The Tim Ferriss Show Transcripts: Josh Waitzkin and Tim Ferriss on The Cave Process, Advice from Future Selves, and Training for an Uncertain Future (#498)

Please enjoy this transcript of my conversation with Josh Waitzkin, author of The Art of Learning: An Inner Journey to Optimal Performance. Josh is an eight-time national chess champion, a two-time world champion in Tai Chi Chuan Push Hands, and the first Brazilian Jiu-Jitsu black belt under nine-time world champion Marcelo Garcia.

For the past 13 years, Josh has been channeling his passion for the outer limits of the learning process toward training elite mental performers in business and finance and to revolutionizing the education system through his nonprofit foundation, The Art of Learning Project. Josh is currently in the process of taking on his fourth and fifth disciplines, paddle surfing and foiling, and is an all-in father and husband.

Transcripts may contain a few typos. With some episodes lasting 2+ hours, it can be difficult to catch minor errors. Enjoy!

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Tim Ferriss: We have beautiful Ossa, Dutch shepherd of small stature next to us, growing quickly. We have Josh Waitzkin, polymath of medium stature. This is the Tim Ferriss Show. I’m Tim Ferriss.

And Josh, baby. It’s good to see you again.

Josh Waitzkin: That’s an interesting label, polymath of medium stature, Timbo. That’s good. I like it.

Tim Ferriss: I’ve got excellent coffee, strong, to fuel our conversation.

Josh Waitzkin: Yes.

Tim Ferriss: I feel good about this thing.

Josh Waitzkin: Me too, because I’m going to turn the tables on you a little bit.

Tim Ferriss: Yeah. Let’s get into it.

Josh Waitzkin: Our plan here is for me to interview Tim a little bit, and open up some questions, and we’ve been having a beautiful few weeks of dialog over meals, and ice plunges, and saunas. Over the last bunch of days have been really intense conversation. And one of the patterns I find really powerful in our dialog is that when we talk about ideas, and potential projects, you consistently have the ability to ask gating questions that frame the discussion differently.

And I tend to think I’m pretty good at that, but what I find surprising is how, and one thing I love, is when I bring ideas to you, you take it to another level, and it’s consistently jolting, and after our conversations I often look at something quite differently, and I love that. And so, how would you deconstruct your relationship to gating questions? How do you approach them?

Tim Ferriss: Let’s do a deep dive. First, could you define, or describe, for me what a gating question is?

Josh Waitzkin: If we’re talking about an idea, or let’s say someone were to approach you with a project that they’re thinking about, you tend to go at it with first principles, and you have a way of approaching the subject with a different framing, and so I observe your approach exposes, like in the David Foster Wallace This is Water, a fish isn’t aware of its water, you are very good at showing people what their water is, and you have a way of tackling the subject that they’ve been thinking about for days, or weeks, or months, or years, and very quickly showing them angles of it that they haven’t considered.

And I’ve watched you do that with a lot of people. I think it’s one of your power zones, and I just thought it would be really cool for you to talk about how you approach it.

Tim Ferriss: Yeah, this is fun. I don’t often talk about this, or I suppose even think about it explicitly. When I talk to folks who are presenting an idea, a plan, a hope, a goal, I think the first thing that I do, and this is probably honed over many, many, many years of getting pitched hundreds of times with startups is there are a few stock questions, so I think I cheat in that respect.

I have a handful of triage tools that I use on the intake, so if somebody comes in just like, “Are you having trouble breathing?” Let me check your pulse. Let me check your vitals, and there are a few questions like that that I use repeatedly. One would be asking someone what assumptions they are making to see if they’re even consciously aware of the assumptions that are being made, which is also a really good test to see how rigorously they’ve examined other aspects of whatever the plan or goal might be. What makes this attractive? What are the aspects of this that you assume to be true that make this attractive if it’s an idea, or something like that.

The answer they give, or don’t give, it’s like the Sherlock Holmes, the case of the dog not barking, sometimes it’s the answer they don’t give that really says a lot, and removes the need for a lot of follow-ups. Another one that I ask all the time, and I think this is in part because I get asked a lot about writing books. I’m thinking about writing a book, or I’m about to start writing a book, or I’m going to be selling a book, and I’ve talked to dozens of friends about this, and the way I pose it, and this will sound familiar is I’ll ask them if it takes twice as long and you get half the rewards, or a quarter of the rewards, and it’s not a best-seller, is this still a no-brainer for you?

The wording there is really important, the no-brainer part is important. It’s not “Is it still a good idea?” because a good idea could be pro and con list, and you come to the conclusion 51 percent good, 49 percent bad. Yes, it’s a good idea. That’s different from a no-brainer. If it’s a whole-body yes —

Josh Waitzkin: This question is fishing for how intrinsic the motivation is?

Tim Ferriss: It’s fishing for how intrinsic the motivation is. It’s also fishing for a few other things. The first might be worded a different way in the case of books. Is it easier to write the book than to not write the book? For me, I rarely, and there are different motivations for writing books, there are different catalysts, but for me usually I can’t find something I’m looking for and it bothers me so much that I just have to write the goddamn thing because I’m not going to have it otherwise, and in that respect it’s easier for me to write it than to not write it, because it bothers me so much that it’s not written in some way.

The other is taking into account all of the things outside of our control. You could put the perfect plan into motion. You could write an outstanding book, just a genre-defining, category-killing book, and then 9/11 happens the week of your book launch, and nobody ever sees your book in effect, because it’s crowded out. there are so many things outside of our control. Certainly, the last year has highlighted that, and so I want to know are you going to in some sense find reward, and gratification, and edification through the process in case a curve ball hits you square in the face because it’s not a black swan event?

It’s very common that this happens. If you just come out in the wrong week in the case of books. Those are two questions, and then for me I think in the last handful of years in particular thinking of energy management over time management has led me to think of experiments that can be done that might be alternatives to what people are considering that allow them an easier termination clause, if that makes any sense. I’m using that metaphorically, but it’s sometimes very easy to get into plans, and then you have employees, or you have a company, or you have your identity potentially wrapped up in something that has gone out, and now you feel like you can’t remove yourself, or shut it down, because it will be viewed as a failure.

