming regularly.

Ryan Holiday: Yep. It’s a great time for that.

Tim Ferriss: It is a great time for that, yeah. Yeah, you live at Barton Springs.

Ryan Holiday: Yeah.

Tim Ferriss: It’s a great location. There are a lot of pools here. So swimming regularly, I always feel better and I always feel more energized, I feel more emotionally resilient after swimming.

Ryan Holiday: Yeah.

Tim Ferriss: And it’s not a “Hell, yes,” like for some people going to Burning Man for the first time or something, it’s not that—

Ryan Holiday: It’s not like “Chocolate cake? Hell, yes!”

Tim Ferriss: No, it’s not that volume of like, jump up and down on the table, “Hell, yes!” but it is a great investment for building up energy reserves.

Ryan Holiday: Yeah.

Tim Ferriss: And so I’ve tried to make more and more decisions keeping that in mind.

Ryan Holiday: Yeah.

Tim Ferriss: And I’ve turned down a lot of what on paper would look like fantastic opportunities because it would involve dealing with a huge bureaucracy, which I know is going to drain my batteries and historically has always drained my batteries. It’s like, “You know what? It is on paper a great opportunity, but this is going to take 10 times longer than it’s expected to take, and it’s going to be draining.”

I would much rather do something smaller that doesn’t have that effect on my energy, even though one could argue that this would be better for my career, whatever the hell that happens to be. I still don’t know what my career—

Ryan Holiday: I think a lot of—you were talking about the difference between good and bad decisions is not the same as good or bad outcomes, and so I think a lot of people make decisions, and I do this if I have to counteract it, but we go like, “Is this going to make me more or less money? Is this going to make me more or less famous? Is this going to make me more or less successful? Is this going to make me more or less interesting?”

We think about the outcomes. And often, that outcome is very far in the future, and very much—the decision, it isn’t like an, “If you do this, you are guaranteed X, or if you do this, you’re guaranteed X.” It’s like, “Hey, if you can continue to do this over and over again, you might get this thing in 20 years.”

Tim Ferriss: Yeah.

Ryan Holiday: And I think one of the things that I took from The 4-Hour Workweek and that I’ve gotten from you regularly is you tend to think more about like quality of life right now. So 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 the access to the beach in the intermediate or short term.

So I tend to think more like—

Tim Ferriss: As an experiment. Right?

Ryan Holiday: Yes.

Tim Ferriss: Specifically.

Ryan Holiday: Yes.

Tim Ferriss: Because you may get—

Ryan Holiday: You may hate the beach actually.

Tim Ferriss:—to the end of the line, and you’re like, “Oh shit, I actually don’t like selling. And this was my made-up dream for 50 years, for which I sacrificed all these other things.”

Ryan Holiday: Yeah, so I think it’s like, “Is this giving me day to day what I like more or less?” That’s my version of the energy thing, is like, “Am I having the time and the life that I want?” Not, “Am I doing this so maybe I get that in the future?” And it seems like, as a person who popularizes lifestyle design, that’s kind of your core message. It’s like, “Are you designing a life you actually like living in?”

Tim Ferriss: That is, I think, a huge piece of it. And if we wanted to parse that out even further, it’s really trying to cultivate an acute awareness of knowns and unknowns, and if you look at lifestyle design for people who aren’t familiar with the term, so lifestyle design would effectively be a contrasting philosophical lens through which to look at career and personal development, that is juxtaposed with the kind of slave, save, retire.

I am going to cash in my chips in 20, 30, 40 years, that will then redeem this period of doing many things that I dislike doing, which is not to say you’re always going to enjoy doing everything.

Ryan Holiday: Yeah.

Tim Ferriss: I don’t know many people who love doing their taxes.

Ryan Holiday: Yeah.

Tim Ferriss: There are things that you need to do, but outside—

Ryan Holiday: No one gets exactly what they want when they’re 20 years old.

Tim Ferriss: Right.

Ryan Holiday: You know what I mean?

Tim Ferriss: Yeah.

Ryan Holiday: You have to earn and build and invest. Yeah.

Tim Ferriss: There’s a period of testing that goes on to determine where you are particularly adept, looking at—we don’t have to do a rehash of the book but suffice it to say there are ways that you can test and should test the hypothesis that in X period of time, when I do Y, it is going to give me Z amount of pleasure that will make up for these decisions I’m making in the interim.

That is a theory that is contingent on many things being accurate, and in my experience, effectively lifestyle design is effective testing and awareness. Investing is, for me at least, has been effective testing and developing keen awareness of things that most people don’t pay attention to, or a lot of people don’t pay attention to.

So if we’re looking at for instance living in New York City versus living in Austin, so I might say, “Well, I’m just going to live here for another 10 years. I’m going to have these following promotions in my investment banking job, and then I’m going to move to Hudson Valley, I’m going to move to Santa Barbara, I’m going to move to—and then live the good life.”

Ryan Holiday: Sure you will.

Tim Ferriss: Right, yeah. So if that is your life plan, let’s spend some time developing experiments to prove or disprove that before you dedicate the next 20 years to it, but people will very often spend more time planning their Memorial Day weekend than they will speccing out out tests.

Ryan Holiday: Right.

Tim Ferriss: So A, is there anything in your historical record to suggest that you will be able to walk away from something like that?

Ryan Holiday: Right.

Tim Ferriss: Anything, if you’re a type A, right?

Ryan Holiday: Yeah.

Tim Ferriss: And by definition, in that circumstance, you’re probably type A.

Ryan Holiday: Yeah.

Tim Ferriss: And there are many, many, many, many faulty assumptions.

Ryan Holiday: Yeah.

Tim Ferriss: So I think that I am very, very accepting of the fact that there are many things I don’t know and there are many things that I take for granted, and there are many things that I don’t see.

Ryan Holiday: Yeah.

Tim Ferriss: Therefore, I spend a lot of my time developing experiments. That’s my constant framework, “How can I be sure that I know X?” Which relates to, in 2015, walking away from startup investing. So I was like, “All right, if I look at the track record of these various companies, not only in my portfolio but others, for the biggest wins, it’s taking— if we’re looking at say Shopify, Uber, et cetera—it’s taking seven to 12 years to come to fruition, and your final tally is not known until you’ve liquidated all of your holdings effectively.”

