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Oliver Burkeman
Author, Four Thousand Weeks and Meditations for Mortals

Learning This Sooner Could Have Saved Me Decades - Oliver Burkeman

📅 Feb 19, 2026 Chris Williamson 92 MIN 39824 VIEWS 139 SEGMENTS · 2 SPEAKERS
Oliver Burkeman is a journalist, a writer for The Guardian, and an author. How does the insecure overachiever evolve? You think success will quiet the doubt, then you hit 30, and it’s still there. More achievement, more stress. So how can you feel proud of what you’ve built without always fearing it’s not enough? Expect to learn if it possible to be the best in the world and relaxed at the same time, how to deal with uncertainty more effectively, the biggest changes insecure overachievers will face as they age, the cost of constantly asking, “Am I living my best possible life?“, how to know...

Questions asked in this interview

12
  1. 0:00Is it possible to be the best in the world and relaxed at the same time?
  2. 3:01So how do you healthfully pursue goals without tying your self-worth to the outcome, given that the only sort of goals you do pursue are ones you care about, and in the caring, the disappointment, and in the disappointment, the self-worth?
  3. 15:25You're a fan of Krishnamurti's secret of existence: 'I don't mind what happens.' What's that mean to you?
  4. 20:18What's the problem it's looking to solve?
  5. 27:31Can you read what that says?
  6. 30:41Do you ever think about engineering enjoyment as a productivity strategy?
  7. 45:20Isn't that — that's such a great point because what is it?
  8. 57:44Have I given you this one?
  9. 58:49Who's going to carry the TV remote and the Cheetos?
  10. 1:20:07You might think, why do I need to be more hydrated?
  11. 1:21:22Is this in tension with the creature inside of us all that desires maximization and novelty and creativity?
  12. 1:26:13Have you got a new book?
Chris Williamson 0:00 ↗
Is it possible to be the best in the world and relaxed at the same time?
Oliver Burkeman 0:08 ↗
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, a very personally motivated mission to prove is not how it works. 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.
Chris Williamson 1:14 ↗
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.
Oliver Burkeman 1:36 ↗
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 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 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 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 that's just like a... and therefore I'm sort of rigid and clenched and muscles tensed and everything, the more you sort of pop into this awful self-conscious space where nothing works, and it's much better to lose yourself in the activity than to be trying to control it.
Chris Williamson 3:01 ↗
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. Like if I — 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 healthfully pursue goals without tying your self-worth to the outcome, given that the only sort of goals you do pursue are ones you care about, and in the caring, the disappointment, and in the disappointment, the self-worth?
Oliver Burkeman 3:46 ↗
So I mean, there's a sort of ideal way of doing this, which I don't claim to have, you know, totally pulled off or anything, but I think the distinction is 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 a 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 at large. They're 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.
Chris Williamson 5:03 ↗
Mhm.
Oliver Burkeman 5:04 ↗
And that sort of 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 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 know, 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 like who are you? What are you? There is this whole other way of thinking about caring about goals, right, which is to say, like 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 in flight from something, but it can be challenging to get there.
Chris Williamson 6:31 ↗
I love this. It's been one of the central questions. I think it's why I'm such a huge fan of your work and your newsletter as well, that everyone should go and sign up to, The Imperfectionist. 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 song 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.
Oliver Burkeman 7:35 ↗
Yeah. Yeah.
Chris Williamson 7:37 ↗
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 at this thing and before realizing that that meant next year I have to be better than that was...
Oliver Burkeman 8:08 ↗
Yeah. Right. Right. Approximately probably 15 minutes or maybe less.
Chris Williamson 8:15 ↗
And a beautiful 15 minutes. 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 grindset. I don't think — I think it's more him, which is why 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. You're number whatever, one 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 got to get back to writing the next book.' And I was like, 'Ryan, come on, dude. It's like you're supposed to be the [__] 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.
Oliver Burkeman 9:27 ↗
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.
Chris Williamson 10:16 ↗
Yeah.
Oliver Burkeman 10:17 ↗
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?
Chris Williamson 10:37 ↗
Yeah.
Oliver Burkeman 10:37 ↗
Like 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 talks, 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. It's the... what does an existential...
Chris Williamson 11:14 ↗
Existential crisis. He's triggered, right? Yeah. Exactly.
Oliver Burkeman 11:16 ↗
What does an existential crisis look like from the outside? And that's what we're — that's the [__] bullseye for me. That's exactly what I'm going for.
Chris Williamson 11:24 ↗
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.
Oliver Burkeman 11:32 ↗