To mitigate against all those things I’m constantly looking for cheap, fast ways to test. How can you test your assumptions? How can you test your assumptions about the upside? How can you test your assumptions about the downside? How can we find comparables? Have you spoken to any of the people who are at the helm of X, Y, Z at those comparables? I really don’t view myself as a risk-taker even though at points I’ve had that label, or reputation, but I view myself as first and foremost a massive risk-mitigator. I do a lot of testing. Those are a few things.

Josh Waitzkin: If you were to invert that, if you think back on to all those conversations you’ve had with people pitching you on something, if you were to take their perspective, what do you think the patterns would be in what those people said about the insights they gained from the conversation, not the tactics, but the insights about themselves and how they relate to their project?

Tim Ferriss: I look at everything with an editorial eye, which is part of the reason why I almost never read friends’ manuscripts, because I can’t just give them a paragraph of feedback. I’ll end up copy editing the whole goddamn thing. When I look at a deck, like a pitch deck, and then I go down a level deeper and I look at the bios of the people involved, I spot weaknesses and red flags that would turn off, oftentimes, other investors they want involved, or the types of investors they would want involved.

I’m answering this somewhat indirectly, but I get to see also how founders in the case of startups, but this could apply to almost anything, this could apply to books also, book ideas, it could apply to any idea, how people respond to constructive criticism. And what’s really interesting about not just startups, but book ideas, business ideas, career switching ideas that people have is very often people around them feel like support means giving positive feedback, so their baby, even if it’s ugly, never gets called ugly.

And then, I come in, and I’m like, “Well, the first thing I noticed is on the first page of your deck you misspelled profile. It might seem like a minor thing, but I would fix that.” It’s low-hanging fruit. It’s easy to fix. And that’s not a massive correction, but I get to see how people respond to that. Another question, there are a lot of questions I like to ask, and this was a question I was asked in the last year, I want to say. I can’t recall the source, but it’s not mine. I borrow most of what I use and ask.

And the question is: flash forward three years, the company has failed, what went wrong? What is the most likely reason the company will have failed? Also, if it’s due to an incorrect assumption, which assumption do you think is most likely to be wrong? And if someone can’t answer that, or is unwilling to answer that because they’re getting a lot of adulation, and say in the case of a startup they have more demand, in other words investor interest than supply, that’s definitely a red flag for me.

What people get to see then, if they really take those questions seriously, and assuming someone else hasn’t asked those questions, is they very often find blind spots that are real risks. There are risks that they have not accounted for. Like most authors think, or potential authors, if I get the right publisher, if I have the right distribution, and I write an amazing book, it is inevitable that the book will do well if I follow a few guidelines for launch if I’m on a big show, and that’s just not true.

Josh Waitzkin: Yep. Building on this, one of the themes that I spend a good deal thinking about is the entanglement of genius and eccentricity. I think that most of the great performers that I’ve known, or competed against, or worked within different fields just had this beautiful connection between their areas of dysfunctionality and brilliance. Sometimes the very thing that helps them excel in their professional life, or their artistic life, or their competitive life, is something that in their personal life can be a little bit awkward. Right?

Tim Ferriss: Or sometimes very awkward.

Josh Waitzkin: Or something very awkward, and it can be extremely subtle, and it can be fascinating like the recent study of Usain Bolt’s stride and the fact that it’s uneven. People might want to normalize it, but then you can think about how the unevenness of his leg length, or spinal construction, might actually be part of why he is so fast. I think about it a great deal with Marcelo Garcia, and he and I have been having a fun conversation about this theme over the past few days.

Tim Ferriss: For people who don’t know him, just a sentence or two on Marcelo.

Josh Waitzkin: We’ve spoken about Marcelo so much.

Tim Ferriss: I know.

Josh Waitzkin: Marcelo’s the nine-time submission grappling and Brazilian jiu-jitsu world champion. He’s probably, I would argue, pound-for-pound the greatest martial arts grappler to ever live, and he’s a dear friend of mine. We own a school together in New York, and I’ve trained with him for a decade plus, and really an exquisite learner, and a really interesting eccentric learner.

Anyway, this theme of the entanglement of genius and eccentricity is one that I find to be liberating for people because there is a big pressure to normalize oneself.

Tim Ferriss: How does that show up for Marcelo, or why did you bring him up after Usain Bolt?

Josh Waitzkin: I think Marcelo is in a similar league in terms of dominance of his field, and he’s someone who’s really built a game around his idiosyncrasies in a beautiful way. Physically, he’s physically small, short, short limbs, has been an incredible technical repertoire that really revolutionized the Brazilian jiu-jitsu world based on his body type, and the idiosyncrasies of his personality, the way his mind works, his incredibly overdeveloped somatic intelligence versus his many years ago lack of conceptual relationship to what he was doing.

For example, one of the remarkable things about Marcelo is the way he repeats mistakes less than anyone I’ve ever known. It’s incredible, whether it’s a technical mistake, a psychological mistake, and I’ve observed this. I’ve felt this with him. We’ve spent hundreds of hours grappling, sparring, fighting on the mats, and you catch Marcelo with something one time and you don’t catch him with it again, and that’s just not true about people. It’s incredible.

Tim Ferriss: Usually, it’s the opposite.

Josh Waitzkin: Yeah. If you explore a weakness, you can now exploit it.

Tim Ferriss: It’s like when I got guillotined 77 times in a row at your school.

Josh Waitzkin: Oh, yeah. That was a good time with that one. The amazing thing about, for example, how that manifests in Marcelo’s life is that as he’s told me in really powerful moments of conversation he experiences pain really viscerally. He experiences pain and his body never forgets it in his life, and it’s true on the mats, and so there’s an area that could really make life painful, but that is incredibly powerful in his life.

I think about this a lot relative to myself as well, this entanglement, but I was curious to open up with you. You have a public life, and you and I mostly interact outside of your public life in just the eccentric nature of our friendship, meeting up in the jungle four weeks at a time and having great conversations. And I have my own perspective on this, but I’m curious how you would talk about — you’re so admired in the world, and people think a lot about your brilliance, and your ability to deconstruct, and how much insight you have. How would you describe the underbelly of that? What’s the shadow of it? How does that brilliance manifest in your personal life? Where are the areas of eccentricity or dysfunctionality that people might not see?