I mean, it’s a little more complicated than that, but not by much. So even though on paper, and also in exits it would—I could convince myself that I am good at this, and people tell me I’m good at this, that remains to be seen.

Ryan Holiday: Yeah.

Tim Ferriss: Right? And so I stopped, and—

Ryan Holiday: And the larger assumption, just because you’re good at something does not mean you have to keep doing it for the rest of your life.

Tim Ferriss: Yeah. There are many things I’m good at that I shouldn’t do at all.

Ryan Holiday: Yeah.

Tim Ferriss: I think it’s challenging for anyone, myself included, to shift gears. If you’re good at something, being rewarded for something, and yet you have this creeping dread that you don’t really want to do it, that is a challenging situation for I think just about anyone, and certainly has been challenging for me. But the parachute, right, the safety net is realizing that for almost anything, you can leave and come back.

Ryan Holiday: Yeah.

Tim Ferriss: Almost anything. And I’m sure there are exceptions, but if we’re talking about businesses and professional capacities and careers, if you are really good, that’s a big—

Ryan Holiday: That’s the ultimate leverage.

Tim Ferriss: That is a huge hurdle that you need to be able to pass, but if you are really good and dedicated to your craft or crafts, it could be a combination of unusual crafts, right?

Ryan Holiday: Right.

Tim Ferriss: You might be a quant who’s also really good at writing, and then you have a newsletter.

Ryan Holiday: Sure.

Tim Ferriss: It could be an unusual combination of trades, like Warren Buffett and public speaking and writing, or Jeff Bezos and writing, entrepreneurship, et cetera. You can always come back.

Ryan Holiday: Right.

Tim Ferriss: So I try to keep that in mind in making a lot of my decisions.

Ryan Holiday: You know what’s interesting? It’s like you’re taking it all very seriously, but then you’re also not taking it that serious. I was thinking, as we were talking about the Stoics, more like one of the things that sort of weaves its way through I think the thinking you’re giving. And I know I can give you one of these, but—

Tim Ferriss: Memento Mori!

Ryan Holiday:—one of the reasons you shouldn’t do the thing for the rest of your life just because you’re good at it is that you only get one life, and one of the reasons I think you’re always questioning—it seems like part of your fear-setting thing is like, “What if I die? Does any of this matter?”

Tim Ferriss: Yeah.

Ryan Holiday: Do you know what I mean?

Tim Ferriss: Yeah, the costs of inaction.

Ryan Holiday: Yeah.

Tim Ferriss: Right, I think that thinking very carefully about the costs of inaction and telescoping out six months, 12 months, 18 months, what effect does continuing to do what you do have on you and your loved ones from a financial, emotional, physical perspective. Right?

Ryan Holiday: Yeah.

Tim Ferriss: I think about death all the time, and it’s not a morbid, sullen exercise for me. This becomes easier the older you get because friends start dying, family members die, and you realize this is not an indefinite lease.

Ryan Holiday: Yes.

Tim Ferriss: You have—

Ryan Holiday: Or that it is a lease, you don’t own it.

Tim Ferriss: Yeah, it is a lease.

Ryan Holiday: Yes.

Tim Ferriss: And that, having the, I don’t want to call it time pressure, but awareness of that impermanence, for me, I find—this might sound strange, but greatly encouraging because it drives a sense of urgency.

Ryan Holiday: Yeah.

Tim Ferriss: Or at least time sensitivity to a lot of my decisions, and so that’s one one hand, sort of pricing this fleeting non-renewable resource that is time and realizing that 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.

Ryan Holiday: Right.

Tim Ferriss: And then simultaneously, I guess meditating is the best way to put it, or contemplating how little a lot of this matters or all of it matters, in so much as Naval Ravikant once said to me, he’s like, “Yeah, we’re just a bunch of monkeys on a spinning rock.”

Ryan Holiday: Mm-hmm (affirmative).

Tim Ferriss: And spending time, this is going to sound so highfalutin but whatever, reading about the cosmos or contemplating as—I believe it was Ed Cooke, an incredible memory competitive champion and entrepreneur, Memrise is his company, M-E-M-R-I-S-E, and coach, also writer, had said to me and then he would—

And BJ Miller, who’s a hospice care physician I think, did something very similar, but they would look at say the stars and imagine that it’s possible and I’m not an astrophysicist so maybe this is impossible, but that it’s possible that the star you are seeing is in fact light that is hitting your eye from a star that no longer exists.

Ryan Holiday: Yeah, right.

Tim Ferriss: Right. And to just sort of contemplate that when you’re freaking out because you have some problem with Amex or there’s some disagreement and it’s like somebody badmouthed you at work or whatever it is, you’re like, okay to—

Ryan Holiday: Number one and number two on The New York Times Best Seller list or all the things that we—

Tim Ferriss: Who cares? All dust. Right? As our friend Marcus would say—

Ryan Holiday: Yes.

Tim Ferriss: All dust, nobody gives a shit and—

Ryan Holiday: Right. Not even you in the future will give a shit.

Tim Ferriss: Yeah. It’s all going to be completely irrelevant, so holding those two in my mind has been a practice, and I do think about death a lot and there is a person featured in, I think it was Tribe of Mentors, Muneeb Ali, who’s involved, very heavily involved with cryptocurrency and very, very smart guy. Maybe better put blockchain, and very smart guy.

And it’s funny to me how certain things stick and certain things don’t stick, or certain things have like a time release. And so I read this, and I was like, “Oh, that’s interesting.” And then months later it sort of just resurfaced and I thought about it a lot since, which was he will routinely ask himself when he’s overwhelmed or feeling scattered, “How much would I pay to relive this experience 20 years from now, 30 years from now, 40 years from now?” And I’m paraphrasing, so it’s not perfectly stated, but—and I think about that, where I’ll be—I think about the experiences that I would pay the most for, and I’m being honest with myself, it’s not the professional successes, or the glamor shots. It’s usually something very simple, like—

Ryan Holiday: It’s the moments of stillness, and quiet and peace and relationships.

