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Why You Can’t Stop Your Productivity Addiction - Oliver Burkeman

Oliver Burkeman is a journalist, a writer for The Guardian, and an author. How does the insecure overachiever evolve? You think success will quiet the doubt, then you hit 30, and it’s still there. More achievement, more stress. So how can you feel proud of what you’ve built without always fearing it’s not enough? Expect to learn if it possible to be the best in the world and relaxed at the same time, how to deal with uncertainty more effectively, the biggest changes insecure overachievers will face as they age, the cost of constantly asking, “Am I living my best possible life?“, how to know when it’s a good time to settle and much more… - 0:00 The Hidden Trap of Tying Your Worth to Success 6:31 Making Peace With Our Limited Control of Life 15:25 Why Nothing Going Your Way Might Be a Gift 19:04 What Control is Really Costing You 24:27 Why You Should Do It Anyway 30:41 Can You Actually Design Fun? 41:03 Is AI Just Another Control Fantasy? 46:26 The Insecure Overachiever Paradox 55:14 Is Optimising Your Life Making You Miserable? 58:41 Do High Performers Create Their Own Problems? 01:05:19 Criticism and Congruence: Learning to Relinquish Control 01:21:22 Does Settling Help You Get More Out of Life? 01:26:12 What Is Oliver Working On Now? 01:31:25 Where to Find Oliver - Get up to 20% off the leading longevity and cellular health supplement at https://timeline.com/modernwisdom Get 15% off your first order of my favourite Non-Alcoholic Brew at https://athleticbrewing.com/modernwisdom Get up to $350 off the Pod 5 at https://eightsleep.com/modernwisdom Get a Free Sample Pack of LMNT’s most popular flavours with your first purchase at https://drinklmnt.com/modernwisdom - Get access to every episode 10 hours before YouTube by subscribing for free on Spotify - https://spoti.fi/2LSimPn or Apple Podcasts - https://apple.co/2MNqIgw Get my free Reading List of 100 life-changing books here - https://chriswillx.com/books/ Try my productivity energy drink Neutonic here - https://neutonic.com/modernwisdom - Get in touch in the comments below or head to... Instagram: https://www.instagram.com/chriswillx Twitter: https://www.twitter.com/chriswillx Email: https://chriswillx.com/contact/

Chris WilliamsonhostOliver Burkemanguest
Feb 19, 20261h 31mWatch on YouTube ↗

EVERY SPOKEN WORD

  1. 0:006:31

    The Hidden Trap of Tying Your Worth to Success

    1. CW

      Is it possible to be the best in the world and relaxed at the same time?

    2. OB

      [laughing] Um, the best in the world? I don't know. I, um, I- what I do think is that it is very possible to be really, really good at what you do and relaxed. And actually, my experience is that the more relaxed I can be, the better I am at things. I'm not gonna claim to be the best in the world at anything. But, um, I, I think that notion that you've either got to choose a relaxing life or a, an accomplished one, this is, uh, uh, this is the thing I'm on a mission, very personally motivated [chuckles] mission to prove is not, uh, not how it works.

    3. CW

      I think there's a tension between having high standards, which is hypervigilance, and obsession, and focus, and really paying attention to stuff, and that just tends to bleed into the personality and the ambient anxiety. And, uh, I can see, uh, for instance, if you were to say, um: "Is it possible to be the best in the world and never relax at the same time?" That question would seem pretty obvious to answer.

    4. OB

      Hmm.

    5. CW

      Yes, of course, because the exact same level of resolution that you're obsessing over your pursuit with is the thing that kind of destroys the rest of your life. The interesting question is to work out whether you can kind of be on and off, or if you can hold things a little bit more loosely whilst still getting the right level of output you want.

    6. OB

      Yeah, it's really interesting. I think that, um, there's, there's something... I mean, this runs through a lot of what I try to write about, but there's something about wanting to feel in control of the process of getting better at things or being good at things, which is kind of completely different from the actual process of getting better at them or, or being good at them. So I think there's, you know, this is, on some level, just the banal observation that people who really excel in what they do are very often, or perhaps more often, in a flow state while they're doing it. They're kind of- they sort of let go into the action. They're not sort of sitting back inside their minds, controlling it all in a very, um, sort of, mmm, uh, conscious, uh, controlly, controlly way. So yeah, for me, and of course, I'm talking about things like writing or speaking. I mean, I'm not talking about, um, uh, it may work differently in, to different degrees for kinda sports performance and things, but you find that the more I'm trying to make sure that things go well, that- that's just like a... And, and therefore, I'm sort of unrelaxed and clenched, and m- muscles tensed and everything. The, the more, um, you sort of pop into this awful self-conscious space where nothing, nothing works, and it's much better to lose yourself in the activity than to be trying to control it.

    7. CW

      I think a lot of people are struggling to find a healthy way to pursue goals without tying their self-worth to the outcome.

    8. OB

      Hmm.

    9. CW

      That is-

    10. OB

      Yeah, def-

    11. CW

      ... one of the f- one of the fundamental problem. Like, if I, the only way that I can get myself to pursue a goal is if I care about it.

    12. OB

      Mm-hmm.

    13. CW

      And in the act of caring about it, I'm gonna be disappointed if I don't reach it, and in the act of the disappointment is some sort of value judgment about me, and my worth, and whether-

    14. OB

      [chuckles] Right

    15. CW

      ... or not I sh- Yeah. Uh, so, uh, how do you healthily pursue goals without tying your self-worth to the outcome, given that the only sort of goals you do pursue are ones you care about, and in the caring, the disappointment, and in the disappointment, the self-worth?

    16. OB

      So, I mean, I, the- there's a sort of ideal way of doing this, which I don't claim to have, you know, totally pulled off or anything, but I think the distinction is w- when you say care about, there's a way of caring about goals that basically defines yourself as inadequate and insufficient until you've met them. Um, and there are other ways of caring about goals. So there's a f- concept in, um, psychology, the concept of the insecure overachiever, uh, which whenever I kind of mention it in public audience context or whatever, like, like, half the people in the room, uh, just the, the look of recognition, uh-

    17. CW

      Mm

    18. OB

      ... that passes over their face is amazing, right? So people who do really well in life, and they're driven, and they're probably applauded and celebrated by their friends or by society at large for doing loads of impressive stuff, but on some level, and I was like this for years, they're doing it to try to f- fix something about themselves or to try to feel okay and to try to sort of fill a, a, a void. So loads and loads of really successful people in the world, they ultimately are sort of feeling like they've absolutely got to succeed, otherwise, on some level, they don't really deserve to exist or something.

    19. CW

      Mm-hmm. Mm-hmm.

    20. OB

      And that sort of, that puts you in a perpetual place where everything you're doing for, in terms of goal pursuit, is, um, is, is to try to make yourself feel sort of less bad about yourself. And it, and it puts you in this really awful situation as well, which I definitely used to experience a lot, where anything you achieve in the world, which you might think you could then feel, like, proud and happy about, just instantly becomes the minimum standard that you've got to meet next time. Um, which is a very depressing way to, to, to live, right?

    21. CW

      [laughing]

    22. OB

      Um, [chuckles] and because... And, and so, you know, you, you, you do really well at a, an exam, or you get a certain level of public success with something, and then it's like, that instantly becomes like, if you don't meet that same level the next time, then-

    23. CW

      Mm

    24. OB

      ... then, like, who are you? What are you? There is this whole other way of thinking about caring about goals, right? Which is to say, like, to-... at least to entertain the possibility of, like, what if everything was fine right now, and you feel good about yourself, and you don't have these self-worth psychodramas going on? And then on top of that, you decided to create some cool things in the world because that's a more interesting way to live than, um, than sitting around doing nothing. So I think there is a way of being ambitious and accomplished that doesn't need to be, um, like, in, in flight from, from something. But it's, uh, it can be challenging to get there.

