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

Modern Wisdom

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  • Relaxation Improves Performance
    • Excellence often emerges when you relax and lose self-conscious control during action.
    • Trying to micromanage performance usually produces tension that worsens outcomes. Transcript: Oliver Burkeman 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. And 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 Chris Williamson It works. 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? Yeah, it’s really interesting. Oliver Burkeman I think that there’s something, I mean, this runs through a lot of what I tried 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 way. So, yeah, for me, and of course I’m talking about things like writing or speaking. I mean, I’m not talking about, I 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’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 Works. And it’s much better to lose yourself in the activity than to be trying to control it. (Time 0:00:40)
  • Achievement As A Fix For Insecurity
    • Many high achievers pursue goals to fix feelings of inadequacy rather than for intrinsic interest.
    • Achievements then become minimum standards, creating a perpetual treadmill of dissatisfaction. Transcript: Chris Williamson That is one of the fundamental problems. 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 should. 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 ones you care about and in the caring, the disappointment And in the disappointment, the self-worth? Oliver Burkeman 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 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 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 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 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? (Time 0:03:37)
  • Fifteen Minutes Of Joy
    • Chris enjoyed 15 minutes of genuine joy after discovering his podcast charted before anxiety set in.
    • That brief relief highlighted how quickly success becomes pressure for the next cycle. Transcript: Chris Williamson 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. (Time 0:08:43)
  • Accept Finitude To Reduce Grip
    • Recognize finitude: many attempts to control life stem from denying limits and mortality.
    • Letting go of the need to avoid failure frees energy for meaningful choices. Transcript: Oliver Burkeman 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, 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. 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 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 um 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. (Time 0:12:40)
  • Do It Anyway Captures Relaxed Courage Over Grind
    • Chris shows his rotating phone background that reads “Do It Anyway,” depicting a gentleman walking toward an exploding ravine as a visual metaphor.
    • He contrasts “Do It Anyway” with push-through grind: the former means act despite fear, uncertainty, or tiredness, not forceful perseverance.
    • Chris prefers “Do It Anyway” because it aligns with Oliver’s point about accepting uncertainty and acting with calm competence rather than compulsive productivity.
    • The image and phrase emphasize courage to start when success isn’t certain, not a brittle insistence on perfect control.
    • This reframes productivity from relentless striving to taking imperfect action rooted in judgment and timing. Transcript: Chris Williamson And there’s this just 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 Do It Anyway. (Time 0:28:20)
  • Act Despite Fear
    • Do it anyway: act despite fear, uncertainty, or tiredness rather than waiting for certainty.
    • Aging makes embracing ‘do it scared’ increasingly important. Transcript: Chris Williamson 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 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 you don’t have 100 certainty that it’s going to work even though it probably will you maybe it whatever like just fuck just do it anyway dude And i think that that doing it anyway becomes increasingly important the older you get yeah (Time 0:28:32)
  • Follow What Interests You
    • Let your daily interests guide productive work instead of rigid schedules.
    • Use fleeting desire as fuel; harness it rather than forcing fixed tasks. Transcript: Oliver Burkeman 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 um sort of trying to engineer fun experiences is not something that um 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 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 potatoes, right? 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, 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 i among the things i enjoy sometimes is things that involve you know work or administrative things that i would would never Have wanted to try to force myself to do but feel like i need to do those sort of the 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. (Time 0:31:22)
  • Aliveness Beats Tactical Content
    • Audience capture tempts creators to prioritise marketable content over genuine aliveness.
    • Ironically, audiences prefer creators who sound alive and interested, not perfectly tactical content. Transcript: Oliver Burkeman 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. Chris Williamson Before we continue, I am a massive fan of reducing your alcohol intake, but historically, non-alcoholic brews taste like ass. You don’t need to be doing some big reset. Maybe you just want to crack a cold one without feeling like garbage the next morning, which is why I am such a huge fan of Athletic Brewing Co. They’ve got 50 types of NAs, including IPAs, Goldens, and even limited releases like a cocktail-inspired Paloma and Moscow Mule. And here’s the thing, you can drink them anytime, late nights, early mornings, watching sports, playing sports, doesn’t matter, no hangover, no compromise. And that is why I partnered with them. You can find Athletic Brewing Co’s best-selling lineup at grocery or liquor stores near you, or best option, get a full variety pack of four flavors shipped right to your door. Right now, you can get 15% off your first online order by going to the link in the description below, or heading to athleticbrewing.com/modern wisdom. That’s athleticbrewing.com/modern wisdom. So true. Yeah. And, uh, in my experience, the further I’ve gotten away from what is it that I’m interested in, who is it that I want to speak to the worst 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 it’s the parameters of outcome are a bit more tightly defined. Like 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 this, the, all the, 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 fucking shock the world that I’ve said no to, because I just, it just didn’t feel, it just straight up didn’t feel something. It just, I was like, no, the answer, the answer was no. And, um, 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 fuck. I’m just going to do it. Like Rory Sutherland accounts for like nearly 1% of this podcast. Isn’t it? That’s amazing. A non-insignificant amount of hours on this podcast have been Rory Sutherland. And you and I just, I will continue to do it. And yeah, 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 why 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 gets 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. Just connecting to the aliveness of what the thing is that you’re doing. (Time 0:35:19)
  • AI Can Steal Emotional Authorship
    • Chris imagined using AI to craft a loving apology message and then feeling like a fraud.
