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When Matters as Much as What

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Sometimes you really can trade lead for gold. You may have noticed, for example, how much of a time-saver it is to stay a little late to finish a task today that you could finish tomorrow instead. Somehow that last little bit, which would only take a half-hour now, will eat up most of tomorrow morning if you leave it till then. It’s the same work, but somehow its size and complexion change drastically depending on when it gets done.

There should be some metaphysical law that stops you from getting such a good deal, but there isn’t. So you should go for it, and also become a hunter for such deals.

A lot of variables come together to make this sort of transmutation happen. If you’ve been working on something for an hour or two, your system is warmed up in all the right places. You have the relevant information loaded up in your mental RAM, the body is tuned into the relevant actions (flipping between spreadsheets, folding clothes, whatever) and the mind has dropped most irrelevant thoughts. What would take thirty more minutes in this state might take two hours from a cold start tomorrow.

In this scenario, and many others, delay is extremely costly. You’re not simply pushing the same amount of effort to the next day; it will grow four-fold in the meantime.

When I left that thing till Monday

There are times when delay is your friend, though, for exactly the same reason. Momentum, excitement, and other conditions make it much easier to do certain things at certain times — but sometimes you want a thing to be harder to do.

One of Mr Money Mustache’s tips for saving money, for example, is to consciously delay any purchase you are suddenly considering. This is because the moment in which it occurs to you to buy something, you are probably intoxicated with excitement. You’ve gotten it into your head that one of those sleep-tracking rings would change your life, or that having a bottle of XO-grade cognac on hand would make you a hero to your guests. The mind easily justifies such a purchase when it’s been “warmed up in all the right places” by whatever anecdote or advertisement brought the idea to mind in the first place.

At moments like these, bias towards “yes” is probably maximal – it can only dissipate. Instead of telling yourself “No, I can’t have that,” making the desire more persistent, you simply delay the decision. Chances are, the next time you think of that potential purchase, the initial heat-bomb of excitement and covetousness has faded. Even though you still want the thing, you don’t want it enough to spend hundreds of dollars on it. This time, reason prevails, because it doesn’t have to overcome nearly as much exuberance.

This or a year’s worth of cheese

You may have heard similar advice about delaying dessert or second helpings. The time when you most want more food is when you’re still eating something delicious, or right after. At that time, the system is warmed up in all the right ways again, this time for eating more food, which may not be what your wiser self wants to do.

If you wait fifteen minutes before making the call about dessert, the mind’s fever cools, the body begins to report its distinct opposition to further eating, and the prospect of filling a bowl with ice cream might go from hyper-attractive to something more blah.

Making use of this principle isn’t just a matter of “delayed gratification.” Delayed gratification, made famous by the Stanford marshmallow experiment, is about the benefits of impulse control – you can often get better rewards in life by not taking the reward that’s right in front of you.

Sucker’s bet, scientists say

You might use some impulse control to push to the end your Friday-afternoon task, or to delay your prospective cognac purchase, but the more important idea, the real alchemical miracle, is about understanding and exploiting the huge swings in ease and salience that different activities have at different times. Just by doing something at a different time, under different conditions, you can make good things feel much easier and more natural to do, or make not-so-good things harder.

There is some cultural awareness of this principle (“Don’t go grocery shopping when you’re hungry”), but we talk much more about what to do than when. Often when I make some sort of personal breakthrough, it’s not because I’m doing a new thing, but because I’m changing when and under what conditions I’m doing an old thing.

I basically know already what’s worth doing – exercise, getting work done, sleeping enough, yada yada. But finding the best conditions for a given worthwhile thing – the best when – is usually what makes it finally work smoothly.

There is a time and place for all things

For example, I began exercising consistently only when I started doing it mid-day, rather than before or after work. At mid-day, I always have energy, the gym isn’t busy, traffic is light, evening plans never compete with my training, I don’t dread my workout, and it no longer feels cathartic to skip it. These are way better conditions. I actually want to lift heavy weights at noon; at 5pm I want to do the opposite of that. Doing it at 5pm is like adding a second kind of gravity to the barbell.

It’s like alchemy, this conditions-swapping game. You can often trade a bad situation, at a one-to-one ratio, for a good one. You really can pay twenty-five minutes of late afternoon work to spare yourself two hours of morning work. Lead-to-gold deals like that are out there.

If you tend to use your morning hours better than your evening hours, for example, by shifting your bedtime 30 minutes you’re essentially trading a low-quality half-hour of aimless screen time, which probably makes your sleep worse, for a high-quality half hour of morning reading on the porch. Good deal!

Inner landscape of lifting weights at 5pm

The best whens for a given person are an idiosyncratic matter. The deals you’re getting – and you’re getting a deal of some sort no matter what — depend on what your particular inner landscape is like in different situations, and inner landscapes vary tremendously between people, as you know if you’ve ever had a roommate.