  2. 6:3115:25

    Making Peace With Our Limited Control of Life

    1. CW

      I love this. I, I've- it's been one of the central questions. I think it's why I'm such a huge fan of your work and, and your newsletter as well, that everyone should go and sign up to, the, The Imperfectionist. Uh, it, it's one of the central questions that I want to achieve things, but I don't want to miss my life, might, might, might be a, a pithy way to, to sort of describe it. And, um, I called it the curse of competence, this, uh, situation where if, if things go well for you sometimes, or, or even worse than that, most of the time, then success is no longer a reason for celebration. It's the minimum level of acceptable output. And there's a line from a John Belli and Luke Combs song that says, uh, "If the higher I climb is the further I fall, then why love anything at all?" And he's, he's talking about it with regards to falling in love with somebody, but the same thing is true. [chuckles] The, the insecure overachiever in me pattern-matched it to personal development. [laughing]

    2. OB

      [laughing] Yeah. Yeah.

    3. CW

      [laughing] And I thought-

    4. OB

      I was, um... Go on.

    5. CW

      I just thought it's so funny. I, I'd found out in the middle of December last year that the podcast charted r- really high globally on this, this Spotify thing, and the, the Goldilocks zone period, after not knowing that I was- w- that I'd charted at this thing-

    6. OB

      Mm-hmm

    7. CW

      ... and before realizing that that meant next year I have to be better than that-

    8. OB

      [laughing]

    9. CW

      [chuckles] was-

    10. OB

      Yeah. Right, right.

    11. CW

      A- approximately s- probably 15 minutes or maybe less.

    12. OB

      [laughing] And a beautiful 15 minutes.

    13. CW

      [chuckles] It was so good. It was... I got to actually enjoy the thing before I thought, "Well, 2026's chart is only, whatever, 11 months and 30 days away, so I must, I, I must get my nose back to the grindstone." I remember I saw this-

    14. OB

      Right

    15. CW

      ... Ryan Holiday video. I brought this up to him. Um, and I, I think Ryan's a super balanced guy, and I, I really, really like him, but, um, I had seen this... It's almost like performative grindset. I don't think- I think it's more him, which is why it's less... It feels less contrived.

    16. OB

      Mm.

    17. CW

      He got a call from his publisher, and he was sat in, in his office, and it was to say, "You've hit the New York Times list. You're number, whatever, one," or s- something like that, "Congratulations." And Ryan took, like, three minutes or less, like 90 seconds on this call, and it's videoed, and he put it on his Instagram and then was like: "All right, I've gotta get back to writing the next book." And I was like: [chuckles] "Ryan, come on, dude. Like, you're supposed to be the fucking guy." Anyway, curse of competence, um, uh, if, "If the higher I climb is the further I fall," and me, my Spotify debacle last year of-

    18. OB

      Mm

    19. CW

      ... of y- yeah, realizing this is the minimum level of acceptable output for 12 months' time, um-

    20. OB

      Mm

    21. CW

      ... it's, it, it's a real pervasive challenge.

    22. OB

      Yeah, absolutely. I was speaking to an author more successful than me, talking about how, um, I shouldn't name names. He was talking about how, you know, when his first big successful book had, um, hit right at the top of the charts, he was, like, following along with his friends on WhatsApp, and they were just, like, completely amazed that this thing was happening-

    23. CW

      Mm

    24. OB

      ... and everyone was just overjoyed. And then realizing when that happened to his, like, I don't know, fourth, fifth, sixth bestseller or whatever it was, and it fin- and it did get to the top very soon after release, that he sort of felt only, uh, relief. [chuckles] And then realizing that there was something amiss about only feeling relief in a situation where you should be, you know, you should be just sort of amazed and celebrating that it's happening. But now it's become the, the bare minimum.

    25. CW

      Yeah. That... I, I asked a question at my live show, so the people who came to see me in North America last year would have heard me ask this. It's one of the final questions, which was to work out basically whether you're gripping life too tightly. Um, and it is, when things go well, is your presiding sensation one of joy or one of relief?

    26. OB

      Yeah.

    27. CW

      Like, is it, is it the, uh, sort of congratulation of self-love or simply the abatement of fear? And, uh, [laughing] I just think, like, this, you see, it's strange doing talk- I'm sure you do live, live stuff, too, and it's strange giving talks like this because, a, a musician wants hands in the air and, and shouting, and a comedian wants laughter and clapping, and if you're us, what you want-

    28. OB

      [chuckles]

    29. CW

      ... is this kind of this sullen, fearful look on someone's face. [chuckles] And the, what, what does an existential crisis-

    30. OB

      Existential crises trigger, right?

  3. 15:2519:04

    Why Nothing Going Your Way Might Be a Gift

    1. OB

      your life.

    2. SP

      You're a fan of Krishnamurti's secret of existence: "I don't mind-

    3. OB

      I am.

    4. SP

      -what happens." What's that mean to you?

    5. OB

      So just, um, for anyone who's not familiar with it, right, he's, he-- this is the, the, the legend or the anecdote here is that he's, um, leading some group in California in the 'seventies or something, and, uh, this is, um, uh, Krishnamurti, the spiritual teacher, and he, he sort of... He, he asks everyone who's present: "Do you want to know my secret?" And of course, all these kind of spiritual junkies, absolutely obsessed, lean forward, desperate for the secret. And his secret, as he says: "I don't mind what happens." And for me, uh, that is a sort of ultimate statement of a kind of approach to life that, um, that, that recognizes the limitations of the control that we have. Recognizes how much of our lives are spent sort of anxiously leaning into the next hour or the next day or the next week-

    6. SP

      Mm-hmm. Mm

    7. OB

      ... just waiting to make sure that things are okay. And then, of course, they are okay, usually, and all you do is lean forward into the next, into the next week. I don't think he means like-

    8. SP

      You perpetually lean through your own life.

    9. OB

      Right. Exactly, exactly. And I don't think Krishnamurti, in that, in that, uh, line, I don't think he means, uh, that some things that happen aren't better than others, or that you shouldn't try to have things in your life or the world, or the people you love, like, go well instead of badly. It's just that when whatever happens does happen, um, there isn't this sort of automatic stressful collision between, like, what you, um, are demanding [chuckles] that reality do and, and what reality does do. And you can still put huge amounts of effort and time and focus into trying to, you know, have things go the best way. But then when they don't go the way that you were hoping, you're not sort of completely bent out of shape by it. Who knows how perfectly even he manifested this attitude, right? I think a lot of what we're talking about here is kind of a, a, a, a, a, a shift of perspective that, um, that, uh, you know, one, one hopes to embody on one's best days. But, uh-

    10. SP

      It's a-

    11. OB

      Yeah

    12. SP

      ... a largely unreachable gold standard, I think, but it's definitely-

    13. OB

      Yeah

    14. SP

      ... a dir-- it's a direction that you can be, or an orient, uh-

    15. OB

      Yeah

    16. SP

      ... orienting principle would be a good way to put it.

    17. OB

      Yeah.

