Oliver Burkeman

Interview by Madeleine Dore

Oliver Burkeman: author and journalist

Full transcript

“The kind of planning that works is very near-term planning, so planning what you’re doing in the next hour is much more in tune with reality than planning even what you’re going to do with your week, let alone your month or your year. So I have given up completely the idea of ‘in six days’ time, I’m going to reach that milestone and that milestone’. Instead, I’m really trying to zero in on ‘in 45 minutes time, there will be 400 more words on this document’.”
– Oliver Burkeman

Madeleine Dore: In a poem called The Summer Day, the late Mary Oliver describes how a grasshopper has flung into the palm of her hand to eat sugar before snapping its wings open and floating away. She writes:

“I don’t know exactly what a prayer is. I do know how to pay attention, how to fall down into the grass, how to kneel down in the grass, how to be idle and blessed, how to stroll through the fields, which is what I have been doing all day. Tell me, what else should I have done? Doesn’t everything die at last and too soon? Tell me. What is it you plan to do with your one wild and precious life?”

Figuring out what we plan to do with our one wild and precious life is no small feat. Our relationship to life is a relationship to limitation. The limitation of one wild and precious life, the limitation of how the moments will unfold, the limitation of not being able to get everything we plan to do done in our lifetime.

As Sylvia Plath once wrote in her diaries, “I can never read all the books I want. I can never be all the people I want and live all the lives I want. I can never train myself in all the skills I want. And why do I want? I want to live and feel all the shades, tones, and variations of mental and physical experience as possible in my life. And I am horribly limited.”

We might be horribly limited, but our limitations can also be motivating. It can help us let go, to stop midway through books we aren’t enjoying, and focus on the ones we do. To seize the next 45 minutes in front of us, instead of planning an entire day, week, month, life that can go in any direction or actually be not what we want in the first instance.

This weeks’ guest has spent the last few years delving into this topic of limitation through researching and writing his latest book on time. Oliver Burkeman is a British author and journalist living in Brooklyn. He writes a popular weekly column for The Guardian on social psychology, productivity, and the science of happiness called This Column Will Change your Life. And he’s also the author of The Antidote: Happiness for People Who Can’t Stand Positive Thinking.

Back in 2017, I met Oliver for a coffee in New York and we spoke a lot about how routine can serve as an emotional need for control, as well as giving up the fantasy of the perfect routine. Something we’re both drawn to but also resent and resist.

In this conversation, we continue on from these discussions and delve further into how he’s moved through a rut, really centred around the book writing process. We also speak about how goals can become redundant very quickly, his love of the Kanban method, self-control and distraction, parenting, shadow work, insomnia, and also how we can get out of a rut by breaking our own rules.

And so in honour of how our lives ebb and flow, about how sometimes we can be really in a routine but sometimes we can be in a rut, and how that can change hour by hour, here is Oliver Burkeman on how he’s doing today.

Oliver Burkeman: Today has not been a good day workwise. Today has been a day where I’m too tired and the morning got off to an annoying start and I have not really done any of the things that I intended to. Now, as I can also say, if you want to know, I think this day has occurred in the context of a really good, slightly broader period of time, but I won’t lie about today. This may be the most constructive and enjoyable thing I’ve done, or indeed do, with my day.

MD: Well, not to put any pressure on it. So I guess if we take a step back then, into this broader context of better days, what have you been working on?

OB: I’m working on a book, which I was working on when we last met a long time ago, and what has happened in the interim is that, well, I think my wife had had our son when we met, but only a few months ago, and he just turned three and it turns out that the first two years of having a child, if you’re me anyway, make it very, very different to do all that much else.

So I’m now several extensions to my contract later, I’m now really in the closing phase of finishing this book manuscript, the main first draft.

MD: Obviously time, potentially, could’ve been a struggle or just changes to your routine with a newborn, but what else is difficult about the book writing process? Is it the coming up with the idea and actually settling with something you’ll enjoy enough to explore?

OB: The main thing that’s been difficult for me has been a really good thing. This is probably true of all large creative projects, but certainly when you’re writing about psychology in a book form, but if you’re on your own psychological journey, like we all are, I think as time passes through the project, it is itself like an act of discovering stuff. 

And so it’s not a question of you decide the topic, you research it, and then you write it out exactly as you thought about it. You realise that you have to change in certain ways to be able to write what the book wants to be, and you have to get quite good at waiting on parts of your psychology that are maybe outside your conscious mind to see what’s happening. But at the same time, you do actually need to get a move on and produce stuff.

MD: Well I would imagine as self-help writer who questions self-help in their writing, there would be a lot of overthinking, a lot of changing your mind, and that need for more time. So what is the book about currently and how has it changed through this process?

OB: I think everything I ever write is, on some level, is like here’s my current way of thinking about the world. And again, I suspect that’s universal, but maybe more disguised in some forms of creative work than for me. The working subtitle is Time Management for Mortals. The idea is to think about time and how to use it and how to be productive, or whatever you want to call it, in a way that really takes account of our limitations and the fact that we only have a limited amount of time on the planet, that we don’t actually get to control an awful lot of what goes on in that time, or the talents and resources, and social positions, and money, and all the rest of it that we bring.

