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One day, 20,000 times: the evolution of a daily routine


The most daunting thing about going jobless is working out some sort of answer to that question of how to fill the space of each day. (I also talked about this in The longest weekend). Of course, a day gets filled with something, whether you like it or not. You can’t stop it from happening. But that also means that questions arise, maybe not in the first few weeks, but after three weeks, a month, six months. Hard questions: What should I do today? What can I do today? Should I be doing something else right now? Am I going to run out of money? Should I be doing something about that? Is it better to worry now or later? These are questions about survival, meaning, purpose.

It seems especially impossible when you’re thinking that, once you’ve got this all figured out for today, now you have to figure it out all over again tomorrow: 365 times this year, and 365 again next year, and the year after that. A new existential crisis every day!

But what I propose here is that you only really have to figure out one day. One perfect day that encapsulates everything you most want to be present in your life. Once you have that, you just repeat it 20,000 more times. (20,000 days is about 54 years. Maybe I’ll have much less time, maybe much more, but I’ll just shoot for the middle here.)

By the way, this isn’t just for people who are jobless and have all day to fill. You have some control over what to do with some nonzero amount of time, at least one minute of your day or week. If you don’t have any control over any of your time, it’s unlikely you would be reading my blog, but even so, you can still control your experience of time, which is almost the whole thing.

Am I suggesting that the plan is to do the exact same things at the same times every single day? No. This idealized prototype day is a container you build that you can then rely on to encase the living soul of each day–which cannot and should not be predicted–and to protect it from dribbling out and being stolen away by distractions that you don’t want to give your days to. It’s also a default which you can stray from completely when being spontaneous, but, just as many people prefer to have a geographical home base available even if they’re usually not found there, your perfect day is a home base for a way of being, that you’ll know is bespoke-crafted for you, by you, and to which you can always return when you’re not sure what else to do. It eliminates decisions, and “fewer decisions” is one of the best gifts you can ever give yourself. Decisions drain willpower. Willpower is a finite, and rather limited, renewable resource. When we’re completely drained of willpower, we do crazy shit. Wondering “what should I do now?” every hour or two will severely complicate your life and hold you back.

As Annie Dillard put it in The Writing Life:

How we spend our days is, of course, how we spend our lives. What we do with this hour, and that one, is what we are doing. A schedule defends from chaos and whim. It is a net for catching days.

Crucial to this whole enterprise is the idea that how you spend any one day can and does represent how you go through your entire life. I find myself believing this more and more strongly. Of course the literal activities change across the days, years, and decades. But if I don’t spend my day today being thankful to be alive, how can I expect to ever do so? If I don’t make time and space in my day today for myself and for my friends, I won’t do so on any other day. If I don’t take a risk today, I won’t take a risk tomorrow. I’ve procrastinated enough in my life to know that if I put off living for long enough, pretty soon I’ll be dead. So, to live the life I want, I have to get today right.

This is the making of a routine.


First, it’s helpful to know what you’d actually like your day to look like, not right now but in your wildest dreams.

In 10 years from now I mention an exercise I did last year for envisioning what a typical day would look like, 10 years from the time of writing, in my perfect life. This exercise was passed from legendary graphic designer Milton Glaser to designer & podcaster Debbie Millman, then to me, and now I’m passing it on to you.

The exercise took me no more than an hour or two, and not only was it fun, it brought me massive and instantaneous clarity. It’s effective because it asks what your day would actually look like, from the time you wake up to the time you go to bed. Often future-envisioning exercises only ask what you’d want to have accomplished, or what you want to have. I think that if you wake up 10 years from today, and you have everything on your list, like a fancy house and the partner of your dreams, and an award for something, but you still don’t know what you would want to do with your day, so you let it all go to reactive things and responding to what people want from you.. it’s going to be hard to feel like life is meaningful, or that you’re exactly where you most want to be.

I didn’t realize it at the time, but my answer to this exercise, and the fact of having done it, became part of the foundation for building my daily routine as it is now.


I was stumbling slowly towards something maybe resembling a working process for iterating on my current routine and making it better, when the current pandemic hit, and changed up daily routines for just about everyone. I was totally not expecting this, but quarantine life seriously powered up the development of my routine. It removed most potential variables from most of my days, which leaves only routine. No longer can I say, as I would say on most days, “But today is an exception because [reason].” And if I’m not able to say that, then every day is either a perfect day, or it’s a day that tells me something helpful about myself, tells me what I might need to adjust. And when I adjust my routine then the change can go into effect today, instantly, because today is not going to be an exception. Since I am one of the lucky ones whose lives are rendered less chaotic by the current situation, quarantine life has been, for me, basically a highly controlled lab that accelerates experiments in routine–and, therefore, accelerates learning.