    18. SP

      A quick aside, if you've noticed your energy isn't quite what it used to be, even though you eat well and stay active, there might be a reason for that. As we age, our mitochondria, which is the parts of our cells that produce energy, become weaker and make less energy, which is why I'm such a huge fan of Timeline. They developed this pill right here.

    19. CW

      ... that helps clear out damaged mitochondria, so your cells can actually renew themselves. And this isn't just theory. In clinical trials, people saw mitochondrial renewal increase by more than forty percent in just sixteen weeks, along with improvements in their overall energy. Timeline is backed by over a decade of research, has more than fifty patents, and is the number one doctor-recommended mitochondrial supplement on the planet. I started taking it nearly two years ago because it was recommended to me by my doctor, and that is why I've used it for so long, since way before I knew who made the product, and that is why I partnered with them. Best of all, there's a thirty-day money-back guarantee, plus free shipping in the US, and they ship internationally. So right now, you can get up to twenty percent off and that thirty-day money-back guarantee by going to the link in the description below or heading to timeline.com/modernwisdom. That's timeline.com/modernwisdom.

  4. 19:0424:27

    What Control is Really Costing You

    1. CW

      You know, the place that I get this, [chuckles] this looking over the shoulder of the present moment thing the most is when I go to comedy shows, especially if you go to the mothership here in Austin, because lots of comedians... I, I-- this is probably the same way it is at many other comedy clubs, but I haven't gone to them. When you see a lineup, and there's eight comedians in a night, and it's ten-minute spots or, you know, five minutes maybe for the first few guys, and then some tens, and then maybe a f- one or two fifteens, and then a thirty or a f- a sixty at the end. And what it means is that there's kind of a, a regular carousel of these new comics stepping out on stage. And me at my most juvenile and worst and most dopaminergic is me going: "Ooh, I can't wait for the next guy," as the current guy starts, and then I next guy my way through every comedian. [laughing]

    2. OB

      Yeah.

    3. CW

      Until the show's out- over, and then I can't-

    4. OB

      Yeah

    5. CW

      ... wait to get into bed, and then it's the morning. And, um-

    6. OB

      Yeah

    7. CW

      ... this, you're, you're so right that people sort of lean toward the thing that's happening i- in an attempt to control it, in an attempt to deal with the uncertainty. I think our first-ever conversation that we had, I'd, I'd identified that most of your work is around control.

    8. OB

      Yeah.

    9. CW

      It's around people's need for control, their desire to control. Do you see... Just to dig into that a little bit, is control the reduction of uncertainty? Like, what, what is control trying to achieve? What are the, what are the component parts? What's the problem it's looking to solve?

    10. OB

      Yeah, it's a really, um, deep and interesting question. It gets to the point where I don't know if I have the, the answers. I guess what I think ultimately, [clears throat] the idea that I'm tracking, which is, of course, you know, me doing personal therapy and coming to terms with my own issues, is that there's something really, really sort of overpoweringly intense and, and vulnerable feeling about being human and consciously showing up for the human life that we have, to sort of really take account of the fact that we're here, that we didn't make-- didn't choose to be born, that w- that we have limited time, limited, or limited ability to steer how things go, that we're gonna die. All of this is just, like, super intense, and I think that very, very often, what we're doing, without necessarily realizing it, um, is, is pursuing strategies for feeling like not that we've got out of this situation, 'cause you can't get out of it until death, but feeling like we're, [chuckles] we're-- feeling like we're engaged in a project of, like, getting a little bit out of it or sort of up on top of it sometimes, is the-

    11. CW

      Mm

    12. OB

      ... is the way I think about it. It's like we're trying to sort of lever ourselves into a position where we're kind of controlling life instead of being in life, which, uh, all of us inevitably are. And so, you know, you can do that in ways that involve... I think, you know, a lot of mainstream productivity culture is all about developing that feeling that, like, you know, I'm really in the driver's seat of the, of the, of the thing now. But also, sometimes it's a more kind of numbing out and distracting ourselves response, right? A lot of, a lot of kind of time-wasting is probably best understood as the fact that if you were really to focus on what you wanted to be doing, you'd feel vulnerable again because, like, who knows if this difficult plan would work out? Who knows if this awkward conversation is gonna go the way I, I want it to go? And that manifests in all sorts of ways. I mean, the thing you're saying about the comedy clubs is interesting to me because there's a cliché about how people put off life until they get married, until they get a promotion, until they retire, these big milestones, and that's true. Um, but even after I felt like I kind of got over that, uh, which to some extent, you know, getting older will cause you to get over it because you pass some of these milestones and, and, uh, realize that there's just more milestones. But you're referring to this thing that I've really noticed in myself, too, which is the capacity to sort of live not a decade in the future for when you get that big promotion or retire or something, but, like, about an hour in the future or twenty minutes, right?

    13. CW

      Mm.

    14. OB

      Like, like even once you-

    15. CW

      Such an amount of time that's-

    16. OB

      [laughing]

    17. CW

      ... so fucking unimpressive. It doesn't even achieve anything.

    18. OB

      Right. And it's just that sort of waiting for the next thing to happen, checking it went okay, and not even checking it went okay. In the case of comedy club, uh, a night at a comedy club, what's gonna go wrong, right? Like, I mean, actually, and I would be... I'm terrible in those situations 'cause I have sort of too much weird, vicarious empathy for the performers, and, like, I'm-

    19. CW

      Me too.

    20. OB

      When people, when people die on their feet in comedy clubs, I can't bear it, but, um, that maybe doesn't happen at the high-class Austin ones that you go to. I don't know.

    21. CW

      Typ- typically, the guys are not bombing all that much, although I'm, I'm sure if it did happen, I would feel the exact same. I'd, I'd want-... to do, throw some sort of a lifeline. I'd feel obliged to make this performance night okay. Like, how is it my responsibility

  5. 24:2730:41

    Why You Should Do It Anyway

    1. CW

      to do that? So you, you, you hit on something that, uh, I think is real interesting. So I'm 38 next month, and, um, what I'm interested in, speaking to a slightly older gentleman on a similar set of r- rails to me, what changes for the insecure overachiever as they age?

    2. OB

      It's interesting. Uh, I turned 50 th- well, actually, technically last year, but I am, I am 50. Um, which is completely alarming, and, uh-

    3. CW

      Mm

    4. OB

      ... I'm still constantly going through the weird experience of realizing that people in their 20s or even their 30s are relating to me as a, as someone from an older generation, when... I'm not talking about now in this conversation, but, like, you know, when I was just kind of assuming we were having a conver- "Oh, so oh, I see, right, I'm an old person." Um, uh, what changes, uh, is, you know, I think that gradually there's this accretion of experience that gets big enough that you realize, um, that firstly, you know, the world does not, uh, collapse when you don't meet, um, when you don't- when you break a streak of some kind of, uh, achievement. That, um, th- that, that, you know, you can sort of relax in that sense, and you sort of develop... I have developed, I think, um, uh, a greater level of sort of basic confidence that I sort of know what I'm doing when it comes to, to writing things, [chuckles] which I sort of until quite recently don't think, don't think I had. Um, but then also there's just the kind of, if you, if you healthily manage your midlife crises and your dawning sense of mortality and being in the sort of much more decisively being in the likely second half of, of life and, and, and all the rest of it, there is just that kind of, um, awareness, whether panicky or quite sort of, uh, down-to-earth, that it's sort of got to be now, right? It's like, like, wh- when, you know, when are you going to-

    5. CW

      Mm

    6. OB

      ... when are you gonna do that thing or travel to that place or learn that skill? Like, I mean, at some point, it's gonna have to be, it's gonna have to be in a, in a now. Um, you'll be familiar, I'm sure, with the, the book, um, uh, Die with Zero, about, um-

    7. CW

      Bill Perkins

    8. OB

      Uh-

    9. CW

      Good friend.

