#1061 - Oliver Burkeman - Why You Can’t Stop Your Productivity Addiction

Summary

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Modern Wisdom #1061: Oliver Burkeman — Why You Can’t Stop Your Productivity Addiction

Date: February 19, 2026
Host: Chris Williamson
Guest: Oliver Burkeman

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Episode Overview

In this engaging and reflective episode, Chris Williamson sits down with writer and thinker Oliver Burkeman to probe the dark underbelly of productivity culture. Together, they explore the addictive nature of achievement, the endless chase for self-improvement, and how our frantic attempts to “maximize” life may actually rob us of living it. The conversation weaves between personal anecdotes, psychological insights, and pithy wisdom on how to loosen our grip, find true agency, and perhaps finally learn to unclench our white-knuckled hold on existence.

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1. High Achievement vs. Relaxation: Is It Possible to Have Both?

[00:00–03:30]

• Theme: Can you be “the best” and relaxed, or does hyper-competence demand constant tension and anxiety?
  • Oliver: “The more relaxed I can be, the better I am at things... I’m on a personally motivated mission to prove [relaxation and accomplishment] aren’t mutually exclusive.” [00:37]
  • Chris notes the “ambient anxiety” that comes with hyperfocus and asks if it’s possible to hold ambition more loosely.
  • They agree that the urge to control often sabotages genuine excellence; real mastery emerges more often from a flow state than brute-force vigilance.

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2. The Productivity Trap & The Insecure Overachiever

[03:30–07:00]

• The Central Problem: Most people struggle to pursue goals without tying their entire self-worth to outcomes.
  • Chris: “The only way I can pursue a goal is if I care... and so disappointment when I fail becomes a judgment about my worth.” [03:30]
  • Oliver introduces the concept of the “insecure overachiever”: people lauded for success but internally anxious, forever raising their minimum acceptable output.
    • “Anything you achieve... just instantly becomes the minimum standard that you’ve got to meet next time, which is a very depressing way to live.” [04:15]

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3. Success as Relief vs. Success as Joy

[07:00–12:00]

• Joy or Just Not-Failing?
  • Chris shares a personal story: after his podcast achieved global charts success, joy lasted “probably 15 minutes” before panic over next year’s standard set in. [08:43]
    • Notable quote: “If the higher I climb is the further I fall, then why love anything at all?” [07:00]
  • They discuss how the celebration of achievement can devolve into mere relief—wiping away fear rather than generating real joy.

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4. The Plane Has Already Crashed: Acceptance, Finitude, and Failure

[11:53–15:54]

• Key Insight: Much of suffering comes from the belief we can avoid all failure.
  • Oliver’s metaphor: “We go through life braced, like we’re in a plane that might crash... but in a way, the plane has already crashed. Here you are, on the desert island in the smoking wreckage. That’s what life is.” [13:23]
  • Accepting limits, finitude, and already-missed opportunities can be liberating, not depressing: “It's so invigorating to realize I don’t have to go through life trying to stave off the great failure, because that’s just being alive.” [13:48]

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5. Krishnamurti’s Secret: “I Don’t Mind What Happens”

[15:54–18:14]

• The Wisdom of Letting Go:
  • Oliver recounts Krishnamurti’s ultimate secret: “I don’t mind what happens.” [16:04]
  • This stance isn’t about apathy—it’s about ending the chronic collision between “what you are demanding that reality do and what reality does do.”
  • Chris notes we spend much of life “leaning through your own life” instead of inhabiting the moment.

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6. The Addiction to Control and the Problem of Uncertainty

[20:28–24:08]

• The Drive for Control:
  • Chris describes “leaning forward,” always hungering for the next thing, even on a simple night at a comedy club.
  • Oliver: The urge to control is a way to temporarily insulate ourselves from the vulnerability and terror of life’s uncertainties and finiteness.
  • Many time-wasting behaviors can be a symptom of wanting to avoid the vulnerability that comes with meaningful engagement. [21:14]

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7. Aging, Acceptance, and the Midlife Perspective

[24:41–29:20]

• How Does the Insecure Overachiever Change With Age?
  • Oliver: Accumulated experience teaches that the “world does not collapse” when you break a streak, and basic confidence may finally settle in.
  • Nearing midlife brings a “hurry the fuck up” motivation: “At some point, it’s going to have to be now.” [27:56]
  • Chris shares his phone background: “Do it anyway”—embracing action despite uncertainty, tiredness, or fear. [28:14]
    • Oliver offers the British equivalent: “You might as well.” [29:41]
    • Oliver quotes Elizabeth Gilbert: “You’re scared to surrender because you’re afraid of losing control. But you never had control. All you had was anxiety.” [30:14]

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8. The Pursuit of Aliveness—Interest, Enjoyment, and the Trap of Optimization

[31:09–38:57]

• Can Enjoyment Be Engineered?
  • Oliver distrusts attempts to “engineer” fun, arguing that enjoyment cannot be monitored or forced as a productivity hack.
  • He shares the revelation that letting productivity be guided (at least in part) by authentic interest produces better work and greater satisfaction.
  • Chris: “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. The numbers may have gone up, but if it’s something that I don’t care about, it’s just vibes.”

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9. Marketability vs. Aliveness: Audience Capture and Staying Authentic

[38:57–42:02]

• The Temptation to Please the Crowd:
  • Both discuss the risk of being “captured” by the audience or market, losing personal aliveness in favor of what is popular or effective, and how this ultimately hollows out meaningful work.
  • Oliver: “At the end of the day, why do you care? If the thing you’re doing isn’t a meaningful experience overall, then... why would you do it?”

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10. Authenticity, A.I., and the Fraud Paradox

[42:02–45:49]

• A.I. as Productivity Cheat:
  • Chris outlines a chilling example: using AI to compose a heartfelt message for a partner, and then feeling like a fraud when it’s well received—because “you do not get to capture what’s truly happening here. It wasn’t you.”
  • Oliver notes the subtle difference between authentic experience and “therapy speak” or LLM-generated content: real meaning and intimacy arise from risk, repair, and genuine presence.
  • Together they reflect on how increasing digital mediation and editability have fostered a “self-assessment and cajoling energy” that distances us from the rawness of life. [45:46]

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11. The Frankl Inverse & The Problem With Never Accessing Joy

[47:39–51:46]

• Overdevelopment of Meaning, Underdevelopment of Joy:
  • Chris reads from his essay “Frankl’s Inverse Law,” addressing those who substitute constant meaning or hard work for pleasure, because they find joy inaccessible.
  • Oliver: “A lower efficiency but higher reliability fuel is to just do hard things, because the sense of satisfaction can kind of always be achieved, even if the sense of joy can’t.”
  • They discuss the importance of embodied experience, grace, and being present—not merely using productivity or even the body as another tool for control.