And then also I hope it brings the idea of time management into something which absolutely was not really on my mind when I very first had this idea, because it was a number of years ago now, which is this sense that I think a lot of people have now, but there’s a civic, political, and beyond that, of course, environmental stages that we all feel a bit more that we need to be doing something, than certainly I did five years ago.

So it’s rather a trademark, I think, that some time management and productivity books, that they just assume that building your startup business and maybe managing your household. Maybe. Those are the two things that anyone is going to want to care about. But I want to be able to care about things like activism and whatever it means to be a good citizen. Things like that as well. 

The problem is, as soon as I talk about this, it sounds like I’m trying to write a book about the meaning of life. But then again, I think we all are, and what other topic is worth writing about?

MD: Exactly. Time and our relationship to it and our limitations and our limited time really does speak to this idea of… it’s like Mary Oliver’s “what will you do with your own wild and precious life?” That does have an inherent relationship to time.

Just a teeny more about this idea of limitations. What has been your discoveries with limitations?

OB: I can take that question in two senses, and one that I know that you’ve thought about and written about is the idea of constraints that you, in some sense, apply on yourself as a way of generating output or creativity or whatever, and we can talk about that, I think it’s really interesting.

But mainly, I suppose what I’m thinking about is it’s not a question of whether it’s good to have limitations. I’m talking about the kind of limitations that just are, and so the question is always to do with, are you going to confront that fact? Or not?

And I suppose part of my critique of a lot of traditional productivity advice that has really come into focus for me over the last few years is that it really acts to enable denial. And so one of the things I try to explore is this idea that there’s more pressing in on you then you can possibly do in the time available, whether that comes from all your ambitious creative dreams of your life or it just comes from all the obligations and duties and tasks that your position in life puts on you.

If there’s more that you feel you need to do than you actually can do, then you’re not going to do it all. And if you don’t take account of that fact and if you try and stand to use ways of becoming more and more high proficient and productive so that you might one day get on top of it all, you won’t succeed, but what will happen, for various reasons that I go into, is that you’ll feel much busier and you’ll also probably end up dedicating less time to the stuff that really does matter to you.

So I suppose the underlying ethos of at least part of this book is, okay, you’re definitely not going to get done all or even most of the things that you want to do or you feel you ought to do. Now what?

I don’t personally find this to be a recipe for a counsel of despair at all. I think it’s absolutely brilliant and incredibly energising to really understand, as I think I have in my personal life. A bit more than I did anyway. That a lot of the time, the thing you’re trying to do to prove yourself or whatever it is, was impossible all along. 

So the idea that you’re ever going to render yourself into this absolutely perfectly efficient, hyper-productive… the idea that any of this is ever going to be achieved is nonsense, that’s just a huge relief, because then you can get on with spending your limited time and using your limited abilities and resources to do as much stuff that matters as you can, without this agenda.

MD: Feels like an immediate burden off the shoulders if you accept that you’re never going to accomplish that all. I have a tendency to create systems for myself, but the next day comes and I fail to stick by that system or that routine, and then, by the end of the day, feel like a failure because I didn’t meet that. But maybe it’s not actually you that’s the problem, it’s the routine that you’ve invented.

OB: Yeah, I resonate with that so much. I mean, I still do this to some extent, but what I have come to understand, I think, is how much of the time, I’m going to say we, but I suppose really I just mean me, and I hope that I have some wider elements, how much the time we are acting to try to feel in control of time and life and ourselves, and I think those kind of system building things, certainty for me and it sounds like for you, have served that purpose a lot in life. Right? 

It’s like now I’m finally going to put this system in place and then I can cruise in autopilot through a brilliantly, high-achieving life. But one thing that happens a lot is that you set these kind of goals, and then they feel really stale and dead within about 48 hours or something, because I think they’re not authentically suited to the actual experience of life. You don’t have the kind of control over life that you, or I, have been seeking. 

You can either constantly chase this thing that you will never achieve, or you can, at least to some extent, at least on the good days, understand that you don’t. And it’s not that you have no control. It’s that once you see what you can’t control, you fall back into the agency and effectiveness that you do have and you can do things much more usefully, and have a bigger influence on the world, I think, if you’re not chasing this level of total control.

MD: I would love to invite more surprises into my life somehow because I think the best things happen as a surprise, whether it’s our career or meeting someone that we fall in love with or whatever opportunities. They’re often not what we planned for.

But another little thread that I want to pick up there is that you have spoken a lot about goal setting and how much of goal setting can be quite futile but having process goals can be a way to counter this control.

OB: I think in my last book where I was on a real tear against goals, it was always the part of the book that, and I think I did say this actually, it was always the part of the book where I was the least comfortable with a total rejection stance because, apart from anything else, I think as biological organisms, we just have some goals, whether we like it or not. And then it doesn’t seem sensible than to have no other goals at all for your career.

