#1 - Not Everything you do is going to be great, and that’s okay.

”Aisha Tyler: Bombing makes you invulnerable. To constantly skin your knees. The older you get, the older you know how little you learn. A posture of perfection needs to be weaned off.” — July 19th, 2018

👍👍 Hey friends, you are reading the inaugural issue of Not Everything, a newsletter where I reflect on one personal learning from a trove of daily notes kept since 2018. This week, you will follow me in real time as I procrastinate on writing this issue.

I had to set a timer, a Pomodoro timer, to get started on this at all. I wrestled excuses: I have a cold. I’m sleepy. I am way behind on the dining room cupboard that I need to assemble for my wife, Lisa. All the things. I’ve barely begun and I already feel exhausted from indecision.

All this foot-dragging because I am petrified of starting this newsletter.

It’s already five days too late. How am I supposed to sustain a weekly newsletter, I rage to myself internally, if it takes me five days of putting things off before I relent to the tried-and-true (but always annoying) tomato timer?

Procrastination is my middling attempt at contending with perfection.

"If you’re procrastinating on something because you’re worried you won’t do a good enough job, you can relax—because judged by the flawless standards of your imagination, you definitely won’t do a good enough job. So you might as well make a start." (Oliver Burkeman, Four Thousand Weeks)

It’s not a huge leap of logic to see how the fear of starting something is related to our latent perfectionists being comfortable with inaction – because who wants to risk being mediocre? In Procrastination: Why You Do It, What To Do About It, Jane B. Burka and Lenora Yuen patiently explain that the roots of procrastination is entirely an emotional problem: we are afraid of what the piece of work will become. (Imperfect. Like us.)

I get it. We want to be fawned upon as humans, so everything we do needs to be great. We relish the affirmation of our own genius. As children, we got our heads pat and told our futures are bright whenever our work was above a certain threshold. Our formal education systems have lined us up in neat little columns, and firmly explained that if we weren’t brilliant, our worth as a human being is deferential to those who are. Thank goodness none of this translated to adulthood.

Finite time brings existential angsts.

If only it were as simple as just anxiety around the work: there’s something more insidious and nuanced happening here. Like in Four Thousand Weeks, Burka and Yuen happily note that some of us procrastinate because we feel that our time on this planet is finite. Or rather, the idea that our time on earth is finite scares the living crap out of us. The pressure mounts for us to want to do everything. Our minds, delirious, begin measuring and stack ranking the things we’re currently doing, against comparisons with our hitherto achievements; which are then violently collided and qualified ungenerously against our peers.

And so we quickly collapse into a paralyzed mess of neuroses where the most comfortable thing to do is nothing.

This is perfectionism, except a thousand times worse. In this narrative, ‘perfectionism’ decides to team up with ‘existential angst’ and conspires to trick our self-esteem into crawling into a grungy gunny sack, where they are then thrown headfirst into the muddy street gutters, and then kicked senseless.

I know I’m not alone. I watch my wife pace from her desk to lying on the couch, to watching the birds outside my home office window, to raiding the kitchen, and back to the couch.

“How is work?” I ask her as she passes my desk for the fourth time this hour.

“Two sentences.” she said, then curtly ignored me for the chirping cardinal outside my window. She’s a professional writer. She knows what she’s doing.

Embracing the suck.

The way I see it, dealing with perfectionism – and thereby procrastination – is all about surrendering to the realization that our work will always actually kind of suck. Not in a defeatist, let's just give up now, sort of way; but one that is actually liberating. Flipping the Oliver Burkeman quote around: knowing that our work will suck gives us permission to move forward in spite of the impossibly high standards that we have set for ourselves.

And going back to Aisha Tyler, nothing gets us to feel that visceral, gut-wrenching feeling of sucking, as bombing.

So here I go: maybe I'll let this first issue 'bomb'. This first issue will never be perfect. In fact, I think it's still a bit lacking. It's sparsely researched. Mostly anecdotal. Borne from lots of books and articles I might have remembered. There could have also been more examples of when I've bombed in the past as well, but I am thinking now I might save that for another issue. (This newsletter is long enough as it is and I need to wrap up soon, chop chop, so here we are.)

Surrendering to imperfection bombing.

Yes, I know it's simply a perspective shift, but it seems to help recovering perfectionists like me. See, once we know we are bombing/have bombed/will bomb again, we surrender to the comfort that we were never in full control of our work and lives no matter what we do. Real life is a chaotic, beautiful, tumultuous mess of variables, chance, and happenstance. We make our best, most-informed choices with the limited information that we have at the point in time. That makes every new thing that we do an evolution of ourselves. Since we're always adapting, learning, and growing – seeking perfection just slows us down.

So instead, we seek the numbness, the invulnerability, to dive off the deep end; because meaningful change come from big, bold, crazy moves that feel gross and uncomfortable; crazy moves that put you out there in front of a public who will judge you no matter what you do.

So let's bomb hard.

Bomb so hard that starting over becomes easier, knowing it only gets better from there. Screw procrastinating. Just go. Dive in. The water’s cold and freezing but you will survive. Get to work. It will never be as good as you want it to be... and that’s okay. Just show up. Every single day. Do the work. And let it bomb, if it must.

The tomato timer beeps, and my 25 minutes is up.

Relatedly, but tangentially.

• I’ve found the Pomodoro Technique to be helpful for me to start something, because small chunks of time are easier to commit to and less overwhelming for my tiny brain. If you know of a better way to get a task started (other than a looming deadline – everyone knows that works but only in small doses – let me know!)
• In recent years I’ve been a fan of time-boxing time for work. Nir Eyal spells out the reasons why it works here and I can’t help but attest meekly that it works for me. I’m currently testing out reclaim.ai as a way to help automate my schedule, meetings and time-boxing for tasks. Will report back on how it goes!
• Toxoplasma gondii is a parasitic microorganism that changes the behavior of rodents to be take riskier behavior, be less anxious, and less averse of predators. In humans, it is generally asymptomatic but there are hypotheses that it is linked to ‘entrepreneurship behaviors’ across some individuals. The inhibition of ‘fear of failure’ via an infection vector. I shudder at the thought, but take that as you will.

Thanks for joining me on the first issue of this newsletter! If you found this helpful, please feel free to share or forward to your friends. Also, if these lessons and reflections resonated with you in any way, or if you have suggestions and learnings that you'd like to share; I'd love to hear all about it!

Till next week,

-- David