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12. Control vs. Agency: Shades of Power

[52:55–54:38]

• Difference Between Agency and Control:
  • Chris argues for the value of agency, yet sees a limit—a need to sometimes “be on a set of guardrails.”
  • Oliver: “Agency and control are in some sense fundamentally different things... To relax the need for control is the extent to which I acquire what I think of as agency or power.” [53:51]
  • Fragile self-worth results from making accomplishments the criteria for existence.

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13. The Cost of Chasing Your Best Life & The Mirage of Maximal Potential

[55:55–59:16]

• Downsides of Maximalist Thinking:
  • Oliver is “suspicious of the notion of a best life,” likening it to the endlessly receding horizon of “fully realizing your potential.”
  • Chris offers a powerful self-check: “If I get too self-critical... What else could you have done? ...I probably did pretty close to what I’m capable of.” [56:57]

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14. “Type A People Have Type B Problems” — The Hidden Plight of the Productive

[59:20–63:35]

• Cultural Blind Spots in Self-Help:
  • Chris shares one of his best essays, arguing: “Insecure overachievers need to learn how to chill out and relax, and lazy people need to learn how to be disciplined... Type A people may objectively have better lives, but subjectively they’re ravaged by the sense they’ve never done enough.” [59:20]
  • Oliver notes the “selection bias problem”: Those who most need rest are ironically most susceptible to “work harder” advice, and vice versa.

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15. The Journey of Letting Go: Criticism, Congruence, and Identity Transitions

[65:40–80:35]

• Losing Congruence in Order to Grow:
  • Chris describes the discomfort of public evolution—from high-agency, hustle gospel to advocating for “letting go.” This triggers criticism and, harder still, a “loss of congruence” in identity.
  • Oliver: “Remaining completely congruent all through your life... is a disaster. We all do know people who seem stuck in the wrong age for the psychological outlook that they have.” [73:30]
  • James Hollis is quoted: “The goal of really good therapy is to make your life more interesting to you.”
  • Both agree these phases of incongruence are necessary but uncomfortable, akin to being a crab who has outgrown its shell before a new one hardens.
  • The apparent “unproductivity” and uncertainty of these times is “generative”—something is happening beneath the surface even if you can’t see growth yet. [80:15]

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16. The Value of Settling: When Depth Follows Commitment

[82:17–86:41]

• Will Settling Down Ruin Your Potential?
  • Oliver reclaims the idea of “settling”: Every choice is a form of settling, since every real path comes with downsides and opportunity costs.
  • “A lot of indecision... has this feeling of, ‘I’m just going to keep my options open.’ But you don’t keep your options open—you choose to spend that time without the benefits of commitment.” [84:07]
  • The right time to “settle” or commit is often when you realize you’re just chasing an unattainable fantasy of perfection.

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17. Oliver’s Next Book: Aliveness and the Power of “Unclenching”

[86:41–92:13]

• New Project:
  • Oliver shares he’s writing a book about “aliveness,” the elusive sensation at the heart of meaningful life experiences.
  • He wants to avoid both spiritual platitudes and clinical prescriptions, aiming for a nuanced account of what it means to “relax into the chaos... and unclench.”
  • Chris warns that a book about aliveness could easily become cloying, unless done with subtlety and lived wisdom—qualities he trusts Oliver to deliver.

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Memorable Quotes

• “The more relaxed I can be, the better I am at things.” — Oliver [00:37]
• “Anything you achieve... instantly becomes the minimum standard you’ve got to meet next time, which is a very depressing way to live.” — Oliver [04:15]
• “If the higher I climb is the further I fall, then why love anything at all?” — Chris [07:00]
• “You never had control. All you had was anxiety.” — Elizabeth Gilbert, quoted by Oliver [30:14]
• “Connecting to the aliveness is the ultimate point.” — Chris [39:52]
• “To relax the need for control... that’s the extent to which I acquire agency.” — Oliver [53:51]
• “Every underdog movie has a guy working harder, but none include a guy learning how to log out of Slack at 6pm or finally enjoy a beach holiday.” — Chris [61:00]
• “The goal of therapy is to make your life more interesting to you.” — James Hollis, paraphrased by Oliver [73:50]

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Timestamps for Key Segments

• 00:37 — The myth (and truth) of relaxed excellence
• 04:15 — The curse of the insecure overachiever
• 07:00–09:45 — Success as relief, not joy
• 13:23 — “The plane has already crashed” — Living amid inevitable failure
• 16:04 — Krishnamurti’s “I don’t mind what happens”
• 27:56 — The “hurry the fuck up” spirit of midlife
• 28:14 — “Do it anyway”: embracing action & uncertainty
• 45:46 — Authenticity in the age of edits and AI
• 59:20 — “Type A people have Type B problems”
• 73:30 — The danger of lifelong congruence—time for a “midlife crisis”
• 80:15 — The generative discomfort of growth and transition
• 84:07 — The reality and necessity of “settling”

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Final Thoughts

Oliver Burkeman and Chris Williamson cut through popular self-help dogmas to reveal the uncomfortable truths about productivity, ambition, and the longing for control. If you feel that your life is one long to-do list or that achievement has become its own prison, their insights offer a path—one that paradoxically runs not toward “maximizing” but toward letting go, embracing finitude, re-learning enjoyment, and finally, living with “aliveness.”

Transcript

[A]

Valentine's Day is coming up and whether you want to more deeply connect with your partner or work out whether or not you should break up, I've got the fix for you. I have put together a list of 50 of the most viral and science backed ways to connect with your partner more deeply and 25 questions that will help you work out whether or not you should break up and they're all available right now at the Modern Wisdom Valentine's review and it is completely free. You can get it by going to chriswillex.com valentines that's chriswillex.com/valentine's is it possible to be the best in the world and relaxed at the same time?

[B]

The best in the world? I don't know. 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 going to claim to be the best in the world at anything, but I think that notion that you've either got to choose a relaxing life or an accomplished one. This is the thing I'm on a mission, very personally motivated mission to prove is not how it works.

[A]

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 I can see, for instance, if you were to say, 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. 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.

[B]

Yeah, it's really interesting. I think that 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 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 sort of conscious, controlly controlling way. So yeah, for me, and of course I'm talking about things like writing or speaking, I mean, I'm not talking about. It may work differently and to different degrees for kind of sports performance and things, but you find that the more I'm trying to make sure that things go well, that's just like a. And therefore I'm sort of unrelaxed and clenched and muscles tensed and everything, the more 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.

