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  • How to Use—and Not Use—the Almighty Em Dash

    A few years ago, when I was at Medium, I wrote a piece about em dash usage for their Creator Hub. Considering how often I see people railing against the humble em dash as a hallmark of AI, I thought it might be worth sharing.

    Before we begin, let’s get one thing out of the way—I love em dashes. For instance, that first sentence should’ve used a colon. Let’s get one thing out of the way: I love em dashes. Nope! You’re outta here, colon. Go find a serial list to preface.

    Loving the em dash treads a fine and dangerous line, though. It’s one of the most flexible pieces of punctuation at a writer’s disposal, but that flexibility can lead to pitfalls from overuse to straight-up misuse. In other words, you should probably learn to be judicious in deploying it, lest your work start to look like a second-rate impression of Emily Dickinson. Or a 17th-century pamphleteer. (Which isn’t really a thing you find that often, but still would probably clutter up your writing.) So let’s get a better sense of how it works.

    First, some unnecessary context. An em dash is the most assertive member of the hyphen family; em is typographer-speak for the full width of whatever point size you’re writing in. Looking at the top of my screen right now—and I should admit here that I originally wrote this not in the WordPress editor, but in Google Docs—I see that I’m using Arial 12, which makes an em dash 12 points wide. There’s also an en dash, which is half as wide as an em dash. En dashes are usually used in number ranges, like 1902–1987, which is the lifespan of Clara Peller, the “Where’s the Beef?” lady from Wendy’s mid-’80s ad campaign. And then there’s the hyphen, the tiny but stalwart star of phone numbers and compound adjectives like “ill-advised” (as in “his ill-advised Clara Peller reference ensured that no one would keep reading”).

    It’s easy to type an em dash without hunting through byzantine drop-down menus or Googling lists of Unicode shortcuts: shift-option-hyphen. Try it. Isn’t that nice? In WordPress, you can also render an em dash in WordPress by typing two hyphens. Magic!

    By and large, an em dash serves to insert a break in your thought without ending your thought entirely. (Other things can do that too, but we’ll get to those in a bit.) You can achieve that thought-break in two primary ways: using the em dash as a bookend, or as a bridge. The first is much simpler, so let’s start there.

    Em dashes as bookend

    Using em dashes is a great way to create a sub-sentence of sorts, to nest a thought inside another thought. Think of them as parentheses’ slightly more literate cousin: they’re not snobby, but you know they’ve got a kickass bookshelf in their apartment. In their most frequent and popular application, they let you properly unpack what you mean before moving on to the rest of the sentence. Here’s an example, from a piece I wrote a few years ago:

    By now you’ve become accustomed to the tainted synchronicity of targeted marketing. You email or talk with a friend about a given topic—Instant Pots, hiking boots, desk lamps—and boom, said topic shows up in a banner ad the next day. Isn’t that crazy? you say to yourself, wondering how long it’ll be before the Instant Pots stop following you around.

    But those bookends can also let you break the fourth wall, like an aside to the reader. Hey, take a break from this essay for a second; let’s talk over here in private. I kinda did this above:

    Looking at the top of my screen right now—and I should admit here that I originally wrote this not in the WordPress editor, but in Google Docs—I see that I’m using Arial 12, which makes an em dash 12 points wide.

    Hacky? Maybe. But not as hacky as parentheses would have been!

    Em dashes as a bridge

    Now comes something that feels just as easy, but can run into trouble all the same.

    Used as a bridge, an em dash emphasizes whatever comes after it—like the pause before a punchline.

    But it also has the nifty trick of resetting the sentence’s odometer, so you can add details or even change subjects for the rest of the sentence without hitting run-on territory. Whatever comes next, the em dash tells you, will be its own section of the thought. Here’s an example, from another old piece I wrote:

    While narrative flexibility might be great, social media has wreaked a different kind of havoc on readers’ media habits—and people swiping through a series of panels is by no means a foregone conclusion.

    That em dash could have been a comma, right? But think about what would have happened:

    While narrative flexibility might be great, social media has wreaked a different kind of havoc on readers’ media habits, and people swiping through a series of panels is by no means a foregone conclusion.

    If you read the two sentences out loud to yourself—something you should be doing with your own writing already—you’ll hear the difference. With the comma, you probably keep the same cadence from the sentence’s beginning to its end. With the em dash, you take a longer pause, maybe even hit the rest of the sentence in a slightly different register. And whatever your voice is doing, your reader’s brain is doing, too.