I think the way I’d frame it in the context of what I’m writing about now is, there’s the kind of goal, which is fundamentally an effort to try to control the future, to get some reassurances from the future about how things are going to go. Then there’s the kind which is more a statement of intentions. 

There’s a writer who you may well know, or know his work, David Kane. The way he puts it is that you don’t actually ever have any time. You have intentions. You do not have three hours in which to complete a project in the same way that you might have $3 in your pocket. You don’t really have it. You expect it, but anything could happen, and so what you really have are intentions towards time. You can absolutely formulate your best case scenario or how you’re going to respond if certain things happen, but you withdraw from that idea that it’s you throwing a lasso around the future and bringing it in and taming it.

And I think the reason that distinction matters is if you do go and head into the time, constantly thinking that you own it and that it’s yours to decide and that you have it under control, then every single second of your day is going to provide contrary evidence of that fact, and it’s going to be very stressful because you never can predict how long something is going to take. 

The famous Hofstadter’s Law that says everything is always going to take longer than you expect, even when you take Hofstadter’s Law into account. In other words, you can’t ever get out of this problem. People aren’t going to do what you want them to do, certain kinds of distraction can overwhelm you.

I think having a child was a really good way to see that. I don’t want to make it sound like a self-help technique and I also don’t think any of this unique to parents at all, but here’s among many, many other wonderful things, a constant source of destabilisation of any rigid plan I might have made for any hour of the day. And that’s useful.

MD: I would love to move into your routine in a moment and hear about what the shape of your days look like at the moment, but I’m interested with this talk of goal setting and the futility of it perhaps, but also this idea of having intentions and not necessarily time. I’m just curious to hear what you make of manifesting and things like setting intentions and setting ten-year plans.

Debbie Millman has a wonderful example. She does this exercise with her students of writing out a five-year plan and time and time again she has students come back to her and say that everything has come true, even if it was wild and ambitious. 

So where do you think that comes in?

OB: I think some of that law of attraction business gets quite wild in terms of the supernatural claims being made and I can remain fairly mocking about all that probably, but on the other hand I think I do have more than I used to, anyway, on some level, I hope, of appreciation for, or humility towards, all the parts of my brain that are outside of my awareness.

So it’s not for me to say that if I write down how I want things to be in five years’ time and put it in an envelope and put it in the attic, but that won’t lead to something. How would I know? I mean, nothing has gone the way I planned it in my life, and surely that’s true for most people.

So I think it is probably important that that exercise, as you described it, is not the same as the kind of classic self-help goal setting, which involves thinking all the time about your monthly, quarterly, annual objectives. And that, in my experience, just becomes absolutely intolerable within about a week because you’re no longer responding to the moment or to what matters most to you. You’re trying to carry out this prearranged map and it feels like someone is bossing you around, even though that person is yourself.

MD: It’s you. I forget that I’m the worst boss sometimes.

OB: Well, we’re all the worst boss to ourselves. I don’t know if you do manage anyone, I basically never have in my life. You’d probably be a lot nicer to them.

MD: Oh, I would hope so. But the exercise, I think there’s a website called My Ten Year Plan that I can send to you, but I think it really does circumnavigate a few things because it’s about going big, going to ten years, five years, but then bringing it back to what you want your day to look like. And I think that comes back to, how do you want to spend your time intentionally?

So on that note, what do your days look like at the moment? You’ve described them previously as a mash-up. Are they still a mash-up?

OB: Yes, although now I wonder if anybody’s day that doesn’t apply to… just before me and my wife moved in together and before our son came along, I had got to a point in my life where I was pretty set in my ways, and I had figured out the exact routine that I wanted to implement on a given day, and I was doing it.

And I think already, for a while then, I’d started to feel like something had gone a bit calcified.

MD: What was it like? Just as a brief overview.

OB: I’m someone who likes to get up early.

MD: Is that like five? Six?

OB: Five is the earliest, yes. I realise this is a subjective judgement. Sometimes I hear people say that they like to get up really early, 8am, and I’m like what?

MD: Yeah. I love when people say that.

OB: I have never consistently, for more than about two days, got up any earlier than 5:00. I’m a morning pages person, so I’ve done that for years and years now.

MD: That’s from The Artist’s Way I’m assuming?

OB: Yes. Well, I’m not sure I’m following her instructions properly. But yeah.

MD: Oh, okay. Did you ever read The Artist’s Way?

OB: I did. Well, I read the section on Morning Pages, I didn’t complete the whole course.

MD: Ah. I just completed it for the first time this year, which is quite an achievement.

OB: Do you recommend it?

MD: I’ve been putting it on and off for five years, and finally did the 12 weeks, and it was great to have that bedrock for 12 weeks. I ended up in New York at the end of it, so that was some kind of magical ending.

OB: As far as possible, I have kept The Morning Pages up. There were big chunks of our son’s earliest days when that was not going to be feasible. The big thing for me, just to treat you too much like a therapist, but the big thing for me over the last few years has been unclenching from those routines.