[A]

I think a lot of people are struggling to find a healthy way to pursue goals without tying their self worth to the outcome. That is one of the fundamental problems. The only way that I can get myself to pursue a goal is if I care about it. And in the act of caring about it, I'm going to 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 or not I, you know. So 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, are ones you care about and in the caring, the disappointment and in the disappointment the self worth.

[B]

So I mean there's a sort of ideal way of doing this which I don't claim to have totally pulled off or anything, but I think the distinction is 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. And there are other ways of caring about goals. So there's a concept in psychology, the concept of the insecure overachiever, which whenever I kind of mention it in public, audience context or whatever, like half the people in the room, just the look of recognition 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, 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 fix something about themselves or to try to feel okay and to try to sort of fill a void. So loads and loads of really successful people in the world I think 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. And that sort of. That puts you in a perpetual place where everything you're doing in terms of goal pursuit is to try to make yourself feel sort of less bad about yourself. 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, which is a very depressing way to live, right? And so you do really well at 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 who are you? What are you? There is this whole other way of thinking about caring about goals, right? Which is to say like, 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 sitting around doing nothing. So I think there is a way of being ambitious and accomplished that doesn't need to be like in. In flight from. From something. But it's a. It can be challenging to get there.

[A]

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. It. It's one of the central questions that I want to achieve things, but I don't want to miss my life. Might be a pithy way to sort of describe it. And I called it the curse of competence. This situation where if things go well for you sometimes 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 Bellion and Luke Coombs songs that says if the higher I climb is the further I fall, then why love anything at all? And he's talking about it with regards to falling in love with somebody. But the same thing is true. The insecure overachiever in me pattern matched it to personal development. Yeah, I just thought it's so funny. I found out in the middle of December last year that the podcast charted really high globally on this Spotify thing and the Goldilocks zone, period. After not knowing that I charted this thing and before realizing that that meant next year I have to be better than that.

[B]

Yeah, right, right.

[A]

Approximately. Probably 15 minutes or maybe less.

[B]

And a beautiful 15 minutes.

[A]

It was so good. 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 get my nose back to the grindstone. I remember I saw this Ryan Holiday video. I brought this up to him, and I think Ryan's a super balanced guy and I really, really like him. But I had seen this. It's almost like performative grind set, I don't think. I think it's more him, which is why it's less. It feels less contrived. He got a call from his publisher and he was sat in his office, and it was to say, you've hit the New York Times list. Your number, whatever, won, or 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 gotta get back to writing the next book. And I was like, ryan, come on, dude. Like, you're supposed to be the fucking guy anyway. Curse of competence. If the higher I climb is the further I fall. And me, my Spotify debacle last year of realizing this is the minimum level of acceptable output for 12 months time. It's a real pervasive challenge.

[B]

Yeah, absolutely. I was speaking to an author more successful than me, talking about how I shouldn't name names. He was talking about how, you know, when his first big successful book had 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. 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 did get to the top very soon after release, that he sort of felt only relief 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 bare minimum.

[A]

Yeah. 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, and it is, when things go well, is your presiding sensation one of joy or one of relief? Is it the sort of congratulation of self, love or simply the abatement of fear? And I just think, like this, you see, it's strange doing talk. I'm sure you do live stuff, too. And it's strange giving talks like this because a musician wants hands in the air and shouting and a comedian wants laughter and clapping. And if you're us, what you want is this kind of sullen, fearful look on someone's face. What does an existential crisis.

[B]

Existential crisis trigger, Right? Yeah, exactly.

[A]

What does an existential crisis look like from the outside? And that's the fucking bullseye for me. That's exactly what I'm going for.

[B]

Yeah, brilliant. No, I think. And I think that's a great. It's a great question. It's a great way of putting it. It obviously raises the question of what the answer is to this. And I think it's really one of those things where, first of all, just seeing the dynamic is far more powerful than any technique or method for goal setting or anything that I've ever come across. Just like realizing that you're doing that and that it kind of makes no sense that you're turning your successes into reasons to beat yourself up. And I guess also. I guess this is sort of part of this overarching idea that I end up writing about, you know, because we are finite creatures, because we're all going to die. Because there are limits of all sorts of other kinds. The control you have over your life or the number of avenues that you can pursue with finite time. There's this really powerful and incredibly liberating and I insist, not depressing sense in which you've kind of already failed. And so this desperate kind of white knuckle clinging to the cliff face, attempt to not fail. You can sort of let it go because like metaphor that I've used in my writing before, right? It's like we go through life braced, like we're in a plane that might crash. And you're adopting the brace position or whatever, and it's like everyone's terrified, but in a way, the plane has already crashed. And it. And you're, you know, and here you are, right? You're on the desert island in the smoking wreckage of the plane. And that's what life is, right? It's just sort of doing what you can with what's in front of you. And I definitely. There are Definitely people who think that this is a very sort of unambitious, depressing, sort of resigned attitude to life. But I think it's absolutely, like, it's so invigorating to realize that, like, I don't have to go through life trying to stave off the great failure, because that's just being alive. And now I just get to.

[A]

It's an interesting version of what the actual situation is, right, that I've said this before. I often think about the fact that one day I'll die, but my inbox will continue to accumulate emails that will forever go unanswered and unopened. So given the fact that you're not going to be able to do everything that you want, you cannot do all of the things. There will come a day where there are still things that you want to do and time will be up. So in that perspective, 100% there is already failure as the set point. If that is your criteria. If your criteria is to do everything that you want to do, complete all of the tasks, answer all of the emails or whatever, one day you will fail at that. And, yeah, it is an interesting inversion of what might be more accurate.

[B]

And, yeah, not just to fail to do everything, but even to fail to reach kind of perfect standards in the things that you do do or fail to have uniform, positive responses to the things that you do. It's like once you see the way that all these things are kind of outside our control, it becomes a lot easier to waste less time trying to control them and thereby sort of, you know, free up time and energy and focus for doing a few of the things that you want to do with your life.

[A]

You're a fan of Krishnamurti's secret of existence. I don't mind what happens. What's that mean to you?

[B]

So just for anyone who's not familiar with it, right, this is the legend or the anecdote here is that he's leading some group in California in the 70s or something. And this is Krishnamurti, the spiritual teacher. And 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 you say, is, I don't mind what happens. And for me, that is a sort of ultimate statement of a kind of approach to life 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, 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.

[A]

And you lean through your own life.