    But wait!

    As you’ve probably already realized, em dashes aren’t unique. A semicolon also gives you the freedom to stop and change direction entirely, while still leaving a connection between the two thoughts in the sentence. A pair of commas can also create a parenthetical thought. A colon can also tee up details to unpack what came before. So it’s also helpful to think about when not to use the em dash, and instead to pull another tool from the box. To wit:

    Don’t use an em dash in a sentence that already uses “advanced” punctuation.

    Commas? Sure. But packing an em dash into a sentence that already has a colon or semicolon is a sure sign that you’re trying to do too much. Chances are you’ve got three sentences packed in there, and they’re all suffocating each other. Instead, think about how you can break them up and still give the reader a lovely through line. Paragraphs have rhythm just like sentences do, and consistency has a sneaky way of turning into monotony.

    Don’t use them instead of simple commas.

    I’ve seen this sort of thing a lot in inexperienced writers’ drafts: Before I had a chance to get out of bed—my phone rang. If it’s a straightforward sentence with a single thought, chances are a comma can do the job. Let it.

    Don’t use them when you don’t need to.

    Em dashes are seductive in large part because they feel naturalistic. We talk in loops and asides, interrupting ourselves and doubling back to qualify our own statements, so seeking to capture that quality is an understandable impulse. But writing doesn’t need to replicate the foibles of speech in order to sound conversational—and clarity often comes from brevity.

    Don’t use them, period. (Or at least try not to.)

    If you can’t make it through a paragraph without using them, think about why you’re using them. Do you need that many punchlines? Does the reader really want to be interrupted that many times? If you look at something you’ve written and you can see more than two occurrences in a single screen’s worth of writing, see if you can pare them down. Chances are the piece’ll be better for it.

    No one is immune to these issues. (Seriously, ask my editors.) But keep them in mind and keep things simple, and you’ll have a new favorite tool. Just make sure it’s a scalpel, not a hammer.

  • Slouching Toward Natural: Can AI Approximate Our Individual Writing Voices?

    At work, my team has been doing a lot of experimentation around how (read: if) AI can help us in our editorial work. Generally, I’ve assumed that its greatest impact will be non-creative, especially with the rise of reasoning models and agentic capabilities. For instance:

    • Distilling and synthesizing meeting notes
    • Automating financial reporting
    • Logistical planning

    After all, AI writing is … AI writing.

    But I started wondering how we might help AI absorb our natural writing voices—not what we think it should sound like, but how we sound after many years of writing. My colleague Cheri proposed pointing an LLM at her editor’s picks, which is a promising angle. I thought I’d take it in a slightly different direction. Each year, I keep a running doc with every blurb that I write for Longreads‘ Top 5 newsletter. These blurbs are longer than our usual picks (200-250 words is probably the average), and incrementally more complex: They involve more critique and usually have a more personal approach. Giving AI one of those yearly docs—around 50 blurbs, and well over 10,000 words in total—seemed like a good place to start, with no agent behavior necessary.

    I did this using Perplexity and ChatGPT, so let’s try a side-by-side approach.

    Prompt 1:
    The attached document has about 50 blurbs written about magazine stories. Based on the blurbs, describe my writing style and voice in a way that would let me use that description as a prompt for you.

    PERPLEXITY

    Insightful, engaging, and intellectually curious. You have a knack for distilling complex topics into accessible prose while maintaining depth and nuance. Your writing is marked by a blend of analytical rigor and conversational warmth, often employing wry humor and cultural references to connect with readers.

    You demonstrate a wide-ranging interest in diverse subjects, from technology and sports to literature and social issues. Your commentary is thoughtful and often critical, but rarely cynical – you approach topics with a balance of skepticism and openness.

    Your voice comes across as well-informed yet unpretentious. You have a talent for finding the human angle in abstract concepts and for highlighting the broader implications of specific stories. Your prose is crisp and economical, with a good ear for memorable phrases and analogies that illuminate your points.

    You seem to value both intellectual substance and readability, crafting pieces that are both informative and engaging. There’s an underlying current of empathy in your writing, even when discussing controversial subjects.

    Overall, your style combines journalistic clarity with essayistic depth, resulting in writing that is both accessible and thought-provoking.

    CHATGPT

    Your writing style is incisive, conversational, and deeply engaged with the material. You blend sharp analysis with wry humor, balancing intellectual rigor with a relatable, sometimes personal, voice. Your tone often carries a mix of enthusiasm and skepticism, and your descriptions are vivid, sometimes poetic, without being overwrought. You’re adept at threading cultural references into your critiques, making your observations feel both insightful and accessible.