Tim Ferriss: Waking up in bed with my girlfriend on a beautiful, sunny day and patting the bed and having my dog jump up and having a little snuggle fest. It’s very, it sounds so cheesy, like the 20-year-old Tim would just be vomiting all over himself right now, but nonetheless, 20-year-old Tim was a pretty miserable fuck.

So I feel like I’ve improved on that front, and asking yourself like, “All right, if I were 80 and Molly has long since passed away, maybe my wife has passed away. How much would I pay for that?”

Ryan Holiday: Yeah.

Tim Ferriss: Right? And that really, to me, is part and parcel of the valuing of time, these slivers of experience, as more valuable than making a speculative decision about earning more in the future based on doing something that takes you away from those people.

Ryan Holiday: Right, or agreeing to some thing because you might get some honor, or—

Tim Ferriss: Mm-hmm (affirmative). You know—

Ryan Holiday: Go ahead.

Tim Ferriss: I’ll say one more thing, which is I really think that even if you keep all your money in a mattress, studying good investors is worth a lot.

Ryan Holiday: Yeah.

Tim Ferriss: Not necessarily in financial return, but in temporal return, right? In how you think about time, because humans overall are very sloppy. I’m no mathematician, so I’ll put myself in the same category when it comes to thinking about probabilities.

Ryan Holiday: Yeah.

Tim Ferriss: Probabilistic thinking is not, it’s not a strong suit for humans, and so you might hear like, “Oh, my God, there’s a room with 300 people and these two people have the same birthday. That’s crazy!” But mathematically speaking, it’s not that crazy.

Ryan Holiday: Right.

Tim Ferriss: And in fact, at some point, it becomes totally expected. Right?

Ryan Holiday: Yeah.

Tim Ferriss: And similarly, developing a basic mathematical literacy with respect to investing, so I think most people watching or listening to this will have, as I did, I mean, I stopped taking math in high school because I had one bad math teacher. Even though I was good at it, I became totally turned off. My brother went on to get a PhD in stats, and it was the same year.

He had a good math teacher and I had one who was just a ball-buster, and you can see how we split in different directions. But I have a deep-seated insecurity when it comes to math. Nonetheless, studying investing has helped me to develop my understanding of certain concepts, like expected value.

So if you think that you are going to—you could make $100,000 or $1 million or $10,000 at Y point in time. Is making that decision, in your mind, actually worth 10, 100,000, or whatever it might be?

Ryan Holiday: Yeah.

Tim Ferriss: Well, it depends a lot on the probability of that happening, and then you can do some basic multiple and be like, “All right. Actually, the expected value of that, given that it’s a low probability, or 50 percent, or 30 percent, is instead of $100,000, it’s actually worth $25,000.”

Ryan Holiday: Right.

Tim Ferriss: That could very, very deeply influence how you make that decision about how you’re going to spend your time over the next six to 12 months.

Ryan Holiday: Right.

Tim Ferriss: Right?

Ryan Holiday: Sure.

Tim Ferriss: Because if there’s a sure bet, it’s a $50,000 return, but it’s 80, 90 percent likely to happen—

Ryan Holiday: It’s worth more.

Tim Ferriss: It’s worth more. Right? If you’re thinking about it in a structured way. And there’s some really fun books on investing that don’t necessarily touch on this, and exactly—one is called More Money Than God, it’s about hedge fund investors. It’s a super fun book. It’s kind of like Liar’s Poker, but instead of purely bonds, it’s all sorts of different characters and types of investing.

There are other books, I think there’s one called How to Measure Anything, which is worth taking a look at, that was recommended by the co-founder of Zocdoc named Nick Ganju, who is a fantastic teacher. Really, really good teacher. He’s taught me a lot about music and math.

Math is too scary, it’s just like how to think probabilistically? Because life is probabilities, and whenever for instance, and I’m dragging myself into the deep end a little bit here because I’m not a scientist, but if look at science and studies, you will very—this is another reason to become probabilistically literate, is you’ll be better able to separate fact from fiction, and fact from hyperbole, and medicine and science.

People get so confused about these things, and people end up dying and making bad decisions and choosing quacky doctors without this basic literacy. There’s a great book called Bad Science by Ben Goldacre that I recommend to everybody.

I excerpted some of those chapters in the appendix of 4-Hour Body because I think it’s so important. But suffice it to say, if someone says these studies prove X, it’s not really true.

Ryan Holiday: Right.

Tim Ferriss: They suggest at a high probability—

Ryan Holiday: They suggest for a very small sample size, it has a slightly greater than average probability that—

Tim Ferriss: Yeah.

Ryan Holiday: Yeah.

Tim Ferriss: And it could be an incredibly strong signal, but it is not 100 percent certainty, so—

Ryan Holiday: Might never have been replicated.

Tim Ferriss: It might never have been replicated, there could be experimenter bias, who knows how tight the design was. And it changes how you relate to the world and decisions and opportunities and risks when you start thinking in terms of probabilities.

Ryan Holiday: Yeah.

Tim Ferriss: Right? Because to remove all risk is a fool’s errand.

Ryan Holiday: Right.

Tim Ferriss: I spent a lot of time trying to do that, and chasing that tail end of the last let’s just call it 10 percent of risk, you could spend all your time 24 hours a day every day trying to do that, and you would still not succeed. You just have to lock yourself in solitary confinement in a box and—

Ryan Holiday: Right.

Tim Ferriss: It would be no life worth living. But this has been a real game-changer for me, even though I don’t do—I mean, I invest. Anyone who’s alive invests.

Ryan Holiday: Right.

Tim Ferriss: You are investing time, energy, capital. You’re choosing where to allocate resources.

Ryan Holiday: Sure.

Tim Ferriss: But I read all these books on investing, or Think Twice is another one that’s good, related to cognitive biases, not because I’m playing the stock market at all. That’s not why I’m reading these books. I’m reading it because it helps me to think in a more structured way about good decision-making.

Ryan Holiday: Yeah, I want to come back to the studying thing because I had a question for you, but I was—when we were talking about happiness, money, young, old, Sep Kamvar, who we both know—

Tim Ferriss: Yeah, brilliant guy.