[B]

Right, exactly, exactly. And I don't think Krishnamurti in that, in that line, I don't think he means 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 go well instead of badly. It's just that when whatever happens does happen, there isn't this sort of automatic, stressful collision between what you are demanding that reality do 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 shift of perspective that, you know, one hopes to embody on one's best days.

[A]

But it's a largely unreachable gold standard, I think. But it's definitely a direct, It's a direction that you can be. Or an orienting principle would be a good way to put it 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 am such a huge fan of timeline. They developed this pill right here that helps clear out damaged mitochondria so your cells can actually renew themselves. And this isn't just theory. In clinical trial saw mitochondrial renewal increase by more than 40% in just 16 weeks. Along with improvements in their overall energy. Timeline is backed by over a decade of research, has more than 50 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 30 day money back guarantee plus free shipping in the US and they ship internationally. So right now you can get up to 20% off and that 30 day money back guarantee by going to the link in the description below or heading to timeline.com modernwisdom that's timeline.com modernwisdom the place that I get this, 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. 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 10 minute spots or, you know, five minutes maybe for the first few guys, and then some tens, and then maybe one or two 15s and then a 30 or a 60 at the end. And what it means is that there's kind of 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.

[B]

Yeah.

[A]

Until the show's over. And then I can't wait to get into bed. And then it's the morning. And this. You're so right. That people sort of lean toward the thing that's happening 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 identified that most of your work is around control. 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? What is control trying to achieve? What are the. What are the component parts? What's the problem it's looking to solve?

[B]

Yeah, it's a really deep and interesting question. It gets to the point where I don't know if I have the answers. I guess what I think ultimately 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 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 we have limited time, limited ability to steer how things go, that we're going to die. All of this is just like super intense. And I think that very, very often what we're doing, without necessarily realizing it, is pursuing strategies for feeling like not that we've got out of the situation because you can't get out of it until death. But feeling like we're feeling like we're engaged in a project of getting a little bit out of it or sort of up on top of it sometimes 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 all of us inevitably are. And so you can do that in ways that involve. I think a lot of mainstream productivity culture is all about developing that feeling that I'm really in the driver's seat 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 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 going to go the way 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 cliche 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. But even after I felt like I kind of got over that, which to some extent, getting older will cause you to get over it because you pass some of these milestones and 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 20 minutes. Right.

[A]

Such an amount of time that's so fucking unimpressive, it doesn't even achieve anything.

[B]

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, a night at a comedy club, what's going to go wrong? Right? Like, I mean, actually. And I would be. I'm terrible in those situations because I have sort of too much weird vicarious empathy for the performers. And like, I'm. When people, when people die on their feet in comedy clubs, I can't bear it. But that maybe doesn't happen at the high class Austin ones that you go to. I don't.

[A]

Typically the guys are not bombing all that much, although I'm sure if it did happen, I would feel the exact same. 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 to do that? So you hit on something that I think is real interesting. So I'm 38 next month, and what I'm interested in speaking to a slightly older gentleman on a similar set of rails to me. What changes for the insecure overachiever as they age?

[B]

That's interesting. I turned 50 that. Well, actually technically last year, but I am 50, which is completely alarming. And 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 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 conversation. Oh, I see. Right. I'm an old person. What changes is, you know, I think that gradually there's this accretion of experience that gets big enough that you realize that firstly, the world does not collapse when you don't meet. When you break a streak of some kind of achievement, that you can sort of relax in that sense and you sort of develop. I have developed, I think, a greater level of sort of basic confidence that I sort of know what I'm doing when it comes to. To writing things, which I don't, until quite recently don't think I had. 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 life and all the rest of it, there is just that kind of awareness, whether panicky or quite sort of up, down to earth, that it's sort of got to be now. Right. It's like. Like when, you know, when are you going to. When are you going to do that thing or travel to that place or learn that skill? Like, I mean, at some point it's going to have to be. It's going to have to be in a. In a. Now you'll be familiar, I'm sure, with the. The book Die With Zero, about Bill.

[A]

Perkins, good friend, lives here in Austin, Texas.

[B]

Right. Right. About how dangerously possible it is to defer gratification for too long. And, you know, so I've had, to the extent that, you know, to the extent that I'm a calmer person and a 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.

[A]

Hurry the fuck up.

[B]

That's a good combination of motivations.

[A]

That's nice. I don't make a habit of showing my phone 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?

[B]

Do it anyway.

[A]

Do it anyway. It's a gentleman walking up what appears to be a completely exploding ravine and there's this, like, cosmic hellfire coming down. It's quite artistically done. I think my prompting was. My prompting was lovely. But that's rotating. That's rotating on my phone background with different versions of Do It Anyway. And 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 sort of. The just do it thing feels a little bit more forceful and grippy. And maybe this is just like total bias because, like, I did this one, but I really love. I really love Do It Anyway and Do It Anyway, I think speaks to what you're talking about here, which is. Yeah, you don't know how. Maybe it won't. Maybe you don't have 100% certainty that it's going to work, even though it probably will. Maybe it. Whatever. Like, just fuck. Just do it anyway, dude. And I think that. That the Doing it anyway becomes increasingly important the older you get.

[B]

Yeah, yeah. And I feel like the. Maybe it's not. Maybe it's not quite the same point as Do It Anyway. Or maybe it's identical, but the slightly more. The slightly more. The one that evokes a more British atmosphere for me is. Is like, you might as well.

[A]

So much more British. Yeah, it is.

[B]

You might as well, like, it's like. Yeah, the stakes shift in such a way that, like, you have less to lose or maybe you never had what you thought you had to lose in the first place. Elizabeth Gilbert has that wonderful line about how you. You're scared to let go or to surrender because you're afraid of losing control, but you never had control. All you had was anxiety. Which I think is a brilliant story.

[A]

Where is that from?

[B]

That is Elizabeth Gilbert writing somewhere. I don't know which book it comes from.

[A]

Yeah, yeah, yeah. How great. Isn't it? I think there's a lot of pithy lines about, you know, True hell is when the person that you are meets the person you could have been or whatever, whatever, whatever. A really painful version of hell is you getting to the end of your life and finally realizing that you had nothing to lose, but you feared it all along. Like, oh God, like now, now it's gone. And I spent my entire life fearing that I would get here, the place that I was going anyway, like I was always gonna be here. And now the time to do anything else is sort of pass me by.

[B]

Yeah, yeah. Genuine tragic situation.

