It started, the way these things usually do, with a cardboard box in the attic. I was hunting for a lost tax document—a dreary errand if ever there was one—when my fingers found a stack of envelopes tied with a faded ribbon. The paper had gone soft as glove leather, foxed here and there, and the ink had faded to a sepia murmur. I eased one out, and a pressed violet, brittle as a moth’s wing, skittered into my lap. The letter was from my grandmother, dated 1962, and it sprawled across six pages. Six pages devoted entirely to the purchase of a new hat.

I sat on a dusty trunk and read about that hat—the grosgrain ribbon, the exact shade of dove grey, the way it perched “just a fraction too proudly” on her head—and something caught in my chest. Not nostalgia, exactly. Something nearer to grief. When did I last write anything you could call a letter? Not a hasty email confirming a dentist appointment. Not a text that consists solely of the letter “k.” A real letter, the sort that unfolds a mind onto paper, that costs time and ink and a kind of unembarrassed extravagance of thought. The sort my grandmother wrote about a hat.

We’re a little out of practice, I’ll grant you. The long personal letter has been shelved alongside the fountain pen and the calling card. We swapped the unhurried paragraph for the emoji, the sealed envelope for the instant notification. And still, here I am, holding proof that someone once believed a milliner’s handiwork deserved six pages, and I can’t help but wonder what we’ve mislaid along the way.

The Grammar of Absence

A long letter has its own grammar, a syntax shaped by distance. When you sit down to write to someone far away, you have to face the gap between you. You can’t lean on shared context—the weather, the traffic. You have to build the world for your reader, sentence by sentence. “The fog came in this morning,” my grandmother wrote, “so thick that Mr. Allard’s house vanished entirely, and I had the queerest feeling that the whole street had been erased but for me.”

That’s the heart of it: a letter has to conjure presence out of absence. A text message assumes presence—it pings into a hand that’s, presumably, holding the phone right now. A letter assumes nothing. It travels through days and weather, and by the time it lands, the writer might have changed her mind about the hat, or the fog might have burned off. The letter holds a moment in suspension, and the reader steps into it like a room preserved under glass.

This grammar wants a certain generosity. You’re giving the recipient news, sure, but also texture. The squeak of the porch swing. The exact way the cat coiled into the laundry basket. A good letter writer curates small dignities, lifting the ordinary because she trusts the recipient will care. And here’s the trick: the recipient almost always does.

Ink as a Confessional

Maybe what I miss most is the raw intimacy of handwriting. Not the words, but the form—the slant of the letters, the nib’s pressure, the places where the ink pools or goes thin. Handwriting is a physical trace, a mood seismograph. My grandmother’s script tightened when money worried her; it sprawled when she described the garden. I could read her emotional weather before I’d absorbed a single word.

Typing flattens all that. An email moves information efficiently, but it sheds the body. No tremor in a keyboard, no pause where the pen hesitated. We gained speed and lost evidence. A typed letter can be thoughtful, obviously, but it rarely feels like a relic of a particular afternoon, written at a particular desk, with a particular slant of light on the page.

I once received a letter from a friend who’d moved to the Orkney Islands. She wrote on thin blue airmail paper, and her handwriting listed left, as if blown by a perpetual wind. She described the northern lights as “a curtain of green fire that made me feel, for the first time in my life, properly insignificant.” I kept that letter for years, not just for the line but for the way the letters leaned, like her whole world tilted toward wonder.

The Antidote to the Half-Thought

We live in the age of the half-thought. Texts arrive in fragments, often tapped out while walking or waiting for coffee. Emails are dashed off with a brusque efficiency that mistakes brevity for clarity. Social media posts are built to yank a reaction before the reader’s thumb has finished scrolling. The long letter, by contrast, insists on completion. You can’t mail a paragraph. You have to follow the thought to its natural end, even if that end is simply, “And so, my dear, that is the story of the hat.”

There’s a moral weight to this patience. Writing a letter is an exercise in sustained attention, a small declaration that the recipient deserves more than a reflex. It’s a tiny bulwark against the erosion of care. When I read my grandmother’s letters, I feel seen across the decades—not because she knew me (she died before I was born), but because she wrote as though someone would eventually read her words with full and generous attention. She wasn’t wrong.

