The Joy of Missing Out

I have a crippling fear that the sun might never come back up again. So there I sit day in and day out, tensely watching it get closer and closer to the horizon, trying to find a way to make sure it doesn’t leave. I explore tools, read books, try harder and smarter - but somehow, it just keeps going down.

That’s a pretty pointless endeavour, isn’t it? If I just looked my fear in the eye for once, I would quickly realise the simple truth: It’s not my lack of smarts and/or effort that’s keeping me from solving this problem - because I was never dealing with a problem in the first place. Take it from Seth Godin:

“Problems have solutions. That’s what makes them problems. A problem without a solution isn’t a problem, it’s simply a situation.”

I won’t change the nature of the universe, at least not anytime soon. So why don’t I leave this tense, stressful anxiety behind and enjoy the sunset?

Well, by holding on to my fruitless attempts, I can keep the hopes alive that I am theoretically capable of solving this problem - I just haven’t found the right approach yet. A part of me prefers the fear to the alternative: Sitting down to enjoy the sunset would mean admitting to myself that I'm very much human, constrained by human constraints, and I’m stuck with this human condition.

This all sounds very silly, I know. But by now, I’m sure most of you have made the connection. This ridiculous example of my rather rare fear sets up a point about a more common one.

The Fear of Missing Out. The idea that there is a rewarding experience somewhere else - and you’re not experiencing it. The anticipation of regret, of failing to spend your time right. A mistake in the making. What a sneaky way to run away.

🌏 How to Get the Worst of Both Worlds

You see, recently I’ve found myself back in an odd predicament. By virtue of ridiculous serendipity, I landed a role managing a co-living company last month. The setup sounds ideal: I don’t have set hours, I can work anytime, anywhere. The only condition is: The work gets done.

This is lovely until you realise that “the work” is endless. After finishing the day-to-day tasks, there’s an ever-expanding list of ways to grow the community & enrich the member experience. New events for members to connect & learn, adding on new houses to expand what we can offer, a new member portal to answer all their questions, a better way to process payments & other day-to-day hassles - the list goes on. Each and every item seems like a worthwhile way to spend my time.

Even worse: that's only work. Human life has so much more to offer. There is basketball to be played, surfing to be learned, plus mobility & strength to keep the body healthy through it all. There are books to be read, conversations to be had, essays to be written - and I’ve been meaning to get into creating videos around these topics for ages! Add to that languages to be learned, pianos left unplayed, meditations to be meditated - and I’ve been meaning to learn the guitar for ages! All of these endeavours seem to me to be perfectly wonderful ways to spend my time. Not good, not great - they’re all perfect.

Yet, in light of the sheer infinite variety of potential, the day has the audacity to stubbornly remain at a fixed 24 hours. No matter how hard I try, it won’t give me the tiniest bit of leeway. I don’t even get a measly five minutes - It’s 24, take it or leave it.

So there I find myself, constantly anxious if I'm spending my time right. Whatever I do, I am tensely aware that there are about a million other things I could be doing right now. Each of them would be a wonderful way to spend my time.

Just this morning, I was sitting on the beach with my friend having a coffee - but my mind wasn't. Instead of enjoying this blissful start to the day, it was busy beating myself up for not starting to work earlier. It’s a pretty impressive accomplishment: I get the worst of both worlds. Neither really here in this wonderful moment with my friend, nor making any headway on my work projects. Neither here, nor there - just existing in this limbo. Surely, this ain’t it. So what do we do about it?

🏔️ Just wiggle it a bit and it should fit

Well, if you’ve ever dipped your toes into the realms of self-improvement and productivity, the answer you get is rather simple:

The reason you feel like this is because you’re a) not working hard enough and b) not working smart enough.

The promise: If you only used this new matrix to organise your to-do list and applied these 5 life hacks to make smarter choices about your time, all those problems would vanish. Case in Point: Pickle Jar Theory, a long-standing favourite among the productivity crowd. It’s often explained in this parable:

“A teacher arrives in class one day carrying several sizable rocks, some pebbles, a bag of sand, and a large glass jar. He issues a challenge to his students: Can they fit all the rocks, pebbles, and sand into the jar?The students, who are apparently rather slow-witted, try putting the pebbles or the sand in first, only to find that the rocks won’t fit.Eventually—and no doubt with a condescending smile—the teacher demonstrates the solution: He puts the rocks in first, then the pebbles, then the sand, so that the smaller items nestle comfortably in the spaces between the larger ones.”

The moral of the story: It is because you suck at prioritising that you feel overwhelmed by choice. Do the big things first and it’ll all fit in quite nicely.