So it’s not to do with discovering the perfect routine, but actually easing up a little bit on the need for one. One of the things I have found really useful is the idea of decoupling all this from specific times. So it’s not like I try to get up at X o’clock and then I try to do this for this amount of time.

When it works well, I have a running order in my mind, right? So it’s as and when I get the opportunity this morning, I’m going to write in my journal for three pages, do ten minutes meditation, that’s as much as I’m doing at the moment. Maybe sometimes there are light bodyweight exercises in the mix there as well, whatever.

So these kind of things that previously I would’ve been like, I’m going to do this at 5 o’clock every day and this at 5:45pm every day, which was very frustrating because even then I wasn’t reliably hitting those times until I would feel like a failure for no good reason.

But now I’m just like, I’m going to slot those three things in and sometimes they can all be done by 6:15 in the morning and sometimes it’s going to be 10:00 because I’ve spent an hour playing with playdoh.

MD: And living.

OB: Yeah, and making breakfast for people. So that’s the middle way. I feel like that idea of having a running order of things that you want to do.

MD: Yeah, I like that. Austin Kleon, who I interviewed earlier this year, has checkboxes, so he’s reading, walking, and writing, and that’s a day. If he checks those boxes, that’s a good day, but not every day.

OB: You don’t want to set up a system that makes spending time with your child, or whatever other important thing you might have in your life aside from your work, you don’t want to make it so that you’re somehow subtly failing at implementing your life plan, when what you’re doing is as rewarding and important as hanging out reading storybooks or whatever.

And I think there is a risk of that. Obviously many people have far less flexibility of their schedules than me or you, and they have to be at a desk at a certain time, and that’s the way of the world. I don’t want to overlook that, but I still think that, for me, just caring about all these kinds of orderly, control-ly things a bit less is the challenge, and I’m no ways through it yet. I’m not really some position of perfection on any of this.

MD: It sounds like what you’re talking about in some ways is attention or being present in the moment, rather than thinking about a to-do list.

OB: I think I’m better at that than I was. I might just be much better at seeing myself doing it. I think I definitely understand my kind of built-in anxiety and control-iness and all this stuff much better than I did. I think I deal with it somewhat better than I did but, you know, maybe it comes in stages. You sort of figure out your patterns ahead of letting go of them completely. I don’t know.

I just recently read a book by a psych therapist called Bruce Tift called Already Free, which made a big impression on me, and an interesting part of his outlook is to take these things that frustrate you about yourself, or about your relationship, or about any other aspect of your life, and be like, what would it be like if that never went away? Basically if the end of my days, this frustrating problematic trait was present, and it’s actually very liberating in many ways, to be like I might be okay. Yeah.

I probably am not at this point. I’m going to wake up one day in a few years’ time and be like, oh, great, now I’m a perfect person and really easy to get on with and never wastes any time and blah, blah, blah.

And again, that’s realising that you’re not going to get everything done. I know it’s an embrace of limitation.

MD: Yes. I like that a lot. So I am curious then, as someone who has a weekly deadline with the weekly column, and you’ve been writing it for over a decade now.

OB: Oh, yes.

MD: That’s a lot of ideas. The column is called This Column Will Change Your Life. I’m curious to hear maybe how you research that column, how you keep track of different studies that might be coming out, what kind of things you read? What goes into that column if you do have more of a mash-up of a day, but still that weekly deadline?

OB: It’s a big mix. One of the things that I realised, quite a long time now I think in writing that, is the idea that you need a peg for everything you’re doing. A hook. The thing you’re writing has to respond to something that happened in the news in the last few days, or an article or an essay on a similar subject has appeared in another publication in the last few weeks, then you can’t do it yourself.

And it was really, really helpful, I think. I don’t know, maybe some of my editors would disagree, but I think it was really, really helpful to learn to say, what do I feel like is really important to say? What do I think might be really useful to people?

And sure, if it can be related to new research, that’s often what provokes a given topic, but it doesn’t need to be. Surely what matters in a column like that is that you’re saying something that you think is worth saying.

I’ve completely, you could say, abandoned standards, I suppose, so it’s totally eclectic and the most difficult part for me is literally keeping track. Like how do I make sure that if, I’m in a swimming pool and I have some random thought, that it doesn’t just flee my tired brain once and for all then, and that it’s there to be selected from.

MD: So do you use a notebook then or do you have notes in your phone?

OB: The swimming pool is a bad example because I have nothing in a swimming pool. I’m sure that someone has invented something for recording ideas in the swimming pool. I have found an app really useful, an IOS app called Brain Toss. It’s not the greatest of names perhaps, but this is an app that just does one thing. You open it, you type something in, you press send, and it goes to your email inbox. That’s literally it.

It’s not like sending yourself an email because then you see your inbox and you’re like, oh, I’ve got to deal with all these other things. I think you can do a voice memo with this as well, but I don’t usually do that.

So that is one simple way of doing it and it means that, as long as you have a point in your day or your week where you’re properly processing your email, which I’m not necessarily great at, you will pick those all up and add them to a list. 

