Every December marks Longreads’ annual Best Of package, a series of pieces published over a two-week period that celebrate the editors’ favorite stories from that year. We tried something new this year, and in keeping with that spirit, I tried something new as well.

For the past few years, we’ve structured the package to concentrate on journalistic categories: Personal Essays, Investigative Reporting, Profiles, that sort of thing. The structure makes sense. It has a clarity of purpose that benefits the editor and the reader. (People don’t talk enough about how clarity is a two-way street, and also a feedback loop of its own.¹) Its focus invites deeper thinking. If someone were to publish something like “The 50 Best Stories of the Year,” they’d need to weigh personal essays against deeply reported investigations; when we filter by genre, we’re able to discuss each piece’s merits without feeling like we have to create some sort of universal value system in order to do so.

But the structure has a downside, too. In addition to editing stories, Longreads editors write about other stories all year long²³. They (we) do so in the form of editors’ picks—around 600 a year—but also in slightly longer form for the Top 5 weekly newsletter. This means that whatever stories they (we) write about in a year-end package, they (we) have invariably written about before, and in basically identical form. All well and good, but once you write 200 words extolling the virtues of a feature, writing a different 200 words extolling the virtues of the same feature doesn’t feel particularly additive.

Which brings us to this year. Instead of doing those genre-based roundups, we decided that each editor would revisit all the stories they’d written about this year, and then write a short essay teasing out one of the themes they’d noticed in their own reading patterns. We had readers in mind with this change, but we also had ourselves in this mind with this change—speaking for myself, just the act of switching things up flicked on a different burner in my brain.

First, I went back to revisit my recommendations. I wrote 93 editor’s picks, and wrote longer blurbs about ~50 of those for the Top 5 newsletter⁴. When I fuzzed my eyes and looked at them in the aggregate, I could see a few constellations.

1. Cultural shifts, especially the (d)evolution of media in the digital age
2. Deep reporting that animates a story with a very narrow scope.⁵
3. Fascinating subcultures⁶
4. Esoterica and the self.⁷
5. Slow thinking: intellectual history, cognitive science, etc.⁸
6. Breaking through archetypes/stereotypes.
7. Cottage industries and power structures.
8. Interrogating pop culture.

I went back and forth on a few of these, but ultimately settled on the one that felt the most . . . fertile, I guess. I wanted to seed some sort of argument in there, not just point at stories that prove I like that kind of story.

So I was armed with a loose framework. I also wanted to try a new writing process, though—something that felt like the continuation of some changes I started making earlier this year. But I’ll save that for the next post.

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Tenuous Thematic Tie: Dirtsman, “Hot Dis Year”

Dirtsman’s death is one of the great tragedies of dancehall. After a slew of big singles—1992’s “Hot Dis Year” arguably the most enduring among them—he signed with BMG, only to be gunned down at his own house in 1993. If you hear shades of Peter Tosh in that, you’re not wrong. Dirtsman’s contemporary Panhead had been shot dead in the street just months before, and the twin murders (along with Garnett Silk’s killing the next year) cast a pall over reggae, with songs like Buju Banton’s “Murderer” mourning the situation. Capleton’s smash “Tour” even recounts learning the news on his return to Jamaica: “come back mi hear Panhead skull bore / come back an’ hear Dirtsman skull bore . . . seem like di people dem nuh love God no more.” Thankfully, songs like this remind you of the talent he brought to the world.

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1. Is that two metaphors, or one? One if the two-way street is a track, I guess. ↩︎
2. Internally, we shorthand this as “curation,” so if I use the word again, that’s what I mean. Also, I don’t know why I’m hiding that in a footnote, though I’m going to assume I have a decent reason for it. ↩︎
3. Okay, I realized why I hid it in a footnote. I tried it in a few places in the graf, and it never quite fit. It felt either interruptive, or like it was arriving too late to matter. So: footnote. ↩︎
4. Those longer blurbs totaled somewhere north of 12,000 words, which I only know because I keep each year’s blurbs in a single doc. ↩︎
5. These sorts of pieces usually centered on one or two people, but they weren’t profiles. They hinged on intimacy and a lot of scene reconstruction. ↩︎
6. This is the least surprising thing I can imagine. I’ve always loved subculture/microscene stories. Read hundreds or more, written a few. ↩︎
7. These were all over the places: a wild Harper’s profile of “the QAnon Shaman,” a very cool Nautilus story that explores a lingering (and mind-blowing) question about psychedelic experiences, a Paris Review essay about having been Mike Mew’s patient as a young man. ↩︎
8. Even typing that made me feel like a productivity/performance bro. I apologize. Let’s just say “stories about brain shit.” ↩︎

I don’t do a lot of freelance writing these days, but last weekend, a friend hit me up to see if I could contribute a quick humor piece to a company’s newsletter. He’d already figured out the concept; all I had to do was write it. A container and some rules. Perfect. It’s the kind of thing he and I have done together dozens of times over the years in various outlets and various formats: print, online, newsletter.