    10. OB

      Yeah.

    11. CW

      Lives here in Austin, Texas.

    12. OB

      Right, right. About how, uh, dangerously possible it is to defer gratification for too long.

    13. CW

      Yeah.

    14. OB

      Um, and, uh, you know, so I've had... To the extent that, you know, to the extent that I'm a calmer person and a [chuckles] happier person than I was, which is, you know, it's a mixed picture, but I think one of the big reasons for that is sort of this combination of, like, I kind of know what I'm doing, and also, even if I didn't, I would have to do it now.

    15. CW

      Hurry the fuck up.

    16. OB

      That's a kind of... That's, that's a good combination of, uh, motivations.

    17. CW

      That's nice.

    18. OB

      Yeah.

    19. CW

      I, I, I don't make a habit of showing my phone on the, on the episodes all that much, but you might be able to read my new background. Come on, there we go. Can you read what that says?

    20. OB

      Do it anyway.

    21. CW

      Do it anyway. It's a gentleman-

    22. OB

      Love it

    23. CW

      ... walking up what appears to be a completely exploding ravine, [chuckles] and there's this just, like-

    24. OB

      [laughing]

    25. CW

      ... cosmic hellfire coming down. It's quite art- a- artistically done, I think.

    26. OB

      It's nice.

    27. CW

      My prompting was, my, my promp- prompting was lovely, but, uh, that's rotating-

    28. OB

      [laughing]

    29. CW

      ... that's rotating on my phone background with different versions of do it anyway. And d- do it anyway, for me, is kind of do it scared, do it uncertain, do it tired. It's not push through and grind. Like the-

    30. OB

      Right

  6. 30:4141:03

    Can You Actually Design Fun?

    1. CW

      What sort of person do you think is having the most fun? Do you ever, do you ever think about engineering enjoyment as a, a productivity strategy?

    2. OB

      [laughing] Um, I mean, I started off very skeptical about any kind of engineered fun, right? Especially in kind of corporate settings, but frankly, even in one's own life, because, uh, as the moment you're, the moment you're engineering it, isn't it- doesn't it stop being fun?

    3. CW

      Mm.

    4. OB

      Uh, the moment you're doing it for some outcome other than itself, aren't you just sort of monitoring it all the time-

    5. CW

      Mm

    6. OB

      ... vigilantly to make sure that it's, uh, that it's having its, having its effect? So I'm not sure this is the s- quite an answer to your question, but what it makes me think of is, um, sort of trying to engineer fun experiences is not something that, um, I, I feel I've had much success with. But asking myself s- in the moment, in the context of, of the day, w- what I feel like doing or what I would enjoy to do, letting my productivity be at least somewhat guided by the question of like, what I feel like doing, has been a huge revelation for me. I think a lot of us, probably the insecure overachievers, right, we go through life with a sort of deep, uh, lack of trust in ourselves. We think that if we were to just do what we wanted, we'd just like unspool and spend all day-

    7. CW

      [laughing]

    8. OB

      ... on the sofa eating potato chips.

    9. CW

      I love that image.

    10. OB

      Right?

    11. CW

      Yeah, yeah, yeah.

    12. OB

      Um, and of course, it's not true. Like, you know, if you're interested in being productive or ambitious in the first place, you can pretty much assume that you're not the kind of person who's just gonna become a, a wreck if you were to, uh, ease up on yourself a bit. And the big revelation for me was finding that when I can pursue some kind of approach to productivity that allows me to take note of what I want to do, [chuckles] firstly, you get to harness that energy instead of trying to, um, squash it all the time, right?

    13. CW

      Mm.

    14. OB

      It's like crazy to come up with these incredibly, um, rigid, straitjacket productivity systems that say, like: Even if you feel like working on X, you've got to work on Y, because that was what you-

    15. CW

      Yeah, yeah, yeah, yeah

    16. OB

      ... that was what you assigned. You're just wasting your own energy. Um, and then secondly, the big discovery is that actually, you know, I, I, among the things I enjoy sometimes is things that involve, you know, work or administrative things that I would, would never have wanted to try to force myself to do, but feel like I need to do. Those sort of the things that belong to the world of obligation.

    17. CW

      Mm.

    18. OB

      Actually, there, there does come... there do come moments in the day or the week when that's the thing that you want to do, 'cause you wanna be the kind of person who keeps your commitments and is organized, and all sorts of things like that. So it's kind of a no-lose situation if your professional situation permits it at all, I think, to, um, to, to navigate by fun and enjoyment at least, uh, a little bit more than you probably are doing.

    19. CW

      Yeah, you wrote about the idea that interest is everything.

    20. OB

      Mm.

    21. CW

      "When you're procrastinating on a project, wondering why your outwardly successful career doesn't feel as vibrant as it could, or feeling stuck on a difficult life choice, it's worth asking if you've forgotten the importance of building your days, as far as you're able, around what actually interests you." And I think this sort of explains the bind that many people are in, where they struggle to do what they want because they think it won't be as effective in the marketplace or something, or it's, i- it's not right. For some reason, what they want to do is not right, what interests them is not right, so they nerf that.

    22. OB

      And, you know, I've, I've- I'd be fascinated about, to hear about your experiences with this, because I think one of the, um, one of the places this is really evident is in any kind of, um, any kind of digitally mediated stuff, including, you know, most of what I do, um, but especially, uh, a lot of what, of what you do and at the scale that you do it, right? You have the capacity to really know what other people respond well to-

    23. CW

      Yeah

    24. OB

      ... when you do it. This, this phenomenon is famous in podcasting and elsewhere for leading some people, uh, sort of, uh, astray, the kind of audience capture phenomenon and the rest of it. But even if you're not being audience captured, you're still liable or susceptible at any moment to really decide that what you're going to try to do is, is give people what they want. And I think, as opposed to what you want [chuckles] to give them, because it's more, um, interesting for you. And the big irony, of course, I think, um, at least my limited experience has been-

    25. CW

      Mm

    26. OB

      ... actually what people want is to read, watch, listen to things from people who are really alive with interest in what they're, in what they're talking about and, and dealing with.

    27. CW

      Before we continue, I am a massive fan of reducing your alcohol intake, but historically, non-alcoholic brews taste like ass. You don't need to be doing some big reset. Maybe you just want to crack a cold one without feeling like garbage the next morning, which is why I am such a huge fan of Athletic Brewing Co. They've got 50 types of NAs, including IPAs, goldens, and even limited releases, like a cocktail-inspired Paloma and Moscow Mule. And here's the thing: you can drink them anytime, late nights, early mornings, watching sports, playing sports. Doesn't matter, no hangover, no compromise, and that is why I partnered with them. You can find Athletic Brewing Co.'s best-selling lineup at grocery or liquor stores near you, or best option, get a full variety pack of four flavors shipped right to your door. Right now, you can get 15% off your first online order by going to the link in the description below or heading to athleticbrewing.com/modernwisdom. That's athleticbrewing.com/modernwisdom.... So true. Yeah, and, uh, in my experience, the further I've gotten away from what is it that I'm interested in, who is it that I want to speak to? The worse the show's got. Now, the numbers may have gone up, but if it's something that I don't care about- like, m- maybe if you run a charity or something, right? Or you- you- you're a, you're a, a pediatric neurosurgeon or something, like, it's on you... Your job is in service of this thing.