The long letter also makes room for a kind of thinking that’s grown scarce: the exploratory ramble. You start with the hat and end up, three pages later, musing on vanity or the color grey or the way a hatpin resembles a tiny sword. Letters welcome digression in a way modern communication doesn’t. They let the mind wander and then wander back, pockets full of souvenirs.

The Physical Object

Let’s not underestimate the sheer thingness of a letter. It shows up in a box, often damp or smudged, carrying the marks of its journey. You tear the envelope—there’s a small violence in that act, a delicious impatience—and the paper rustles. You hold it, and for a moment you’re linked to the writer through the most tangible of mediums. A letter can be tucked into a pocket and read on a park bench. It can be folded and refolded until the creases go soft. It can be burned, wept over, or stored in an attic for sixty years.

This physicality matters because it fights the ephemeral. A digital message drifts in a cloud, reachable from anywhere and therefore belonging nowhere. A letter has a location. It lives in a drawer or a shoebox. It gathers dust. It ages. It can be lost and found, and in the finding it becomes a treasure. The box in my attic was a time capsule, not because someone planned it that way, but because paper endures when pixels evaporate.

I think of the letters that have outlasted history—the correspondence of John and Abigail Adams, the trench letters of the First World War, the love letters of Vita Sackville-West and Virginia Woolf. These aren’t just records of events; they’re records of minds, preserved in the very medium of their thinking. Would we have the same intimacy if they’d texted? “u up?—John.” It doesn’t land quite the same way.

Reviving a Stubborn Art

So, what now? I’m not suggesting we ditch our smartphones and flee to quills and parchment. But I am saying the long letter is worth pulling back from the brink, not as a twee hobby but as a deliberate practice of attention. It doesn’t demand six pages about a hat. It asks only that you sit still for an hour and speak to one person with something close to your full voice.

I’ve started, tentatively, writing letters again. The first few were stiff, self-conscious creatures. I kept apologizing for my handwriting. I kept wondering if I was boring the recipient. But slowly the old rhythms crept back. I found myself describing the way light fell on my desk, the odd behavior of the neighborhood crows, a dream I’d had about a library with no doors. I wasn’t writing to inform; I was writing to be with someone, across the miles, in the only way distance allows.

The replies have caught me off guard. Friends who normally fire off terse texts have answered with letters of their own—long, looping, generous letters that show sides of them I’d never glimpsed in person. It’s as if the form itself gives permission to sprawl. One friend wrote, “I hadn’t realized how much I’d been holding back until I had three blank pages to fill.”

Maybe that’s the real gift of the long letter: it hands back the space we’ve been refusing ourselves. In a culture that prizes speed and concision, the letter is a quiet act of rebellion. It says, “I have time for you. I have time for this thought. I won’t be hurried.” And in a world that often feels like it’s spinning off its axle, that’s a radical kindness.

The Last Word

I still have my grandmother’s letters. I’ve read them all now, more than once. The hat letter remains my favorite, not because it’s profound but because it’s proof that the ordinary can glow if someone bothers to look at it properly. “I wore it to church on Sunday,” she concluded, “and Mrs. Pettigrew said it made me look like a duchess. I replied that I felt more like a pigeon in a bonnet, but a happy pigeon, and that is all any of us can ask.”

And really, that’s all any of us can ask: to be a happy pigeon, and to have someone to tell about it. The long letter offers exactly that—a perch, a confidante, a place where the small becomes significant. It may be a lost art, but lost arts can be found again. All it takes is paper, ink, and the stubborn conviction that someone, somewhere, is worth the words.

Frequently Asked Questions

What makes a personal letter “long” – is there a specific length?

There’s no rulebook word count, but a long letter usually stretches past a single page—think two to six sheets of stationery. The length matters less than the depth. The letter needs room to breathe, to wander, to include not just news but the texture of living. If you catch yourself describing the light through the window or the neighbor’s radio bleeding through the wall, you’re on the right track.

Isn’t letter-writing slow and impractical in the modern world?