What a lovely idea. It means there’s hope for me. If I only become more productive, I’ll be able to do all those wonderful things listed above. I won’t have to choose between them and I’ll never have to miss out on anything. Right? Right???

Yeah, well, here’s the slight issue: The teacher’s a cheeky liar. He brought just enough rocks to fill up the jar - so naturally, it all fits wonderfully. The human experience, however, is a little different. Compare your list of things absolutely worth doing this week with the things humanly possible in a week, and you find a little mismatch:

🙏 There's Hope?

In this sneaky way, the fear is actually a way of holding on to hope. To be afraid of Missing Out assumes that you could, theoretically, not miss out. You’re afraid that your suboptimal choice could lead to you not experiencing everything worth experiencing - and that if you could only improve your decision-making, you wouldn’t face this problem anymore.

The Fear of Missing Out implicitly lives on the hope that there is a point in the future where you’ve got it figured out. A point, often seeming just around the corner, where you don’t have to choose between two wonderful choices anymore. Like my odd crusade against sunsets and the attempt to put Mt. Everest in its little jail-jar, you can play this game forever. Or you can look the truth in the eye:

You are missing out - every day. More importantly: You’ve been missing out - every day - from the moment you were born. You will continue to miss out for as long as you live. Every "Yes" is an irreversible "No" to a million other things. Many of those might have been absolutely worth doing - but you won't do them.

Gooooood morning. Sorry to drop in on your Monday like that. I swear, this is going somewhere. On the surface, this sounds pretty damn depressing. But take closer look and you see that it’s actually a huge liberation in disguise:

The thing you’ve been tensing up against, you’ve been working so hard to avoid, you’ve been so deathly scared of - it’s been happening all along. But look here: You’re still around. Still fine. Alive & kicking. We all are.

Here we all are, finite human beings, bathing in an ocean of infinite possibility. Blessed with a chance to experience this vivid spectacle we call life, but cursed with the awareness that there’s only so much time to check it out (if you live to 80, you get about 4000 weeks). What a bummer. If only we could live forever - that would solve the problem, right?

✔ Just Do It (later)

Well, let’s look into that. Just for argument's sake, imagine you’ll never die. You wake up on a Monday Morning, trying to decide what to do. Learn Spanish? Play the guitar? Go to Greece? Or just spend the whole day in bed, because you could just do it all tomorrow?

You see, when the limitation of finitude is lifted, our choices become meaningless. Don’t feel like leaving the bed today? Do it tomorrow, or in 12 years, or in 28917 eons - who cares? It doesn’t matter, because there is absolutely nothing at stake. Steven Bartlett put this so wonderfully:

Make a decision and rest peacefully in the wisdom that it was the need to make a decision that made the thing you've chosen so special.

If "Missing Out" has been inevitable all along, why not try embracing it? Introducing: The Joy of Missing Out. How? There’s a simple framing shift I’ve been working with:

As one does when trying to solve the problem of finitude by means of efficiency, I have a wonderfully sorted arrangement of lists overflowing with things worth doing. To-Do, To-Read, To-Write, you name it. These sorts of lists, however, always come with a feeling that you have to clear them. Tick it all off, one by one. If you can’t, you’re missing out. You weren’t productive enough. But there’s another sort of list - one you’re all very familiar with.

🍽️ What do I get to choose today?

Have you ever left a restaurant in deep depression because you didn’t manage to eat every item on the menu? Googling new techniques to eat more, beating yourself up that you didn’t put in enough effort tonight?

I’ll take a guess and say no. Simply because you never expected to “finish” this list of items all absolutely worth eating, you can go home content with the meal you had. So why not apply the same logic to your to-do list? Once the pressure is off to get through it, the list magically becomes less daunting. Instead, you're free to choose from the Menu. Resting peacefully in the wisdom that it was the need to make a decision that made the thing you've chosen so special.

While we’re on this matter, there’s one last thing I want to share. I see that whenever we’re confronted with our mortality, it feels somehow like someone’s taking something from us. Here we were, peacefully minding our business in expectation of immortality, and there comes the party pooper the spoil all the fun. Compared to the perspective of endless life, 4000 weeks seems, in the words of Oliver Burkeman, “terrifyingly, insultingly short”.

But here’s something I like to remind myself of every birthday: I’m entitled to nothing. So this year, I got to note to myself: “None were promised, 23 were given.” There’s nowhere I can point to that would justify this feeling that I can expect even 100 weeks. So yeah, compared to infinity, 4000 is a pretty small number. But compared to nothing, even the 1300 weeks I’ve had so far are an incredible gift. It's funny how framing changes everything.

So, go and peruse the menu. I'm sure there's something exciting you get to do today.