    If you wanted me to replicate your voice, here’s how you might prompt me:

    “Write in a style that is analytical yet conversational, blending sharp critique with wry humor. Use vivid descriptions, cultural references, and an engaging, personal tone. Avoid overly academic language but retain intellectual rigor. The writing should feel lively, incisive, and slightly skeptical—curious but never credulous.”

    Would you like me to refine that further based on any particular aspects of your style?

    Thoughts
    Immediately, you can see hallmarks of AI communication. They’re both clear, but . . . voiceless. As for the diagnosis itself, many of the same assessments emerge: “Rigor,” “wry humor,” “cultural references,” etc. I appreciated that Perplexity gave me more details—each insight is an ingredient in the recipe of any writing-voice simulation, and I thought more ingredients would lead to a richer, fuller result.

    Prompt 2:
    How would you describe my writing from a mechanical standpoint? What kind of sentence constructions do I use? Are there any stylistic flourishes I over-rely on?

    PERPLEXITY

    Based on the writing samples provided, I would describe your writing style from a mechanical standpoint as follows:

    1. Sentence structure:
    • You frequently use complex sentences with multiple clauses, often separated by em dashes or parentheses to add context or commentary.
    • You balance these longer sentences with shorter, punchier ones for emphasis or to conclude thoughts.
    1. Stylistic elements:
    • You employ a conversational tone, often using contractions and occasionally addressing the reader directly.
    • Your writing is rich in cultural references and analogies, which you use to make complex ideas more relatable.
    • You frequently use rhetorical questions to engage the reader or transition between ideas.
    1. Vocabulary and diction:
    • Your vocabulary is diverse and sophisticated, but not overly academic.
    • You often use industry-specific jargon when discussing media or technology, but generally explain or contextualize these terms for a general audience.
    1. Structural techniques:
    • You often open paragraphs with a hook or provocative statement, then expand on it.
    • You frequently use lists or series of examples to illustrate points.

    As for stylistic flourishes you might over-rely on:

    1. Em dashes: You use these frequently for parenthetical asides or to add emphasis. While effective, overuse could potentially disrupt flow.
    2. Pop culture references: While these add color and relatability, very frequent use might date the writing or alienate readers unfamiliar with the references.
    3. Rhetorical questions: These are effective for engagement but could become predictable if overused.

    Overall, your writing style is engaging, informative, and demonstrates a strong command of language and structure. The potential over-reliances noted are minor and generally serve your writing well when used judiciously.

    CHATGPT

    From a mechanical standpoint, your writing is characterized by:

    Sentence Construction:

    • Varied Sentence Lengths: You frequently mix short, punchy sentences with longer, more complex ones. This creates a natural rhythm that keeps the reader engaged.
    • Parentheticals: You often use parenthetical asides (sometimes for humor, sometimes for clarification), which add a conversational tone and a sense of spontaneity.
    • Em Dashes: You favor em dashes for dramatic pauses or to introduce an additional thought—almost like a quick sidebar within a sentence.
    • Colons and Semicolons: Colons introduce sharp clarifications or dramatic reveals; semicolons appear in compound sentences, adding balance to your ideas.
    • Parallelism: You often structure phrases or clauses in a parallel way to enhance readability and impact.

    Stylistic Flourishes & Patterns:

    • Rhetorical Questions: You frequently use them to create engagement and invite the reader into your thought process.
    • Conversational Repetition: You’ll sometimes repeat a phrase or reframe it for emphasis, often in a buildup to a punchline or a sharp insight.
    • Casual Yet Elevated Tone: You seamlessly blend informal phrasing (“that’s not a judgment!”) with sophisticated analysis.
    • First-Person Anchors: Even when discussing a broader cultural or analytical topic, you often include a personal touch—an anecdote, a reaction, or a subjective stance.
    • Dash of Polemic: While your writing is fair and nuanced, it often carries a persuasive undercurrent, leaning into a strong point of view without feeling heavy-handed.

    Potential Over-Reliances:

    • Parentheticals & Em Dashes: They’re effective, but since you use them frequently, they could occasionally be streamlined for sharper clarity.
    • Conversational Self-Interruption: Sometimes, the way you backtrack or add a quick self-aware qualifier (“Not to brag, but…”) can slightly dilute the impact of an otherwise strong assertion.
    • Sentence Length Variation: While generally a strength, some longer sentences can get a bit winding when packed with multiple clauses.