So that I find really useful, and what’s great about it is that it doesn’t do anything else. I mean, what’s great about it is that you don’t get to see your emails or surf the web while you’re trying to do it.

MD: Exactly. Maybe you’ve experienced both conundrums, but is it ever idea overwhelm with the amount of Brain Tosses you’re sending? Or has there ever been a period where you think, I can’t think of what to write for this column anymore?

OB: It’s so cyclical, but yeah, I’ve sort of given up ever thinking I can’t think of what to write anymore because it literally is just what’s on my mind. It’s evolved. I mean, not that anyone cares apart from me, but what I do in that column has got nothing to do with what I did at the beginning, really, I don’t think.

Because it’s this amazingly privileged position that I don’t expect to have forever to just sort of write for 500-600 words about what I think is interesting and important. So the other thing I definitely can blatantly do is experiment with things that I’m thinking about for part of the book I’m writing. Sort of put out an idea in a prototype form and see how people respond to it.

I mean, it really is just, hopefully, my side of a big disorganised conversation about stuff that seems important. I think, in some sense, I write about politics and global things much more than I used to because as I say, for me anyway, that suddenly seems much more urgent than it used to.

So I don’t know that I have a great technique for doing this specific kind of thing, more than the time, for whatever reason, has seemed to have lucked into a thing that’s infinitely flexible to do whatever, almost, I want. Although if there is a lesson to be drawn from that, I think it’s probably just to the extent that you’re writing about stuff or producing in any other medium. Stuff that you seriously care about. It gets you a long way to finding an audience. I think, I hope, rather than trying to gain it by following some other strategy.

MD: Well, I think it also speaks to doing one thing well or having one quite strong focus, be it in a week or a day or a career, whereas I feel sometimes I can be quite scattered, especially as a freelance writer who doesn’t necessarily have a set column. 

It can feel like you’re sort of opening the door somewhere, trying to push it down somewhere else, it’s closing over there, and it can be hard to get momentum. But do you think that having that column for as long as you’ve had has allowed for momentum, and then maybe even been able to tackle bigger projects like a book?

OB: I think that’s probably true. I mean, the less flattering way of putting that would be I’ve got people breathing down my neck if I don’t get a move on, right? And so a good thing about external deadlines is there comes a point where you just have to say, well, no, this isn’t a very good idea, but I don’t know any others. I’m going to be a bit late, I’m usually a bit late anyway, but I’m going to be unacceptably late if I don’t go with it. And what you find then, fascinatingly, is at least sometimes those are the best columns.

MD: Interesting. Because you haven’t over-thought it?

OB: Yeah, or because, I don’t know, because you just have to make the best of what you’ve got, and then you actually really put the effort into making the best of it. The other thing that I probably got to go on and on about, or for 30 seconds anyway, is in terms of getting these things done and not just opening 20 doors at once, in the last year or so has been the personal Kanban, which I know is not brand new, you’ve probably done a lot of them, but for me, it was a big discovery. So that’s also been really important to finishing things that get started.

MD: So do you have a big wall of Post It’s for the Kanban?

OB: Just a folding file with mini Post It’s, but I think that’s very important, that visualised part, but the rule that is so central to this, that has made a big difference to me, is this idea of limiting your working progress. So I don’t know how universal this is to different Kanban implementations, but just this idea that you have, say, three things that you’re working on at any one time, or maybe one major project and two to three small tasks, or something like that. And you don’t put anything new into the column of what you’re doing right now until one of those has been completed and moved out. Or abandoned. You can just say this is a dead idea, I’m going to throw it away.

So when my column is that thing, I’m going to be working on that column until it’s done, and I’m going to resist the urge to move to an interesting bit of the book or to, I don’t know, try and redesign my website that’s desperately needing redesigned, until I’ve moved that one out.

Sounds like you do all this already, so I don’t know, I’m probably telling you things you know very well.

MD: Oh, no, I definitely am not very good at having that one thing.

OB: Well, the really fascinating thing about it is it’s got all these weird effects that you’re not expecting. So, for example, it really sort of naturally forces you to right sized tasks because if you’re going to be working on one or two major things at any one time, you can’t put ‘write book’ in that slot.

MD: Mm, it doesn’t linger there forever.

OB: That’s right, and that’s going to deadlock your whole system for ages. So then you have to be like, okay, well, what could I actually do in the next hour or maybe it’s the next few days? What would be the chunk that would make sense?

The other thing that really helps, and I mention it in my book because it is relevant to this idea of limitation, it feels like you’re imposing a limitation on yourself, but really all you’re doing, mainly, is bringing into conscious awareness a limitation that you already had. And it makes you realise that if you don’t approach work in this way, like before I did this, on some weird subconscious level, I would think of myself as having 35 irons in the fire at any one time.

But it was bullshit because I obviously wasn’t getting around to 33 of them. And then the other problem when you’re in that situation, in my experience, is that when any one of them gets tough and difficult, you just bounce off into another one, right? So you never actually push through when you need to push through.

MD: That’s where I’m at, Oliver. This is very hard.