Tim Ferriss: I’m glad you used the word dysfunctionality because sometimes eccentricity can be used as a nice substitute for crazy when somebody is successful in a given field, so it’s true, but different adjectives sometimes apply to the same thing depending on how well someone was done by luck, or design, or both, and it shows up a lot. It shows up a lot in many, many different ways, and I’ve thought about this quite a bit because there have been times when I’ve wanted to, and there still are times, warranted times when I want to fit certain dysfunctionality, and there’s occasionally a fear that in attempting to snuff out those areas of dysfunction, or those exhibitions of eccentricity that I’ll also snuff out whatever the pixie dust is that allows me to do certain things.

This is very true I know for a lot of comedians for instance. Some comedians don’t want to get therapy. They don’t want to fix the pain because they feel like the gift that pain provides is a certain degree of insight or cynicism, and also wittiness, that leads to what they’re able to do, which is a really tough position in a lot of respects to find yourself in, or to put yourself in. I’d say on the more amusing side of things a good example would just be, as I mentioned, the editorial eye. Let’s take that same editorial eye, that seems like a huge gift when you’re reviewing a manuscript, but when you look at a countertop — and I’ll give a friend of mine a nod here. I won’t mention his full name, but Popi. Let’s call him Popi.

Josh Waitzkin: Popi. He’s a character.

Tim Ferriss: I was with Popi in Panama at one point. This is a very long time ago. This is 2004, so for those who have read The 4-Hour Workweek, this is right before I went to Argentina, and had the entire saga of tango unfold. I was in Panama, and it was actually a friend of his, initials JM, Micho, who said I had to go to Argentina. But backing up to the point I was going to make, I would sit there, and I would write, and I was working on various things at the time, and I was running this sports supplement business, and I had all of my notebooks, and all of my pens, and everything laid out almost like an unboxing photograph, or a pack trip photograph that you would see on Instagram.

Everything was either parallel, or perpendicular. It was like it was set up by some type of Japanese artist on graph paper. It was perfectly organized to my liking, and Popi would come over and very slowly he’s looking at me like a cat, like your cat, Loki, and he’d look at me, and just with his index finger push the edge of one pen to knock it off-angle like 10 percent, and then we would just go back to whatever he was doing, and I knew he was trying to fuck with me, so I would leave it. I’d be like, “I’m not going to succumb. I’m not going to succumb.” And I’d leave it, and I’d leave it, and I’d just be like, “I can’t do it,” and I would fix it.

After a half-hour of this he came over and he’s like, “Tim, you’re behaving like American Psycho.” This monk-like sensitivity, especially visual sensitivity, can be really problematic, and that can certainly lead to domestic strife, and that’s on me. That’s on me.

Josh Waitzkin: I should note by the way that we’re having this conversation in front of my desk, and I have the exact opposite dynamic of Tim, so entering my world is just pure chaos created consciously.

Tim Ferriss: It is just chaos. It is chaos.

Josh Waitzkin: He’s functioning quite beautifully without a single thing in a straight line.

Tim Ferriss: I’m not even going to mention the stuff underneath the desk. It’s terrible! 

If we take it as true for the moment, which I think it is, that hyper-function and dysfunction are often right next to each other. I think another way to think about that is that your superpower is very often right next to your wound, like your biggest wound.

Josh Waitzkin: Yes.

Tim Ferriss: I think that’s an interesting way to reflect on it, or journal on it, or think about it, is how did this possibly develop if it developed through a wound, or traumatic event, or challenge of some type in my life? Many of these things are fed by innate qualities. I think that Usain Bolt, it doesn’t matter how many coaches he has for sprinting, if he’s built like me, it’s going to be the story turns out differently. Nonetheless, I think the superpower being right next to your wound is very often the case. They’re often two sides of the same coin.

And I think it is possible to work on the areas of dysfunction whether they’re minor or major without subjugating and muting your superpowers. I do think that’s possible. You have to track it. I’m not saying it’s always possible, but in my experience so far I think that it is very possible. And I’ll just say another thing, which is a phrase that I used to use a lot, and I hear a lot of my type-A friends use a lot when it comes to considering meditation and therapy, fill in the blank, is that they’re afraid of losing their edge. “I just don’t want to lose my edge, and I’m afraid I’m going to become complacent. I don’t want to lose my edge.”

Lose my edge, this phrase is used a lot, and in my experience the edge that they have in mind almost inevitably cuts both ways, like that intensity and that edge that they view as a pure advantage, which helps them most often professionally usually has a lot of consequences personally. Those are just some of the ways that I relate to it, but I definitely agree that they are side-by-side.

Josh Waitzkin: This framing of your around the wound is really beautiful and really powerful, and I relate to it. In the last stretch I’ve been writing about training, and one thing that I’m very careful about is for anyone that’s trying to convey something to be able to see their context, because any kind of teacher, or coach, or writer, or anyone who’s not aware of their own context can be trying to impose something on somebody else that doesn’t fit them, and so I’m trying to be explicit and introspective about my context, and my context relative to training comes from a wound, which was, in a nutshell, I started playing chess when I was six years old. When I was seven and eight at that point I was the top-rated in the US for my age, and so I was the target.

My whole childhood, from age seven into my 20s, I was the target, and as a kid that means that not only other kids focused on beating me because I would be the person to beat in the tournament, but their coaches, who were adults, who were masters, international masters, grandmasters, every weakness that I showed would be seen very clearly because the adult coaches were much stronger players than me, and would be focused on and exploited. And any strength that I had, I had to refine it, or else it wouldn’t work.

As a child, as a really young child, I had this experience, it was almost Pavlovian, of not taking on an error led to pain. Taking on an error, or refining a strength, led to flow, pleasure, love of the game, winning, all those things. Now, as an adult, what I’m aware of is that not taking on a weakness is almost outside of my conceptual scheme unless I really consciously try.

Tim Ferriss: “Josh, can you just make a mediocre turkey?” As one friend recommended. “Josh, try not to make the best turkey in the world. Just make a mediocre fucking turkey for once.”

Josh Waitzkin: Our friend, Jim Dethmer, who’s a brilliant man who Tim interviewed recently, has been saying to me for a long time, “Josh, just try to cook like shit. Just practice mediocrity.” And it’s a beautiful, wise piece of counsel given my madness. It’s something I grapple with, and that is really important for me to see. It’s a core area of strength of mine, but of course it can lead to complexities in interpersonal relationships and in my own life, and so I have to be able to see it.