[A]

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

[B]

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 as moment you're at the moment you're engineering it, isn't it, doesn't it stop being fun the moment you're doing it for some outcome other than itself? Aren't you just sort of monitoring it all the time vigilantly to make sure that it's having its effects? So I'm not sure this is quite an answer to your question, but what it makes me think of is. Sort of trying to engineer fun experiences is not something that I feel I've had much success with. But asking myself in the moment, in the context of the day, 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 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 on the sofa eating, right? Yeah, yeah, yeah. 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 going to become a wreck if you were to 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, firstly you get to harness that energy instead of trying to squash it all the time, right? It's like crazy to come up with these incredibly rigid, straight jacket 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. That was what you assigned. You're just wasting your own energy. And then secondly, the big discovery is that actually among the things I enjoy sometimes is things that involve work or administrative, things that I would never have wanted to try to force myself to do but feel like I need to do. Those sort of things that belong to the world of obligation, actually, they're there do come moments in the day or the week when that's the thing that you want to do, because you want to 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 navigate by fun and enjoyment at least a little bit more than you probably are doing.

[A]

Yeah, you wrote about the idea that interest is everything. 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 not right for some reason, what they want to do is not right. What interests them is not right. So they nerf that.

[B]

And you know, I'd be fascinated to hear about your experiences with this, because I think one of the places this is really evident is in any kind of any kind of digitally mediated stuff, including most of what I do, but especially a lot 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 when you do it. This phenomenon is famous in podcasting and elsewhere for leading some people sort of 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 give people what they want. And I think as opposed to what you want to give them, because it's more interesting for you. And the big irony, of course, I think at least my limited experience has been actually what people want is to read, watch, listen to things from people who are really alive with interest in what they're talking about and dealing with.

[A]

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[B]

That's amazing.

[A]

Non. Insignificant amount of hours on this podcast have been Rory Sutherland. And, and you, you and I, you know, I just, I will continue to do it. And yeah, this tension between what is marketable, what is effective, especially because people, unfortunately momentum is so much more important than ability or quality for a lot of things. And that means that if you play the game enough, you can then sort of burn and coast with. I've applied some momentum and then I sort of get to come into land and then I do the same. So that's where playing the game, but knowing it's not about it. That's why I do think that there's an argument to be made. Well, yeah, you know, like this movie star or musician or whatever, that maybe they're interesting, maybe, you know, we'll see, see how you get on with them. And sometimes it's really great. Often there's times it's really great, like rolling the dice in that way to be like, okay, we're going to pick up a bit more steam and then I'm going to bring more people in to learn about some more niche ideas. That's not necessarily the worst thing in the world, but fucking hell, there is an upper bound. And if I start to stray beyond that, whatever Overton window thing, it's so dull. And that's why you've got this line in that blog post where you say connecting to the aliveness is the ultimate point, like just connecting to the aliveness of what the thing is that you're doing.

[B]

Well, because the other, I mean, the other point is like, yeah, when you said that you can take certain decisions that, that are not like that, but the numbers might go up, you know, firstly, you might want to argue that the numbers wouldn't, wouldn't indefinitely go up if you kept doing it. There might be a short term boost, but also like, you know, at the end of the day, why do you care? Right. That's what it always comes back to is like if the thing you're not doing is an overall and in aggregate a sort of a meaningful experience, then once you've got like, you know, basic food and shelter taken care of, why, why would you, why would you do it? And it's, I mean, I say it as if it's an easy thing to remember. It's obviously we're all forgetting it all the time and kind of pursuing these instrumental goals that lead to other instrumental outcomes and kind of losing sight of whether they're all. Yeah, it's the thing about climbing a ladder and realizing it was the wrong. Up against the wrong wall, leaning against the wrong wall or whatever. Yeah, yeah, yeah.

[A]

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

[B]

Right, right. People have done it in organizations and stuff at a lower scale. Right. Taking credit for what their underlings produce.

[A]

But this is like, you know, but this is nuclear. Yeah, it really. 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, 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 your partner goes, baby, I'm so glad you sent me that message. It made me feel so good. 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. Liar, liar. Contrived, conceitful. Like, because you do not get to capture what is truly happening here. It wasn't you, it wasn't your genesis. What some are saying is, thank you for showing me you, and thank you for how wonderful for me to be the progenitor, the muse, the inspiration for your thoughts. And because you didn't do it, you don't get to capture any of that goodwill.

[B]

Yes. No, that's a great. It's a great and kind of chilling example. Although I know that lots of people are doing it. And I think that, Yeah, I mean, I think that 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 a lot of what happens when you use LLMs in that kind of context to sort of, again, it's like wanting to stay in control, right? It's wanting to sort of 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? So you have to sort of go wrong first. But somebody was making the argument that, you know, 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. And I always want to, I always want to kind of say these are two totally different things, right. And I couldn't really put words to it, but I 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 really the kind of generic outputs of both of large language models and of the kind of brains that use them too much and come to think 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 and absolutely doesn't need to be full of, you know, so called therapy speak and jargon terms and you know, turning every human experience into a sort of technical pathology or something, it's completely different. But that feeling that everyone is kind of thinking too hard about what they're saying, figuring out what to say first. Even just the nature of text based communication and email and messaging has allowed.

[A]

The ability to delete and right, you.

[B]

Think about it first, you work it out. You know, even that is a bit secondary.

[A]

Isn't that interesting? Isn't that, that's such a great point because what is it? Written language has been around for basically no time at all for human history and spoken language has been around for way longer and like editable written language has been around for a microsecond essentially. And yeah, I've never even thought about that, but that's a really, really great idea that it does. But how could that not create an environment of self assessment and cajoling energy and this sort of semi manipulative coercion of. Was that really. What I meant to say was that. Well, it's what you said, it's what you said the first time and the second or the third time when you got to go back. No, that's. That's more like what I meant to say. I'm not. I'm not by any means. If all books had to be published on the first pass, the world of literature would be a fucking mess. But I think that's a really interesting insight. Going back to the dare do 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. It's kind of like inverse stoicism. You're insulated from the good things happening to you when you manage to turn everything into something negative. So I had a little essay that I quoted you in that I wanted to read to you, and it's called Frankl'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 a 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, Frankl's inverse. 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.

[B]

Oh, I love that. And feel confronted by it.

[A]

Yeah, I've got your line. It's significantly longer than that and I didn't want to subject you to the whole thing, but one of my favorite 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 raging 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 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 satisfaction can kind of always be achieved, even if the sense of joy can't.

[B]

That's really interesting, and I love your use of the word grace in the bit that you wrote. 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. There's an aspect to this which is also. Which also maps onto the distinction between like living entirely in your head and in your intellect versus being kind of embodied in the world. Right. Because a big part of enjoying life and showing up for things is. Is embodied, you know, even just in the most basic sense of like feeling the air on your skin when you're.