    Overall, your writing is sharp, dynamic, and highly readable. If you were looking to tweak anything, it would be in paring back certain stylistic habits (like em dashes and asides) in favor of a bit more directness at times. But that’s a minor adjustment—your voice is strong, distinctive, and highly engaging.

    Thoughts

    I AM ATTACKED.

    • Love of em dashes: ✅
    (I’m always seeking to minimize these, in my own writing and others’)
    • Varying sentence lengths: ✅
    (Anyone I’ve ever worked with or mentored knows how I go on and on about cadence and rhythm in writing!)
    • Parallel structure: ✅
    (This one impressed me—I do use it a lot, but only ChatGPT picked up on it.)

    Interestingly, ChatGPT illustrated my overreliance on self-interruption (valid!) with a completely misread example. Here’s how I actually used “Not to brag, but”:

    I’ve never read Moby Dick. I know that’s considered a grievous sin in certain circles. However, to those people, I say: well, how familiar are you with Pittsfield, Massachusetts? That’s what I thought! Not to brag, but I saw Dumb and Dumber in a mall there.

    Anyway. On to the next part.

    Prompt 3:
    Distill both sets of observations about my writing into a single prompt that I can use when asking you to write something.

    PERPLEXITY

    Write in a style that is insightful, engaging, and intellectually curious. Use a blend of analytical rigor and conversational warmth, employing wry humor and cultural references where appropriate. Craft prose that is crisp and economical, with memorable phrases and analogies that illuminate key points. Balance complex ideas with accessibility, maintaining depth and nuance while being relatable to a general audience. Use a mix of sentence structures, including longer, multi-clause sentences (often with em dashes or parenthetical asides) balanced by shorter, punchier ones for emphasis. Incorporate rhetorical questions and lists to engage the reader and illustrate points. Approach topics with a balance of skepticism and openness, finding human angles in abstract concepts and highlighting broader implications. Aim for a voice that is well-informed yet unpretentious, combining journalistic clarity with essayistic depth to create writing that is both informative and thought-provoking.

    CHATGPT

    Write in a style that is analytical yet conversational, blending sharp critique with wry humor. Use varied sentence lengths, mixing punchy, direct statements with more complex constructions. Incorporate parentheticals, em dashes, and rhetorical questions for a lively, engaging rhythm—but don’t overuse them. Maintain a casual yet intellectually rigorous tone, balancing cultural references, personal asides, and polemic flourishes. Structure sentences dynamically, using parallelism, well-placed colons, and occasional repetition for emphasis. The writing should feel incisive, curious, and slightly skeptical—inviting the reader in while maintaining a strong point of view.

    Thoughts

    Not bad! Also, very similar! While I appreciated Perplexity’s fuller description, I overall preferred ChatGPT’s more balanced approach.

    To see how these pay off, I asked both models to write a blurb from the actual piece I blurbed a week ago. This is mostly to handicap the AI—it wouldn’t have read my actual blurb in the provided corpus, so was flying blind.

    Prompt 3:
    Using that prompt, write a 200-word blurb about this story: https://www.esquire.com/entertainment/tv/a63613027/seth-rogen-interview-2025/

    PERPLEXITY

    In the twilight of his early 40s, Seth Rogen has morphed from Hollywood’s favorite stoner-bro into a multi-hyphenate mogul with a Midas touch. Esquire’s profile paints a portrait of a man who’s traded bongs for boardrooms without losing his signature laugh or his penchant for pushing boundaries. Rogen’s latest venture, “The Studio,” is a meta-comedy that turns the lens on Tinseltown’s executive suite—a world where dreams and spreadsheets collide in a haze of anxiety and Kool-Aid IP.

    But what’s most striking about Rogen 2.0 is his zen-like approach to an industry in flux. While others bemoan cancel culture, he shrugs it off with the ease of a man who’s found the perfect strain. “Maybe comedy was too easy before,” he muses, challenging the notion that edgy humor is endangered. It’s a refreshing take from someone who’s navigated the tightrope between provocation and progress with the grace of a pothead parkour artist.

