Annie and I had sold our book, Good Writing: 36 Ways to Improve Your Sentences. Well, our agent had sold it. A couple of weeks later, in the blissful early days between signing the contract (easy) and completing the manuscript (hard), I was strolling down the street with hardly a care. Our dead-end block is lined with sycamore trees that form a 30-foot-high bough over the narrow asphalt, so it’s a pretty nice place to set to thinking. And pow! A thought made it all the way into my brain.

“These so-called rules are algorithms. Maybe the book is also an app.” That’s two thoughts. I praised my septuagenarian cranium.

CLICK TO TRY THE APP

The last time I programmed anything it was 1981 and I needed to get a 5 ¼-inch VisiCalc floppy disc to talk to my Radio Shack computer, which thought in Basic. I remember a command called Poke, which did just that and got snatches of new code inserted into long lines of old code.

I set up a Zoom with an LA couple I know who create augmented reality art works. They bit, and agreed to build a prototype. In a few months we had a good-looking interface, some proof-of-concept success in getting a handful of rules to interact properly, and a great marketing video.

The idea is that you paste a writing passage of your own into the app on your phone or tablet, and it returns a mark-up with suggestions for changes. It doesn’t rewrite or even offer new wording, just points out the weak areas for you to work on, and tells you the rule so you can relearn it or refer back to the book.

This was midyear 2025, and with dismay I watched AI race through puberty and careen into adolescence. What need for an app if anyone could train AI to do the same thing? Having spent all the money I had budgeted, I prepared to bail out.

But just in case, I asked my friend Jon in San Diego whether he might take a look. An expert programmer working a corporate management job, Jon happened to be developing an AI program to take over his own job.

Before continuing, let’s be clear on the boundaries I believe in for working with AI.

1. If you are not a writer and don’t expect to ever become one, go ahead and use AI to write as you wish. You are not my concern.

2. If you care about writing, don’t let AI take over the task. Make your own sentences, and make them better yourself. Writers puzzle out sentences; in doing so they find meaning. If AI solves the puzzle for you, why write?

3. If you are pretty sure of your grammar but know that you’re no expert, go ahead and let Grammarly or the like copyedit a final version. If Grammarly is finding more than one mistake a page, take a break to study syntax or spelling or whatever’s your problem.

4. If you’ve already written a first draft, with a structure and a theme and characters and events in place, it’s OK to ask AI to write an editor’s note for you. It’ll be a humdinger. AI is great for suggestions from 10,000 feet. You’ll eventually have a human book editor, but in the meantime AI can be a great support.

5. And finally, Rule 2 again. If you care about writing, don’t let AI take over the task. Make your own sentences, and make them better.

Let’s now get back to Jon, who unexpectedly is laid off from his nine-to-five job before he can get his bot to take it over. Jon now had time on his hands, and enough of a cushion to dive into my app for a while. My LA friends retired from the project. I told Jon that if he wanted to, he could work on it, but if he didn’t, I was happy to shut it down: “It’s your call. I can’t pay you, and I can’t vouch for the app’s potential. You’re the AI expert. The risk is all yours now.”

As Jon tinkered with the app, he realized that the algorithms only looked simple, as if anyone could get AI to quickly code them. As it turns out, human language is not particularly logical; this is the core of what Noam Chomsky discovered in the late 1950s, changing the study of linguistics forever. Some of our app’s algorithms would require multiple AI platforms and weeks and months of training the AI platforms to reduce false positives and negatives. The degree of difficulty in getting the app to work was convincing Jon that it had a future.

Jon, by the way, had readily agreed to my requirement that the app remain pedagogically sound. It would reinforce the rules, but wouldn’t rewrite. Our first idea for a marketing slogan was, “It’s a teacher, not a cheater.” The Good Writing app would offer real-time reinforcement of good writing habits, even to the point that teachers using the Good Writing book in class could support the app’s use. I didn’t have to explain the boundaries to Jon. His wife is a writer, and he knew what was good for the marriage. “My friends are nice people who hate all writing apps,” she said with her arms crossed. “You better not piss them off.”

Sooner than I expected, Jon had a beta version of the app out to a number of volunteer writers for testing. The feedback was more than encouraging. People were using it. Some leaned into it, feeding it multiple writing projects and learning along the way.

“I love that it gooses the writer to do better without providing exact suggestions,” beta tester Tracey T. wrote to Jon. “This is AI at its best – assisting without taking away the writer’s voice.”