OB: Well, that is why I would seriously recommend saying three things on my plate at any one time. And again, it doesn’t need to be record and produce a podcast series. It just needs to be one identifiable task related to that, and when that space is freed up, then you can put pay bills, or write an old friend, or whatever it is. I just love it. And the sense of achievement is much more genuine. It’s much rarer, I think, when I’m using that system well, that I feel like, well, what did I do today? It’s like I did those six Post Its today.

MD: There you go. It’s very tangible. I love it. In so many senses, it’s really that one step at a time, and also you’re not going to do everything. Limitations.

OB: Right, right, right. And you already weren’t going to do everything.

MD: Yes, exactly.

OB: That’s the thing I keep trying to emphasise. It’s not that you’re somehow accepting a lower standard, it’s that the low standard is called being human, and we can either confront it or not.

MD: Yes. How do you think you’ll approach writing the book? How will you chunk it down step by step?

OB: I tend to try to do the writing in very short bursts, but lots of them, so I try to do a 45-minute writing period and try to get a few hundred words down in that time. And if you do a few of those in a day, that’s a good days writing.

The kind of planning that works is very near term planning, so planning what you’re doing in the next hour is much more in tune with reality than planning even what you’re going to do with your week, let alone your month or your year. So I have given up completely the idea of ‘in six days’ time, I’m going to reach that milestone and that milestone’, but I’m really trying to zero on ‘in 45 minutes time, there will be 400 more words on this document’. 

But books are very strange. It really feels like I’ve worked very hard and written many, many days, a good thousand words. But it feels like I’ve done that on hundreds and hundreds of days, but I can’t have done because a full-length book is 70,000 words and I’m not there yet, so I can’t have done 1000 words on 70 days, mathematically by definition. It’s very odd because I don’t feel like I was lazy. If we knew where the time went, we wouldn’t necessarily go there.

And, you know, I do do other things. I freelance for other people and there’s plenty of other stuff that goes on, so it’s not like I can’t come up with things to fill the time when I’m trying to avoid confronting some difficult part of the book or something.

MD: So what are common distractions?

OB: Well, the one that most closely resembles a struggle with a Class A drug, or something is Twitter for sure, for me. I go between days of spending far too many hours on it and using those apps to ban myself from it for three weeks at a time.

MD: Do they work?

OB: They do. Well, I finally found one called Self Control. Though you can remove it once you’ve put it down. It’s just about complicated enough.

MD: Yeah, I’m just terrible with the self-control element of deleting the app designed to help me with self-control.

OB: Right. These kinds of things where you block the external source of the irritation are helpful, but the thing I’m trying to get a handle on is this idea that it’s true that Twitter distracts us. It’s true that there is a huge corporate industry designed to monetise our attention and take our attention away from the goals we have for it.

But it’s also true that we kind of want to be distracted in a way. We’re fleeing some kind of inner distress or pain every time we do that. And the simplest form of pain is just writing this passage in the book is kind of hard and difficult, and it suddenly feels so much easier and lovelier to go and dive, plunge into Twitter.

Equally, it could be worse. I mean, when you’re going through something much more serious in your personal life or something. Again, there are reasons. And it’s not that we can overcome that all the time, but I do think that it’s really great to see that you are sort of trying to run away from something when you seek out distraction and that, to some extent, just expecting difficult work to feel a bit unpleasant is the answer.

As soon as you stop thinking my day at my writing desk should be unbroken bliss becomes way easier to stay with it when it isn’t.

MD: Yeah, or even that you have to feel like doing the work. The muse will appear only when you actually sit down to do it.

OB: Firstly, yes. If you do it, you’ll probably feel much better about it. But even if you don’t feel much better about it, that’s okay. It’s okay to spend a few hours doing something important and it not to feel blissful. And most of the problem, for me, with distraction is when I’m in a rut of expecting it to be otherwise.

I came across an amazing quote just the other day from Charlotte from Joko Beck, the Zen teacher who died a few years ago. “What makes it unbearable is your mistaken belief that it can be cured.” It’s such a great life philosophy and it applies certainly to work sometimes feeling not pleasant in its difficulty.

MD: So I guess after a day of a complete mash-up, of column writing, book writing, Kanbanning, what does late afternoon, evening tend to look like?

OB: If I’m going to exercise properly, that’s where it’ll happen at about 3:00, 3:30pm. Because I’m starting so early, I’m getting very tired by about 2:00, 2:30, 3:00 o’clock. We really have got into no particular routine with my son and my wife’s work, so some days I’ll be picking him up from preschool at 2:45 and we’ll spend the rest of the afternoon and evening together. And then at the other extreme of that, I might get back five minutes before he goes to bed to read a story.

MD: Is that just managed day by day with yourself and your partner with just texting?

OB: It’s all over the place. We make some plans. It’s not literal. He goes to preschool three days a week and doesn’t on the other two, so there are some certain rhythms. It’s been a very interesting experience. In some ways, I feel like cohabiting, which I only had really started doing very little before becoming a parent, and in some ways even more of a challenge to your routines and your control-iness than having a child.