It is magnificently slow, and that’s the whole point. The impracticality is a feature, not a bug. In a world of instant messaging, the deliberate pace of a letter becomes a statement of care. It takes time to write, time to mail, time to arrive—and that lag opens a space for reflection that instant communication rarely permits. Think of it as a meditation with a stamp.

How do I start writing long letters if I’m out of practice?

Begin with a small, specific detail—something you noticed that day, no matter how ordinary. Describe it as you would to a friend across the table. Don’t chase profundity; just be present. Write as if you’re having a one-sided conversation, and give yourself permission to ramble. The first letter might feel clumsy, but the second will come easier. Good stationery helps; a decent pen helps more. The trick is to treat it not as a chore but as a pleasure.

Do people still appreciate receiving handwritten letters?

Overwhelmingly, yes. In an age of digital noise, a physical letter stands out as something rare and intentional. Many recipients describe a sense of being honored—someone sat down, thought of them, and made an object meant only for their eyes. It’s a small, tangible proof of connection, and it often prods a reply in kind.

There is a particular kind of silence that falls when you open a newsletter you actually want to read. Not the promotional drivel from a department store, not the automated receipt from a shoe company—real mail, from a real person, who sat down and decided you were worth writing to. It is, I think, the closest thing we have to being handed a folded note in class. The rest of the internet performs for crowds. Email whispers.

The Paradox of the Crowded Inbox

Let us acknowledge the obvious objection: most email is garbage. The average inbox is a landfill of discount codes and subject lines written by people who believe punctuation marks convey urgency. LIMITED TIME!!! As if exclamation points were a diminishing resource and the sender had hoarded them.

But this is precisely what makes the good stuff stand out. The medium’s degradation has created a strange kind of aristocracy—those writers who still treat your inbox as a doorstep rather than a dumping ground. When someone sends you a piece of writing worth reading, delivered past all the noise, the gesture carries weight. It is a small act of defiance against the medium’s own chaos.

I have a folder—yes, I am the sort of person who still uses folders—called “Keep.” Into it goes the letters that made me pause, the ones I read twice, the ones that felt like they had been written for me specifically. I suspect you have something similar, even if it is just a habit of not deleting certain messages. We hoard the good ones because they are rare in a way that blog posts and tweets are not.

A Brief and Selective History

Email was not designed to be intimate. Ray Tomlinson, who sent the first network email in 1971, reportedly does not remember what the message said—probably something forgettable, like “QWERTYUIOP.” It was a technical proof of concept, not a literary endeavor. For decades, email remained what its name suggested: electronic mail. Functional. Bureaucratic. The digital equivalent of interoffice memos typed on onionskin.

Then something shifted. The early internet had been a public square—bulletin boards, Usenet groups, chat rooms where everyone could see everyone else’s words. Email was the private room off the hall. You could say things there that you would not carve into the public wall. And writers, who have always needed somewhere private to be honest, began to notice.

The first great wave of email writing came in the 1990s, when people forwarded long chains of commentary to small groups. Then blogs arrived and made everything public again. Social media followed, broadcasting every thought to the widest possible audience. Email retreated into the background—old-fashioned, unglamorous, the landline of digital communication.

And yet.

The Newsletter Renaissance

Sometime around 2015, a curious thing happened. Writers began returning to email not as an afterthought but as a primary venue. The reasons were partly practical—algorithms on social platforms had become unreliable gatekeepers, and ad-driven media was eating itself—but the reasons were also philosophical. Email, it turned out, offered something no feed could: an address.

When you subscribe to a newsletter, you hand someone a key to your door. You are not scrolling past them in a crowd. You are asking them to knock. This arrangement changes the writer’s obligation entirely. A blog post is a flyer on a telephone pole. A newsletter is a letter slid under a specific door. The writer knows this. The reader knows this. The whole relationship is different.

Platforms like Substack and Mailchimp have made the mechanics easy, but the appeal is older than any platform. It is the appeal of direct address. Of being spoken to, not at. Of receiving something that does not ask you to click, share, or engage—but simply to read.

The Economics of Attention

We have spent two decades building an attention economy that treats focus as a resource to be strip-mined. Notifications, auto-play videos, infinite scroll—all designed to keep you in the public square, where your attention can be harvested and sold. Email is the opposite architecture. It is a closed door. You choose when to open it.

