#1: Finishing things in an uncertain time

Reconciling "perfect", "good", and "done" during a pandemic

Maplewood Memorial Park, May 19, 2020.

As I like to pretend my dog says every morning: hello hoomans!

Today is my family’s 67th day of COVID-19 lockdown, my 76th day working from home. Things are… fine? We’re among the lucky ones: my job has been unaffected by things, we have plenty of space and a nice park nearby, our kid is young enough for her life to not have been that disrupted by not going to school for months. Ask us how we’re doing a month from now, when it’s been more than a hundred days without friends, brunches, or a feeling of safety, and we might answer differently.

For some reason, newsletters are the format I turn to when the world has turned upside down. The last time I was even a little consistent about trying to write one was the ~year after my daughter was born, with a few updates spanning the time I was changing jobs. (Longtime e-friends may also remember a newsletter I wrote back in high school, which was also a crazy time just by virtue of being high school. No, you cannot read it, and we will not speak of it again.)

You might be getting this because you subscribed to the last iteration—or “season 1”—of this newsletter on TinyLetter, or because you signed up since I posted a teaser on Twitter. Or you might be reading this on the web. Either way, welcome to Season 2!

The subject of this first issue of Season 2 is finishing things (or not), and my worst habit here is boldly starting something and then dropping it for something newer and shinier.

So I’m pleased to report I’ve already started writing the next few upcoming posts. Issue #2 will be an all-recommendations edition about “plague merch,” issue #3 will be about iPads and keyboards, and topics past that will include OKRs, variable fonts, and working from home. If you have any topic requests for me to get into, hit me up on Twitter (DM @ddemaree) or email david@demaree.me.

Finished > in progress

I have always had a problem finishing things. Speaking of high school: in my junior-year art classes, I used to ruin perfectly good paintings by continually reworking them. The process felt more interesting in the moment than landing on a finished product.

Like a lot of people, I started the lockdown times thinking I’d finally have time to take on and finish some side projects. First I thought I’d make that to-do list app I’ve always dreamed of making, then I thought I’d make my own headless CMS app. Most recently I’ve re-stacked and re-designed my personal site/blog for the millionth time.

As with my paintings in high school, I’m chasing the feeling of working on something but (depending on the project) either don’t have a clear plan for what I’m doing or why I’m doing it, or I have a plan but I ignore it because, god help me, part of me enjoys redrawing a face, refactoring a database layer, or switching React frameworks every 2 weeks. Perfecting (or “perfecting”) elements of craft/technique is a great way to procrastinate while still feeling productive.

And a real toxic combo is to have things I want to do (that aren’t getting done) that are blocked or dependent on me doing other things (that aren’t getting done). If I want to start a blog, I could just start a blog in a number of ways, but if starting a blog is dependent on me designing my perfect WordPress (or Ghost, or Gatsby, or…) site design, I will end up with several unfinished design projects, and maybe some rambly article drafts, but no blog.

This is a bad habit. And though you could argue a pandemic is a bad time to work on breaking bad habits, on the other hand, the feeling of not finishing things is a drag on my soul. And now is a time to avoid unnecessary drag on my soul.

Earlier I thought of this modified Eisenhower Box:

It’s… well, it’s nonsense, but hopefully, you also get the point?

As Steve Jobs is said to have said, real artists ship. Some of the things I’m trying in order to ship more:

  • At work, in the spirit of Matt LeMay’s One Page/One Hour pledge, instead of letting PRDs, decks, roadmaps, or whatever else linger in an undone state, I’m trying to instead focus on delivering something clear (if imperfect) in an hour of working time, then getting feedback.

  • At home, I’m trying to maintain “inbox zero” on chores—doing laundry as soon as it needs doing, not procrastinating on taking out the recycling, or doing dishes.

  • And on my personal projects, I’m trying to find ways to just get things done and embrace imperfection. Like this newsletter—Substack isn’t perfect, but it’s fine, and I can publish things. Eventually, I want what I write to be on my own web site, but that can come later. (And while writing on someone else’s platform is a wee bit problematic, it does let me avoid lots of bike-shedding opportunities.)

I think “don’t let the perfect be the enemy of the good” is good advice at all times. But especially now, in these times, when “perfect” and even “good” seem like high bars to clear, it’s healthy to not let what you’re not doing distract from what you’ve done. Especially if it’s hard to predict what you can get done or how it will be received.

So, 1) optimize for getting something done, even if it’s imperfect, 2) be kind to yourself about the level of work you expect to produce, and 3) try to push past doubts about whether you’re spending time wisely, and embrace the opportunity to have more opportunities to do things. It’s better to ship an imperfect thing, possibly followed by a better thing than to do nothing at all.


Recommendations

I was going to close with some links to what I’m calling “plague merch”—products for or inspired by the pandemic, mostly from DTC startups—but it ended up long enough to be its own newsletter, so watch for that soon.

Even before the current situation turned my daily dog walks into 45-minute, 1.5-mile hikes, dog-walking time has been podcast time. My daily news routine is NPR’s Up First and Crooked Media’s What A Day—sometimes in that order, sometimes flipped, depending on mood. On Fridays, my first listen is Eater’s Digest, “a show about all things food and dining,” which as you might imagine has undergone a real 180º change in tone lately.

The most delightful thing I’ve heard recently is this episode of NPR’s Rough Translation about very different people coming together in a COVID quarantine hotel in Jerusalem.

If you are, like me, a huge nerd with strong keyboard opinions, you may harbor a secret ThinkPad fetish even if you can’t bring yourself to go all-in on Windows. And if this is you, I have good news: Lenovo has finally released a standalone wireless keyboard based on the iconic ThinkPad design, complete with the little red nipple pointer thing. I bought one of these (on day one) to use with the Chrome OS computer I have set up just for video conferencing, and it is 100% as ThinkPaddy as I dreamed it would be. One caveat for Mac users: this Lenovo keyboard has a true Windows layout—its Alt and Win/Cmd keys are swapped, with no built-in way to switch them. But you can use an app like Karabiner-Elements to remap the keys in software. 🤓

One quarantine project I’ve stuck with is trying to up my home cocktail-making game. After a semi-ridiculous struggle to get all the ingredients, I made a decent version of a Brooklyn, following Jim Meehan’s recipe from Meehan’s Bartender Manual (a book full of both pitch-perfect classic cocktail recipes and more than you could ever wish to know about what goes into operating the world’s greatest bars). If you’re going to try to fill a craft-cocktail-bar shaped hole in your life while at home, I recommend Cocktail Kingdom’s Essential Cocktail Set, which includes a fancy mixing glass and high-end steel instruments (jigger, shaker, spoon, and strainer) for about $100.

Stay safe, stay home, stay weird.

—DD