    Rogen’s evolution—from “Freaks and Geeks” to freak-in-chief of his own empire—offers a masterclass in growing up without selling out. He’s proof that you can build an adult life without kids, stay creatively fulfilled without compromising, and yes, still get high while aiming higher

    CHATGPT

    Seth Rogen has spent decades refining a public persona that’s equal parts stoner philosopher, comedy workhorse, and deeply unserious businessman (see: Houseplant, his genuinely gorgeous line of weed accessories). But in his latest Esquire profile, we get a slightly different version of Rogen—one that’s older, more thoughtful, and maybe even a little wistful. Ostensibly pegged to his new Apple TV+ series Scotty & the Secret History of Hollywood, the piece quickly becomes something bigger: a meditation on fame, creative control, and what happens when your industry starts moving in ways you don’t like. Rogen, never one to mince words, has plenty to say about the state of film and TV today—particularly when it comes to superhero movies and the streaming economy—but he’s also refreshingly honest about his own evolution. He’s still funny (the man can’t not be funny), but there’s a self-awareness here that feels sharper than usual. As he talks about aging, ambition, and the kind of work he actually wants to be making, you get the sense that Rogen, for all his success, is still figuring things out. And honestly? That might be the most interesting thing about him. —PR

    Thoughts

    Stylistically, this isn’t much of a contest. It’s ChatGPT, hands down. I 100% would have written this sentence:

    Ostensibly pegged to his new Apple TV+ series . . . the piece quickly becomes something bigger: a meditation on fame, creative control, and what happens when your industry starts moving in ways you don’t like.

    Meanwhile, Perplexity’s version has an over-eagerness that I see in a lot of AI writing:

    While others bemoan cancel culture, he shrugs it off with the ease of a man who’s found the perfect strain.

    Might I have written that? Sure. But hopefully I would have edited it before it went any farther.

    But here’s the issue: ChatGPT makes shit up. Like, a lot. (Of course it does. All LLMs do. They create ostensible “facts” out of whole cloth. Fake legal citations. Research papers that don’t exist. The list goes on.) And many of its claims about this Esquire piece are demonstrably false.

    • Rogen’s new series is called The Studio, not Scotty & The Secret History of Hollywood

    • The conversation never turns to superhero movies or streaming services

    • Rogen never talks about aging or ambition, at least not in direct terms.

    So, still at square one. Yes, I’m impressed at its ability to sound like me with sufficient coaching. But I also don’t trust it as far as I can throw it—which, it being software, is exactly 0.

  • Welcome to CHUNE

    I’ve been in love with hip-hop since I was eight years old. I’ve been in love with reggae nearly as long. But the words I’ve written about the former outnumber the words I’ve written about the latter by two orders of magnitude. Maybe three.

    Most of that is due to cultural prominence. Hip-hop being the dominant engine of pop culture gave me plenty to write about, and plenty of places to do it. Hell, it gave me a career: My very very very first clips were artist profiles in Paper and a book review of Douglas Century’s Street Kingdom. Reggae, though? That was the exception, not the rule. (One of those exceptions being this piece from [gulp] 20031.)

    I still love hip-hop. Always will. I keep up with it as well as I can, try not to yell at clouds too much. The thing is, it doesn’t hold many rabbit holes for me. How could it? I was there the whole time. It’s my security blanket, my Madeleine.

    But with reggae, there’s always a new trail of breadcrumbs, a new thrill of discovery. Fifty-plus years of interconnection, innovation, creation. I wanted to find a way to share that thrill. And so: CHUNE.

    It’s not much. A little subdomain to this site that posts a song every day. Mostly dancehall. Some roots. Some lover’s rock. A little history mixed in there, because how could there not be? Whether you’re a deep fan or you’ve never listened to anything that wasn’t by Bob Marley, I hope there’ll be something for you in there. A surprise. A connection. A tune you can’t get out of your head. Some breadcrumbs for you to follow, just like I’ve followed them over the years and decades.

    I hope you enjoy it. I know I enjoy making it.

    1. Disregard, if you will, the apostrophe in the word “ting.” Not my choice. ↩︎

  • Trap Muzik

    I’ve been making a living as a writer since I was 22 years old. Even when I was mostly editing, I was writing. Even when I was running a section or department, I was writing. I knew first-hand that the idea of “inspiration” had almost nothing to do with it.

    Sure, inspiration happened sometimes—a bolt of an idea out of the blue, a lede or framing or kicker that helped me get unstuck—but I also couldn’t wait for it. (Deadlines: they’re magic!) So earlier this month, when I decided that I’d post every day on LinkedIn for 40 days, I never considered that I’d fall into the inspiration trap.

    That was dumb. Of course I fell into it.

