How to Write a Trying! Essay

The advertiser for today’s 100th edition is, perhaps fittingly, Trust & Will, an online estate-planning service. For each of you who clicks, I get $1.60, which I should probably spend on Trust & Will itself, since Jean and I don’t yet have a will. Always fun to start these essays with a late-capitalist consideration of our own mortality, isn’t it?

One hundred days ago, when I sat down to write the first edition of Trying!, I had only a vague sense of what I was doing. Ideas had been swirling in my head for months, some of them maybe for years, and I’d started to compile a list, in the Notes app, of course, of potential topics: the wrong timeline, pins and pencils, zany face, feeling more at home when I’m not at home, how and why to quit, 2,000 words about Luke Skywalker. But how to transform each of those slugs into a full-fledged essay?

Sure, I’d done such things before, in both my life as a professional journalist and in a fun weekly speed-writing project I dubbed “Ballet Up to the Bar.” Getting words out wasn’t going to be difficult, but I didn’t know if I would be settling into a rhythm of regular structures and approaches or reinventing the essay all over again every single day (including weekends).

As it turned out, I found a formula that has mostly worked! Not that I was necessarily looking for it, or trying attempting to lock in a particular style of argumentation, but over time a pattern emerged.

First I would begin with an anecdote, as I’ve clearly done with this very essay. Usually, these would be very minor events in my life, sometimes recent, sometimes long since past. The important thing was that they be small, homey, almost forgettable incidents—but not entirely forgettable, for it was from such incidents that I would start to mine meaning. Usually, the interpretations would be highly personal: That first day writing the very first Trying! was both one small step and one great leap. It was a return to the practice that had sustained me as an adult, both professionally and emotionally, and that would upend my routine, reshaping how I approach everything in my day-to-day. But I would also start to connect, if tentatively, those interior and singular analyses to the larger philosophical, literary, or political world. That first essay, and every one afterwards, was a leap of faith in the Kierkegaardian sense, an experiment in bridging the gap between what I felt and what I could say, what words I could conjure and how they would be received.

Once I was partway in, I would consider writing a nut graf. For those of you who haven’t immersed yourselves in insider journalism terms, a nut graf is the paragraph or two in a feature article that comes after the introductory anecdotes and scene-setting, and that aims to tell readers what the story is about. A nut graf sets up the real stakes behind the opening anecdotes, and lays out where the remainder of the piece will take us—without revealing too much of what’s to come. Learning to write a nut graf is a vital skill for professional journalists, because you have to write them all the time, and when they’re well done, they’re beautifully concise crystallizations of themes and action. But I have chosen, for the most part, to reject them, often because I don’t know where these essays are going, and I want the structure of the essay itself to reflect this journey into my own mind. The stakes are always the same, but the destination—even the direction—is never certain. So no nut graf.

But then, usually in a single sentence right before the ad, I would state that everything I’d just written was completely wrong.

More after the highly clickable ad…

Breaking for the ad not only lends the essay a sense of drama—cliffhangers work!—but also gives me a few moments to refill my coffee² (or, depending on the time of day, whiskey) and think about how to proceed. Not that I really need to think much, because I knew from the start I was giving you a false interpretation of my opening anecdote.

Or not so much a false one as a misleadingly comforting one. Because don’t we want to imagine Matt Gross sitting nervously at his computer 100 days ago, hesitantly pecking out sentences, unsure of what he’ll create or where it will go? That’s our idea of most writers—fragile figures, anxious, neurotic, always coasting on the edge of failure and catastrophe. And while I’m happy to set things up that way, to let you believe what you naturally believe, it’s a ruse. I am in control here, and I was from the very start. And it’s that very control over my language and my thoughts that allows me to frame this as a journey of exploration, destination unknown.

But hey, I still want to make this a fun journey! Which is why I’ve prepared a snack bag full of delicious literary tricks to make it more enjoyable, especially for my paid subscribers. There’s one right there! I like to think of such things as Greek epithets—regular refrains like Homer’s “rosy-fingered dawn” that anchor us to a piece of writing and to its author, from whom we can come to expect, anticipate, and even love the repetitions, as hoary and hackneyed as they may become. Another epithet you’ll find in Trying! is a reference to this as a “reasonably high-quality newsletter,” which is a blatant theft from my actual professional colleagues M.D. and S.B., who came up with it one day for our work email, Need2Know. Maybe “blatant theft” is too strong. I like to think of it—there’s another phrase I use all the time—as an homage, or as a secret dialogue between two seemingly unrelated email products. I guess the secret is out. Oh well!

What other devices will I deploy? Will there be an entire paragraph of nothing but questions? Will the questions in fact develop the essay’s ideas still further? Or will they allow me to toss concepts out into the world without really having to commit to any of them? Is this, quite literally, rhetoric? Will I ever bother to respond to one of them, or can I just leave the answers just dangling, sensed but unspoken? Should I just dodge it all by distracting you cocksuckers with an unexpected curse word? Or should I change tacks entirely and implore you to fill out the survey telling me what to do next with this project?

As the essay goes on and crests 1,000 words, which it did right before the block quote, I’ll have to start figuring out how to end it. This is where I’ll most likely reread everything I’ve written up to this point, removing excess repetitions of the words truly and fundamentally and trying attempting to identify ways to reference the starting point of this journey, so that it feels satisfying and complete.

And pretty often, I’ll do that by reversing course once again: The interpretation that I offered you at the very beginning was the true one. The idea that I am in control of all of this, for instance, is just a mask for my very real anxiety about this entire project. I know that I can write about and around anything, and that I can produce in my readers a sense of recognition, sometimes even revelation, about our mutually challenging circumstances by shedding the sillier, more casual diction found earlier in the essay and shifting into a more structured register. This—this is how I can convincingly convey to you that we are all born into a world that can stun us with its beauty and its depravity, that we must endure and enjoy both for as long as we are able, because if we don’t—if we don’t even endeavor to try—then the bad guys win. The struggle is all there is, the rock is our thing, yada yada yada³.

Look, it’s time for me to get emotionally naked and be as honest with you as I can—which is a godawful hedge. “As honest with you as I can”? Why not just “honest”? There’s so much I want to say, but truly the words get in the way⁴: They’re there to communicate, but they also obfuscate. They represent what’s in my heart and my brain, but as sharp as they can be, as convincingly truthful and powerfully precise, they’re still only representations. It takes a leap of faith to get them out, and I rely on you to make a faithful leap back into my soul when you read them.

So I'll say this to you, my friend, with all the love in my heart and all the wisdom of the universe⁵: Words matter. Words come free, so we all, rich and poor alike, have access to all of them, and we can use them to perform magic, for good or for ill but, I hope, for good. When I sit down to write and you sit down to read, we get another opportunity, a miraculous opportunity, a Sisyphean opportunity, to create a new world—every single goddamn day (including weekends). 🪨🪨🪨

Actually, I’m going to take tomorrow off. I’ll be back Monday through Friday, then I’ll take a longer vacation, nine whole days, before returning with some new variation on Trying! What will that be? Take my survey and tell me!

It’s Good and I Like It: Good-bye, Pamela Paul

Notes

1. Which is what I just did.

2. This is the 100th email, so I figure I’ve written easily 150,000 words, which is equivalent to a 400-to-600-page book, depending on how you lay it out.

3. Injecting a bit of more casual diction makes the hifalutin language and naked emotionality of the finale more tolerable.

4. It’s always necessary to make oblique references to 1980s and ‘90s pop songs.

5. And definitely always quote sitcoms, especially toward the end of the essay, as you start to get emotional.

Read Yesterday’s Attempt