In Praise of Worst Practices

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As far as I can tell, today’s email marks the 98th daily essay I’ve sent you guys. And one of the things I’ve noticed in that long, long march is no matter what hot topic I take on, no matter how inflammatory (if ironic) my rhetoric, it’s been quite difficult to generate conversation around my writing. Some of you email me back, a few of you comment on mattgrossistrying.com, and once in a while I’ll see responses to my posts on Facebook or LinkedIn. But that’s okay! I’m not mad! It’s not your fault!

As we say in my family: It’s not a criticism, it’s an observation¹.

On the one hand, I understand. These essays are so perfectly formed, so exquisitely jewel-like in their presentation, so thorough, so inarguably correct that your natural response is merely to gape in wordless wonder as you attempt simply to absorb the magnitude of my insights. Who could possibly think of a social media share at a time like that?

But also: I am definitely not doing the work to get engagement, as we are required to call it these days. I don’t end the essays with a call to action (except to get you to fill out my future-of-Trying! survey). I don’t post the essays on social media with open-ended questions engineered to get you to like/share/comment/subscribe. And I’ve refused as well to narrow the scope of the newsletter, to focus its goals and make them relatable and actionable, to reduce the frequency (and somehow raise the quality), to make specific promises and then fulfill them. In short, I’ve been rejecting the commonly accepted best practices for publishing on the Internet, and trying to make a go of it anyway.

This has not been easy!

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I am naturally inclined toward optimization and efficiency—toward doing things the right way. To pick a hoary bourgeois cliché: the dishwasher. If you load it the correct way, you can fit more dishes in, and they will get cleaner. We can argue about what the correct way is, but as long as you believe there is a correct way—versus just throwing everything in there willy-nilly, as some people do—then we’re basically in agreement. The best practices are there to make our dishes cleaner.

So it goes for so many things in my life: There’s a right way to run and to climb rocks. There’s a better way to shave. There are techniques for shoveling snow, both literal snow and figurative snow. Proper procedures for folding laundry. In cooking as in math, there are algorithms that will lead you to the desired conclusion. Ignore these truths, and you cannot expect the same results.

This is not to say that because I know the best practices exist, I execute everything flawlessly. Far from it! I fail all the time. I get distracted, I get lazy, or I just don’t care. One look at my apartment and you’ll know I’m not a neat freak. I accept a certain amount of mess in my (and my family’s) life. I mean, at least until I trip on a pair of black Uggs some daughter left in the hallway and go on a rage-cleaning spree that leaves the floors temporarily spotless. Okay, yes, I may have some control issues, but that’s the point: If we all followed, or tried to follow, best practices—say, lining up our shoes neatly against the wall after taking them off—then no one would stumble over them in the middle of the night, and we’d all be better off.

At the same time, I’m sick to death of best practices. Recently, I learned that keeping the subject line on these emails to 40 characters or fewer will increase the likelihood that you’ll open and read them. Over 40, and you’ll probably skip over them. But what if the ideal title for one of the essays was 45 characters, or 72, or 111? Why should I have to sabotage the work just to get people to read it? And if I get you to open the email, I know that you’re more likely to read the essay within if it is either less than 600 words or more than 2,000—that’s what the research says. And while I’m sure that the vast majority of you would prefer I hit the 3,000-word mark every single day, I find that I can usually make my point in half that space. Sometimes even less!

I optimize so much—we optimize so much—that I just want one space free from it, and I want you, my subscribers, free and paid alike, to appreciate that. Here you will get what I think and hope is simply good, not what the data (sadly backed up by many experiments) says is effective. Here you will get what is thoughtful, surprising, and on rare occasions insightful, not what is useful, except in the most abstract sense. Except for the moments when I tell you what to do, I won’t tell you what to do, because I barely even know what I should do. These essays are, as the novelist Alexander Chee recently put it, “a device that shows me my own thoughts.” With Trying!, I am thinking out loud, on “paper,” so that I can learn to think more clearly. If that’s of service to you, if that helps you think your own thoughts more clearly, then great! And while I could steer these essays in that direction, and thereby make them more functionally useful to a broad swathe of the reading population, that’s just not my aim. So I won’t! 🤪

And therefore I’ll have to face the consequences: a smaller, less measurably engaged readership. And I’m okay with that. I guess.

What I would like to do is to break my own brain, not mention yours, out of the habits that allow optimization to penetrate. We react to the optimizations because they work: the emoji grab our attention, the video cut 3 seconds in keeps our eyes locked, the cliffhangers keep us bingeing. And they work because we are trained, or we’ve trained ourselves, or it’s innate to Homo sapiens, to recognize them as interesting. Can we undo that training? Through practice and discipline, can we learn to untangle the 45-character subject line, to watch the videos that begin with slow and static shots, to transform what might appear to be boredom or consternation into intrigue? I’d like to think we can, if we try put some effort into it. It won’t be easy, but we can escape our own internal algorithms by paying closer attention, by willing ourselves to have a bit more patience, and by giving ourselves the freedom to think and reflect. And once we make that second nature, maybe we’ll find we’ve freed ourselves from other algorithms as well.

Look, I’m not telling you you should do this. But you should. I don’t know if this is the best practice or the worst practice, but it’s practice. And you know what they say practice makes. 🪨🪨🪨

It’s Good and I Like It: Paint Drying

TKTK

Notes

1. If you perceive it as a criticism, that’s on you—maybe it hits a little close to home, eh?

Read Yesterday’s Attempt