Stop Wasting Time Planning Your “Perfect Day.”

Image created by the author in Procreate #byHumansForHumans

Usually it’s something like this: “Describe your perfect day. Don’t let reality get in your way, just imagine from the moment you wake up until you go to bed if you had everything you wanted.”

The first few times I saw the prompt, it felt too painful to write. I was in a pretty rough time in my life, and writing about things that I was sure I’d never have — travel, physical health, a stable relationship, money in the bank, time to spend with my kids and my art and my writing — just seemed cruel.

But one day, as I sat down to do my morning pages in a house that had the rent paid up in full, several clients in the docket for me to do the work I cared about, kids at school, and a happy good morning text from my wife when she got to work — it seemed safe enough to try.

I let my imagination wander. I wrote about having time to exercise, about having uninterrupted time to write my own work, about having lunch with clients and spending time with my kids and grandkid, about having an assistant to take care of the invoicing and the (at that point, imaginary) travel details. I wrote about having a comfortable evening with my partners, sharing the days’ joy over wine and a sunset.

Something like that, anyway. I don’t remember the details.

My life up to that point felt like a comic tragedy of poor decisions and unfortunate circumstances, so just feeling able to dream that big was a breakthrough of sorts.

Fast forward about a decade, and my life was almost completely different. A new career (but still self-employed) that included traveling all across North America and occasionally over the pond. New relationships, new grandkids, and better understanding of my health as I aged (though I still wasn’t aware that all of this was happening alongside undiagnosed ADHD).

I didn’t expect my perfect day, but I recognized it when it happened. Everything — everything — I’d described. Time to write. Time for art. Pastoral polyamorous bliss and the bliss of enjoying my role as pater familias minus the patriarchy (at least, as best I could).

I even had lunch with a new client, reconnected with friends, and wrote a draft of an article that had been marinating in my mind. To add cream to the coffee, a client paid their invoice that morning and for at least a while I wasn’t even stressing about money.

And when I finally crawled into bed that night, I realized something about Perfect Days.

They are exhausting.

Nobody tells you that about the “Perfect Day” exercise. It wants you to pretend that not only do you have limitless resources and few obligations, but it never talks about the energy that perfection demands.

Yet the expectation is that this Perfect Day essay will serve as some kind of epistolary vision board, with the things that you should work towards for the rest of your life. It’s some kind of twist off of the “if you shoot for the moon, at least you’ll land among the stars” affirmation, which is both trite and astronomically implausible. If you’re always working towards your perfect day, keeping it in mind, you’ll at the very least have some pretty good days, right?

Wrong.

A much less inaccurate (but admittedly trite) aphorism comes to mind: The Perfect is the Enemy of the Good. That is truth; if you hold up some standard of “perfection”, then no matter how good a day you have, it will fall short of the imagined ideal.

I felt cheated at the end of my Perfect Day, because it turns out that what I’d thought I wanted was what I wanted, but I hadn’t realized that it would come with such an energetic price. It was the classic be careful what you wish formoment because, as I lay in bed thinking about the day, weary to the core, all I could think was I hope tomorrow isn’t this tiring.

Of course it wasn’t. But that’s the other thing about Perfect Days: they are not sustainable. As much as productivity gurus and self-help bloggers (myself included) would like to pretend, routines are, at best, good intentions via wishful thinking; reality has all the subtlety of a sledgehammer through a spiderweb.

No daily routine survives contact with the first ping of your phone.
—Prussian Field Marshal Helmuth von Moltke the Elder (translated from the original Klingon)

Which begs the question: Why plan for a perfect day when it is at best rare and at worst demotivating?

There’s a much more effective exercise, I think, and it’s something I wish I’d done a lot sooner.

I’m not talking about existential crisis, death, or other specific tragedies. I’m talking about the equivalent of Alexander’s Terrible No Good Very Bad Day.

Imagine every particular personal thing in your life that could go wrong doesgo wrong.

• Your alarm doesn’t go off.

• Your cat threw up on the bed.

• Your kid “reminds” you that they need cupcakes for their class at 10am by telling you about it for the first time.

• You can’t find your keys.

• Your car’s “check engine” light goes on.

• There’s no clean underwear (or there is, but the dryer mysteriously shut off and so it’s all still damp).

You get the idea. The Worst Day Ever. When it really, truly feels like the universe is conspiring against you.

And then…write what would get you through that. Not what would preventthe thing from going wrong, but what would mitigate the impact of each of them?

Because no matter how much you try, s#$% happens.

But there may be ways to increase your resilience and make things easier to deal with.

• No alarm, but the cat wakes you up just a few minutes past when it would go off

• …by throwing up on the bed, but there’s a laundry chute in the closet and now you get to look forward to sleeping in fresh sheets tonight

• You have the bakery department of the grocery store on the way to your kids school on speed dial with your credit card number on file with them. Bonus: now you have an excuse to pick up donuts for work. Siri, run the “morning sugar rush” shortcut

• You don’t need to find your keys, because you had a spare set made that is in a magnetic box next to the door. You also know that when you are about half-mile from the house the Apple Tag keyring will sohelpfully let you know you forgot them — but at least you’ll be able to find them later.

• The local mechanic (who you’ve also made friends with) is also on speed dial, and you can make an appointment for that blasted light. Meanwhile you text your group of three friends who also have cars and flexible schedules to let them know you may need rescuing from the side of the road — but regardless, your Lyft account has $30 in it already and AAA is paid up.

…I currently define security as the absence of unmitigatable surprise.
— Daniel E. Geer, Jr., Harvard Law School National Security Journal

Have you ever seen a heist movie like The Thieves or Ocean’s 8? There’s usually a part in the movie where everything seems to be going wrong for the protagonists, and there’s absolutely no way out of the disastrous consequences.

And then there’s a flashback.

There’s a bit of “little did you know…” the writers will introduce, showing how the intrepid thieves/heroes/whatever anticipated this outcome, maybe even counted on it, and took measures to make sure it didn’t interfere with their plan. It might have been a friendship with an influential person (like, say, the bakery manager or a mechanic). It might be a well-placed piece of equipment exactly where they needed it (like an emergency car key by the door). It might just be a graceful way of cleaning up a mess (like a laundry chute and spare sheets).

The one thing that the Worst Day has in common with the Perfect Day is that it rarely happens. But sh—er, stuff definitely happens all the time. When it does, and you realize you have exactly what you need to deal with it — you feel like frikkin’ Batman, MacGuyver, and Atomic Blonde all rolled into one.

If you want a miniature version of this, you might want to try putting together an “everyday carry” first. I made one specifically for my own ADHD brain trying to exist in a world as an artist, grandpa, and nonprofit professional — and there is such a delightful rush of dopamine when I get to use it. For example: thanks to time blindness I rushed out the door, and only later realize I forgot to take my meds…but there’s a spare pill case with a dose in my EDC, and as long as I carry it, I don’t have to worry.

Let me know what you do to keep your worst day from being all that bad. Or maybe just think back to times that stuff happened that could have been mitigated — and start there.

But forget planning for your perfect day. Let it surprise you. If you don’t see it coming, you’ll have a lot more of them than you ever expected.