A friend of mine, Jonathan Rowson, who just wrote this great book called The Moves That Matter. It’s a book of life wisdom, but he’s a chess grandmaster, so it’s kind of through the lens of chess, but he has some very interesting observation there about how actually, at least for maybe the first few years, it’s not becoming a parent for a man in a heterosexual relationship.

Even if you’re doing a bit chunk of your duties, as I hope I am, that’s not the hard part. It’s actually kind of really fun to hang out with small children. The hard part is the different relationship it places you in with your adult partner and, I don’t mean to say this in any way that implies anything other than the best things about my wife, but sharing your life with another adult human being with their own interests and projects and personality, it’s super challenging.

MD: With or without child, as you say.

OB: Yes, right. Absolutely.

MD: Negotiating their routine and the shared calendars. It sort of doubles everything.

OB: Absolutely, yeah. And it’s a sort of famous and justified critique from feminist writers and labour historians of people that, even when a couple shares the responsibilities in a household, it’s often the woman who does the coordinating, they call it the worry work or designated warrior, or whatever it is, right?

MD: Yes. The emotional labour.

OB: Right, but also you have to keep track because often I think how couples organise the work is that they may do something like 50% of the tasks, but it’s basically the guy going and getting told tasks by his wife from a to-do list. She still has to maintain the to-do list and make sure everything is on it.

I don’t think we do that in my relationship. I think we’re much better at splitting the worry, coordination, are we looking ahead to this and that. But even then, you realise that someone’s got to coordinate who is worrying about what, so there’s a kind of infinite regress, and it does seem like it’s exponential. 

I don’t know if that’s the right word, but it’s not just that you have to think about one other person, or two other people if you have a child, or something like that, it’s just the whole extra layer of complexity to everything. And also sort of emotional complexity because people are in good moods and bad moods, and sometimes one person is totally exhausted and the other person can pick up the slack, but sometimes both people are totally exhausted.

MD: How people do it baffles me. So you wrote quite beautifully about shadow work, if I recall?

OB: Yeah, as I recall, it was a while ago now, I think what I was writing about there was more these kind of tasks that get created in the world. One of the things that others have observed a lot is the convenience revolution of the internet makes it looks like everything is much easier, but it actually has the effect of shifting a huge burden of admin onto us.

So, back in the day, you might ring a travel agent, lay out what you needed for a trip, get a bill, and it was all done. Now you don’t have to worry about that, you can do it directly, but that just means you have to pick through all the flights. And so that kind of shadow work, or even just self-service checkouts in stores, my particular hate. It’s like, why don’t you do that work as well? It’s like okay.

MD: Exactly. Well, I guess having said all of that, it either makes for a very restful sleep because you’re exhausted or not so much if there’s a head full of worries. So how are you with your sleep?

OB: My issue has always been that I get to sleep very easily, but then in a cyclical way I wake up too few hours later and have a patchy rest of the night. So I do, in some areas, there has been a thing for me. I think I’ve basically got it managed now. Not eliminated.

MD: Anything that helped with insomnia?

OB: Well, this is like the archetypal, like the canonical case of if you could only give up your mistake and belief in a cure, you would be fine, right? Because the only problem with being awake for an hour or so, or two, in the middle of the night, I mean there’s much more chronic insomnia that I don’t suffer from, but the only real problem is that you’re trying to get back to sleep, I think.

If you just be fine with it, if you could remind yourself and remember that actually it doesn’t usually totally sabotage your day to be a little tireder, if you didn’t have the anxiety about the fact that you’re awake, you probably wouldn’t be awake. So it’s the purest expression of that stupid paradox about trying too hard to do the thing that you want to do. So that is helpful. Just that recognition.

And then the other thing that I’ve done is tried successfully to give up everything that looks like a crutch. Like over the counter medication, or herbal tea, or having to have things just right. The more that you can give all that up, the more you find yourself trusting yourself to sleep again. I don’t know. Is this a thing for you?

MD: Not insomnia. I find it difficult to wake up in the mornings, so I suffer more from sleep inertia. The snooze alarm is very appealing, whereas getting to sleep is usually fine if I haven’t had too much coffee that day.

OB: Right. Well, I just wonder also, is it time of day related? Because my wife’s big challenge is that, in her ideal sleep world, she would not be even thinking about going to sleep until 1:00am, and then she would probably get up at about 10:00am. But that’s just not compatible with the world as its organised. It’s not laziness, it’s just a different phase and rhythm.

MD: Well then, yeah, maybe it’s just about being okay with that. And I’ve got more flexibilities with being a freelancer, so I could have that rhythm if I let go of the guilt about having that rhythm.

OB: Right. It’s always the same thing, isn’t it?

MD: Were there any other parts of your day before winding down?

OB: I don’t know. I feel like my account of my afternoons and evenings hasn’t given proper focus to how they are, on one hand, the loveliest parts in many ways, and then, on another way, there’s meals that need to be cooked, and there’s dishwashers that need to be loaded, and it’s not really anything to do with what my creative ambitions for my life might be.