[A]

Present in a place enjoying the coffee as opposed to using it at the maximum possible survivable temperature in order to get the caffeine into your system.

[B]

Exactly, exactly. And so, yes, I think another thing that characterizes these 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, 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 that doing the driving through sort of cognition and living in your frontal cortex or whatever, this very specific feeling. And I think you sort of see it, I feel like as I've got, but older and more experienced with what I've been doing, you sort of. 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. And there is something crucial about remembering that you're a body as well 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 kind of really obsessive kinds of physical fitness or whatever that are just as much about the future progress.

[A]

Well, I think the crossover between those people 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 together because the desire for control in the cerebral world has moved into the physical world as well. And the reverse has happened too. Yeah, I think you're right to say people hope for, they want this. I make life happen and that's beautiful. Agency. My friend George Mack is writing what will be the seminal book on agency right now and it's going to be fantastic. And I think I massively value agency and high agency in my own life. But there is a, a limit to the art of agency, I guess you could say, like learning when to just be able to be on a set of guardrails.

[B]

Well, I want to say even I'm going to read that book very energetically because I want to say that it's not so much that agency's great and all, but there comes a point where you have to. I think it's that agency and control are in some sense fundamentally different things. And that's interesting. My experience anyway has been that to whatever extent I can relax the need for control, that's the extent to which I kind of acquire what I think of as agency or power or something. Right. It's like when I'm going through my life trying to make sure that it goes the way I think I need it to go. Trying to bend reality in the direction that I've decided, but for a fundamentally deep buried emotional reasons. Right. I need it to go. I'm actually sort of disempowered. I'm. I'm kind of chained to.

[A]

You're fragile, kind of. You're very fragile, right?

[B]

Absolutely. Yeah. And, and again, maybe it's not everybody, but I've. When I, when I don't need, when I don't absolutely feel like my basic worth needs something to happen, that's when I can get to it.

[A]

That's when you can fully lean into it. Yeah, that's wonderful.

[B]

Yeah, no, absolutely, that's wonderful. So yeah, I don't think there necessarily needs to be any limit to agency. We just need to see and appreciate the sense in which it isn't to do with sort of this kind of control domination based urge which has another agenda always than just creating and building for the joy of doing so.

[A]

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[B]

That's a good question. I mean, most obviously, I suppose it's just that you. That is, that's a, that's an invitation to find your life as it is right now, wanting, as opposed as compared to some fantasy that you have of what your best life would be. I'm quite suspicious of the notion of a best life. It reminds me of the notion of sort of fully realizing your potential. Right? 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. No, I really are asking that. That's where you're going to end up.

[A]

There's a really interesting tweet that I saw a couple of weeks ago by this lady who's a communications professor and there's a clip of her 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? And why would be, why would being basically an overachiever with regards to your capacity and it's all just social signaling. It's all just you being able to say as the observer, I am the sort of person that is able to detect in another that which hasn't been recognized by other people on both sides. 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 realized it yet. 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. But the what I think I can do is plucked out of complete fucking obscurity. And it is like you say, a fantasy. Because 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 in order to assuage whatever deep feelings of insufficiency are currently swimming through you? Like, what else would you have done? And when you actually go through it, you're like, fuck me. I mean, I could have gone to bed half an hour earlier on Tuesday and then that would have meant I could have got it. But I'm really, you know, I'm playing in the margins here. I really, I really gave it a good shot. Just when you ask what else could I have done? You in my experience, you find out probably not that much. I probably did pretty close to what I'm capable of. And again, what was have I ever done my type A people, type B problems thing to you? Have I given you this one?

[B]

It's not ringing a bell, so maybe not.

[A]

God, let me give you, let me give you this. I mean, this is. I am just so shameless with how much I get inspired by people like you and Alain de Botton. But 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. 1 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 6pm 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, well, 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 rest harder than me. Type B problems are just as tough as type A ones, but they require a much less sexy solution piece. One that you can't actually achieve by simply working harder.

[B]

Nice. I agree, I have those problems. I have had those problems. You know what, it also makes me something that came up in the middle of listening to you read that. Which is lovely is there's like a weird selection bias problem here as well, isn't there? Which is that the. See if I can express this. The people who are drawn to the hard charging, self punishing, you know, work harder stuff are going to be pretty much by definition the people who don't for whom that message is something they don't need. Right? The temptation is going to be for people to pursue those messages and consume that kind of stuff Read those books, watch those videos, because they're already in too deep with the idea that that's what they need to do and they need more sort of fuel to help their sort of driving of themselves. And probably the reverse is true, right? Which is that people who are kind of already pretty relaxed and into relaxation are going to be consuming a lot of relaxing content. So it's almost like, you know, it's like democracy. 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 consuming the message that they just need to.

[A]

You just. You. You keep fucking activating my trap cards, all of them. 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. I did. I'll just send you it. Yeah, I'll send you it and you can read it afterwards. Please do. If anyone wants to read it, it's called Advice Hyper Responders and they can just search it on my. On my blog.

[B]

Oh, there you go. Yeah. The title shows me that that is.

[A]

Basically the people who most need the medicine don't take it. And the people who are likely to overdose have taken too much already. And the most spicy example of this that I think still holds true was around MeToo, which was telling men, don't be pushy caused men who really could have actually done with a bit more confidence around women to take it to heart, while the guys that were just blowing through boundaries all along disregarded it entirely. So advice is not taken evenly by people. It amplifies their existing fears and predispositions and worldviews.

[B]

Yeah, no, absolutely. And it's also the idea that I'm not going to try and successfully quote Poets Live, but it's the idea that the worst people are full of intensity and the best lack all conviction. Right. It's the same wherever that comes from. Well, this is why I'm not going to pretend that it was some sort of strategy in any of the books that I've written. But I do sometimes think in hindsight, and one or two people have said it to me, that I am. That I might be performing some kind of useful and edifying bait and switch in some of the stuff I do, in the sense that sometimes I think it appeals to people who think what they need is more time management advice or something like that. And then I sort of, you know, if it works, completely destroy their worldview from the inside, lulled them in under.