Ryan Holiday: He did this massive study where he scraped all these blog posts about, and social media posts, about what people were saying. I think the book is We Feel Fine, is the result of the findings, but he was talking about how young people, when they say, “I feel happy,” it tends to be followed with statements about accomplishments or activity.

And as you get older, the statements drift steadily towards feeling self-contentment or connectedness, and so we can make a lot of decisions—it’s like we know objectively that’s where we’re going to end up, that’s what we’re going to care about, but then we spend most of our lives focusing on piling up accomplishments.

Tim Ferriss: Mm-hmm (affirmative).

Ryan Holiday: Do you know what I mean?

Tim Ferriss: Yeah.

Ryan Holiday: And knowing—I think that idea of thinking about what you’re going to care about if you are lucky enough to get old is really important, because it puts the things that feel important in perspective.

Tim Ferriss: Yeah, Sep’s an amazing computer scientist.

Ryan Holiday: Yeah.

Tim Ferriss: And just a sweetheart of a guy.

Ryan Holiday: Totally.

Tim Ferriss: And this observation that you just made, and that in younger years, let’s just call it 20s, and maybe 30s or early 30s, “I am happy; I’m doing great because…” and then accomplishment.

Ryan Holiday: Yeah.

Tim Ferriss: Versus the contrast with connectedness and so on when older, raises a lot of interesting questions for me. Right? So is it that, independent of how well someone does professionally, that that shift exists?

Ryan Holiday: Yeah.

Tim Ferriss: Or is it that those people who are being polled happen to be at say, Stanford, where Sep has spent a lot of time? So—

Ryan Holiday: You know people are being—

Tim Ferriss: Oh, this is from blog posts. Okay.

Ryan Holiday: This is unsolicited statements that you make on social media.

Tim Ferriss: Okay, I got it.

Ryan Holiday: Yeah.

Tim Ferriss: So that answers that. It’s important to me, at least, to immediately not be a cynic, but to ask a lot of questions so I understand the nature of what is being implied. Right?

Ryan Holiday: Yeah.

Tim Ferriss: Because could it be that the people who experience or value connectedness in later years, sort of paid their dues, cut their teeth, and therefore they’re like, “All right. I’m on my second home. I have checked off all these rungs on Maslow’s hierarchy of needs. Great, now I can focus on self-actualization.”

Or does that happen independently? I think, if I had to place a bet, I would imagine that it probably happens still, independently, as you become more aware of your mortality.

Ryan Holiday: Yes. I think that’s what it is.

Tim Ferriss: But this is another facet that I think underscores how beneficial it is to study good investors, and that is, or good scientists, but it’s—I think that investing has more sex appeal for a lot of people. The distinction between correlation and causation.

Ryan Holiday: Yeah.

Tim Ferriss: Right? Is it possible that there’s a third or fourth factor that could be causal, or at least highly correlated? Right? So you might see an observational study of some type where women who do yoga between the ages of this and this report a higher level of well-being and lower blood pressure, therefore the headline in some—

Ryan Holiday: Huffington Post is, yes.

Tim Ferriss: Wherever. Therefore, yoga decreases blood pressure and stuff. But wait a second. Where was this done?

Ryan Holiday: Yeah.

Tim Ferriss: Oh, San Diego, okay. What’s the median household income? Okay. What else are they doing? Oh, they have a PPO instead of HMO and they’re seeing some of the best doctors in the country, oh, okay. All right. And you begin to realize how tricky it can be to establish a causation. Right?

Ryan Holiday: Yeah.

Tim Ferriss: But I don’t find, at least the more I dig into this stuff, I find that more enriching and exciting than anything else. I know that it’s frustrating because it means you can’t rely on say most media reports of scientific findings or studies to be accurate, and the claims that are extrapolated.

But at the same time, to me, what it highlights is how much there is in plain sight that is really misunderstood. And that’s exciting for me, because to me that spells opportunity. If it’s possible for instance—there’s some pretty good examples of this.

I think that if you even look at, for instance, before we started recording we were talking about The Big Short, and if we look at some of these mortgage-backed securities, short bets ended up producing these multi-billion-dollar windfalls.

Ryan Holiday: Right.

Tim Ferriss: Some of those positions were based on looking at publicly available data and drawing some pretty common sense conclusions.

Ryan Holiday: Right.

Tim Ferriss: Right? It wasn’t—

Ryan Holiday: We think—

Tim Ferriss:—AI, proprietary AI from the Chinese government that was cracking this code, it was looking at what’s right in front of certain people and seeing something different. And also, asking a lot of questions about incentives.

Ryan Holiday: Right.

Tim Ferriss: Right? If you ask a venture capitalist if things are going to turn south, it’s—They’re highly, highly, highly, highly, highly subconsciously or consciously disincentivized from saying things are going to go south because—

Ryan Holiday: What if they have a large bet that things are going to go south?

Tim Ferriss: Which they would have to have either outsider venture capital so it wouldn’t be associated with their fund, or they’d have to have something like counter-cyclical startup bet, which they may or may not. Right?

Conversely, if you’re looking at say hedge fund investors, I know that’s a term that’s falling out of favor, but nonetheless, people who can place both long bets, “We think this is going up or growing,” and short bets, “We think this is going down or decreasing in value,” their view of the world is going to be very different.

Ryan Holiday: Sure.

Tim Ferriss: And what they’re willing to talk about. Right?

Ryan Holiday: Yeah.

Tim Ferriss: I find it incredibly, both really exciting and entirely terrifying that there are so many blind spots.

Ryan Holiday: Well, Tyler Cowen talks about this with the three-point revolution in the NBA. Three-pointers have always been worth more than two-pointers, and so you can miss a higher percentage of them and still score more points. Right?

Tim Ferriss: Yeah.

Ryan Holiday: So percentage making of a three-pointer is on average worth more than a field goal. Right?

Tim Ferriss: Yeah.

Ryan Holiday: And he’s like, people were paid millions of dollars, billions of fans watch this thing, and no one was like, “Hey, why don’t we shoot more three-pointers?”

Tim Ferriss: Right.

Ryan Holiday: And then somebody did it, and the entire game changes.