On good days, there’s something I really like about that. There’s something about domesticity that is just totally great. And then there are other days. The other thing I think is a big change is that weekends are really weekends now in my life.

I do tend to, at the moment while I’m completing this book, grab a few hours on Saturday morning to do some writer, but apart from that, there’s a much clearer boundary than there used to be. And I still don’t particularly find it easy to think about Sunday as just being like, oh, we’re just going to all hang out, go to the park, and do things like that.

A part of me is like, why am I not producing things? But that’s another point that I know you’ve thought about before, that we all need to rest some more, but it’s actually quite hard to bring yourself to rest, even though you have the privilege to be able to do it in your life.

MD: Yeah, I think that’s probably the number one commonality between everyone I’ve interviewed. Often they’ll say, I don’t know how to do nothing. I don’t know how. So yeah, it’s definitely something to learn, I think, is to be restful without any of the beating yourself up for being restful part.

OB: Well, just like, again, stop expecting it to feel great at the beginning. Because if you’ve got momentum and you decide to stop, it’s not going to feel great at first. And there’s a lot of the retrick, I feel, around just savouring the moment. It just implies that the moment you go on a walk in the park instead of working, you’re going to feel ecstatic. But why would you? The flywheel is still going to be slowing down at that point.

MD: Yeah, the rest almost isn’t for that moment of rest, it’s for later. Maybe it was Hemingway who said, “Stop while the going’s good, so that you’ve got something to come back to,” but that stopping is incredibly difficult when you’re mid-sentence, but the payoff is later.

OB: And it gets easier if you don’t expect it to feel great at the moment you’re doing it.

MD: Yeah. So this podcast is routines and ruts and we’ve had a great impression of how both elements are found in our days and how you’ve gone through… you didn’t phrase it as a rut for the book, but what would you call it?

OB: I think it counts. I’m happy to call it a rut, yeah.

MD: Okay, we can call it a rut. What would be your insights that you’d share with someone else who might be going through a similar rut, or something’s taking a lot longer than they thought it ever would?

OB: To not expect things to be otherwise. I think that’s important. I spent a significant proportion of one or two of the last few years being like, well, why can’t I just, having got up with a small baby at 5 o’clock in the morning and then come into work, like why can’t I just keep going? It’s like, well, this is an unrealistic expectation.

Books just take a weirdly long time. For some reason, it is much, much more than ten times harder to write a 70,000-word book than a 7000-word article. I mean, when you phrase it in those terms, it’s like, why aren’t we writing books every month? It’s ridiculous. But nobody is, really. Well, not good ones.

MD: Or not themselves.

OB: Right, exactly. So, you know, who am I to know how hard a given thing is going to be is a useful thing. Beyond that, for me anyway, it has been very easy to get into a rut as a result of trying to meet some kind of criteria, which isn’t what actually the creative work needs to be.

Actually seeing that it was meant to be something different and shifting, that was the way I got out of that rut. Another sticking point, I think, was the idea that I had to have figured it out. I think it’s far more relatable, actually, and makes for better writing. Just be like, this is where I’m at with this stuff, and I hope that if I’m bringing something to the reader that they don’t have , having thought about it some more and read around it, but it certainly isn’t having created the perfect life, which I will now lay out so that you can copy me.

MD: There’s a lot of emphasis placed on getting started when it comes to creative projects. “Just do it”, “make it happen”, “don’t wait for inspiration”, “begin now”, “start before you’re ready”. 

But something that keeps coming up in my conversations with creatives is how getting started has actually a lot to do with how we stop. It came up in my previous conversation with Lauren Martin in Episode 7. This idea that you can become afraid of the work if you step away from it.

Another side to it came up in this conversation with Oliver Burkeman, about how it can be difficult to stop when we’re in flow and how we might actually resent our downtime or feel guilty about doing nothing because we were in the zone with something, and it feels wrong to stop mid-motion.

In both instances, I’m reminded of when I started running. I started really, really slowly, just two minutes at a time, that built up to five minutes, to ten minutes, and over the course of many months, I reached my goal of being able to run five kilometres without stopping.

There was one afternoon when I was actually going for a run with someone far more experienced than I am, and we were running and then they just sort of stopped, and they said, “Well, that’ll do for today.” And I remember saying, “But I can keep going. I can run for much, much longer than.”

And they said, “Great. That means that you’re going to be excited for your next run”. You’re not going to resent it because you didn’t exhaust yourself or you didn’t injure yourself or you didn’t push yourself to a point of then dreading it next time.

And I think that has a lot of resemblance to the creative process. As Hemingway said, “Always stop while you are going good, and don’t think about it or worry about it until you start to write the next day. That way, your subconscious will work on it all the time. But if you think about it consciously, or worry about it, you will kill it and your brain will be tired before you start.”

So the key to starting is actually to stop at the right point so that you’re not tired the next time that you go for a run, or sit down at your desk to write, or to illustrate, or whatever creative pursuit it is.

So there’s my two takeaways from today. Start small with the 45 minutes you have in front of you, and stop when the going is good.