Tim Ferriss: As we’re talking about this it makes me think of a story in the book Essentialism by Greg McKeown, which I’m very fond of. I think it has a lot of gold in it. And I’m going to paraphrase here. I’m not going to get it exactly right, but it tells a story of I believe it’s a man in his 30s or 40s who flames out completely, professionally. He just kills himself through overwork. And at the end of the story his advice to others is something along the lines of, “Okay, you’re a type A, hard-charging competitive winner in life.” And he’s like, “All right. You want to try something hard?” He’s like, “Something hard is not working seven days a week.” He’s like, “Try going home in the middle of the day and taking a nap.” He’s like, “Do you want to prove how tough you are? Try that, because that’s the harder thing for you to do.”

Josh Waitzkin: Yeah. Let’s keep exploring this relative to you, so let me throw out two themes and see where you go with them. One is efficiency. You are a master of efficiency. You’re also an athlete, and you’ve had an identity as an athlete your whole life, but you have a very specific physical dynamic relative to your lungs that could lead somebody to really need to take on the art of being crazy efficient. What do you think about that dynamic and how it might have informed where you’ve become incredibly overdeveloped?

Tim Ferriss: For people who are not aware, I have a number of very obvious scars on me. You can still see that one on the wrist, which looks like a cigarette burn, but it’s actually where I was intubated. I have another one on the left side where my left lung collapsed when I was born, or probably collapsed possibly before I was born, or in the birth process, and I was preemie in the NICU, the neonatal intensive care unit for a really long period of time.

I have issues with, in particular, thermoregulation is how that shows up, and that may or may not be related to the lungs, but I do have some pulmonary complications. If you’ve ever seen a dog pant, that is to dissipate heat. Dogs don’t really dissipate heat through sweat very much. 

In my case, I overheat very easily. I’ve been hospitalized for heatstroke a few times. And what that meant from an athletic perspective when I was wrestling, which was given how small I was up until sixth grade it was really one of, or the only, sport where I could compete and possibly win because you have the puniest of the puny competing against the puniest of the puny. I developed an approach to wrestling that compensated my propensity to overheat and therefore generally lack of endurance.

I think that led to thinking about efficiency, although at the time I don’t think I would’ve labeled it that way, and then much later with language learning, and Japanese, and so on when I was 15 also led me to think about efficiency a lot. I think those were the two seminal chapters, the wrestling, and then the language learning that led me to think about effectiveness and efficiency both. I think even though it gets talked about less I think about effectiveness, that is choosing the right things, choosing material so to speak, 80/20 analysis style more than efficiency because doing something really well doesn’t automatically make it important, but I do think about both.

To use your phrasing from earlier, the shadow side of that in the case of wrestling I identified and Greco-Roman upper body techniques as places where I could really shine. And if you continue to chunk down, chunk down, chunk down so you get to a place where instead of using, I’m making up these numbers, but 100 techniques, you’re using 10 techniques, and they’re very shoulder dependent, and on top of that you’re cutting, in my case, I was cutting from my senior year in high school 178 to 152 twice a week, which is insane.

Josh Waitzkin: That’s crazy.

Tim Ferriss: It’s insane, and it’s very dangerous. I don’t recommend it. I ended up having, and still have chronic shoulder issues, so I know. You’ve got to take care of those shoulders. I think Ossa’s letting out some wicked dog fog mist, also. In any case, I digress. I do think striving for the minimalist 80/20 analysis in the physical realm can be quite dangerous because you can end up with overuse syndrome, and dislocating shoulders, and in my case having reconstructive shoulder surgery and so on.

I think more and more these days about how I can change things in my life so I don’t need to think, or I’m not inclined to think about efficiency, same with competition.

Josh Waitzkin: Say more about that.

Tim Ferriss: I think we as humans gravitate to what we are good at, in general. I think we all like the validation intrinsic or extrinsic, or perhaps otherwise, that comes from feeling good about doing something well, and I’m really good at figuring out process improvements. What was his name? Deming, in the manufacturing world with Toyota and so on, like I’m very good at identifying steps, looking at a process, figuring out which steps can be removed, which steps should be removed, which should be inverted. I’m very good at that.

I’m also, and we could talk in length about this, but in certain ways a good competitor. I’m very driven by competition. I find it exciting. I like stakes. I do well when there are consequences usually, and I’m almost always able to perform better in competition than I am in training, but I think competition, much like positional economics, in other words, someone is inclined if they make $75,000 a year let’s just say to feel much better about that if all their friends make $50,000 versus if all their friends make $100,000 a year, even though their life, and quality of life, may not change at all objectively at that $75,000. It just depends on the peer group.

Competition I feel like has value in certain areas certainly, and it’s been incredibly valuable to me, but if you default to efficiency and competition that you can make yourself miserable depending on who you feel you’re competing with, and you can focus on doing things really well whether or not you should be doing them in the first place, whether or not they are in fact the element, or the piece of the puzzle, that makes a real difference. Those are a few of the things that I’m shifting and thinking about a lot in my life. The last six months, especially the last three months, has been a hitting of the pause button. The pause button is currently on for me, and this is the awkward part, not so much think about these things, figure these things out, but to watch the conditions of my life and see if I notice anything that pulls me in a different direction, or that compels me in a different direction, or draws me in a different direction.

You and I’ve spoken about this a bit, and I’m probably mangling your intention of what you said, but rather than doing something right now, trying to slightly change the conditions to see what emerges from that new set of conditions, or to set the correct conditions. Right now, the question for me would be, correct for what? I don’t know, because the what is the next step, and right now that’s a void for me. I just don’t know. And so I come here to the jungle to spend time with you. It’s like, all right, let’s have a shift of a couple of variables, create some space, and see what emerges from that.

Josh Waitzkin: It’s a beautiful entry into this idea of when we talk about the entanglement of strengths and weaknesses, or genius and eccentricity, or dysfunctionality, however you want to frame it. It opens up the discussion of how much we should be focusing on our strengths and how much we should be focusing on our weaknesses, and I tend to believe that, in life, we should really embrace our funk. An overdeveloped power zone is incredibly powerful and potent.

On the other hand, we do need to acknowledge our weaknesses, and one thing I’ve really come to admire about you is how you do that. And so, for example, what you’re saying right now you’re a person who really loves to get shit done, but you’ve hit pause, and the pause button is revealing some things. The theme of control is also quite interesting. When you speak about a power zone of yours as risk mitigation, trying to think about how things can go wrong on projects, you also have a very interesting relationship to control.

Tim Ferriss: Yeah, and hypervigilance.

Josh Waitzkin: And hypervigilance.