Tim Ferriss: Yeah. I wonder who that was? Steph Curry or someone comes in and just—

Ryan Holiday: But that it was even, not just within our lifetime, it was within the last half decade—

Tim Ferriss: Yeah, yeah.

Ryan Holiday:—that the game fundamentally changed. And it’s not like they’ve figured out the physics of shooting the three-pointer better, just now there’s incentives and so people shoot more three-pointers and they make more and the—a game literally that millions of people watched, just nobody noticed this thing right in front of them.

Tim Ferriss: Yeah, yeah. Or if you look at certain inventions. Right? Wheels on luggage.

Ryan Holiday: Yeah, we were talking about this.

Tim Ferriss: For God’s sake, you know?

Ryan Holiday: Yeah, right.

Tim Ferriss: How long did that take? And it’s sitting there, right in plain sight.

Ryan Holiday: Yeah.

Tim Ferriss: And I think there are still, I mean, practically an infinite number of opportunities like that. And for me at least, it all comes from just a better set of questions and if you look at the process behind, or that has been developed at places like IDEO or frog Design or these different product development and industrial design firms, a lot of it’s asking questions. Right?

Ryan Holiday: Yeah.

Tim Ferriss: And trying to not just test the assumptions but find the assumptions, identify the assumptions in something like grocery cart design. Right? What if we’re just completely taking it for granted because this is the way it is and this is the way it’s always been?

Ryan Holiday: Yeah.

Tim Ferriss: And I find that really exciting. When it comes to—and I like to try to ask a lot of those questions. There’s a great documentary called Objectified.

Ryan Holiday: Yeah.

Tim Ferriss: Which is about a lot of this. And then, I saw it a long time ago, maybe by the same filmmakers, I believe, who did a film called Helvetica.

Ryan Holiday: Such a good—I remember it, yeah.

Tim Ferriss: Yeah, such a great doc, that brings up a lot of this and when I see something that doesn’t make sense or it doesn’t feel good, it doesn’t work well, I like to ask a lot of questions and also combine that with studying incentives.

Ryan Holiday: Yeah.

Tim Ferriss: Is there any reason besides a design blind spot that there weren’t wheels on luggage earlier? Is someone incentivized in such a way that would make that—did that idea exist 30 years ago but whatever, but it never came to fruition? And if so, why might that be the case? Okay, let’s do that as a thought exercise.

Ryan Holiday: Yeah.

Tim Ferriss: For instance, I remember when—Uber is a great example of this, right? I mean, I was involved with Uber before it was called Uber, it was Uber Cab LLC way back in the day, like 2008.

Ryan Holiday: Yeah.

Tim Ferriss: And we’ll just refer to it as Uber for simplicity, was widely mocked. It was put on AngelList, which is another company I’m involved with, angel.co, if people want to check it out. It was offered to investors and turned down, I want to say by hundreds of investors, as ludicrous.

Ryan Holiday: Yeah.

Tim Ferriss: And the math behind some of the ridicule looked at the existing market for, I want to say black sedan car services and limousines. In that analysis, in retrospect, we can see there were a bunch of false assumptions.

Ryan Holiday: Right.

Tim Ferriss: Right? They thought it was always going to be high-priced, where many things start out being prototyped among the privileged.

Ryan Holiday: Yeah.

Tim Ferriss: Recycling, another great example of that. But then, with scale, prices go down. They also assumed a relatively fixed market size. It’s like, “Here’s the existing market of black sedan use; we only see X percent of single-digit growth. This is a shitty business because they’ll never capture more than Y percent.”

Ryan Holiday: Right.

Tim Ferriss: Missing the possibility and ultimately the reality, which was that ride sharing would create, expand that market exponentially and create its own market. All right? And then you look at let’s just say incentives of media coverage.

Ryan Holiday: Yeah.

Tim Ferriss: Right? Okay. At the time, and even more so now, it’s very much in fashion to sort of attack anything that seems like it’s catering to the one percent. Right? Even though it’s really critical to prototype with people who are price-insensitive in the early stages of a lot of product development because—

Ryan Holiday: Sure. If you’re subsidizing—

Tim Ferriss: If you’re making one-offs, they’re going to be fucking expensive, and if you’re testing things and it’s very rough around the edges, you can have these rich people, exactly, subsidize the product development that will ultimately lead to mass adoption.

Ryan Holiday: Yeah.

Tim Ferriss: I find the whole thing just endlessly fascinating.

Ryan Holiday: Yeah.

Tim Ferriss: And I think it’s also safe to assume that at almost any given point in time, that almost everybody’s getting it wrong.

Ryan Holiday: Yeah.

Tim Ferriss: With many, many, many, many, many things. And that, to me, says that if you just have—because this is not an intrinsic capability that I have. This has been, if we’re talking about it from an investment perspective, or opportunity-spotting perspective, it is absolutely something that I have honed over time.

And there are many people much better than I am, but when I’ve found questions I like, I borrow those questions and I put them into an Evernote notebook, under investing. Okay. I have these questions. When people point out misperceptions to me, and I’m like, “Holy shit, I totally missed that. How could I have missed that?” I write those down.

Like, “Wow. This never would have occurred to me. Now that they’ve said it, it’s entirely self-evident. How did I miss that?” Right? And why did they not—”Wait, why did they not miss it?”

Ryan Holiday: Yeah.

Tim Ferriss: I really think about these things. And over time, you can develop this very learnable skill of seeing things that other people don’t see, which for me is mostly a byproduct of asking a lot of questions.

Ryan Holiday: Well, that actually ties into what I was going to talk to you about next. There’s a quote—in Ego Is the Enemy, I have a quote from Bismarck, where he says, “Any fool can learn by experience, so I prefer to learn by the experience of others.”

Tim Ferriss: Right.

Ryan Holiday: And it seems like—so you’re doing experiments, you’re doing trials, but you’re also—it seems like that’s one bucket of learning for you, then the other bucket is a network of smart people you ask lots of questions of, and then the third one is you read widely and deeply from different kinds of books, from history, from philosophy, from psychology. So you’re not spending 30 years of your life learning a lesson you could’ve learned on a $3 used Amazon purchase.