But the more I looked past the shape of the piece, the more I realized that a dotted line runs from magazines—the media vessel of the past, like it or not—to newsletters, the media vessel of the present¹.

Magazine fans know what a “front of book” section is, even if they don’t know the name. Those are the quick-hit sections. They feature shorter pieces, lots of elements on a page, and generally feel busier than the rest of the issue. When you get to the “feature well,” the design shifts to keep you immersed in the longer pieces, generally with a two-column layout and maybe the occasional sidebar. In other words, where features are the entrées, FOB pieces are the appetizers. But if editors are doing their jobs well, each one of those appetizers distills a magazine’s overall sensibility. It’s a flavor bomb—powerfully enjoyable, but one that gets its point across in a single bite. You might think you. Another colleague of mine used to say that good FOB sections act as a spiritual table of contents for the magazine: simply by reading them, you knew the general vibe of what you were getting into later.

So in Wired‘s culture section, Start, which I worked on for my first few years at the magazine, you could find a a page mocked up to look like Yelp in Game of Thrones‘ Westeros. Or a poem about the sameness of disaster movies. These were both pegged to cultural happenings the month each issue hit newsstands, but they also embodied Wired‘s larger approach: irreverent, enthusiastic, and steeped in genre. Were they also an opportunity for me to be a smartass? Possibly².

Good newsletters, though, are at their best when they reverse that structure. They start with the “main bar”—the central element of the edition—and continue to shorter-form pieces. A great example of this comes from Ryan Broderick’s Garbage Day, which is basically my lifeline to whatever’s happening in the various nano-niches that add up to Online Culture. In the most recent installation, the main bar clocks in at just under 900 words; after that comes a series of quick hits in the 100–300 word range. Each of those shorter bits is consistent with the newsletter’s overall scope and tone, just as FOB pieces are, but here they act as palate cleansers rather than table-setters. You open the email because you’re interested in whatever Ryan’s going deep on in the main bad, but by the time you’ve read through everything you feel reasonably up on the things that you wouldn’t possibly know otherwise but seem somehow indicative of where society is heading. (Spoiler: nowhere good!)

You can find this everywhere, from the massive to the micro, from business to humor, from Morning Brew to Backseat Freestyle. Sometimes the quick-hit bits are a linkdump, sometimes they’re mini-pieces in their own rights. (Some newsletters even break themselves into named sections, which for my money is a smart play: the more concrete vocabulary you can give someone to talk about the thing you make, the easier it is for them to recommend it to the next person.) But when you abstract away the words themselves and squint, these are basically magazines in reverse.

Importantly, this isn’t the only structure that great newsletters use, but it’s common enough that you’ll start seeing it everywhere you look. And it’s a staunch corrective to the idea that magazines faded because they’re static and fusty. The ideas are still big—it’s the pages that got small.

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Tenuous Thematic Tie: The Heptones, “Book of Rules”

No disrespect to The Wailers, but it’s tough to find a vocal trio that means more to Jamaican music than the group that started life as The Hep Ones. Not only did they embody the musical shift from rocksteady to reggae, but lead vocalist Leroy Sibbles was a monster on the bass, and lent his skills to Studio One hits like “Full Up,” which would go on to be one of reggae’s foundational riddims. Like The Wailers, The Heptones signed with Island Records in the ’70s, part of the push that exported reggae around the globe; their Island album Night Food contained re-recorded versions of many of their classics, this gem among them.

1. Not the only one, obviously, but the one that—together with podcasts—best represents how journalists have adapted to the decline of print media and the rise of the creator economy. ↩︎
2. I worked on a handful of FOB sections over the years—GQ, Complex, King, Wired—but the one thing that they all had in common was that the editors putting it together tried, above all, to entertain each other. We would be reading these magazines if we didn’t work there, and so it wasn’t much of a jump to use ourselves as stand-ins for the reader. Focus testing was basically baked into the process. ↩︎

For nearly 25 years, my career has revolved around magazine writing. Editing too, but that’s a harder thing to describe to people, mostly because it involves so many things: overseeing a section, working on a special package, editing a feature story, even nudging a piece that’s already been edited. It’s easiest to just use “journalist” rather than either word.

Working in magazines for 25 years, though, has done some weird things to my brain. Well, that’s not quite true. What it’s actually done, I think, is create conditions that hyperdevelop certain aspects of creativity, while ignoring other aspects. It’s like the guy who spends every day in the gym working his upper body but has never done a squat or deadlift in his life, so he waddles around on chicken legs looking like Johnny Bravo. But, you know, the brain version. As a result, despite doing creative work for my entire adult life, I’ve become creatively imbalanced¹.