[A]

A false, false sense of dopamine and then pulled the rug out from. Yeah, I mean, so it's a good point to make. And 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 Meanie spoke, 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 enjoy it? Can I try and produce at a high standard and not grip life too tightly? And one of the problems of 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. Me saying that 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. That feels like non insignificant number of comments said something to the effect of bro sold us the problem and now he's selling us the solution. And I'm like, well look, if I did, if I did do that, I fucking sold it to myself as well because I believed it. So I apologize, I apologize for that. That also being said at the time, I've never said this is the way to live your life. This is 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 end up with a lot of criticism. I think you end up with more criticism being 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 and like the obviousness of just work hard, the sort of just work harder, grip it more tightly advice is so much more pithy. And much of my channel has been built on, you know, analogies, analogies of that, in 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 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. 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 damaging, I think, to some of his 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 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 my sort of worldview. And 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 going to try and go on. But as you do that, your real world results briefly and maybe even for actually a medium, a pretty significant chunk of time, get a little bit worse because you've got to relinquish some of the strategies that you were using previously before. You've got mastery in the new ones, and 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 newly enlightened. 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. 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 honestly.

[B]

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

[A]

Having a stroke. You're having a stroke. It's nothing to do with the camera fading in and out at the beginning of the end. This is how you go.

[B]

It's Lovely, You know, having an interesting conversation. There's worse, there's worse ways. That's obviously a professionally specific thing. And I had a slightly different journey in that I was being sort of sarcastic about, sarcastic in public for about sort of self help related things from an early point in my career and then became, went on a sort of journey towards more sincerity which, so it does, is, does leave you open to some of the same criticisms to some extent. Right. It's like you said, this is all rubbish. And that like the question I've been asked a lot is like you spent lots of your earlier career criticizing self help gurus, but now you've become a self help guru. How did that happen? And it's like, I don't think either of the arms of that criticism are quite accurate. But anyway, that's a separate, separate matter. I think the incongruence thing is really, is really an interesting point and I do think that, yes, the process that sounds like we're sort of both on is one where you have to kind of be willing to move away from strategies that have served their time. And in one definition, right, that is the original, highly respectable definition of a midlife crisis, right, not some kind of terrible problem where you start acting out and being weird, but just where you shift from the first part of adulthood to the second part of adulthood and things that you use to get yourself established in the world or to ultimately the therapist would say probably to sort of separate off from your family of origin and your parents, right, and become sort of fully, fully existing individual adult human. They stop working. They're no longer the, they're not going to get you all the way through the process of sort of coming to, or further along through the process of coming to sort of understand life and yourself and the endless fascinations and difficulties of relationships with other human beings and all the rest of it. And I think, you know, I think an argument could probably be made that kind of, that remaining completely congruent, as you put it, all the way through your life and from early adulthood through to, through to late adulthood is like a disaster. Like, I think that's kind of a, I don't think that's anything to be, to be celebrated at all. Because I think, you know, we all do know people who seem. Maybe we don't. I mean, I know people, we know people who sort of stuck in. They're sort of the wrong age for the psychological outlook that they have.

[A]

What do you mean there?

[B]

Well, people who are sort of, you know, there's something amiss about people who are acting in their late 50s who seem to have the attitude of. Some aspects of. The attitude of being in your late 20s. Right. Not necessarily any particular lifestyle choice. I'm not saying everyone's got to be, like, married and settled down and with adult children by the age of six. It's nothing like that. It's just that sort of. There's something almost hard to put into words that is a bit too sort of. Right. They're sort of too intent on establishing themselves in the world or something. They're too intent on. Too intent on sort of. Yeah, I think that is a kind of a. I think that is some. There's something. There's something kind of wrong about that. On the other hand, you know, it's never too late and people go whatever route they need to go to get to their midlife crisis. James Hollis, who. I know we both are admirers of the. Of the work of. I think the Jungian psychotherapist has this whole very excellent kind of riff about how the goal of really good therapy is to, like, make your life more interesting to you and how. And how the wide world just sees this as, like, nothing. Like, what a pathetic goal in life to have a. To become more and more interested in being alive. But he says, like, you know, he makes the point that really, that's like. That's the whole game. It's the most that psychotherapy can do, but it's also. It's also all you need for a absorbing and meaningful and fulfilling life. It's that it. And I think it's. That requires this kind of change and development and I'm sort of going on and on. Now, you can cut this out, but the bit that. The bit of what you said as well, that resonated with me, like. No, I have quite recently gone through phases of feeling like I'm completely unable to work for, like, weeks at a time, being completely, like, unclear about the direction I'm taking and, like, really sort of out of sorts in ways that, when I describe them in very simple language, sounds like I was going through, like, a depression or something. But it wasn't that. It was. It wasn't pleasant at all. But I think it's better understood as these phases of, like. Yeah, the. The. The last way of doing things falling away. And you just haven't figured out the. Yeah, the new way of doing them. Yeah.

[A]

One of the particular pains that you feel as you go through this. Whatever we want to call it, this chasm of incongruence, one of the challenges is if you're around people who are highly congruent at the time, you feel so inferior by comparison, because these people know what they're doing. They're waking up and thinking about it. And you used to be peers or are comparable or maybe even ahead of them in whatever version of a hierarchy you've conceived in your mind. And you're like, I'm falling behind. I'm falling behind. Look at this person. This is how I should be. This is how I should be behaving. I should be a singular spear of reason and intention and action, and it should all be moving in the same direction. And what I feel like is one of those red ropes that kids eat sweets and I'm floppy and flaccid and I'm all over the place. How their congruence is throwing my incongruence into harsh contrast. And that's a really dangerous situation to be in, because what it causes you to do is it causes you to. It's kind of like being a crab that's outgrown its shell come out of it and is now trying to force itself back into the old one. Like, that simply is not going to work. But it will delay your growth in moving forward. It'll make you feel like fucking shit the whole time that you're doing it, because you're just going to. It's going. You're not going to have the nobility of your evolution or the congruence of your past version of yourself. Like, both of those things don't exist, if that makes sense. And, yeah, it's a challenge. Being in a period of transition around people who aren't is a challenge.

[B]

Yeah, no, totally. And the sort of, you know, you can get some way through it by reminding yourself smugly that the reason they're so congruent is because they haven't, you know, grappled with the truths that you're right. Exactly. But, no, I think it's a real. I think that's not enough. And it's. And it's a. It's a real issue. It's one of those times where. And I think these. We're not easily susceptible to the advice that what's required of you in that moment is just to kind of stay, just to not restlessly leave the situation, whatever they call that middle stage of the alchemical process, right. Where all the things that are happening. It's like the skill you need or the quality you need there is to just sort of remain there and to stand firm or whatever the phrase is right to not let yourself be lured by the temptation to just fix it all and sort of nervously, irritably start, start tampering and like it's true. But it never gets. I don't. In my experience it never gets like easy, but it is. Or pleasant but, but you can have. You know I said before that these, these periods of non productivity in my recent past have not felt like depressions. I think you can, you, you can feel on some intuitive level when this bad situation of being incongruent compared to other people or not being super productive when you want to be being super productive, you still can connect, I find to some kind of intuition that this is growthy or generative.