Tim Ferriss: Oh, yeah. Yeah, I much prefer to not make my own mistakes if I can avoid it, recognizing that of course I’m going to make all sorts of terrible mistakes. To give an example of the second category, learning from other people and how I might approach that, we can talk about something we were discussing very briefly before we started recording, which is right now I’ve noticed and my team has noticed some kind of a odd behavior when it comes to email deliverability and open rates.

And we have a, by most measures, a large list, 1.5 million or something like that, for 5-Bullet Friday and these various newsletters. And we have already looked on Google, we’ve already talked to some of the parties involved, but these parties have various incentives that may or may not be totally aligned with ours.

Not to say they’re in any way malicious or nefarious, it’s just different companies, different people, different parties, and a different collaboration or transaction at different setups. So I and my team have been putting together an email, a draft email, to send to people like yourself.

It’s really five or six people I know already who have large lists, to ask a handful of questions. But if I simply email all of you with a handful of questions, it’s a very one-sided interaction.

Ryan Holiday: Yeah.

Tim Ferriss: Right? I’m asking someone to take time out of their day to help me with nothing in return. So what we’ve done is underneath each question, we are adding what we’ve tried. We’re like, “Here are the three things we’ve already tried to address this. Here are the results, but we’re still looking for more. What have you done, or what would you do?” Right?

Step one, or Question 1, Question 2, Question 3, Question 4. And that could at some point turn into, “We were joking earlier, the conversion cabal, registered trademark. I am funnel, here we go.” I’m not going to do that, but that could turn into some type of brain trust.

Ryan Holiday: Sure.

Tim Ferriss: With a handful of people who then exchange best practices, right, where everyone is currently—or most people are—very silent.

Ryan Holiday: Yeah.

Tim Ferriss: So they’re all trying to solve similar problems and have similar aspirations, yet, even though all the newsletters that I’m thinking of, which are owned by people like yourself and these other folks, they’re all non-competitive. They’re all in different areas with different demographics.

And it would make a lot of sense to have some information exchange and that will start, the initial volley will be this email. Right? Where I’ll share a bunch of stuff, and we may or may not get replies. I hope we get replies. That would be an example of trying not to just make our own mistakes.

Ryan Holiday: I’m going, tomorrow, I’m flying to Arizona, and I’m meeting with five or six authors who you know, we go to this house in Sedona.

Tim Ferriss: Yeah.

Ryan Holiday: Each one of us has sold hundreds of thousands of books, best-selling authors, and we just shoot the shit about stuff that’s going on. We ask each other questions, and you could even argue that some of us are competitive. I don’t think books are competitive, but the point is why would we compete where we don’t need to compete?

Let’s compete on making great stuff, and let’s get the—you know what I mean? That’s what’s been amazing for me with sports, watching these coaches give book recommendations to each other. You think they would be competitive, but it’s like actually they’re getting the easy stuff out of the way, and then on Sunday, they’re competing.

Tim Ferriss: Yeah.

Ryan Holiday: And I think people can be really precious with information, when actually, you’re almost always better sharing information.

Tim Ferriss: Yeah. And on top of that—I can very safely give my playbook for almost anything to thousands of people and almost no one’s going to implement any of it. I mean, that’s not to say that prescriptive how-to stuff doesn’t get used, it does.

Ryan Holiday: Right.

Tim Ferriss: Particularly when it’s simple, right? Like slow-carb diet, 4-Hour Body. Hundreds of thousands of people, maybe millions, have used this diet successfully. It’s simple, it’s easy to follow. Everyone is following a diet, whether they choose to or not, but when it comes to say launching a book, and I lay out this monstrous post because I got tired of answering these questions as one-offs.

I think it’s called How to Publish a Bestseller. How to Publish a Bestselling Book This Year, or something like that. How to Write a Bestselling Book This Year. I can’t remember the exact title, but it’s this monster compilation post of everything you can imagine related to writing, prepping, titling, publishing versus self-publishing, marketing, PR, all of it. Blurbs, you name it.

Every stone is turned. And people don’t do it. They’re just like, “No, I want the silver bullet, easy answer.”

Ryan Holiday: They’re like, “Can I hire someone to do that for me?”

Tim Ferriss: Yeah.

Ryan Holiday: Yeah.

Tim Ferriss: And it’s like, “Yeah, no. I mean, maybe you can, but this is my blueprint. I’ve used it repeatedly, it works. But guess what? You still have to write a fucking good book.”

Ryan Holiday: Right.

Tim Ferriss: And not to say my books are the best in the world, they’re not, I mean, I would like to think they’re very useful, but I’m not Tolstoy. I recognize there are better writers out there.

Ryan Holiday: Sure.

Tim Ferriss: Nonetheless, I take the vast majority of energy and it goes into the writing, but man, yeah, it’s pretty wild how little adherence there is.

Ryan Holiday: Well, to go to that last bucket, maybe that’s a place to wind up. What do you think about reading? How do you find what you read? What’s your methodology for breaking down books? Where do you get the knowledge that saves you painful trial and error?

Tim Ferriss: I very rarely read anything that isn’t recommended to me by either someone I know is very selective and snobby about book choice.

Ryan Holiday: Yeah.

Tim Ferriss: Like say, Naval Ravikant or my brother. There are certain people who already have such a tight filter that anything they read has passed a very high bar, and anything they recommend has passed an even higher bar.

Ryan Holiday: Yeah.

Tim Ferriss: That is one way I get books referred to me that I take seriously. Another would be triangulating multiple points of recommendation, and then very often what I’ll do is let’s just say I get a book recommended from people on social media, or readers or listeners. And I will prompt recommendations quite often, by asking for the best books on a certain topic.

And perhaps a year ago, or two years ago, I was very interested in learning more about the contemporary art world, not just the artists but the gallerists and—

Ryan Holiday: Yeah, the whole industry.

Tim Ferriss: The entire industry, the market, the black box, all the craziness that goes into that. And this book called The $12 Million Stuffed Shark popped up repeatedly.

Ryan Holiday: Yeah.

Tim Ferriss: I’m like, “Okay. Let me take a look at that.” And I looked at it, seemingly written by an economist, I go down then on Amazon in this case to the reviews. I don’t read the one-star reviews, because they’re like, “I thought this was an Instapot. This is stupid.”