    28. OB

      Mm-hmm.

    29. CW

      And, and it's- the parameters of outcome are a bit more tightly defined. Like, it's not- if, if you do the surgery and it goes well, it doesn't matter if you enjoyed it or not.

    30. OB

      Right.

  7. 41:0346:26

    Is AI Just Another Control Fantasy?

    1. CW

      that's a really good point. I, I've been thinking about this with the advent of AI, because everybody has now- anyone that writes or, or, or speaks or fucking anybody, uh, has the potential to augment their process by using AI. And [clears throat] one of the things that it's given us the opportunity to do is basically put out- i- take credit for work that we didn't do at a scale that no one's ever been able to in the past. [laughing]

    2. OB

      [chuckles] Right, right. People have done it in organizations and stuff at a lower scale, right?

    3. CW

      Correct.

    4. OB

      Taking credit for their, what their underlings produce.

    5. CW

      Yeah.

    6. OB

      But this is like-

    7. CW

      You know, but it, it-

    8. OB

      This is nuclear. Yeah.

    9. CW

      It really d- yeah, it is. It is, and it's available to everybody, and it's available in sort of micro ways. For instance, let's say that you and your partner had an argument, and it would be really good for you guys to make up. And you go to ChatGPT, and you load the last few messages in, and you say: Can you write me a reply that is meaningful and loving-

    10. OB

      Mm

    11. CW

      ... that compromises without completely destroying my boundaries and will make my partner feel great? Please refer to as many psychological principles as you can, but keep it light and light-hearted. We've been together for about five years. Send. They send you that back. You send the message over to your partner, let's say.

    12. OB

      Mm-hmm.

    13. CW

      Your partner goes, "Baby, I'm so glad you sent me that message. It made me feel so good. I, I just... You know what I love about you?" And then all that you hear coming into your ears is, "I'm a fraud. I'm a fraud. I'm a fraud. I'm a fraud-

    14. OB

      Mm

    15. CW

      ... liar, liar, contrived, conceitful." Like, [clears throat] because y- you do not get to capture-... what is truly happening here. It wasn't you, it wasn't your genesis.

    16. OB

      Right, right, right.

    17. CW

      What someone's saying is, "Thank you for showing me you, and thank you for, uh, how wonderful for me to be the progenitor, the muse, the inspiration for your thoughts." And because you-

    18. OB

      Yeah

    19. CW

      ... didn't do it, you don't get to capture any of that goodwill.

    20. OB

      Yes. No, that's a great [chuckles] it's a great and kind of chilling example, although I know that lots of people are, are, are, uh, doing it. And I think that, yeah, I mean, I think that, um, I wish I could attribute this argument because it's not my own. I'm borrowing it from something I read, and I can't remember where I read it. But I think that, um, uh, a lot of what happens when you use, um, LLMs in that kind of context to sort of... It's, it's, again, it's like wanting to stay in control, right? It's wanting to sort of-

    21. CW

      Mm

    22. OB

      ... control and direct the process, make sure you say the right thing. It's totally not about the fact that a lot of relationship happens in the repair that follows saying the wrong thing, right?

    23. CW

      Mm-hmm.

    24. OB

      Um, so you have to sort of go wrong first. But somebody was making the argument that, you know, uh, it's a very, very old observation that everyone seems to speak in therapy speak these days, and sometimes this leads people to go on tirades against therapy itself. Um, and I always want to, I always want to kind of say these are two totally different things, right? And I, I couldn't really put words to it, but I s- saw this argument made that actually a lot of the therapy speak, especially in the, obviously, in the last couple of years or whatever, is, is really the kind of generic outputs of, um, both of large language models and of the kind of brains that use them too much and come to think and, and speak like them. It's the exact opposite of really good therapy, which is about, you know, at least in the tradition that I'm familiar with, is about like long-term, real relationship with another conscious, emoting human being.

    25. CW

      Mm.

    26. OB

      And absolutely doesn't need to be full of, you know, so-called therapy speak and jargon terms and, um, you know, turning every human experience into a, into a sort of, uh, technical path- pathol- pathology or something. It's completely different, but that feeling that everyone is kind of thinking too hard about what they're saying-

    27. CW

      Mm

    28. OB

      ... figuring out what to say first. Even just the nature of text-based communication and email and messaging has allowed some of that, right?

    29. CW

      The ability to delete and-

    30. OB

      Right

  8. 46:2655:14

    The Insecure Overachiever Paradox

    1. CW

      really interesting insight. Going back to the, uh, the idea about engineering enjoyment, I think the really impressive magic isn't in just grinding out difficult tasks. It's the very elite strata of people who are able to turn something enjoyable into a drag. Like, that is-

    2. OB

      [chuckles]

    3. CW

      ... it's, it's kind of like inverse stoicism, w- you're, you're- [both laughing] you're insulated-

    4. OB

      Yeah

    5. CW

      ... from the good things happening to you when you manage to turn-

    6. OB

      Yeah

    7. CW

      ... everything into something negative. So I had a little essay, uh, that I quoted you in, that I wanted to, I wanted to read to you, and it's called Frankel's Inverse Law. "When a man can't find a deep sense of meaning, they distract themselves with pleasure." That's Viktor Frankl. Frankl is arguing that lack of meaning causes people to seek temporary relief in superficial pursuits, rather than addressing the underlying existential void. Perhaps for many, maybe even most people, this is a big issue. But there is another group who suffer with the opposite problem: Frankel's Inverse Law. When a man can't find a deep sense of pleasure, they distract themselves with meaning. If ease, grace, joy, and playfulness don't come easily to you, one solution is to ignore moment-to-moment happiness entirely and just always pursue hard things. You become a world champion at winning the marshmallow test. You convince yourself that delayed gratification in perpetuity is noble because you struggle to ever feel grateful. The TLDR is you prioritize meaning over happiness because happiness doesn't come easily to you.

    8. OB

      Oh, I love that, and feel, uh, confronted by it. [laughing]

    9. CW

      Yeah, you've got-- I've got your line. It's, it's significantly longer than that, and I didn't want to subject you to the whole thing, but o- one of my favorite l- lines, paragraphs from you is: "You need to do at least a bit of what you care about now, as opposed to banking on finding time for it in the future. Once the decks are clear and life's duties are out of the way, life's duties will never be out of the way. And so if you really mean it, when you say you'd like to write a novel, or spend more time with your aging parents, or fighting climate change, or having fun, at some point you're just going to have to start doing it." And I think that, uh, the, the, the category of people for whom ease, grace, joy, moment-to-moment happiness are more difficult to access, they have learned that a-... lower efficiency, but higher reliability fuel is to just do hard things, because the sense of-

    10. OB

      Yeah

    11. CW

      -satisfaction can kind of always be achieved, even if the sense of joy can't.

    12. OB

      That's really interesting, and I love your use of the word grace in the bit that you w- wrote. It is kind of, is kind of really interesting to me as well, because I think there is... I'm slightly changing the subject maybe or developing the subject, but there's a, but there's a, there's an aspect to this which is also- which also maps onto, uh, the distinction between, uh, like living entirely in your head and in your intellect, versus being kind of embodied in the world, right?

    13. CW

      Mm.

    14. OB

      Because a big part of, um, enjoying life and showing up for things is, um, is embodied. Um, uh, y- you know, e- even just from the most basic sense of like, like feeling the air on your skin-

    15. CW

      Mm-hmm

    16. OB

      ... when you're present in a-

    17. CW

      Mm-hmm

    18. OB

      -in a place or something.