    Every time I went on there this week, I saw the same things. People arguing about that guy who did that thing. (We all know what I mean. Don’t bring it up in the comments.) People making grand pronouncements about a certain technology. I get it. It’s LinkedIn. But it also felt … barren. There was no springboard to propel from, nothing to respond to unless I wanted to perpetuate the same navel-gazing, counterproductive tropes.

    And somehow, that turned into me feeling barren. If I’ve got nothing to say, I reasoned, why would I say it? So I didn’t post anything that day. I didn’t post anything the next day either.

    None of this mattered to anyone else, obviously. But it mattered to me. I couldn’t figure out what had changed. Until I realized I was doing the thing I knew I should never do: waiting for something that might not even exist.

    That’s the inspiration trap.

    Anyone with a meditation practice is familiar with the idea that “emptying your mind” is a canard. Inevitably, a thought will float through your head. What’s key is to watch it float by without becoming attached to it—without following that first thought to the next thought to the next thought. You notice it, and you let it go.

    Noticing the inspiration trap changed it from something I felt to something I saw. That didn’t mean that I suddenly had world-changing insights about RTO or AI or [choose your preferred acronym]. But once I noticed it, stepping out of it got a lot easier.

    Why bother writing this out? Believe me, it’s not because I like talking about myself. It’s because chances are you’ve fallen into the same trap at some point. You might not think about it as a trap. You might not even realize you were waiting for something.

    But maybe you are. Take a look. See what you notice.

  • Comfortability with Efforting

    The English language is a beautiful, malleable thing. Slang, neologisms, and portmanteaux push at its edges constantly. Other languages contribute terms; patois and pidgins intermingle. Homophones and near-homophones turn ambiguity into a playground1. Even the way we use a given word shifts over time, making the idea of “definition” little more than a snapshot. In the age-old fight between prescriptivism (words should mean what they mean!) and descriptivism (a word’s definition should reflect its popular usage!), my soul lies with the latter.

    But I can not deal with the word “comfortability.”

    I didn’t say anything when “impactful” arrived, because it was not meant for me. Go off, Deborah in Product Design2.

    I didn’t say anything when “operationalize” shambled through the door, because it was not meant for me. I’m sure there’s a strategy document somewhere that just wouldn’t be the same without it.

    I didn’t even say anything when so many people used “comprise” and “nonplussed” incorrectly that the words started to mean the opposite of what they actually mean. “English is a beautiful, malleable thing,” I reminded myself through what I hoped was an encouraging smile but was really a rictus.

    And then people started to say “comfortability,” and I realized that I’m not the descriptivist I thought I was.

    First off, there’s already a word that means what it means. Can you guess what it is?

    That word is “comfort.”

    I love a wide-ranging vocabulary. Even words that feel like interchangeable synonyms hold different hues, making them fraternal twins rather than identical. When someone uses an unexpected word that really nails what they’re trying to communicate, that’s not showing off. It’s artistry.

    But when you add more syllables to a word to make a longer word—without even changing the part of speech it is—then the only thing I hear3 is “check out this gravitas, y’all!”

    It gets worse. Apparently, Comfortability has brought a cousin along, and they’re waiting outside in a Cybertruck. The cousin’s name is Efforting. I don’t know if I’ve met Efforting in person yet, but I’ve heard about them, and I have to be honest: Efforting sounds like they’re named after what it takes to survive a conversation with them.

    1. Yes, this means that puns are in fact the highest expression of art, and I will go to my grave defending that idea. ↩︎
    2. I don’t work with anyone named Deborah, and any resemblance to any person alive or dead is purely coincidental. ↩︎
    3. And you will only ever hear this word, because no one would write it down unless they were taking up arms against its tyranny. ↩︎

  • Trying a Second Brain (aka Thinking Different II)

    [Announcer voice] So when we left off, Longreads had decided to try something different for its year-end package: a series of essays from the editors that reckoned with some larger theme in the year’s best journalism. After looking over all the reading I’d done in 2024 for editors’ picks, I had isolated 8-10 pieces, all of which spoke to the idea that technological “progress” had come at palpable cultural cost.

    But I also wanted to try something different with the way I wrote the piece.

    In the past, I probably would have tackled this essay the way I always approached criticism. I’d have consumed the relevant texts—be that a book, a documentary, an article, or anything else—and waited for a thesis to fight its way to the surface, which more often than not happened when I was in the shower. (Showers and walks: easily my two favorite ways to knock ideas loose.) If a thesis refused to show itself, I’d sometimes just start writing to see what would happen.