    • The example shows how AI can steal the sense of authorship and emotional repair in relationships. Transcript: Chris Williamson 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 lighthearted. 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 somebody’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. Oliver Burkeman 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. (Time 0:42:14)
  • The Value Of Imperfect Speech
    • Repairing relationships often requires saying the wrong thing first; perfect scripted replies can bypass necessary human vulnerability.
    • Over-editable written communication reduces spontaneity and deep relational repair. Transcript: Oliver Burkeman And I think that, yeah, I mean, I think that, um, I wish I could attribute this argument because it’s not my own. I’m borrowing it from something I read and I can’t remember why I read it. But I think that a lot of what happens when you use LLMs in that kind of context, 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 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, at least in the tradition that I’m familiar with, is about long-term real relationship with another conscious, emoting Human being, and absolutely doesn’t need to be full of so-called therapy speak and jargon terms and 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 some of that. The ability to delete and refine. (Time 0:43:40)
  • Meaning Can Mask Joy Deficits
    • Some people chase meaning through hardship because they struggle to access simple pleasure.
    • Prioritizing meaning over happiness can become a lifelong avoidance of joy. Transcript: Chris Williamson 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 law. When a man can’t find a deep sense of pleasure, they distract themselves with meaning. If ease, grace, joy, and playfulness don’t come easily to you, one solution is to ignore moment-to 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. Oliver Burkeman Oh, I love that. And feel confronted. Yeah, I’ve got your line. Chris Williamson 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, duties will never be out of the way and so if you really mean it when you say you’d like to write a novel or spend more time with Your aging parents or fighting climate change or having fun at some point you’re just going to have to start doing it and i think that uh the the category of people for whom ease, grace, Joy, moment-to 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. (Time 0:47:22)
  • Start The Things You Care About Now
    • Do at least a bit of what you care about now instead of waiting for future perfect conditions.
    • Small present actions prevent perpetual postponement and lifelong regret. Transcript: Chris Williamson 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. That’s really interesting. Oliver Burkeman 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, to this which also maps onto the distinction between living entirely in your head and in your intellect versus being embodied in the world, right? Because a big part of enjoying life and showing up for things is embodied, even just in the most basic sense of like feeling the air on your skin when you’re present in a place or something. Chris Williamson Enjoying the coffee as opposed to using it at the maximum possible survivable temperature in order to get the caffeine into your system. Oliver Burkeman Exactly, exactly. And so yes, I think another thing that characterizes these insecure overachievers of which we speak, and that has definitely been part of my biography, and I see it all over the place As well, is being really in your head. And really sort of not only driving towards the future, but assuming that the only way to, but doing the driving through sort of cognition and living in your frontal cortex or whatever, This very specific feeling. (Time 0:49:11)
  • Agency Vs. Control
    • Agency differs from control: chasing control can be disempowering while true agency grows from relaxed engagement.
    • Letting go of self-worth-tied outcomes increases genuine power to act. Transcript: Oliver Burkeman 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 is 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. 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 that for fundamentally Deep, buried emotional reasons, right, I need it to go. I’m actually sort of disempowered i’m i’m kind of uh chained to you’re fragile kind of you’re very fragile right absolutely yeah and and again maybe it’s not everybody but i’ve when I when i don’t need um when i don’t absolutely feel like my basic worth needs something to happen like that’s when I can get doing that’s when I can fully lean into it yeah that’s that’s Chris Williamson Yeah no absolutely that’s wonderful um (Time 0:52:56)
  • Identity Clash During Change
    • Chris described the painful incongruence when shifting from a grind identity to seeking relaxation; public criticism followed.