    19. CW

      Enjoying the coffee as opposed to using it at the maximum possible survivable temperature-

    20. OB

      Right

    21. CW

      ... in order to get the caffeine into your system.

    22. OB

      Exactly. Exactly. Um, and so yes, I think another thing that, uh, you know, uh, that characterises these, uh, insecure overachievers of which we speak, and that has definitely been like part of my biography, and I see it all over the place as well, uh, is, um, is being really sort of in your head. And really sort of not only driving towards the future, but assuming that the only way to... But, but that doing the driving through sort of cognition and living in your frontal cortex or whatever, this very specific feeling. Um, and I think you sort of see it. I, I, I feel like as I've got older and more experienced with what I've been doing, you sort of... I, um, I sort of pick up on it in people and kind of public figures sometimes, right? Not people I know personally, but it is this kind of... It's not just like we're charging into the future, but we're sort of dragging ourselves into the future by our, by our thinking in some way.

    23. CW

      Mm-hmm.

    24. OB

      And, and it is- there is something crucial about remembering that you're a, that you're a body as well, um, when it comes to... Of course, you can then be sort of obsessed with the body for reasons of like, you know, looks maxing or, or kind of-

    25. CW

      Yeah

    26. OB

      ... really obsessive kinds of physical fitness or whatever, that are just as much about-

    27. CW

      Mm-hmm

    28. OB

      ... the future progress.

    29. CW

      Well, I think the crossover, the, the, the crossover between those people is, is way bigger than you might think, which is why the, in the modern world, the kind of dumb gym rat versus the hyper-obsessive autist with glasses that doesn't lift, those Venn diagrams have gotten closer and closer [chuckles] together.

    30. OB

      Right.

  9. 55:1458:41

    Is Optimising Your Life Making You Miserable?

    1. CW

      What is the cost of constantly asking whether or not you're living your best life? [laughing]

    2. OB

      Uh, that's a good question. I mean, most obviously, I suppose it's just that that is, um... that's a, that's an invitation to f- find your life as it is right now wanting, as opposed- as compared to some, um, fantasy that you have of what your best life would be. I'm quite suspicious of the notion of, of a best life. It reminds me of the notion of sort of fully realizing your potential, right? These are, these are concepts, they're not, they're not, they're not reality, and they're also concepts that have this kind of absolute no, no stopping rule, right? No, no limit. Like, you can-- you could be doing absolutely the most amazing things in the history of the world, and you'd have no objective way to know that you had maximized your potential or that it was your best life, and there couldn't be one better. So maybe I'm taking your question too literally.

    3. CW

      No, I-

    4. OB

      You really are asking that, that's where you're gonna end up.

    5. CW

      There's a really interesting, uh, tweet that I saw a couple of weeks ago by this lady who's a communications professor, and it was a, a clip of her, [clears throat] and she was talking about how being underrated is a compliment, but being overrated is an insult, and how if you actually think about that, what you're saying is, why would not being as popular as you're supposed to be, be a compliment?

    6. OB

      [chuckles] Right.

    7. CW

      And why would be... w- why would being basically an overachiever with regards to your capacity- and it's, it's all just social signaling. It's all just you being able to say, as the observer: "I'm the sort of person that is able to detect in another that which hasn't been recognized by other people on both sides."

    8. OB

      Yeah, yeah.

    9. CW

      "Like, I know that they're full of shit, when actually people think they're good," or, "I know that they're actually brilliant when no one else has re- realized it yet." And, um-

    10. OB

      Yes

    11. CW

      ... that is kind of happening with our own judgments of our potential. That what we're saying is, "I have an estimation of where I should be based on what I think I can do."

    12. OB

      Mm-hmm.

    13. CW

      But the what I think I can do is plucked out of complete fucking obscurity, and i- it is, like you say, a fantasy, because-

    14. OB

      Mm-hmm

    15. CW

      ... well, this is a good question that I sometimes ask myself if I get too self-critical, which is: what else could you have done? What else could you have done that you didn't do-

    16. OB

      Mm-hmm

    17. CW

      ... in order to assuage whatever deep feelings of insufficiency are currently swimming through you? Like, what else, what else would you have done? And when you actually go through it, you're like: "Fuck me, like, I mean, I, I could have gone to bed half an hour earlier on Tuesday, and then that would have meant I could have got up..." But I'm really, you know, I'm playing in the margins here. I, I really-

    18. OB

      [chuckles]

    19. CW

      ... I really, I really gave it a good shot. [chuckles]

    20. OB

      [chuckles]

    21. CW

      And, uh, just when you ask: what else could I have done? Um, you, in my experience, you find out, probably not that much. I, I, I, I probably did pretty close to what I'm capable of. And again,

  10. 58:411:05:19

    Do High Performers Create Their Own Problems?

    1. CW

      what was-- have I ever done my type A people, type B problems thing to you? Have I given you this one?

    2. OB

      [chuckles] Uh, it's not ringing a bell.

    3. CW

      Oh.

    4. OB

      So maybe not.

    5. CW

      God, let me give you-

    6. OB

      Oh. [laughing]

    7. CW

      L- let me give you this. I mean, this is-

    8. OB

      I'm excited.

    9. CW

      I am, I am just so shameless with how much I get inspired by people like you and Alain de Botton. But, uh, this, this is one of my best ones, and this, this came out of a conversation between me and George. I think type A people have a type B problem, and type B people have a type A problem. Insecure overachievers need to learn how to chill out and relax, and lazy people need to learn how to work harder and be disciplined. Given that you subscribe to me, I'm going to guess you're probably type A, some version of a walking anxiety disorder harnessed for productivity, as Andrew Wilkinson says. Here's the thing you may have already realized: type A people with a type B problem get very little sympathy, because a miserable but outwardly successful person always appears to be in a much more preferential position than a content being lazy but on the verge of bankruptcy one. Problems of opportunity will always get less sympathy than ones of scarcity. One feels like a choice, the other like a limitation. One is a bourgeois luxury, the other is a systemic imposition. "I need someone to teach me how to be disciplined and work harder," feels noble, upward aiming, and charitable. "I need someone to teach me how to switch off and relax," feels dopaminergic, addicted, and opulent. Every underdog movie ever has a training montage of someone sorting their life out by working harder. None included a guy learning how to log out of Slack at six PM-

    10. OB

      [laughing]

    11. CW

      ... or finally enjoy a beach holiday. So yes, type A people may objectively have better lives, but subjectively, they're ravaged by the sense that they've never done enough. They wake up every morning feeling as if they've already fallen behind, and only if they dominate their entire day flawlessly will they have dragged themselves back up to some minimum level of acceptable output, which means they can go to sleep that night without feeling like a loser. Congratulations, you might be very successful, but you also might be very miserable. "Just work harder, bro" advice reliably makes everyone more successful in the only way they can be judged.... outwardly. There are very few issues in life which can't be solved by just working harder, so everyone treats it as a panacea, not a purpose-built tool. And on average, maybe more people do need to hear David Goggins screaming in their face to go harder than Eckhart Tolle whispering in their ear that they are enough already. But for a certain, perhaps minority cohort of people, they actually need to hear the opposite message. We need a parasympathetic Goggins who's going to carry the TV remote and the Cheetos. Hashtag rest harder than me. Type B problems are just as tough as Type A ones, but they require a much less sexy solution: peace, one that you can't actually achieve by simply working harder.