[A]

Generative is a wonderful way to put it.

[B]

When you really get quiet or write in your journal or whatever it is that you do, you don't. It's not like life is completely meaningless. It's like I'm out of control and I don't know what's going on. And I wish I did know what was going on. But something is going on.

[A]

Ah, it's so good. In other news, you've probably heard me talk about Element before and that's because I am frankly dependent on it. And it's how I've started my day every single morning. This is the best tasting hydration drink on the market. You might think, why do I need to be more hydrated? Because proper hydration is not just about drinking enough water. It's having sufficient electrolytes to allow your body to use those fluids. Each grab and go stick pack is a science backed electrolyte ratio of sodium, potassium and magnesium. It's got no sugar, coloring, artificial ingredients or any other junk. This plays a critical role in reducing muscle cramps and fatigue while optimizing brain health, regulating your appetite and curbing cravings. This orange flavor in a cold glass of water is a sweet, salty, orangey nectar and you will genuinely feel a difference when you take it versus when you don't. Which is why I keep going on about it. Best of all, there's a no questions asked refund policy with an unlimited duration. Buy it, use it all and if you don't like it for any reason, they give you your money back and you don't even have to return the box. That's how confident they are that you'll love it. Plus, they offer free shipping in the US right now. You can get a free sample pack of Element's most popular flavors with your first purchase by going to the link in the description below heading to drinklmnt.com ModernWisdom that's drinklmnt.com Modernwisdom One other contrarian opinion of yours, which I think is real interesting, is unsettling. Basically, that people can sort of get more out of life from settling. That when you commit to a person or a path, more opportunities will arise because of the newfound depth. Is this in tension with the creature inside of us all that desires maximization and novelty and creativity?

[B]

It's been interesting, that thing I wrote in 4,000 weeks about settling, because obviously, apart from anything else, this is a phrase that immediately connotes kind of romantic relationships and dating. And I don't think that's my role on your podcast, actually, Chris. I think to come in and give dating advice. I think that is best left to other guests, probably. But 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 that finitude just means you are settling, right? What we mean by settling is accepting some downside in return for the security or whatever else it might be that you get through taking that option, choosing that relationship, staying in that job, whatever it is. And one way of expressing half of what I write about is just there are always downsides. You can do what you like. You only need to face the consequences, as Sheldon Kopp puts it. So it's not really, I think we get into the situation where we think, well, I'm the kind of person who would never settle, so I'm going to max, I'm going to 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 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, has a downside. 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 deciding to accept a different set of negative consequences, a lot of indecision, a lot of commitment, phobia. I think in relationships and in other domains has this feeling of like, I'm just going to 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, but. But don't go fooling yourself that you're somehow hanging back from. You're in the human condition, you're not getting out of it. And. 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.

[A]

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

[B]

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? How do you know in a given moment which trade off is the right trade off? And I think an awful lot of.

[A]

It.

[B]

Is, annoyingly enough, kind of intuitive and beyond words 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, holding out for a kind of perfection that. That doesn't actually exist in the world. 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 for making it.

[A]

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

[B]

I'm trying to write a new book. I'm trying to write a new book. I am endeavoring to write a book. I should be more. I should be open about what it is, shouldn't. I shouldn't be all coy. And it's probably helpful to the creative process to like put my cards on the table. I'm trying to write a book. Going into. Going in on this topic of aliveness and this idea of this mysterious concept that describes so much of what seems to be missing from so many people's experience and also to be present when things are going really well. This sort of intangible sense of aliveness. I need 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 all the rest of it is a kind of. Well, the word I keep wanting to use is clenching. And then the correct antidote for clenching is unclenching. But my editors are concerned that the.

[A]

Imagery, if I considered it's not talking about clenching and unclenching, 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.

[B]

Well, yes, yeah, no, absolutely. I think that's a huge part of it. But it's all. Yeah. And I. And also it's the kind of. 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 really unnerving historical times and that the sort of wider world is one that causes a lot of people to want to sort of. Clam up or tighten or something. And I think that this move of relaxing into the chaos and the craziness and the uncertainty is one that 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, that trying to sort of shelter from all of that completely is. See, I don't want to write. I'm not an activist. I don't want to write a book about being an activist and making the world's crises better. But I also don't have 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. And you know, building your business or whatever. Like these two some. As ever, I'm sort of annoyed with two camps of writing on these topics. And I'm trying to find what I think people should do instead.

[A]

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. My first sense would be a sort of cloyingly prescriptive framework.

[B]

Spiritual.

[A]

No, it would be a framework. It would be too practical. It would be, well, the components of aliveness ascended by Seligman et Al in 1988. That would. No, thank you. I've been through that world. So I think to. To call.

[B]

I have no plan to tell you. Yeah, I have no plan to tell you about the surprising neuroscience of this. Of this topic or. Or, you know. Yeah. The kind of what studies have shown. There's a place for that writing. And I apologize to anyone. I've.

[A]

No, I'm supposed to. It's supposed to. It's supposed to be there. But is the place for that writing supposed to be around aliveness, like the neuroscience of any. You're right. I like.

[B]

So no. But this is really. This is very useful information for me because I do struggle with the labels and the words. I'm trying to do something that is not a kind of. I'm not a spiritual teacher writing a book about how to transcend the self. But I'm also absolutely not trying to get into that science based on well being stuff. It really is this sense that like there's a quality to the experiences and the activities that we know are the right ones for us to be doing. And there's various aspects of modern culture that seem to sort of systematically squeeze that out. And yes, I think it is all ultimately about control because I always think that.

[A]

Oliver Berkman, 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 that's the.

[B]

Thing to subscribe to? My most recent book is Meditations for Mortals. So that's the other thing to mention here.

[A]

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

[B]

It's a huge pleasure. Thank you so much.

[A]

If you're wanting to read more, you probably want some good books to read that are going to be easy and enjoyable and not bore you and make you despondent at the fact that you can only get through half a page without bowing out. And that is why I made the Modern Wisdom Reading List, a list of 100 of the best books, the most interesting, impactful and entertaining that I've ever found. Fiction and nonfiction and real life stories. And there's a description about why I like it and there's links to go and buy it. And it's completely free. You can get it right now by going to ChrisWillX.com books that's ChrisWillX.com books.