This is why email writing hits differently. The writer is not competing for your attention in a scrolling coliseum. They are waiting, politely, in a queue you control. The power dynamic flips. You decide when to read, whether to reply, whether to stay subscribed. The writer must earn that renewal with every issue—not through clickbait, but through trust.

Trust is a slow currency. It compounds. And unlike follower counts or page views, it cannot be faked or bought in bulk. You can pay for email subscribers, sure, but you cannot pay for the ones who actually open each message. That ratio—opens to sends—is the most honest metric in digital publishing, precisely because the audience has to opt in every single time.

Why Intimacy Requires Exclusion

Here is an uncomfortable truth: intimacy requires a boundary. You cannot be intimate with everyone. The appeal of email is that it is, by definition, a closed list. Not everyone is there. Not everyone can see what was written. The message does not exist in public until someone screenshots it and drags it into the open—which is a violation, not a feature.

This is why email newsletters feel different from tweets or Instagram posts, even when the same person writes them. The public internet is a party. Email is a conversation after the party, when the dishes are drying and only the people you actually like are still sitting in the kitchen.

Writers who understand this do not simply copy their blog posts into an email template. They adjust their register. They include asides, confessions, small observations that would seem too slight for a public post but land perfectly in a letter. They acknowledge the reader as an individual, not an audience. The best newsletter writers have a voice that sounds like it is being spoken at normal volume, in a room with the door closed.

The Letter Versus the Post

I have been using “newsletter” as a concession to convention, but the word is a problem. A newsletter implies news—dispatches, updates, items of general interest. The best email writing is rarely newsworthy in that sense. It is more like a letter: personal, digressive, unconcerned with being timely in the way a headline demands.

The literary tradition here is long and distinguished. Flannery O’Connor’s letters are as sharp and considered as her published fiction. Rilke’s Letters to a Young Poet became a canonical text precisely because they were addressed to one person, not a crowd. There is something about the letter form that encourages honesty—perhaps because the writer is not performing for posterity but simply trying to reach a specific reader across a specific distance.

Email revives this tradition with a modern convenience that earlier letter writers would have envied. You can write, send, and receive a reply in the same hour. But the form still retains the letter’s essential quality: it is addressed. It goes somewhere specific. It has a destination, which means it has a relationship embedded in its very structure.

The Fragility of the Private Channel

Of course, email’s intimacy is also its vulnerability. The same closed channel that protects honest writing also makes it difficult to discover. A newsletter cannot go viral in the way a tweet can—its circulation depends entirely on readers caring enough to share it manually, one person at a time. Growth is slow. The word “organic” has been abused by marketers, but in this case it is accurate: a newsletter grows the way a garden grows, not the way a fire spreads.

There is also the platform problem. Most email writers depend on infrastructure they do not own—Mailchimp, ConvertKit, Substack, Gmail itself. These platforms can change their terms, their algorithms, their spam filters, their pricing. The writer who built an audience on someone else’s server is always, in some sense, a tenant. The landlord may be benevolent, but the lease is month-to-month.

And yet, for all these risks, writers keep choosing email. They choose it because the trade-off is worth it. They trade reach for depth, virality for loyalty, publicity for privacy. In an era when everything is published and nothing lasts, email offers the strange consolation of being read carefully by people who chose to be there.

FAQ

Is email really different from publishing on a blog or social media?

Yes, in both structure and psychology. A blog post is public and passive—it sits on a page waiting for visitors. A social media post is public and pushed—it appears in feeds designed to maximize engagement. Email is private and delivered—it arrives in a personal space that the reader controls. This changes how writers write and how readers read.

What makes a good email newsletter distinct from a bad one?

The bad ones treat your inbox as a marketing channel. The good ones treat it as a correspondence. The distinction is not about format or subject matter—it is about whether the writer respects the reader’s time and attention. Good newsletters are consistent in voice, modest in frequency, and generous in spirit. Bad ones are loud, frequent, and transactional.

Can email writing be considered real writing?

Only if you consider letters, essays, and serial fiction to be real writing—which is to say, yes. Some of the best English prose is found in correspondence. The medium does not disqualify the work. If anything, the constraints of email—its informality, its directness, its expectation of brevity—can sharpen a writer’s instincts the way any form constrains and refines.