    12. OB

      Nice. [laughing] I agree. I agree, I agree. I have those problems. I have had those problems. You know what it, it also makes me- something that w- came up in the middle of listening to you read out-

    13. CW

      Yeah

    14. OB

      ... which is lovely, um, is there's like this weird selection bias problem here as well, isn't there? Which is that the... See if I can express this. The, the people who are drawn to the hard-charging-

    15. CW

      Mm-hmm

    16. OB

      ... uh, self-punishing, you know, work harder stuff, are gonna be pretty much by definition, the people who don't, who, for whom that message is something they don't need, right? That, the, the, the temptation is gonna be for people to pursue those messages and consume that kind of stuff, read those books, watch those videos, because they're already like in too deep with the idea that that's what they need to do, and they need more sort of, um, fuel to, to help their, um, their sort of driving of themselves. And so, and, and probably the reverse is true, right? Which is that people who are kind of, um, already pretty relaxed and into relaxation are gonna be, uh, consuming-

    17. CW

      Mm

    18. OB

      ... a lot of, uh, relaxing, uh, content. So it's almost like, you know, it's like democracy, the, the people who get into power are exactly the ones who shouldn't be in power or whatever. It's like the people who, people who really need to relax are going to be the most prone to, um, consuming the message that-

    19. CW

      Oh!

    20. OB

      -they just need to work a little harder.

    21. CW

      You just... You, you keep fucking activating my trap cards, all of them. [laughing] I can't read you another- I can't read you another essay, but it does go to show how astrally fucking connected we are. Um-

    22. OB

      [laughing]

    23. CW

      ... I did- I, I, I, I'll just send you it. Yeah, I'll send you it, and you can read it afterwards.

    24. OB

      Please do.

    25. CW

      Anyway, um-

    26. OB

      Yeah

    27. CW

      ... if, if anyone wants to read it, it's called Advice Hyper-Responders, and, and they can just search it on my, on my blog.

    28. OB

      Oh, there you go. Yeah. That, the, the title-

    29. CW

      Yep

    30. OB

      ... the title shows me that that is, uh-

  11. 1:05:191:21:22

    Criticism and Congruence: Learning to Relinquish Control

    1. CW

      it's a, a good point to make, and I- there's two things that I've been thinking about recently, especially over the last maybe 18 months or so, which is since the last time that me and you spoke. Um, I have really fucking tried to go on a journey, partly inspired by you, partly inspired by Alan, partly inspired by Joe Hudson and my therapy, and to be like: Okay, can I be really good at what I do and, and enjoy it? Can I, uh, try and produce at a high standard and not grip life too tightly? And one of the problems of that, this journey of relinquishing, of certainty and control and all the rest of it, there's two things that have happened. First off, I've had to publicly say things that sound like they're in disagreement with something that I previously said. Um-

    2. OB

      Mm.

    3. CW

      ... me saying that, uh, just work harder, bro, advice, a sentence that I've almost certainly said at some point, like: "Fuck your feelings, just keep going," blah, blah, blah.

    4. OB

      [chuckles]

    5. CW

      Um, that feels like, uh, uh, a non-insignificant number of comments. It's something to the effect of, "Bro sold us the problem, and now he's selling us the solution."

    6. OB

      [laughing]

    7. CW

      Uh, and I'm like: Well, look, if, if I did, if I did do that, I fucking sold it to myself as well-

    8. OB

      Yeah

    9. CW

      ... because I believed it. So I, I apologize-

    10. OB

      Yeah

    11. CW

      ... I apologize for that. That also being said, at the time, I've never said, "This is the way to live your life." Like, this is-

    12. OB

      Mm

    13. CW

      ... what I'm playing with at the moment, and I think I've caveated a lot around, like, don't just fucking end yourself trying to get this done. So that's the first thing. The first thing is that you've, you end up with a lot of criticism, I think. You end up with more criticism being, uh, g- giving the sort of-... rhetoric, philosophy that you do, because it sounds, it doesn't sound like going from low agency to high agency. It sounds like going from high agency to low agency. [laughing] And, and like-

    14. OB

      Yeah

    15. CW

      ... the obviousness of just work ha- the, the, the sort of just work harder, grip it more tightly advice is so much more pithy, and much of my channel-

    16. OB

      Mm

    17. CW

      ... has been built on, you know, analogies, analogies of that, uh, the, in the, the orbit around that sort of thing. But the second thing, and this is way fucking harder, and this is something that I'm really interested to find out whether you had to deal with, and I think a lot of the audience are dealing with too, is a complete loss of congruence as a person, as you try and go through this. Especially if you've made- you've wrapped a lot of your identity in being the hard charger, "I get things done. I know me. The outcomes I get in the real world are because I do things. I, I go to bed on nighttime, and I think about doing things. I wake up in the morning, and my plan is to do things." Like, you know, thoughts, intentions, actions, goals, outcomes, they're all aligned.

    18. OB

      Mm.

    19. CW

      And say what you want about Trump or Andrew Tate or fucking Mamdani, or whatever it is, but they are highly congruent people. Like, they are just a single line up and down, and this is why Andrew Tate recently lost a boxing fight. That was why it was so, um, d- damaging, I think, to some of his, uh, perception publicly, because he had this sort of very congruent line, and there was now this thing that had got slotted on the side. It would be like if you found out that Trump had started doing meditation or something. You'd go, "Well, this doesn't fit the congruence-

    20. OB

      Right

    21. CW

      ... that we expect," or if you found out that Mamdani secretly owned a bunch of, like, bakeries or something. It's like it just doesn't... I can't slot it in to, to my sort of worldview. And the going through this, I truly believe that there is something on the other side of letting go, and that is a journey that I'm gonna try and go on. But as you do that, your real-world results, briefly, and maybe even for actually a medium, a, a pretty significant chunk of time, get a little bit worse because you've got to relinquish some of the strategies that you were u- using previously before you've got-

    22. OB

      Right

    23. CW

      ... mastery in the new ones.

    24. OB

      Yeah.

    25. CW

      You're saying all of this stuff, and you're talking about embodying emotions and just going with the flow and learning to... And from the outside, what it looks like is not that you've evolved into this-

    26. OB

      Mm

    27. CW

      ... newly enlightened, but it looks like you've devolved back to the thing that you tried to only just get escape velocity from a fucking decade ago. So this-

    28. OB

      Yes

    29. CW

      ... this loss of congruence between criticism and congruence, those are the two things that I've felt in the last 18 months since sort of trying to embody this a little bit more, uh, honestly.

    30. OB

      That's really interesting. I mean, the criticism one feels somewhat kind of professionally specific, right? Because you're... Oh.

  12. 1:21:221:26:12

    Does Settling Help You Get More Out of Life?

    1. CW

      One other contrarian opinion of yours, which I think is real interesting, is on settling. Basically, that people can sort of get more out of life from settling, that, uh, when you commit to a person or a path, uh, more opportunities will arise because of the, the newfound depth. Is this in tension with the, the creature inside of us all that desires maximization, and novelty, and, and creativity?

    2. OB

      It's been interesting that that thing I wrote in Four Thousand Weeks about, about settling, um, because obviously, apart from anything else, this is a phrase that and immediately connotes kind of romantic relationships and dating.

    3. CW

      Mm-hmm.

    4. OB

      And, uh, uh, I don't think that's my role on your podcast, actually, Chris, I think to come in and give, uh, dating advice. I think that, I think that is best left to, uh, other guests, probably.

    5. CW

      Mm.