Tim Ferriss: That would be another example of something that in excess becomes its opposite, like an obsession with security breeds a feeling of insecurity. I’m glad you brought that up because that would be probably the most crippling in a sense, emotional, psychologically, crippling of the wounds/dysfunctions right next to superpowers.

Josh Waitzkin: And in some ways I would think as your friend, and I’m just putting this out as a question, that your grappling with those dynamics is part of what’s led you to this incredibly powerful work you’ve been driving in the world around psychedelics.

Tim Ferriss: Mm-hmm (affirmative).

Josh Waitzkin: Maybe speak to that relationship between control and what your medicine journey has opened up.

Tim Ferriss: I thought you put it really well a couple days ago, or weeks ago. Time changes in the jungle. I can’t even remember. When you said something along the lines of “I find it very interesting that as someone who is controlled so much, and focused on control so much, that one of your primary focuses, if not your primary focus right now, is compounds that create experiences that are not controlled.” They can be safe, but if you think you’re going to take a mega dose of psilocybin, DMT, or LSD, or any of these things and then write the screenplay of your experience and live that out line-by-line, you’re going to be very disappointed.

It may be more like Ulysses strapped to the mast. I experience a tremendous relief when I can completely let go of control, or attempt to let go of control, and feel the beauty of floating downstream instead of trying to swim upriver against the current, because I think most of my life I have prided myself on being the fastest salmon, just fucking thrashing like mad, making it up the rocks, dodging the grizzly bear, and being willing to suffer more than other people. You could dress that up and say developing a pain tolerance, or compete, but ultimately I think if we’re honest with ourselves, and I’m not saying there isn’t a place for this, but I think certainly I have to be very careful about assigning too much dignity and profundity to out-suffering people.

I think if we lionize that and really put it on a pedestal you can paint yourself into a really nasty corner, so with the medicine experiences, and the — let me rephrase that just because that lingo might not make sense to people, but in these transcendental, sometimes certainly transcendental, or transpersonal, meaning that you experience ego dissolution, the concept of I, and Tim, and time, and space dissolves. It’s kind of like sex. It’s really just not going to make any sense unless you’ve had an experience of this type, so I won’t belabor the description. It’s like if some guy’s never ejaculated and you’re like, “Well, it’s like a sneeze in your balls.” And they’re like, “I think I get it,” but you can’t really wrap your head around it.

But I digress. The point is having these experiences where I’m not trying to out-suffer. I’m trying to out-surrender. Not out-surrender. I’m trying to surrender, and also, and lots of people have said this, but I think that experiences of anxiety, depression, et cetera are very often me focused. They’re even in some respects very self-absorbed. They’re very me, me, me focused, and they’re also in the case of depression often past focused, and in the case of anxiety are future-focused.

And if you take five grams of potent psilocybin mushrooms maintaining any type of me, me, me-centric focus in the past or the future is going to be next to impossible. You’re given a reprieve, and once you experience that reprieve you know that it’s possible, and then you can begin to look for avenues for extending the effects into normal everyday sober life, and looking for other modalities or tools to find those spaces. For me, it’s just been a revelation in that respect.

Josh Waitzkin: That’s beautiful. A pattern that I hear you speaking to is that your previous relationship, for example, to efficiency, or control, is evolving increasingly into an exploration of setting the conditions for success, or for X, being downriver, surrender.

Tim Ferriss: Yeah.

Josh Waitzkin: This is just in the exploration of the entanglement of overdevelopment and underdevelopment, and you talked about your friends of yours who have said, “But I don’t want to lose my edge.”

Tim Ferriss: Yep.

Josh Waitzkin: As you feel yourself making that movement, which is really a deep exploration of these core themes, do you feel like it’s taking away your edge or adding to it?

Tim Ferriss: I think it’s multiplying my edge. And this is going to seem like a really mundane, or odd example, but he’s been on the mind because he just stepped down to CEO, Jeff Bezos, and I’m not comparing myself to Jeff Bezos just to be very clear, but one of the massive advantages that Bezos has had for so long, and still has, is his timeframe. He somehow managed to convince and persuade Wall Street to give him different time horizons than everyone else being judged quarter-by-quarter. Now, Amazon is still judged on quarterly results to some extent, but for the longest time the growth of Amazon was, if you read these shareholder letters, and I encourage everybody to look at these collected PDFs of the Amazon shareholder letters, he just had a longer time horizon.

And when you have a 10, 15-year, 20-year time horizon, you can think about making decisions in a very different way. You relate to feeling rushed or pressured in a very different way. And I feel like now I have to be careful here to also recognize that my circumstances have changed a lot in the last 10, 15 years. I might be inclined to say I can just wait for fat pitches, and I feel like I have more of an edge, and that may be also a byproduct of my changing circumstances, so I don’t want to attribute that solely to this ability to wait.

The way that I’ve heard other people describe the shift that I’m tying to embrace is being patient, but I don’t think about it that way. It might be that, but patience to me I think can sometimes — I have a bit of an allergic reaction to patience, just because I think it’s used so often as an excuse for complacency or laziness, so the word is not my favorite to apply here. But paying attention, like really paying attention to the things around me, and the feelings around, and let’s just say the dog that’s lying right next to us. Ossa and Zeus at mealtime, whether they need water or not. I’m constantly tracking all that stuff, but it’s a very light tracking.

And when I cultivate that, I feel like I have less, it still comes up occasionally, but less fear of missing out because I have a confidence that I am going to see things that most people are going to miss simply because they are rushing.

Josh Waitzkin: It’s interesting how universal this theme is, and if you think about it in a multidisciplinary way, there are of course always exceptions, but almost always when you watch for example an athlete over the years and over the decades their progression is from doing more to doing less, just getting more done. And one of the fascinating and mystical looking things about really superb virtuoso fighters, martial artists, is that they can move much slower and always get there first.

Tim Ferriss: Yeah. Yeah.

Josh Waitzkin: It’s gorgeous to see, and it’s really beautiful to really work on embodying, and it’s not because they can’t move quickly, they can move like lightning, but they can move slower and get there first.

Tim Ferriss: Yeah. I don’t know if this name is going to mean anything, because this is dating me, but when I was in Japan, when I was 15, that’s when I really — I had always had an affinity for martial arts, and had trained in various schools as a kid, but had never really seen real hard-hitting fighting in the sense of MMA, which didn’t exist as it does now, but Sogo Kakutogi in Japan, seeing Pancrase and so on, but also K-1 with the big guys, and there was a fighter way back in the day named Peter Aerts, the Dutch Lumberjack, a huge guy. Gigantic. Just a mountain of a guy.