Ryan Holiday: “Mine came damaged in the mail.”

Tim Ferriss: Yeah, or it’s just they clearly didn’t read the description, they’re like, “This wasn’t a novel at all.” It’s like, “Yeah, dummy. It’s not a novel.” So I don’t read the one-star, I don’t read the—what is the highest? Five stars?

Ryan Holiday: Yeah.

Tim Ferriss: I don’t read the five stars, I will read the most helpful three and four-stars.

Ryan Holiday: Right.

Tim Ferriss: Because I already have the gestalt, if the reviews are more than a few hundred reviews, I make the assumption that it is more or less reflective of the reality of the book.

Ryan Holiday: Yeah.

Tim Ferriss: Amazon reviews can very easily be gained on a smaller level, but most authors are not going to be motivated enough to do it over a long period of time, so I assume if there are hundreds of reviews, or even a hundred plus, and I look at them and there are substantive reviews, that the overall star ranking is a broad indicator of how much people have liked the book.

Then, I look at the most helpful three and four-star reviews, because they will very often be, say, three paragraphs to two pages long, and they will really accurately lay out the structure of the book and the strengths and weaknesses of each—

Ryan Holiday: Sometimes they make you read the book better because you—sometimes it spoils what’s in the book, but then you actually understand it when you’re reading it.

Tim Ferriss: Yeah, absolutely. So I do that. And if at that point I’m interested, I download it on Kindle, I try to do almost all of my reading on Kindle, which gives me the ability to highlight very easily, and then I can go to a notebook on Amazon or use any number of other services to grab those highlights and look at them on laptop, put them into Evernote, whatever it might be.

But before I get there, I will look at the most popular highlights. I will also look at Goodreads. I like looking at Goodreads for quotes from given books. If you don’t like—if you don’t love—some of the quotes from the books, that’s like hating the movie trailer and then going to see a three-hour movie.

Ryan Holiday: Right.

Tim Ferriss: You’re not going to like the movie.

Ryan Holiday: Yeah.

Tim Ferriss: So I look at Goodreads, and let’s just say then I have the Kindle version, I will—I’ll read two chapters, three chapters, and if I don’t—if I’m not really grabbed, if I don’t want to take a photograph of some of the highlights and send it to a friend, I will consider stopping reading.

Ryan Holiday: Because life’s too short?

Tim Ferriss: Life’s too fucking short. Tim Urban of Wait But Why has so many great pieces, and one is called The Tail End, and he talks about the number of books he’s likely to read in the rest of his life, and it’s a shockingly frighteningly low number—

Ryan Holiday: Small number, yeah. Totally.

Tim Ferriss: So I don’t have enough time left in my life, if we’re assuming I’m going to die, and I’ve looked at the death ages of my grandparents, great-grandparents, et cetera. Then I’ve isolated the males and I’ve looked at it.

Ryan Holiday: Yeah.

Tim Ferriss: So there’s a pretty decent chance I’ll die somewhere between 80 and 85. I’m 43, there’s not that much time left, especially if you consider sort of cognitive decline and so on.

Ryan Holiday: Yeah.

Tim Ferriss: Right? So I’ve got, let’s just call it, who knows? 20 or 30 years left of good book reading—

Ryan Holiday: You could also get hit by a bus.

Tim Ferriss: I could get hit by a bus. So all that is to say I don’t have enough time to even read the classics I know the titles of.

Ryan Holiday: Right.

Tim Ferriss: Right? That I’ve heard of, I don’t have time for that. I don’t have time to read all of those, so the idea that I would pick up a book and think to myself, “This is pretty mediocre,” and dedicate a week to reading it is pure insanity. So I drop a lot of books.

I put up a blog recently looking at everything I read in 2019, all the books and my favorite articles. And I included all the books I bought from Amazon, and I ended up completing somewhere between 30 and 40 percent of all the books that already made the cut to the point that I bought them.

Ryan Holiday: Sure, sure.

Tim Ferriss: And some of those I simply just never got around to, but a lot of them, I stopped.

Ryan Holiday: I like the rule of 100 pages minus your age.

Tim Ferriss: That’s the taste test?

Ryan Holiday: Yeah, that’s when you quit.

Tim Ferriss: Oh, okay.

Ryan Holiday: So as you get older, you become more ruthless, as you’re younger, you have to give it—because you don’t know what the fuck you’re talking about!

Tim Ferriss: Yeah, yeah.

Ryan Holiday: And I like that.

Tim Ferriss: I like that.

Ryan Holiday: Yeah.

Tim Ferriss: I like that as a—

Ryan Holiday: But no, I think people are, they’re like, “I paid for this.” That’s the sunk-cost fallacy; they’re like, “I paid for this, I should finish it.”

Tim Ferriss: Yep.

Ryan Holiday: It’s like, “You hate this book, so you’re going to give it hours of your life, weeks of your life, just to prove that you could finish a David Foster Wallace book?” I mean, come on.

Tim Ferriss: I know. And I was just thinking, one way you could maybe trick yourself into making better decisions with books is to imagine that the book you’re reading is someone you’re having dinner with, and it’s like, would you really sign up for five more dinners with this person?

Ryan Holiday: Right.

Tim Ferriss: If this is how you felt while you were reading it?

Ryan Holiday: Sure.

Tim Ferriss: No, you wouldn’t.

Ryan Holiday: Right.

Tim Ferriss: And the—

Ryan Holiday: You’d make up an excuse and you’d leave the dinner you’re already at.

Tim Ferriss: Yeah, exactly. Books are also a great way to procrastinate, sort of a socially validated way to procrastinate, so I try to be ruthlessly honest with myself about that.

Ryan Holiday: Interesting.

Tim Ferriss: There are a lot of great books out there.

Ryan Holiday: Yeah.

Tim Ferriss: I could spend all day every day reading great books, and produce absolutely nothing of value.

Ryan Holiday: Yeah.

Tim Ferriss: So I have increasingly tried to block out time. I have less—I would say less and less—time I dedicate to reading.

Ryan Holiday: Really?