Here’s what I mean. Creating inside the confines of a publication or some other existing apparatus? No problem. Give me a container and some rules² and I’m good to go.

Seeing my own ideas through to completion, though? Very much problem. And for very many reasons. So many reasons! The ideas themselves. The getting started. The discipline. Overthinking. Underthinking.

Meanwhile, the larger shape of my day-to-day work is less about writing than it’s ever been—so much so that I no longer think of myself as a journalist, or even a writer. I agonized about that for a while (which is a subject for another time), but it’s starting to look more and more like an opportunity.

Hence, this post. This blog, even. (Which, I’d like to point out, is not a newsletter. It can be! You can sign up to have posts arrive in your inbox. But it’s also something that I own, that looks the way I want it to, and that isn’t a social network in disguise.) The last time I wrote online with any consistency—meaning outside an Official Outlet—was probably the year 2000³. But I want to start doing it again for a few reasons.

1. To address the creative imbalance I mentioned, and to do so through writing as a practice. Inspiration is a rare thing; everyone from Mark Twain to Charles Schulz to Chuck Close has said something to the effect that you’ll never get anything done if you wait for it. (Close’s version, that “inspiration is for amateurs,” has been butchered, attributed to other people, and by now probably appears on a meme of Jesus or Einstein or something.) But to go back to the Johnny Bravo example, creative improvement depends on creative exercise. For me, that means sitting in what my wife calls “the messy part” of creativity. Uncertainty. Disappointment. False starts. Muddling toward clarity. That’s my weakest muscle, and the most painful one to work on.
2. To learn to create authentically. My career has made me into a chameleon of sorts. Writing for Wired is different than writing for GQ or Glamour or XXL or Longreads or Complex or anything else, and I’ve always calibrated my voice to the needs of the publication⁴. It’s still me, and still sounds like me—I’ve got strong enough tells and tendencies, for better or worse—it’s just a version of me. When I’m writing in open space, though, that adaptability turns into uncertainty. I start thinking about who’s reading, which part of me I’m turning up, which part I’m turning down. And before you can say “fractured sense of self,” I look down and my feet are stuck in quick-drying self-consciousness. So I’m also writing to undo that tendency, and to find comfort in my multitudes rather than trying to titrate an ideal version out of them⁵.
3. To open up a little bit. A colleague teased me the other day that I’d finally shared a personal story more than three years after we started working together. Writing as yourself means writing about yourself, and while I’ve published no shortage of essays and stories that I’m a part of, that’s always been a heavily … curated process. (Also: see #2.)
4. Finally, to re-paraphrase an idea that seems to have come from Robin Sloan, I want to start working with the garage door open. I’m fascinated by (and envious of) folks who create like no one is watching, even when everyone can see. It strips away the illusions that creativity is some magical flow state and lays the artistic process bare. It brings people along with you, and helps forge community from creativity. Most importantly, it’s (hopefully) useful to other people, particularly when working across multiple projects or even multiple media.⁶ I work for a company that’s built on the principles of open source—why shouldn’t creativity work the same way?

So that’s the plan. Will it be smooth? Almost definitely not. But considering what I’m trying to do here, that’s a feature, not a bug. Let’s see where it goes.

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Tenous thematic tie: Beenie Man, “Foundation Badman”

In 2006/7, producers Sly and Robbie released the Taxi riddim, a new version of a riddim that had been floating around since 1973. This one, though, became an all-time favorite; it’s got a lovely vintage feel, but meshes well with modern styles. No shortage of massive tunes on it, particularly Buju Banton’s “Driver,” but this Beenie selection is the obvious draw for today. (If you listen to the lyrics, aimed squarely at relative newcomer Mavado, you’ll see why it was originally called “Mi Dis Movado.”)

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1. I should probably acknowledge here that this creative imbalance could easily be nature rather than nurture. Maybe it’s not that my brain spent 25 years thinking in wordplay and punchlines, and so its arms are huge but it can’t climb up stairs. Maybe it’s that I’ve just steered in that direction and away from other directions because I’m not particularly suited to those directions. Either way, though, I’m in the same position. ↩︎
2. The conventions of magazines have given rise to a whole taxonomy of writing considerations: form, length, purpose, tone, etc. ↩︎
3. One short-lived but probably ripe-for-resuscitation newsletter notwithstanding. ↩︎
4. Is this related to code-switching? Oh, very much so. Which is a whole other conversation. ↩︎
5. This is also deeply wrapped up in the phenomenon known as “caring what people think,” which frankly I’m too goddamned old for. ↩︎
6. For whatever reason, I find this much more common among folks who write as an outlet, rather than as a career—particularly people in science and technology fields. Maggie Appleton is a great example. ↩︎