And I think it's really one of those things where first of all, just seeing the dynamic is far more powerful than like 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 is — because there are limits of all sorts of other kinds of 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 a 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 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...
Chris Williamson 13:49 ↗
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 within 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.
Oliver Burkeman 14:50 ↗
And yeah, not just a 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 that 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.
Chris Williamson 15:25 ↗
You're a fan of Krishnamurti's secret of existence: 'I don't mind what happens.' What's that mean to you?
Oliver Burkeman 15:35 ↗
So just for anyone who's not familiar with it, right, 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 week through your own life.
Chris Williamson 16:41 ↗
Right, exactly, exactly.
Oliver Burkeman 16:43 ↗
And I don't think Krishnamurti in that line, I don't think he means that some things that happen aren't better than others, 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 one hopes to embody on one's best days, but it's a largely unreachable gold standard, I think, but it's definitely a direction that you can be — or an orienting principle would be a good way to put it.
Chris Williamson 17:55 ↗
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You know, the place that I get 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 a 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 dopamineergic 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. Until the show's over, and then I can't wait to get into bed, and then it's the morning.
Oliver Burkeman 20:05 ↗
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.
Chris Williamson 20:18 ↗
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? Like what is control trying to achieve? What are the component parts? What's the problem it's looking to solve?
Oliver Burkeman 20:46 ↗
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 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 this situation, because you can't get out of it until death, but 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 know, you can do that in ways that involve — I think, you know, a lot of mainstream productivity culture is all about developing that feeling that like, you know, 'I'm really in the driver's seat of the 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'll say about the comedy clubs is interesting to me because there's a cliché about how people put off life until they get married, until they get a promotion, until they retire, these big milestones, and that's true. But even after I felt like I kind of got over that, which to some extent, you know, 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? Like even such an amount of time that's so [__] unimpressive. It doesn't even achieve anything, 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 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...
Chris Williamson 24:02 ↗
Me too.
Oliver Burkeman 24:03 ↗
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 either.
Chris Williamson 24:12 ↗
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 throw some sort of a lifelong — 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 is speaking to a slightly older gentleman on a similar set of rails to me. What changes for the insecure overachiever as they age?
Oliver Burkeman 24:46 ↗
It's interesting. I turned 50 — 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 — '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, you know, the world does not collapse when you don't meet — when you break a streak of some kind of achievement, that you know 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 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 healthfully manage your midlife crisis 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 down to earth, that it's sort of got to be now, right? It's like 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 in a now. You'll be familiar, I'm sure, with the book Die with Zero about...
Chris Williamson 26:57 ↗
Bill Perkins, good friend, lives here in Austin, Texas.
Oliver Burkeman 27:00 ↗
Right, right. About how dangerously possible it is to defer gratification for too long. And you know, so I've — 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.
Chris Williamson 27:27 ↗
Hurry the [__].
Oliver Burkeman 27:28 ↗
That's a kind of — that's a good combination of motivations.
Chris Williamson 27:31 ↗
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?
Oliver Burkeman 27:44 ↗
Do it anyway.
Chris Williamson 27:45 ↗
Do it anyway. It's a gentleman walking up what appears to be a completely exploding ravine. There's this like cosmic hellfire coming down. It's quite artistically done. I think my prompting was lovely. But 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 '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 '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 — like just [__] just do it anyway, dude. And I think that the doing it anyway becomes increasingly important the older you get.
Oliver Burkeman 28:52 ↗
Yeah, yeah. And I feel like the — maybe it's not quite the same point as 'Do it anyway,' or maybe it's identical, but the slightly more — the one that evokes a more British atmosphere for me is like 'You might as well.'
Chris Williamson 29:12 ↗
It's so much more British. Yeah, it is.
Oliver Burkeman 29:16 ↗
'You might as well.' But like it's like...
Chris Williamson 29:22 ↗
Yeah.
Oliver Burkeman 29:23 ↗
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'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...
Chris Williamson 29:45 ↗
Yeah, that is Elizabeth Gilbert writing somewhere. I don't know which wonderful book it comes from.
Oliver Burkeman 29:54 ↗
Yeah. Yeah. Yeah. How great.
Chris Williamson 29:57 ↗