    • He felt worse productivity then, as old strategies fell away before new ones formed. Transcript: Chris Williamson 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 that, this journey of relinquishing of certainty and control and all the rest of it, it’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 a non-insignificant number of comments said something to the effect of bro sold us the problem and now he’s selling us the solution. 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. Like 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’ve, 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. The obviousness of just work, 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 analogies of that in the orbit around that sort of thing. 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 wrapped a lot of your identity in being the hard charger. I get things done i know me the outcomes i get in the real world are because i do things i i go to bed on night time 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 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 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, maybe even for actually a medium, 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. 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, but it looks like you’ve devolved back to the thing that you tried to only just get escape velocity from a fucking decade ago. (Time 1:06:09)
  • Losing Congruence When Letting Go Of Hustle
    • Chris describes a loss of personal congruence when stepping away from a hard-charging identity: outcomes, intentions, and self-image stop lining up.
    • He gives examples (Trump, Andrew Tate) to show how sudden changes—like adopting meditation—feel inconsistent with a previously single-minded persona.
    • Letting go can temporarily worsen real-world results because you abandon old strategies before mastering new ones.
    • From the outside that transition looks like regression back to the old struggles you once escaped.
    • Chris has experienced increased criticism and this loss of congruence over the past 18 months while trying to embody a different approach. Transcript: Chris Williamson 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 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 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, maybe even for actually a medium, 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. 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, but it looks like you’ve devolved back to the thing that you tried to only just get escape velocity from a fucking decade ago. So this 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. Oliver Burkeman That’s really interesting. (Time 1:08:44)
  • Incongruence Can Signal Growth
    • Midlife transition often requires abandoning old congruent strategies and tolerating temporary incoherence.
    • This period can be generative growth, not mere failure, if you resist premature fixes. Transcript: Oliver Burkeman 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 therapists 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 they stop working um uh they they 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 and all the rest of it and i think you know um i think an argument could probably be made that kind of that remaining completely congruent as you it, all the way through your life And from early adulthood through to late adulthood is like a disaster. I don’t think that’s anything to be celebrated at all because I think we all do know people who seem, maybe I know people, we know people who are stuck in, they’re sort of the wrong age for The psychological outlook that they have. What do you mean there? 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 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 married and settled down and with adult children by the age of 60. 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 sort of, yeah, I think that is a kind of a, I think that is some, 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. Admirers 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 make your life more interesting To you, and how the wide world just sees this as like nothing. Like, what a pathetic goal in life to become more and more interested in being alive. But he says, he makes the point that really that’s the whole game. It’s the most that psychotherapy can do, but it’s also all you need for absorbing a meaningful and fulfilling life. And I think that requires this kind of change and development. And I’m sort of going on and on now. You can cut this out. No, it’s great. 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 weeks at a time, being completely Unclear about the direction I’m taking and really sort of out of sorts in ways that when I describe them in very simple language, it sounds like I was going through a depression or something. (Time 1:11:34)
  • Settle By Spotting Invisible Trade-Offs
    • Recognize every choice involves trade-offs; ‘keeping options open’ is itself a trade-off.
    • Settle when indecision stems from chasing an impossible, downside-free perfection. Transcript: Oliver Burkeman 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 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 a dating advice. I think that, I think that is best left to, uh, other guests probably. But the, but the, but the thing that’s the thing that I was trying to say, and that I think is just true is that it’s not so much that you should settle in that context or any other. It’s, it’s that finitude just means you are settling, right? Like what we mean by settling is accepting some downside in return for the security or 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 like, there are always downsides, right? 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 you 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, um, has a downside. Um, so it isn’t that you should do any one specific thing or that settling down to extend that phrase right into a long-term relationship is necessarily the right thing for any person That 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 don’t go fooling yourself that you’re somehow like Hanging back from like you’re in the human condition, like you’re not getting out of it. And this means that this means that this means that you’re making that kind of trade off in every moment of time. (Time 1:22:22)
  • Settle When You Stop Chasing Impossible Perfection
    • Chris asks when it’s a good time to settle; Oliver reframes it as choosing which trade-off to make in a moment.
    • Oliver says many decisions are intuitive and beyond words, but you can notice the real reason you avoid commitment: a restless fantasy of avoiding all trade-offs.
    • Recognizing that you’re holding out for a nonexistent perfection reveals the game you’re playing and makes the right path obvious.
    • The key shift is awareness: seeing that fear of trade-offs—not lack of options—is what’s blocking commitment.
    • Once you spot that pattern, committing to the trade-off often becomes an easy, clear choice. Transcript: Chris Williamson People know when it’s a good time to settle? Is there such a thing? Oliver Burkeman I mean, rephrasing that question back into what I was saying, it’s like, 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 it 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. (Time 1:25:10)