    Earlier this year last year1, though, I stumbled into the rabbit hole of second brains. (Quick pause for the requisite “have you considered having a functioning first brain?” questions.) First, courtesy of my wife2, came the PARA method, which I started using in my personal life. It’s simple enough to implement just about anywhere3, and powerful enough to use without thinking about it too much. A few months later—again courtesy of my wife4—I read a book called How to Make Notes and Write that completely upended my thinking around reading.

    Waiting to begin reading, researching, making notes, and writing until you know exactly what and how you want to write is unproductive. You learn by writing. The way you begin writing notes, observations, and ideas may not resemble the final form of the output you want to create.

    —How to Make Notes and Write

    Yes, writing begets writing, just as reading begets reading. But crucially, thinking is accretive. I’ve long been conditioned to pitch an idea, then write about the idea. That particular cart-horse system reinforces microwaved takes, and it created a pattern in which I’m loath to write unless I know what I’m writing about. Make posits an alternative—a reversal, really. First, read. Let your curiosity guide you. Second, take notes on anything you find interesting. Small notes. As small as you can make them, really5. Categorize them. Over time, those notes will reach out to one another. Patterns will emerge. Observations, thoughts, connections. Then the writing you’ve been doing becomes a different form of writing altogether. Instead of reaching for the thought as you’re reaching for the word, you’re recording what already in your head (while presumably adding the intangibles that make your writing your writing).

    If you’ve ever used any kind of “personal knowledge base,” this is probably duh territory. But for me, it was revelatory. It was a complete shift in how I’ve always thought about writing, and more importantly, it meshed perfectly with the idea of wanting to write in a way that ignores self and presentation. It’s an intrinsically self-suffused system, in which the words on the page are simply the final manifestation of a long process of collection and synthesis.

    Of course, the distance between “finding an idea compelling” and “putting the idea into practice” can be vast. And to complicate things even more, “putting into practice” can mean multiple things. Some of those things I’ve done: read differently, take better notes, try to keep better track of my own thinking. But I hadn’t found an opportunity to use all that in the service of a specific project. And then came the year-end essay I had to write for Longreads.

    So, this time, I resolved to go notes-first. I re-read all the articles I’d earmarked, taking notes every time a thought occurred to me6; if one thought felt related to a thought I’d already written down, I linked the notes. Ultimately, they started to take some sort of shape, and I could see the ideas that were linking multiple pieces.

    Obsidian’s “graph view” renders all your notes visually, so you can start to see connections between ideas that you jotted down months or even years apart. (This is a zoomed-out view, to spare you the mess of text.)

    That itself wasn’t an earth-shaking shift. It was a small group of pieces that I’d already considered to be thematically linked, so none of the common threads among them were surprising. What was more important was that I was no longer keeping thoughts in my head. Even if something felt like a passing observation, I jotted it down. I didn’t need to remember it anymore; it was just waiting for me, a sentence without a home. This wasn’t a hit-or-miss phenomenon, either: most of those notes made it into the finished piece.

    As people, we like to think that we can hold on to information, but we also hugely overestimate our ability to do so. So many of our thoughts pop up and then disappear. Some are eclipsed by other ideas that feel more important, others are crowded to the margins, and a lot of them just blink out of existence altogether. (Believe me when I say that the four decades’ worth of rap lyrics in my head don’t like making room for new neighbors.) And the things that are easily retrievable aren’t things we’ve recently learned. It’s the things that have been drummed into our brains over time by repetition: the childhood phone numbers; the TV theme songs; the things we actively studied and memorized. That leaves a vast sea of things that we want to remember—that we would probably find helpful to remember—but probably never will.

    I never really took notes when I read because it didn’t seem like it had a point. Scribbling in the margin of a book means that I’d have to go back through that book again, which … why? But now those notes are Lego blocks. Get enough of them together, and they start to fit together in different way—some obvious, some not. The key is that they’re always there when you open the box.