At one point a friend of mine mentioned that every day was starting to feel like Groundhog Day (the movie where Bill Murray literally lives the same day over and over), as a way of saying it was starting to get old. But I didn’t see “Groundhog Day” as a negative thing. I have often fantasized that if only time would stop for everyone except me for a while, I could recover and “catch up” with the rest of the world (see my other post about how I experience time) and with myself: read all the things, watch all the TV, think and write as I’ve been meaning to do for years, actually make decisions about what I want to do. In some ways, our current situation has given me at least some of the same benefits as time literally freezing.

More importantly, the Groundhog Day effect has forced me to think about what actually matters to me in a day. Because nothing eventful is there to distract from that. As Austin Kleon writes in Keep Going (Phil is the Bill Murray character):

In a moment of despair, Phil turns to a couple drunks at a bowling alley bar and asks them: “What would you do if you were stuck in one place, and every day was exactly the same, and nothing that you did mattered?”

I think how you answer this question is your art.

Even when the world isn’t in quarantine anymore, I might still stick closely to the routine I’ve gotten into now, without feeling the vague expectation that my life “should” be more varied. It’s like the quarantine gave me permission to test out the Groundhog Day life. And in fact it’s been devastatingly effective for me.

So maybe Groundhog Day is underrated. You can think of it as drudgery–or you can think of it as the holy grail.


Right after I quit my job, my routine was basically to sleep a lot, wake up at some point, have coffee, think about what I wanted to do, and go from there. Pretty lightly defined. In the 7 months since then, it’s grown incrementally to what it is now, in which roughly the first 5 hours of the waking day and the last 5 hours of the day are all in the routine, leaving about 5 hours in the middle to be decided more spontaneously.

In this current routine, each day includes: a full night of sleep without an alarm; personal hygiene and eating; timing of device usage and news-checking; timing of drinking coffee/tea; planning my day, prioritizing work, tracking what I spend time on, etc; journaling; language practice; stretching/mobility work; time for listening to music and podcasts.

What’s not determined by the routine and happens whenever I feel like it or whenever it happens, are things like: writing for this blog, and other projects; reading; watching movies; doing errands and chores; video chatting or seeing friends; going out for a walk or some event; daydreaming; and so on. It’s not that the stuff in the routine is more important than the stuff that’s not in the routine, or vice versa; just that some stuff I prefer to do as needed/wanted, rather than automatically on a daily basis. I used to try to read every day and journal only every now and then; now it’s reversed. Just my current preference.

This routine is set up so that both maintenance and progress are built in. Progress means that even if I ONLY do my morning routine and evening routine each day, and waste the entire rest of the day (e.g. on Reddit or watching bad movies), every year I will still advance quite a bit in skills I want to get better at and in the work I want to do. Maintenance means that I will be able to do that while getting plenty of sleep and staying physically and mentally healthy. When I had a full-time job, my routine only supported maintenance, and it wasn’t quite enough maintenance, at that. But it was better than not trying.

If you just look at my description of my routine without understanding me or the context behind it, you might think it sounds super rigid and authoritarian. But as with pretty much all things I do and believe in, organic growth and evolution are the right metaphors for how I think about the process, not the Industrial Revolution, efficiency, or modern management theory. I didn’t come up with it all at once and start imposing it on myself. Every practice that got added, got added because I tried it one day (or happened to do it accidentally one day) and decided that it makes my day better, and that I’m happier if I keep doing it regularly. One morning I woke up and thought, “What if I don’t look at my phone at all until after I have coffee?” So I did that, and it felt great. It became part of my routine, and I haven’t checked my phone before coffee for a couple of months. Whenever I feel tempted to, I just remember how awesome that first morning was. I try a lot of things, I double down on the ones that make me feel more alive.

So it’s not like I flog myself through the day, adhering to a schedule where I do specific things at strict times. I have tried that before and it never worked. (See above in section I: relying on willpower is bad.) Instead, I’m gradually building a routine that aligns with what I love to do. My measure of a great routine is that every time I switch to the next thing, I switch to it thinking, “Oh, yay! My favorite!” Lunch and an episode of On Being? Yay! Shower, then dim the lights and do some stretching? Yay! Even when I’m not feeling “Yay!”, what I’m saying to myself is not: “You HAVE to do it Rory, don’t fuck it up,” as if it’s some moral choice, but rather: “You’ll feel better when you’ve done it. Remember?”

I also break routine for good reasons, and I enjoy it when it happens. (I’ve been completely on a different routine for at least a week now, as I’ve been writing all these blog posts, which tends to result in me staying up late at night.) I also break routine for bad reasons, and sometimes regret that. But in the regret, I’m saying to myself: “Well, that explains why you don’t feel so well now. But let’s move on.” I only adhere to my own routine maybe 70% on average. It’s a tool, not a law.

It’s crazy how close my current day is to my “10 years from now” vision already. It probably jumped at least 50% of the way there, in less than a year, just from me getting intentional about it. Gentleness is the way for me to work with myself. Not authority, not judgment. Find the perfect day. Live it 20,000 more times.