You Cannot Try to Fall Asleep

Sleep is only where you notice it first. Much of what matters works the same way.

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It is ten past three. You have done the arithmetic twice already. Five hours if you drop off now, four and a bit if this carries on. So you lie very still, because turning over would be an admission, and you hold your eyes shut a little too tightly, and underneath all of it there is a low, steady wanting. You want to be asleep. And the wanting is the exact thing keeping you awake.

You are failing at doing nothing. It is a strange thing to be bad at.

You are a capable person. You can learn hard things and finish dull ones and drag yourself out for a run on a wet morning when every part of you would rather stay in. Effort is the most reliable tool you own. Most of what you are proud of came out of using it. And then there is this one ordinary thing, wanted more than almost anything at three in the morning, that effort cannot touch at all. The harder you try for it, the further away it goes.

We file that under sleep being difficult and move on. But sleep is not the only thing built this way. It is only the place you notice it first, because you meet it every single night.

The wanting is the exact thing keeping you awake.

Try to stop thinking about someone, and watch what happens to the thinking. Try to be happy, directly, by deciding to be, and feel it thin out into a performance of itself. You cannot make yourself find a joke funny. You cannot force another person to love you by loving them harder; if anything, that is the surest way to send them off. You cannot decide to be interesting at the party, and the second you try, you are the least interesting you will be all evening. You cannot will yourself to relax, which is the cruellest one, because the trying is the tension.

None of these are things you do. They are things that happen to you while you are busy doing something else. Sleep arrives while you are turning over tomorrow’s meeting, and then at some point you never quite catch, you are gone. Happiness turns up on an ordinary afternoon when you were absorbed in something and forgot to check whether you were happy. You become interesting the moment you get genuinely interested in someone else. Love shows up sideways, in the middle of doing something entirely unromantic together. Each one is a by-product. The main thing was always something else.

None of this is new. The Victorians had a name for the trap. ¹ They called it the paradox of hedonism, the plain observation that happiness tends to arrive only when your mind is fixed on something other than your own happiness. Aim straight at it and you miss. Aim at something worth doing and it arrives while your back is turned. Older and gentler still is the folk wisdom your grandmother had. A watched pot never boils. You will meet someone when you stop looking. Sleep comes when you stop chasing it. She was right, and she never needed a footnote.

Which makes it strange that almost everything around us now says the opposite. Try harder. Optimise. Measure it, track it, put a number on it, and by watching the number, improve it.

For plenty of things, that advice is sound. It genuinely works on the steps you walk, the pages you read, the money you put aside, because those are things you do, and a thing you do answers to attention and effort. Point a number at a behaviour and the behaviour usually moves.

The trouble starts when we point the same instrument at something that was never a behaviour. Take the sleep tracker, the small clean example of a very large mistake. It hands you a grade out of a hundred each morning for a thing you did not do, could not have done, and had no control over while it was happening. For someone already anxious about their sleep, that grade can do exactly what you would dread. There is a name now for people whose pursuit of a better sleep score has quietly made their sleep worse. ² They lie there trying to earn the number, and the trying keeps them up, and in the morning the number confirms the bad night, so tomorrow they try harder still. The scoreboard becomes the insomnia.

And it does not stop at sleep. We keep a scoreboard on our own happiness now, rating the day, wondering whether we are as content as we ought to be by this point, which is a reliable way to stop being content at all. We tally our friendships, our rest, our worth, treating the whole illegible middle of a life as figures to be raised. A thing that arrives sideways cannot survive being stared at head-on. Measured, it becomes work. Graded, it becomes a test you are failing. You get all the pressure of a target and none of the thing the target was for.

Measured, it becomes work. Graded, it becomes a test you are failing.

So what do you actually do, if trying is the problem and not-trying sounds like giving up?

You learn, slowly and against every instinct this age has trained into you, to tell two kinds of thing apart.

Some things in your life answer to effort. You can decide the hour you go to bed. You can decide the phone leaves the room. You can decide to show up, to sit down at the desk, to be kind without keeping score, to call your mother, to put yourself in the path of the people you might one day come to love. Those are conditions. Conditions are real work, and they are what you can actually reach.

And then there is everything the conditions are for. Sleep. Ease. Delight. Being loved. Feeling rested. Those you cannot reach for. You can only build the conditions, honestly and without cheating, and then do the single hardest thing a person can do, which is leave the outcome alone.

Leave the outcome alone.

That last part feels like surrender, and it is, and that is exactly why it is so hard. Every part of you wants to grip. Gripping feels like caring. It feels like doing your part. But on this entire class of things, the grip is the surest way to fail, and loosening it is not laziness. It is a skill, and it may be the deepest one a life asks of you. Some effort quietly builds you. This is the other kind, spent on the one thing effort can only spoil.

It is ten past three somewhere, and you are lying very still, doing arithmetic in the dark. You have already done your part. The room is dark, the day is behind you, there is nothing left to arrange. There is nothing left to do but the one thing you cannot do, which is try. So stop. There was never anything there to try for. You have set the conditions. Now let yourself be no use at all for a while.

This is not the usual thing here. I mostly write about AI, product and markets, and the structures underneath them. This is the same habit of looking, pointed at something a lot more ordinary, and I wrote it because I kept meeting it at three in the morning rather than at a desk.

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1. The phrase belongs to the nineteenth-century philosopher Henry Sidgwick, and John Stuart Mill put it plainly in his autobiography: those are happiest, he wrote, who have their minds fixed on some object other than their own happiness, and who find happiness by the way. It is a very old idea with a long line of owners, which is part of why it is worth trusting.

2. Researchers have called it orthosomnia, a fixation on achieving the sleep the tracker says you should be getting. It is a coined term rather than a formal diagnosis, first described in a 2017 case report of a handful of patients who trusted the device over their own clinician. The point is not that trackers are evil. For someone who sleeps well and glances at the score the way they glance at the weather, it may cost nothing. It is the people already lying awake who cannot afford to be graded on it. One boundary, stated plainly: this is an essay about the trying, not a treatment. If sleeplessness has become the ordinary shape of your nights, the thing that works is CBT-I, the only approach carrying a strong recommendation in the American Academy of Sleep Medicine's 2021 guideline, and it is emphatically active: it asks you to change what you do, including getting out of bed when sleep will not come. Leaving the outcome alone is not the same as leaving a real problem untreated.