And he had such impeccable timing, which is certainly in part, very fast perception, and also acute perception that even though he wasn’t the fastest fighter, he almost always got there first, and he was a huge guy, but he was just able to read the ring, and the opponent, and the space so perfectly. It was amazing to watch.

Josh Waitzkin: It’s a beautiful principle, and I think it really manifests everywhere.

Tim Ferriss: One of the mantras that I’ve been repeating to myself a lot recently I learned from a friend who’s former military, which is slow is smooth, and smooth is fast, and really trying to apply that to my writing, trying to apply that to different types of training, trying to apply that to decision making also, which is why almost always just as a rule if someone tries to rush my decision making it’s just no. The answer’s no automatically, as one example. That’s part of what I’m revisiting within this pause period.

Josh Waitzkin: In this pause period where you’re really sitting, and I’ve been watching you sit, in empty space without rush, what’s surfacing, and what are some of the core tension points or areas that you’re aware of being torn?

Tim Ferriss: Massive tension points. Every fiber of my programmed being, like my socialized self that has been rewarded for so long by doing things, it can be very hard to sit with empty space, and it makes me think a lot, and I’ve been thinking about this in the last few weeks a lot, a quote from Tara Brach, who’s a mindfulness and meditation teacher. She’s much more than that, but wrote an amazing book called Radical Acceptance that I recommend to everyone, and she has this, I’ll just call it an expression, it’s probably a story, in one of her books which she says “A famous sage once said there’s only one important question, and that question is: what are you unwilling to feel?”

I think for a lot of people, maybe the majority of people, maybe all people, I don’t know, many of our compulsive behaviors are to mask, or override, things that we don’t want to feel, so if there is something you feel you need to focus on, something you feel you need to do, if there’s a pack of cigarettes you need to pick up, it ties into what Gabor Maté, who I recommend people check out, he’s been on the podcast as well will sometimes talk to with respect to addiction. He says people ask “Why the addiction?” They shouldn’t ask “Why the addiction?” They should ask “Why the pain?” because the addiction is a consequence of the pain and trying to mask the pain, although I’m paraphrasing.

Bringing this back down to Earth, sitting here with empty space, a lot of uncomfortable feelings come up, and it’s been challenging to sit with them and not immediately try to fix them. Fears, feeling a lack of direction, feeling a lack of security, fears, anger has come up a lot, although I think that’s probably in part due to a therapy session a few days ago where I talked about the childhood trauma, which it really is dangerous.

It’s tricky terrain to navigate and can have a lot of aftereffects if I revisit it. A lot of emotions. And there have been great days, yesterday was a great day, and there have been some really hard days where I’m just like, what the fuck am I doing? What the fuck am I not doing? And why am I not doing it? Am I actually going to figure out anything because I just feel like I’m sitting by the pool staring at trees?” You know? Am I expecting some lightning bolt from the heavens to come down, and give me some miraculous epiphany that will solve all my issues? What am I doing?

And so, it’s been really challenging. It’s been super challenging. Not every day, and I’m very fortunate that we’ve been able to spend time together, and able to spend time with your family, and with a number of our friends who are here in strict isolation lockdown. That’s been gorgeous, and I’ve had so much fun, and when I’m by myself, and it’s quiet, a lot comes up because I normally have so many other activities, many of which are great, many of which are productive, many of which are in some way contributing, whatever the adjective we might want to use that allows me, also encourages me, to do those things. When you take all those away a lot of stuff can come up.

Josh Waitzkin: The state you’re in is a version of what so many people are feeling right now. This is such a painful time in the world. So many people are alone, and in pain, in different forms. So many have lost loved ones. So many are forced into isolation, or a lack of socialization, and there’s a lot of heartbreak out there, so you speaking about your own journey here is powerful.

I’m curious, just given where you’re at, I often go with people who I’m exploring with. We do something we call a cave process, which is essentially —

Tim Ferriss: I was going to ask you about —

Josh Waitzkin: — disappearing.

Tim Ferriss: The first thing written down in my notebook.

Josh Waitzkin: Here it is. The cave process.

Tim Ferriss: What the hell is the cave process?

Josh Waitzkin: Essentially, sitting in a space that is empty enough to get away from the inertia or reactivity, the inertia of where we’re coming from, or reactivity away from where we’re coming from, and you’re in a version of that state right now. The last time you and I jammed we talked about this framing that I play with sometimes of how would your future self-guide you, because no one will know you more intimately than yourself 20 years from now, and odds are yourself 20 years from now will be less attached to the things that you are extremely attached to now, so just given your intuitive sense of the direction you’re going in live, what do you think or feel that, say, 20-year future self would say to you? How would he guide you today?

Tim Ferriss: I want to answer that, but first I want to ask you with the cave process, how do you implement that with people you’re working with, or people you advise? Is it a physical relocation to a place of stillness? Is it blocking out the calendar so they have space to remove themselves from the bombardment of stimuli? What does that cave process look like?

Josh Waitzkin: I think it can take many forms, and as you pointed out earlier there are some people who are in a state of privilege where they can really disappear from the world for three or four months, and reflect, and there are other people who can’t do that. Maybe they’ve got families. They’ve got a job. They’re putting food on the table. They can’t just disappear. And so I think there are micro ways of manifesting it. For example, waking up first thing in the morning and journaling is a mini version of this.

Just creating empty space where we can tap into our unconscious is really powerful. I’ve gone through three, four, five-month periods with people where they truly stepped away from everything, and reflected, and tried to blue sky where they wanted to go in life as opposed to getting caught up in the execution concerns.

Tim Ferriss: Is it a structured reflection? Do you have prompts, questions, et cetera that you provide or practices, or is it really just empty space, let’s see what emerges?

Josh Waitzkin: I think the stillness comes first, and then the structure can be layered in, but the structure as you know I would structure it differently for every person who I’d be interacting with because we’re all different. That’s how I honestly relate to that question. I think that the principle of getting away from reactivity or inertia is powerful. Relationships, almost everyone moves from one relationship to the next, right? They rebound, but sitting in space post a relationship is really powerful, post a love relationship, or post a friendship that falls apart.

I just think that we have the impulse to fill space the moment it empties, but sitting in emptiness can be really powerful.