    6. OB

      But the, but the, but the thing [chuckles] that... the thing that I was trying to say, and that I think is just true, is that it's not so much that you should settle in that context or any other, it's, it's that finitude just means you are settling, right? Like, what we mean by settling is accepting some downside in return for the security or, um, whatever else it might be, uh, that, that you get through taking that option, choosing that relationship, staying in that job, whatever it is. And, and one way of expressing, like, half of what I write about is just like, there are always downsides, right? "You can do what you like, you only need to face the consequences," as, uh-

    7. CW

      Mm

    8. OB

      ... Sheldon Kopp puts it. So it's not really... Yeah, I think we get into this situation where we think, "Well, I'm the kind of person who would never settle, so I'm going to max- I'm gonna go for the absolute best thing." But what that gets confused with is, "I'm going to go for this thing that doesn't exist, that has no downside, that has no conseq- no negative consequence," when for finite humans, every choice, every decision on how to use your time or what commitments to make or not make, has, um, has a downside. Um, so it isn't that you should do any one specific thing or that settling down, to extend that phrase right into a long-term relationship, is necessarily the right thing for any person at any given point in life. It's just the recognition that if you don't do that and you do the other thing, you're also settling, right? You're also, um, deciding to accept a different set of negative consequences. A lot of indecision, a lot of, um, uh, uh, commitment phobia, I think-

    9. CW

      Mm

    10. OB

      ... in relationships and in other domains, has this feeling of like, "I'm just gonna keep my options open." But you don't keep your options open. You choose to spend that portion of time without the benefits of a long-term relationship, which might be right for somebody.

    11. CW

      Mm.

    12. OB

      But don't go fooling yourself that you're somehow, like, hanging back from... Like, you're in the human condition, like, you're not getting out of it. [chuckles]

    13. CW

      Ah.

    14. OB

      And this means that, this means that, um, th- this means that you're making that kind of trade-off in every moment of time. I hope this is clear. I don't know, but-

    15. CW

      Uh, it, it is.

    16. OB

      Yeah. Yeah.

    17. CW

      Is there-

    18. OB

      That's, that's the point.

    19. CW

      How do people know when it's a good time to settle? Is there such a thing?

    20. OB

      [exhales] I think that... I mean, rephrasing that question back into what I was saying, it's like, how do you decide which, how do you decide which trade-off to make?

    21. CW

      Mm.

    22. OB

      How do you know, in a given moment, which trade-off is the right trade-off? And I think an awful lot of it is-... is annoyingly enough, kind of intuitive and beyond words and, and all the rest of it. But I do think that you can become aware that the only main reason that you're not committing to something is some sort of restless fantasy of not having to make any trade-off.

    23. CW

      Mm.

    24. OB

      Um, so holding out for a kind of perfection that, that doesn't actually exist in the world. Um, and I think when you become aware of that fact, that when you see what game you're up to, then it's often very easy to see, "Oh, right. Actually, yes, this is the, this is the path I should follow. This is the commitment I should make, because the only reason that's really stopping me from making it is this kind of notion that I might not have to accept any loss or disappointment-

    25. CW

      Mm

    26. OB

      ... um, for making it."

  13. 1:26:121:31:25

    What Is Oliver Working On Now?

    1. CW

      What are you working on now? Have you got a new book? I want you to have a new book. Can you have-

    2. OB

      I'm trying to write a new book

    3. CW

      -a request a new book?

    4. OB

      [chuckles] I'm trying to write a new book.

    5. CW

      Yeah.

    6. OB

      Um, I'm-- I am, uh, endeavoring to write a book. Uh, I should be more... I should be open about what it is, shouldn't I? I shouldn't be all coy and, um, it's probably helpful to the creative process to, like, uh-

    7. CW

      Mm

    8. OB

      ... put my cards on the table. I'm trying to write a book going into, going in on this topic of aliveness-

    9. CW

      Oh

    10. OB

      ... and this idea of this mysterious concept that describes so much of what seems to be missing from so many people's, uh, experience, and also to be present when things are going really well. This sort of intangible sense of, um, of, uh, of, of aliveness. [chuckles] I ne- I need, uh, some other words, perhaps. And also, I'm trying to get at this idea that a lot of what stops us from feeling that kind of deep sense of being immersed in life and doing the right things and the meaningful things, and, and all the rest of it, [clears throat] is a kind of, um... Well, the word I keep wanting to use is clenching, and then-

    11. CW

      Mm-hmm

    12. OB

      ... the correct antidote for clenching is unclenching. But my, um, my editors are concerned that the, um, imagery, if I consider-

    13. CW

      Uh, it's not quite right

    14. OB

      ... talking about clenching and unclenching. [chuckles]

    15. CW

      I, I, I, it's a fraught word. Have you considered grasping? Grasping is... Grasping is quite nice because it suggests that you don't yet have it. I quite like that.

    16. OB

      Yes. Well, yes. Yeah. No, absolutely. Uh, uh, I think that's a, a huge part of it, but it's al- yeah, and I... And also, um, i- it's the kind of, i- it's the degree to which kind of relaxing into the situation that you're in is the pathway to agency and the pathway to enjoyment, and all the rest of it. And part of this, where this comes from in some ways is partly to do with the very widespread sense that people have, that we're living in, like, really unnerving historical times, and that the, the sort of wider world is one that causes a lot of people to want to sort of like, like, um, uh, um, clam up or, or tighten-

    17. CW

      Mm

    18. OB

      ... or something.

    19. CW

      Mm.

    20. OB

      Um, and I think that this, this move of relaxing into the chaos and the craziness and the uncertainty is one that, like, I think is really useful just in day-to-day individual life. But I think it might also be a way of, of relating to the feeling that whether it's politics or AI or a million other crises unfolding everywhere-

    21. CW

      Mm

    22. OB

      ... that, that trying to sort of shelter from all of that completely is... See, I don't wanna write- I'm not an activist. I don't wanna write a book about, uh, being an activist and making-

    23. CW

      Mm

    24. OB

      ... the world's crises better, but I also don't- I've got no time for the kind of argument that is like, just ignore all that stuff and focus on, you know, just focus on your own personal life and your own, and, you know, building your business or whatever. Like, these two... So, as ever, I'm sort of annoyed with two camps of writing on, on, on these topics, and I'm trying to find, uh, what I think people should do instead.

    25. CW

      Walk some balance beam in between them. I think if you were to say a book about aliveness, it would-- if it wasn't you or someone like you, that's gonna do it in a sufficiently sanguine and self-deprecating way, it would f- it would... My, my first sense would be a sort of cloyingly prescriptive framework.

    26. OB

      Spiritual-

    27. CW

      No

    28. OB

      ... maybe? Yeah.

    29. CW

      It would be-

    30. OB

      Oh, okay

  14. 1:31:251:31:59

    Where to Find Oliver

    1. OB

      always think that.

    2. CW

      Oliver Burkeman, ladies and gentlemen. Oliver, you're great. Everyone should go and subscribe to your newsletter, which is The Imperfectionist. Where else are you doing... Is there anything else to subscribe to, or is it just that?

    3. OB

      That's the thing to subscribe to, um, my most recent book is Meditations for Mortals. So, uh, that's the other thing to, to mention here.

    4. CW

      Until the next time, Oliver, I appreciate you very much.

    5. OB

      It's a huge pleasure. Thank you so much. [upbeat music]

    6. CW

      Congratulations, you made it to the end of an episode. Your brain has not been completely destroyed by the internet just yet. Here's another one that you should watch. Come on.

Episode duration: 1:31:59

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