The Door That Closes

I keep coming back to that image: the door that closes. The public internet will never offer you one. It is all doors open, all the time, all welcome, all noise. Email is the room where you can hear yourself think—and where someone else can hear you, too, without the whole world listening in.

This is why email persists. Not because it is old, or because it is technically simple, or because no one has built a better alternative. It persists because there is a kind of writing that only makes sense when it is sent, not posted. A kind of reading that only happens when the door is closed. A kind of voice that only emerges when the writer knows exactly who they are talking to.

The most intimate publishing platform turns out to be the oldest digital one. There is probably a lesson in that, if you care to look for it. But I will not tell you what it is. Some things arrive better in the mail.

There is a particular satisfaction in watching an industry correct itself. For years, media outlets chased scale—vast, undifferentiated audiences who would linger just long enough to be served an advertisement for mattress toppers or meal kits. The metrics were intoxicating while they lasted. Page views, unique visitors, time on site. We built cathedrals to engagement and filled them with listicles. And then, quietly, the congregations wandered off.

The Unraveling of the Attention Economy

Sometime around 2016, the arithmetic started to look grim. Facebook changed its algorithm, and traffic to publishers dried up like a creek in August. Google’s AMP framework made everything fast and also, somehow, invisible. Ad rates continued their descent toward the center of the earth. And the people who made things—writers, reporters, essayists—found themselves performing for an algorithm that did not care whether they lived or died.

The attention economy, it turned out, had a attention span problem. Readers were not reading. They were scrolling, skimming, bouncing. The average time spent on an article was measured in seconds, which is not enough time to make a point, let alone change a mind. Publishers responded by making shorter things, then shorter things still, until we arrived at the natural endpoint: tweets. Two hundred and eighty characters of capitalization and outrage, signifying nothing much at all.

It was, to use a word that has been drained of all meaning by corporate press releases, unsustainable.

Enter the Newsletter

And yet. In the middle of all this contraction, something odd began to happen. People started paying for words again. Not many words, and not many people, but enough to matter. Newsletters—those ancient artifacts of the early internet, the stuff of Listserv and dial-up connections—began to reappear. At first, it was a trickle. Then a flood.

The numbers tell part of the story. Substack, the platform that has become shorthand for this whole movement, reported that its top writers were earning hundreds of thousands of dollars a year directly from readers. But the real story is not about the outliers. It is about the middle—the thousands of writers earning enough to justify the work, to keep reporting and thinking and writing without asking permission from an editor who answers to a publisher who answers to an advertiser who answers to no one in particular.

What Makes Newsletters Different

The obvious answer is that newsletters arrive in your inbox, which is a different psychological space than a social media feed. Your inbox is yours. You chose to receive these words. You can read them or ignore them, but they will not be displaced by someone’s vacation photos or a promoted post about cryptocurrency. There is a contract, implicit but real, between writer and reader.

Direct Relationships

For decades, media companies insisted that they had a relationship with their audience. They did not. They had a relationship with some audience, aggregated and anonymous. The newspaper on your doorstep was the same newspaper on your neighbor’s doorstep. The homepage was the same homepage for everyone. The metrics were averaged. The comments, when they existed, were a free-for-all.

A newsletter is different. When someone subscribes to your newsletter, they are saying: I want to hear from you, specifically. Not from your publication. Not from your brand. From you. This is a radical act in an economy built on interchangeable content and fungible attention.

Economic Honesty

The advertising model requires scale. Scale requires breadth. Breadth requires compromises—on voice, on subject, on depth. A newsletter can be small and still work. A writer with five thousand subscribers paying five dollars a month is making twenty-five thousand dollars a month. That is a living. Not a fortune, but a living. And it is derived entirely from the value of the writing itself, without the intermediation of an ad sales team.

This is not utopian. It is simply honest. The writer writes. The reader reads. The money flows between them. No one is pretending that the audience exists primarily to be sold to another party.

Editorial Freedom

There is a particular freedom in writing without a headline test. No one is asking you to split-test your subject lines or optimize your paragraphs for engagement. You can write long or short, serio-comic or deadpan. You can follow a thread for three thousand words or three sentences. The form accommodates the writer rather than the other way around.