Tim Ferriss: And I’m going to be publishing a post this week, which is a public pronouncement, which helps with setting policies for saying no, describing why I’m not going to read any new books in 2020. So anything that is published in 2020, not—

Ryan Holiday: Oh, that’s—my general rule is that almost always go towards older books—

Tim Ferriss: Can I say one thing?

Ryan Holiday: Yeah.

Tim Ferriss: So I’m going to put out that post also to hold myself accountable.

Ryan Holiday: Right.

Tim Ferriss: Right? Because if I get caught then reading something new, it makes me look like a liar or a hypocrite. And I use [crosstalk 01:50:28]. Oh, I definitely won’t want to do those, and don’t want to do those. So this a single decision that makes, as Greg McKeown of Essentialism, which is a great book I recommend, would say—

Ryan Holiday: Not new anymore, so…

Tim Ferriss: Not new, yeah.

Ryan Holiday: So you can read it.

Tim Ferriss: Oh, yeah. Yeah, that’s a fantastic book. Looking for the single decisions that remove hundreds of decisions. Right? So not reading any new books in 2020 removes a lot of decisions. If someone’s like, “Oh, my God, you should read this book, it’s new.” Sorry, can’t do it.

Ryan Holiday: Right.

Tim Ferriss: Right. It preserves so much of my cognitive decision-making bandwidth and energy for other things, to make that one public, and for me public is to a large audience but for other areas of my life, I make public commitments to one or two or three friends, or to my girlfriend, so that they can hold me accountable.

Ryan Holiday: Sure.

Tim Ferriss: I find great value in that. If you’re trying to guard against your lesser self, I find that really useful.

Ryan Holiday: No, and I think with—the cost of a book is financial, primarily time, and then what you’re going to put in your brain. I don’t want to read things that are going to be subsequently or very quickly proven irrelevant or proven incorrect or out of fashion. You’d be better off sitting down and reading Shakespeare’s plays because that is—

that has not only had 500 years of cultural impact, but will probably have 500 more years of cultural impact, so I think looking at the half-life of information and deciding to consume information that’s likely to remain true over time, it forces you to be both more general but also more timeless.

Meanwhile, if you read a book about the first year of the Trump presidency, or how many books—a couple of years ago, or a year or so ago, somebody wrote a book about Uber, and then the founder was fired shortly after the book came out. The guy who finished that book wasted his time because it’s already irrelevant by subsequent events, and I think we have a newness bias that prevents us from accumulating wisdom where we could be finding it.

Tim Ferriss: Yeah. I’m more interested these days in the pieces of the puzzle, and by the puzzle we could be talking about anything, right?

Ryan Holiday: Sure.

Tim Ferriss: We could be talking about human behavior, we could be talking about the rise and fall of nations that are kind of like the tectonic plates.

Ryan Holiday: Sure.

Tim Ferriss: I’m more interested in those because there’s a bit more certainty and a higher degree of confidence in identifying and understanding some of those elements. Right? If they’ve been shown over and over again throughout history, or proven—or I suppose based on what I said earlier, shown to be very likely repeatedly in science. Right?

Ryan Holiday: Yeah.

Tim Ferriss: This all makes me think of this quote by, I’m thinking I’m getting the name right, Donald Knuth, K-N-U-T-H, who was at, I want to say IBM. Might be IBM, but doesn’t really matter. The point being he stopped using email at one point.

Ryan Holiday: Yeah.

Tim Ferriss: Completely stopped, and he said for people who want to stay on top of things, email is great, he’s like, “But I want to get to the bottom of things.”

Ryan Holiday: Ooh.

Tim Ferriss: And I’ve thought about that a lot.

Ryan Holiday: Yeah.

Tim Ferriss: Because keeping on top of things is a losing game.

Ryan Holiday: Yeah.

Tim Ferriss: It’s just—

Ryan Holiday: By definition, stuff’s happening.

Tim Ferriss: It’s a losing game, and there are people who’re going to be more dedicated and obsessive with current affairs. I have no competitive advantage, I have no information advantage. I actually have a lot of information advantage, but I have no desire or behavioral advantage with current events.

Ryan Holiday: Right.

Tim Ferriss: And it also breathes emotionally and physically a life driven by cortisol and FOMO and so on, whereas if I am able to discipline myself enough, which I partially do through this public accountability, to focus on studying things that have endured, I just feel much better in life in general, and I make better decisions.

Ryan Holiday: Look, they didn’t have the news 250 years ago. You know what I mean? They did fine.

Tim Ferriss: Yeah. Yeah, yeah. Yeah.

Ryan Holiday: They did fine.

Tim Ferriss: Yeah, they did just fine. So, oh man. Yeah, the news. Happy to miss the news.

Ryan Holiday: Yeah, of course. Of course. I’d rather have truth than trivia.

Tim Ferriss: So Ryan, I suppose this is the time when we say goodbye.

Ryan Holiday: Yep.

Tim Ferriss: Tearful, tearful, Stoic, Holiday goodbye.

Ryan Holiday: Yeah.

Tim Ferriss: Where can people find you online, learn more about you? What would you like to tell people about your current projects?

Ryan Holiday: Yeah, maybe check out Daily Stoic, which is a Stoicism-inspired email each morning, also @dailystoic on most platforms, and then I’m Ryan Holiday, pretty much any bookstore.

Tim Ferriss: Across the socials and across the bookstores.

Ryan Holiday: That’s true. Yeah.

Tim Ferriss: If people look at your selection of books and think to themselves, “I don’t know where to start,” where would you suggest people start with your writing?

Ryan Holiday: That’s a good question. I’d start with The Obstacle Is the Way, or Stillness Is the Key. Depending, it’s like if you’re going through something tough, I’d start with The Obstacle Is the Way, if you’re maybe dealing with some of the stuff we were talking about, which is sort of life optimization, what do I want? How do I manage? Maybe I’d do Stillness.

Tim Ferriss: All right.

Ryan Holiday: Yeah.

Tim Ferriss: And there you have it folks. Thank you, Ryan.

Ryan Holiday: Yeah. This was awesome.

Tim Ferriss: And as those listening probably know, this is Tim Ferriss, signing off for now, thank you for listening, and until next time. Experiment well, experiment widely, and test those assumptions.

The Tim Ferriss Show is one of the most popular podcasts in the world with over 400 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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