Finding better whens takes some conscious experimentation. It’s unlikely that you’ve landed on them by dumb luck, because often we’re only doing a given thing at a given time because that’s when other people do it.

What to do is easier to figure out than when because we talk about what so much more. This makes me think that if something’s not working, it’s more likely the when, and not the what, that needs adjusting.


Photos by Rob Wicks, Anita Jankovic, FlyD, David Cain


Joy May 30, 2024 at 7:13 pm

I feel this so much. Hormonal cycles amplify the effects as well. Some days nothing is getting done no matter how much I try and force myself, and the following day it’s all downhill with a tailwind. The hardest part is convincing my boss that 9am really is the best time for me to hit the gym!

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David Cain May 31, 2024 at 8:57 am

Well I mean it’s not the best time to hit the gym if it gets you fired :)

I should say though that sometimes the best time doesn’t seem like the best time at first, especially when it comes to something the body has to adapt to, like working out. Experimentation isn’t easy but the payoffs can be huge.

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Tom May 31, 2024 at 2:41 am

I’ve been reading your posts for a while. I’m routinely impressed with your insight and ability to communicate it. This effort (not to detract from the others, hits me nearly spot on), exceptionally well written, you make a ton of sense. I have a real question though, you make reference to issues with reverting to old ways as a negative. this infers having problems in the past which learned behaviors have begun to correct, but what about the opposite? I’m 45 (I think), and I’m experiencing similar, but for the first time. I was great with focus and work ethic until now, and it’s becoming significantly more challenging. what would come to your mind thinking about it from that perspective? I suspect it’s time to find a new path, but unfortunately, to everyone in my sphere that would likely mean a significant cut in pay which would change everything we’re accustomed to. I’m getting more lost by the day. I just can’t think of what else might be out there.

Many Compliments on your Work.


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David Cain May 31, 2024 at 9:02 am

Good question. The best when for something can certainly change, and maybe the way you do something used to work for some reason and no longer does. There are so many variables involved and they’re all changing all the time. As I said it’s very idiosyncratic, as we’re all subject to a unique combination of variables. I would try making minor changes first, and see what direction the “swing” happens in, before committing to anything drastic. Because there are so many variables, you may not need to change anything too big to effect a different result.

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Agnieszka May 31, 2024 at 7:19 am

As always, an excellent and thoughtful post. My life changed drastically when I aligned myself with my new partner’s sleep schedule after years of trying to align myself with my ex-husband’s. Turns out that decades of insomnia were the result of a lifelong early bird attempting to emulate a night owl. Didn’t work. Now I’m in bed at toddler o’clock, and while it “costs” me evening outings and cultural events, I find the joy of a life with solid sleep and no alarm clocks is well worth it. The robins wake me at 4 am and in those quiet early hours all is as it should be.

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David Cain May 31, 2024 at 9:06 am

Sleep is a big one because it affects so many things downstream. I’m just now figuring out that my sleep has been bad since I moved into this place (7 years ago!) and I think it’s because the ventilation in my bedroom is bad. I’ve adjusted a few things, I’m sleeping longer, and now certain day-to-day tasks are easier, which opens up new possibilities for work, and so on. The benefits of good sleep is worth almost any adjustment.

“toddler o’clock” lol

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Naome May 31, 2024 at 8:36 am

I relate to this so much. I have been trying for years to write first thing in the morning but have finally realized that I am much happier to sit down in front of the screen if I have walked in the forest first. So obvious but took me so long to figure out. This article has inspired me to find other ways of thinking about “when” – definitely going to try that “wait 15 minutes for dessert” experiment.

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David Cain May 31, 2024 at 9:08 am

Good to hear you found the difference-maker. Going outside has a big effect on me too. Literally the moment I get out the door I feel different, and that means different things become possible.

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brettys May 31, 2024 at 10:35 am

The Waiting To Spend is an important issue for me. I had something “in my cart” that I knew would look so good on me! The warning came over that it was Almost Sold Out-Hurry! I decided to step back and read all the reviews. One review mentioned how the material was thin and cheap. It had looked like leather to me. I did not purchase the item, and I felt so good and the feeling continued on into the next day. I didn’t spend money, which is finite. I’ll try to carry this lesson into the future.
Btw, the marshmallow lesson was always lost on me because I hate marshmallows.

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David Cain May 31, 2024 at 6:23 pm

I always wondered about the kids that hate marshmallows skewing the data

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kid June 1, 2024 at 4:07 am

:) :) :)

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JB June 4, 2024 at 8:13 pm

This is so interesting. Often I’m grinding through something in the afternoon that I just know I should put down because tomorrow morning I’ll be fresh and it will take me 10 minutes.

Other times, I know that a bit of prep the night before has a huge impact on my motivation and general well being the next day.

I’ll test out my whens in the coming weeks.

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Eugene June 6, 2024 at 5:40 pm

There’s an old Buddhist saying about right speech: If it’s true and if it’s helpful, find the right time to say it. Taking up difficult conversations with a spouse or loved one, that is so right on.

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