    1. That’ll teach me to wait until January to write something about 2024, I guess. ↩︎
    2. I think it went something like:
      Her: Hey, I got this book, and it sounds interesting, but I feel like I won’t do anything about it. Will you read it too and see if it’s something you want to do?
      Me: Sure! ↩︎
    3. Seriously, anywhere you keep any digital documents: your computer’s file system, Dropbox, Google Drive, Notion, you name it. ↩︎
    4. This time it went something more like:
      Me: I don’t know what’s going on when I sit down to write these days. My brain feels kinda gunked up?
      Her: Oh, you should read this book I have. ↩︎
    5. I’ve seen the term “atomic” used—in part due to the book Atomic Habits, I’m guessing—but the name doesn’t really matter. What does matter is to try to keep each note to a single idea or thought so that later you can find them and combine those thoughts as easily as possible. ↩︎
    6. I use Readwise’s Reader, a fantastic app that handles just about every kind of readable or watchable content: ebooks, PDFs, websites, emails, and more. Anything you highlight in Reader automagically ports over to Readwise itself, as well as to any other note-taking app it can talk to. In my case, those highlights (and notes I make on those highlights) show up in Obsidian. ↩︎

  • Wax Poetics: A Dancehall/Dub Vinyl Haul

    Picked up a few goodies as a holiday present for myself, presented here in no particular order.

    Clockwise from top left:

    King Tubby’s Presents Soundclash Dubplate Style (1988): When sound systems clash, they do so by playing specials—personalized versions of popular songs, with lyrics that exalt or insult a given sound, cut on metal records known as dubplates. Sweet sounds, aggressive sentiment. This LP collects some of Tubby’s countless dubplates, all from the mid-’80s and introduced by the late legendary trash-talker Fuzzy Jones (who rap fans would know from Smif-n-Wessun’s “Sound Bwoy Bureill” and Kanye West’s “Mercy”).

    [Spotify]

    Johnny Osbourne, Nightfall (1981): One of my all-time favorite singers1, backed by my all-time favorite session crew (Roots Radics) and mixed by my all-time favorite engineer (Scientist). This finally got a re-press in 2019, courtesy of producer Linval Thompson; there was apparently a limited colored-vinyl version released for Record Store Day that same year, but I have zero complaints about mine (which is apparently the Spanish version). Listen to “Kiss Somebody” once and tell me you won’t be walking around singing it for weeks.

    [Spotify]

    Barrington Levy, Poorman Style (1982): More Roots Radics/Scientist goodness, this time supporting the incomparable Barrington Levy. This doesn’t have many of his most famous hits, but I’ve loved it since I plucked it out of the CD rack at Jammyland twenty-odd years ago. (Brits may recognize the cover of the UK release on Trojan, which treats “Poor Man” as two words.)

    [Spotify]

    Johnny Clarke, Dread a Dub (2012): Johnny Clarke ran things in the mid-late ’70s, and was the face of the “flying cymbals” and “rockers” sounds that were producer Bunny Lee’s signatures. This compilation gathers dub versions of some of Clarke’s biggest tunes—vocals reduced to snippets, mixed with heavy reverb and lots of space. The musicians on these tracks are some of reggae’s finest, assembled as Lee’s house band The Aggrovators: Sly and Robbie, pianist Jackie Mittoo, flying cymbal originator Carlton Davis, and more. If you’re a newcomer to dub, this is a solid place to start.

    [Spotify]

    Roots Radics, Live at Channel One in Jamaica (1982): This is a great album, and a beautiful reissue, with a white-and-gray vinyl pattern that almost looks like marble; it’s not, however, a great record. Not sure if it’s the pressing or what, but I couldn’t get through a song without it skipping, and that’s straight out of the shrinkwrap. I’ll see if another cartridge helps, but at least it can’t stop you from enjoying it on streaming.

    [Spotify]

    Junjo Presents: Heavyweight Dub Champion (1980): Roots Radics on the music. Scientist at the controls, this time as a dub mastermind. And Henry “Junjo” Lawes producing. You want my exact Venn diagram of perfect music? This is it. Lawes was a giant of reggae’s late ’70s/early ’80s rub a dub era; not only did his Volcano label release massive artists like Barrington Levy and Eek-a-Mouse, but its namesake soundsystem (Volcano Hi-Power) ruled the dance, thanks in no small part to dancehall king Yellowman.

    The first disc in this set reworks most of the songs from Barrington Levy’s 1980 album Robin Hood inna dub style, and the second disc includes the originals, though sequenced differently from the album. A complete package in every sense of the term.

    [Spotify]

    1. Strictly speaking, he’s probably more of a singjay—a singer with a DJ’s chanting cadences. (In reggae, a “DJ” is a vocal artist, and a “selector” plays the actual records.) ↩︎

  • Thinking Different

    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.

    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.

    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.” ↩︎

  • The Front of the Book

    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.

    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. ↩︎

  • New Foundations

    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.

    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.”)

    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. ↩︎