Tim Ferriss: Thank you for that. I’m going to take a stab at your question. I will say as a preface, and I don’t know if I’ve mentioned this to you, the piece of writing that I somehow lost, that made me saddest, was a piece of fiction, and I never write fiction, but it was a story I wrote. I think I was on a train ride and I asked myself this question some time ago. I was like, “What would an older version of me say to me now?” This was a long time ago, 10 years ago, something like that.

I wrote a fiction story of me going skiing, taking a break, going to a ski lodge, sitting by the fire, having some wine, and having this older gentleman sit down next to me, and this is before I read about any Borges because this is straight Borges, and struck up a conversation, and about 10, 20 minutes into it realized that it was an older version of myself, and so we had this conversation about what he learned, what advice he would give me, and it was this 10, 12-page document. It was just an incredible exercise and then I somehow lost it.

Josh Waitzkin: So if you were writing that story today?

Tim Ferriss: If I were writing that story today, I think the core piece that comes to mind if I’m not overthinking it, if it’s just whatever pops into my head, which I’m trying to pay a lot more attention to, that first flash, it’s very different from the number-crunched analytical flash, which isn’t really a flash, it’s more of like a squeezing out of the sponge, but that first flash is that he would say, “Focus on enjoyment, and fun, and pleasure, the things that give you those feelings.”

And there’s a justification, not that there’s one needed, I think those are all very good things, by and large, assuming there’s no collateral damage, I just have so much more energy when I feel one of those things, and my lifelong battle since my teens has been with chronic fatigue, and that led to abusing ephedrine, caffeine, aspirin in high school, which was introduced to me by an upperclassman from wrestling, and now I’m using it two, three times a day. That was a mess for a decade plus. I had severe Lyme disease a few years ago, and this happens all the time on Long Island, to the extent that in the ER in the summers they just have a sign that’s like, “Do you have Lyme disease? Fill out this survey and get a free Amazon gift card.” It’s everywhere.

I had severe Lyme, and the blood test came back, and the doctor said, “You are positive. You have an acute infection, but are you aware you’ve already been infected?” and as more and more people now would recognize with the serologic test, I guess it’s IGG — I might be getting that wrong. I think it’s IGG instead of IGM, but the long-term antibodies for Lyme were present, and I’ve just had this incredible fatigue since I was in my teens, and that persists to this day on some level.

And so, I think that deepening my relationships, thinking about family, I think moving from a deep feeling of obligation and responsibility, which I think has driven a lot of my behavior, there’s a competitive drive, but then there’s also a feeling, especially after almost committing suicide in college that I’m just operating on borrowed time, and I owe a lot, and that I have a moral obligation to do A, B, C, D, E, all the way to Z. Not to say that’s run its course entirely, and maybe there is a place for that. I don’t think I’m at risk of becoming totally irresponsible.

I just don’t think that it’s likely that the pendulum would swing back that far, and I think if I have a family, and I have an embraced, fun, enjoy, and taking time, and taking attention for the small pleasures my kid will receive, or kids, will absorb that type of orientation to the world where it is responsibility, where it is obligation, and it will have a very sterilizing effect, and muting effect, on them.

And so, right now, I’ve found myself, say, years ago, thinking when I have kids I’ll change A. When I have kids I’ll change B. When I have kids I’ll change D, E, and F, and I’ve come to the conclusion that that, I think, is very naïve. You better start becoming the parent you want to be now before game time. You’re not going to just step in the ring and be like, “Okay. Now that I’m here with Mike Tyson, I’m going to learn how to box.” That’s a terrible idea.

Josh Waitzkin: And then, the beautiful thing is all that preparation you have a kid, and the kid just kicks your ass anyway, and teaches you how to parent that kid.

Tim Ferriss: Right. Just to be clear, it’s not so much learning how to be a parent, it’s becoming the person you want to be, trying to train yourself, and instill the habits, and the changes in perspective that you want to have when you’re a parent, so it’s within your locus of control. And then, you get a kid who kicks you in the nuts, and like, okay, now you got to change your strategy, but it’s not a parenting strategy. It’s more a way of thinking about the person I want to be when I’m holding a child in my arms for the first time versus who I am now, and working on that now.

Josh Waitzkin: That’s beautiful, man. I think you’re going to be a hell of a dad. I can’t wait.

Tim Ferriss: Thanks, brother.

Josh Waitzkin: It’ll be so fun to have our little rugrats duking it out together. I love it.

Tim Ferriss: Yeah.

Josh Waitzkin: We have about 11 more minutes, so let’s pick up the pace.

Tim Ferriss: Let’s do it.

Josh Waitzkin: Let’s be a little more tactical about this.

Tim Ferriss: Tactical, practical.

Josh Waitzkin: This is not such a tactical question, but it’s relatively tactical. I personally have this feeling that I observed so many people yearning for return to normal. I don’t personally think that normal is necessarily returning so quickly, and I feel that we’re entering an age in human history where a core thing will be radically accelerating pace of change, so destabilizing events of different forms will become the new normal versus the return to normal that so many people are craving.

And so, I’m not really suggesting we debate that idea, but just roll with me on that idea, and if you were just to play with that framing, how do you think that people would best prepare for the world that we might be entering over the next five, 10, 15 years if that theme has some validity?

Tim Ferriss: It turns out you’re asking Mr. Hypervigilance. I have thought about this a bit. We’ve talked about it a little bit. I think the assertion’s right, certainly with technology, and exponentially ramping technology, global interconnectedness, the curve of all that is going to continue to steepen for a million reasons that we won’t get into right now. I’ll say two things. Number one is, I think you have to — have to is a strong phrasing, but I’m going to use it for simplicity, because we’re doing a lightning round, you have to focus on meta-learning and meta-skills, or you’re just going to be toast, right?

Josh Waitzkin: Mm-hmm (affirmative).

Tim Ferriss: You need to be able to learn to do things that machines have great difficulty doing, and by machine I include software, most software right now, and to embrace your humanness. I think Kevin Kelly’s actually a great person to read up on for identifying opportunities moving forward. A lot of people try to predict technological advances. The big difference with Kevin is that he’s very often right.

He’s given a lot of thought to say AI, and humans, in the next 10 to 20 years. I think meta-learning skills, I think your book The Art of Learning, should be required reading. I think there are aspects of meta-learning that are explored in The 4-Hour Chef, which confusingly is not just a cookbook. It is in fact a book about accelerated learning that can make you not just resilient, but antifragile in the sense that the vast majority of people you might ever compete with, if you end up competing, will not have this toolkit.