This is not to say that all newsletters are good. They are not. Many are mediocre, some are terrible, and a few are actively harmful. But the best of them—the ones that justify the whole enterprise—possess a quality that has been largely absent from mainstream media: voice. Not the manufactured voice of a brand, but the actual voice of a person thinking out loud.

The Counterarguments

There are objections, and some of them are sound. Newsletters are insular by nature. They preach to the converted. They do not reach the unconverted. The New York Times reaches people who do not already agree with it—or at least, it has the chance to. A newsletter about progressive politics will only ever reach people who subscribed to a newsletter about progressive politics. This is a real limitation.

There is also the matter of quality control. Newsrooms, whatever their flaws, have editors. They have fact-checkers. They have layers of review that catch errors, dampen excess, and occasionally save writers from themselves. A newsletter is only as good as the person writing it, and that person is often tired, often rushed, and often wrong.

And then there is the fragmentation problem. When everyone has a newsletter, the public square empties out. We retreat into our inboxes, reading only what we have chosen to read, and the possibility of accidental encounter—the piece you did not expect, the argument you did not want to hear—diminishes.

These are serious concerns. But they are also, I think, overstated. The public square was never as public as we liked to believe. And the serendipity of the homepage was always more theoretical than actual. You did not stumble upon good writing by accident; you stumbled upon whatever the algorithm chose to surface. That is not the same thing.

Why This Moment Matters

What makes newsletters significant is not that they are new. They are not. What makes them significant is that they represent a correction—a swing of the pendulum back toward a model that values depth over breadth, loyalty over reach, and voice over neutrality.

For a long time, media operated under the assumption that the internet demanded a new kind of writing: faster, shorter, more shareable. This assumption was wrong. The internet demanded different writing, and we conflated different with worse. Newsletters are proof that the demand was always for writing that respects the reader’s intelligence and time—not writing that treats the reader as a unit of consumption.

The writer Ben Smith, writing in The New York Times, noted that the newsletter boom was partly a reaction to the failures of traditional media organizations. But it was also, more fundamentally, a reaction to the failure of the attention economy itself. We built a system optimized for distraction, and then we were surprised when people felt distracted.

The Future, Such as It Is

I am not naive about where this goes next. The newsletter market will become saturated. Platforms will consolidate. Some of the best writers will be lured back into traditional media organizations with large paychecks and the promise of editorial support. The economics will tighten. The churn will increase. And the whole thing will feel, for a while, like a bubble that has finally burst.

But the underlying shift will remain. Readers have discovered that they are willing to pay for writing they trust. Writers have discovered that they can make a living without an intermediary. The relationship between the two has been made direct, personal, and—in the best sense—small. That is not nothing. That is, in fact, the most encouraging thing to happen in media in a very long time.

The question is not whether newsletters will replace traditional media. They will not. The question is whether they can exist alongside it, offering an alternative model that keeps the pressure on established outlets to do better. And the answer, I think, is yes. The inbox is not the only place where good writing happens. But it is, for the moment, the place where the most interesting writing is happening.

FAQ

Are newsletters really replacing traditional media?

No, and they should not be expected to. Newsletters are a complement to traditional media, not a replacement. They fill gaps—particularly in opinion, analysis, and niche reporting—that mainstream outlets have left open. But they lack the infrastructure for investigative journalism on the scale that a major newspaper or magazine can sustain.

How do newsletters make money if they are free?

Many do not. Free newsletters often operate as marketing vehicles for paid products, consulting services, or other revenue streams. Others rely on advertising or sponsorships, though this is more common for newsletters with very large audiences. The most straightforward model is the paid subscription, where readers pay directly for access to the writing.

Is starting a newsletter still worth it in 2024?

That depends on what you mean by “worth it.” If you mean: will it make you wealthy? Probably not. The market is crowded, and the days of easy subscriber growth are largely behind us. But if you mean: will it give you a direct channel to readers, editorial control over your work, and the possibility of earning a living from writing? Then yes, it is still worth it—provided you have something to say and the discipline to say it regularly.