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 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 going to be here, and now the time to do anything else has sort of passed me by.
Oliver Burkeman 30:34 ↗
Yeah, yeah. Genuine tragic situation. Yeah.
Chris Williamson 30:41 ↗
What sort of person do you think is having the most fun? Do you ever think about engineering enjoyment as a productivity strategy?
Oliver Burkeman 30:53 ↗
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 the moment you're engineering 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 potato, right?
Chris Williamson 32:12 ↗
Yeah. Yeah. Yeah.
Oliver Burkeman 32:14 ↗
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, straightjacket 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 assigned. You're just wasting your own energy. And then secondly, the big discovery is that actually, you know, among the things I enjoy sometimes is things that involve, you know, 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 the things that belong to the world of obligation. Actually, 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.
Chris Williamson 33:50 ↗
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. 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 digitally mediated stuff, including, you know, 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, 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 in and what they're talking about and dealing with.
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So true. Yeah. And in my experience, the further I've gotten away from what is it that I'm interested in, who is it that I want to speak to, the worse the show's got. Now, the numbers may have gone up, but if it's something that I don't care about, like maybe if you run a charity or something, you're a pediatric neurosurgeon or something, like it's on you. Your job is in service of this thing. And the parameters of outcome are a bit more tightly defined. Like it's not — if you do the surgery and it goes well, it doesn't matter if you enjoyed it or not, right? Like what matters is the outcome. But with these sorts of conversations and largely even blogging as well, it's just vibes. Just what was your vibe that day? What was the kind of language that you used when you put this thing across? What was the sort of energy that you brought into the conversation? And yeah, for me there's been times where, oh, it would be tactically great to bring this person on. It would be useful from an optics perspective or whatever. And I've done pretty well. I've said no to some guests on the podcast that would [__] shock the world that I've said no to, because it just straight up didn't feel something. It just — I was like, no. The answer was no. Mhm. And the more that I've done that and the more that I've been like, 'Yeah, Morgan Housel for the seventh time. Yes, Rory Sutherland for the 11th time. I don't give a [__], I'm just going to do it.' Like Rory Sutherland accounts for like nearly 1% of this podcast. Non-insignificant amount of hours on this podcast have been Rory Sutherland, and 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 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 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 [__] hell, there is an upper bound. And if I start to stray beyond that whatever Overton window thing, it gets so — it's so dull. And you know, 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.
Oliver Burkeman 39:59 ↗
Well, because the other — I mean, the other point is like, yeah, when you said that you can take certain decisions that are not like that but the numbers might go up. Firstly, you might want to argue that the numbers 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 isn't overall and in aggregate a sort of meaningful experience, then once you've got like, you know, basic food and shelter taken care of, 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...
Chris Williamson 40:58 ↗
Up against the wrong wall.
Oliver Burkeman 40:59 ↗
Leaning against the wrong wall or whatever. Yeah. Yeah.
Chris Williamson 41:01 ↗
Yeah. 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 [__] 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.
Oliver Burkeman 41:33 ↗
Right. Right. People have done it in organizations and stuff at a lower scale, right? Taking credit for what their underlings produce. But this is like...
Chris Williamson 41:40 ↗
You know, but this is nuclear. Yeah.
Oliver Burkeman 41:42 ↗
It really 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 someone's 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.
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 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 — it's 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 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 obviously in the last couple of years or whatever, is really the kind of generic output of both 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...
Chris Williamson 45:08 ↗
Figuring out what to say first. Even just the nature of text-based communication and email and messaging has allowed the ability to delete and...

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APA

Burkeman, O. (2026, February 19). Learning This Sooner Could Have Saved Me Decades - Oliver Burkeman [Interview transcript]. Chris Williamson. CEOInterviews.AI. https://ceointerviews.ai/interview/3104687/

MLA

Oliver Burkeman. "Learning This Sooner Could Have Saved Me Decades - Oliver Burkeman." Chris Williamson, 19 Feb. 2026. Transcript, CEOInterviews.AI, https://ceointerviews.ai/interview/3104687/.

BibTeX
@misc{burkeman2026_3104687,
  author       = {Oliver Burkeman},
  title        = {Learning This Sooner Could Have Saved Me Decades - Oliver Burkeman},
  howpublished = {Interview transcript, Chris Williamson. CEOInterviews.AI},
  year         = {2026},
  month        = {feb},
  url          = {https://ceointerviews.ai/interview/3104687/},
  note         = {Speaker-attributed transcript with timestamps}
}