When there’s a shock to the system, like COVID. When there’s a shock to the system like some designer epidemic, or pandemic, that is designed using CRISPR, and released easily out of some basement, and when there is a disaster like fill-in-the-blank. There are so many technologies, 3D printing, blockchain, decentralized social networks, or even assassination marketplaces, miniature drones where the cost of defense is a million times higher than the cost of offense.

The dystopian possibilities for cheap destabilizing events with many players, we’ve talked about, not one, or two, or three, or four players who are state actors, but tens of thousands of people who could implement certain attacks that could be really destabilizing, he or she who is the most adaptable wins I think in many respects, so meta-learning, and then really understanding — I do think for all of his eccentricity I think Taleb and Black Swan, Fooled by Randomness, read those books. If you are not on a very basic level — I never took calculus. I’m not a mathematician by any stretch, but learn to think, learn to understand, probabilistic thinking. It’s so fucking important.

Just start to read Fooled by Randomness and Black Swan. Get a basic understanding of how probability affects your decision-making in life.

Josh Waitzkin: Beautiful. Your point about meta-learning is so powerful. One way to just very simply think about this is that people tend to think about technique, tactics, technique, but if you focus your learning on the principles that house the techniques then you can throw all the techniques away and reinvent new techniques quite easily, as I’ve experimented with a lot, because the techniques are just the external husk. The meta, the principle, is the thing to really focus on learning, and it’s really remarkable how they can be manifested in new places quite quickly. I think the meta-learning and adaptability are so intertwined.

You sent me a doc of some questions from some of your listeners, and I want to hit you with a few of those if you don’t mind.

Tim Ferriss: Let’s do it.

Josh Waitzkin: Andrew T. asks, “What’s the single most important attribute you look for when debating if you’ll bring a new person into your circle of friends?”

Tim Ferriss: The first one, I used to debate a lot more in my head than I do now. The first thing honestly is just gut feeling. Does the animal in me move forward towards that person, does it stay where it is, or does it pull back even a quarter-inch, even a millimeter?

Josh Waitzkin: I love it. That’s a beautiful answer. Boom.

Tim Ferriss: That’s number one. And number two is just trustworthiness, discretion. Intelligence is dime a dozen. I care less and less about what we consider intelligence.

Josh Waitzkin: Every time I’ve overruled my intuition about someone, it’s bit me in the ass.

Tim Ferriss: Yep.

Josh Waitzkin: Every time.

Tim Ferriss: Yeah. And pay attention to Molly. Pay attention to my dog, because even if I’ve had two drinks and my spider-sense is off, if Molly doesn’t like someone, I pay very close attention to that.

Josh Waitzkin: Russell W.: “Do you ever worry you’re mistaking noise for signal with learning from successful people, survival bias, and all that jazz?” It’s an interesting question.

Tim Ferriss: I think about it a lot. I think this is a very smart question, a very observant question, you need to keep in mind. For me, the first thing with world-class performers is, A, can they repeat whatever I admire about them? In other words, once you’re lucky, twice you’re good. Three times you’re world-class if it’s something really outrageous. First, can they actually repeat what is their claim to fame. Let’s just figure that out first, because if not, keep looking.

Number two is: can they teach it? Are there any examples of disciples? Which you can see certainly in the investing world. You see these roll-outs. And then, also the question of are they succeeding because of X, whatever X is that you’re looking at, or are they succeeding in spite of X? And those two things are very often confused where people are like, “This works because I use tough love, and I kick my employees in the face every time they fuck up. I run a tight ship, and that’s why it works.” And it’s like, actually, Jesus, it’d be 10 times better if you didn’t do that, so you’re succeeding in spite of that, in which case you can ask people around them, or who have had exposure to them.

Josh Waitzkin: Yeah. Beautiful answer. Ricky sent two questions I liked, one of which of course is quite personal to me now because we’ve got a beautiful puppy. What have you learned about yourself and the world now that you’ve had a dog for a while?

Tim Ferriss: I’ve learned that we project a lot of our shit on everyone and everything, including dogs. There may be exceptions, but dogs are just so tabula rasa. They come obviously pre-installed with all their gray wolf DNA, and canid quirks, but if you think a dog is — when I was raising Molly, and training Molly, in the beginning looking back I’m so embarrassed by how upset I got at points when she was not being disobedient, not understanding my training, because I wasn’t training well. I wasn’t clear.

It’s so easy to anthropomorphize our animals and assume that they have some internal agenda, or they’re doing A, B, and C to annoy us, and so on, which ends up being such a mirror for what our wounds are, our fears are, our compulsions are, so I think Molly, and dogs, are an incredible mirror. They really show you, I think, your strengths and your weaknesses. And I think Molly has really taught me how to love also as a result of that. Just to just love an animal so deeply and unconditionally I think it’s really opened up a lot in me, and removed a lot of armor that would’ve been difficult to remove otherwise.

Josh Waitzkin: That’s so beautiful, and I see that in you. I see the way you interact with Ossa and Zeus, my brother Light’s dog Zeus, the way you bring love to these big pups that got a whole lot of energy, and they just love you. There’s no bullshitting in that.

Tim Ferriss: Yeah. Sorry about making out with Ossa that first night.

Josh Waitzkin: That was something to behold.

Tim Ferriss: I came in, just for people who are not in the joke, and I was like, “May I give Ossa a little treat?” and he’s like, “Sure,” and this was I guess the first night I arrived. It was the alarm that says “I need to go get my COVID test,” which is — leave it. That’s the alarm saying I need to go get my COVID test, which is appropriate, because I just arrived. And he’s like, “Sure, you can give Ossa a treat,” and I put a little piece of chicken in my teeth, and Ossa grabbed it, and Josh was like, “You’re going to give my fucking dog COVID, and it’s going to give my whole fucking family COVID.” It was pretty great. It was pretty great. We had a fiery start.

Josh Waitzkin: That was a good start to the whole thing. Hey man, this has been a lot of fun. It’s great chatting.

Tim Ferriss: Yeah. It’s been great, man. So good to see you, and so good to jam, and to be continued, brother.

Josh Waitzkin: Absolutely.

Tim Ferriss: Love you very much.

Josh Waitzkin: Love you too, man.

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