It’s always kind of amazing to an author that people actually read the book and dumbfounding when they praise it. Double that surprise for an app that seemed obsolete before it was launched. I remain slightly flabbergasted that it’s actually out there. Hey, it was a stray thought of mine on a walk in the neighborhood, a small notion.

Today is the launch of the complete version. If you click below, you’ll get a free trial of a lite version. And if you already own a copy of Good Writing the book, you can retrieve two months free of the full app capabilities. Don’t thank me. I get a little credit for having the original idea, but Jon gets much more credit for believing in it and persisting until this day arrived.

REALLY, CLICK HERE FOR THE APP

goodwriting.app

Glad you’re here. My new book on writing made the bestseller list, so now I’m an expert, right?

Writing isn’t magic. No one’s born talented. Exactly like plumbing, gardening, driving, and emptying the dishwasher, writing is explored by apprenticing and doing it.

My wife and co-author, Anne Lamott, might tell you that she became a writer because it’s the one career that indulges her favorite pastime, reading. Once she decided to make a living at writing, so she could read more, she bore down on it with the steadfast grind that she had learned as a masterful tennis player (Canadian under-16 doubles champion 1969).

A continent apart (she was raised in California, me in Virginia), we read the same books and harbored the same authorial hopes. I bore down on it starting in my 20s as a newspaper reporter.

Magical writing is sleight-of-hand. Mostly it’s taking observations and filling them with fictional words that have the ring of precision like the tiny triangle’s vibration peeking out of the orchestra.

When I write about anything — my common topics are the inner critic and spirituality, and now writing itself — it’s only because something’s caught my attention. I use writing to explore my interests, refine my understandings, research my blind spots, and collect it all into a rational, economical blather. Only then can I drop that interest and find another one.

So I don’t know where this newsletter will take me.

Also, I like to plug my retreats and the app I thought up that accompanies Annie’s and my little book, Good Writing: 36 Ways to Improve Your Sentences. It’s an app that looks at your sentences and instead of rewriting them itself, flags weaknesses, lets you know why what you’ve got could be improved, and leaves it up to you to make a change. Or not. You can check it out here: goodwriting.app.

Five Days to Better Writing through Self-Trust

Montana Writing Retreat with Neal Allen

September 20-25, 2026

CLICK HERE FOR MORE INFORMATION

That sentence got rewritten in at least a dozen ways, in three minutes. Writing observes the world and explores both the observation and the act of observing. The point of view, even when expressed in the third person, is always internal. The subject matter is my current fascination and I get to explore it by changing the words, adding and removing precision, metaphor, jargon, and atmosphere. As the words of the sentence reformulate, my mood changes, and I notice that, too. The word “Teslas” sneered for a moment, but the entry of a boyhood memory — Matchbox cars in a row — wiped away the smirk, and I softened. Plus the sentence became shapely.

I’ve never thought of writing as anything more than a way to puzzle things out. It’s the same to me whether I’m interrogating my own interests or those of my boss.

So why do I write, if not for finding the artist within or the happy self hidden by the fearmonger? Why don’t I feel a call to self-expression?

In my last post, I wrote about another way I’m not driven to write: I’m not seeking glamor, fame, wealth, or power. I used to, but then I got real. Darn.

Mostly writing has been a job like other jobs I’ve had that weren’t writing: as a publisher, a PR guy, a corporate strategist, a marketing executive, a boss and a prep cook, a bank teller and a student, a coach, a government clerk, and even a father. Some other labels. Mr. Anne Lamott. A San Francisco Giants fan. A gardener. A road biker. None of these roles seemed any less creative than any other. Mr. Anne Lamont engages as the straight man in the improv comedies that Annie cooks up from daily life. (Annie, sighing during a CNN commercial break: “My days as a serial killer are numbered.” Me: “Lost a step with age?” Annie: “It’s not a fair game anymore with Stephen Miller and Elon Musk in the field.”)

In an apocryphal quote, Kierkegaard reminds us that we arrive on Earth carrying sealed orders. The implication is that we die handcuffed to the same locked briefcase. I think that’s right. My ego tells me that my life’s achievements are mine, as if I created my circumstances. Reality tells me that I’ve been dragged through the days by the happenstances of my parents, friends, teachers, family income, children, surroundings, cultural fads and prejudices, all of the winds of fate blown through me by a biological force that cares about only two things: more individuals, and more individuals in more places.

Kurt Vonnegut put it like this:

Oh, a sleeping drunkard
Up in Central Park,
And a lion-hunter
In the jungle dark,
And a Chinese dentist,
And a British queen--
All fit together
In the same machine.
Nice, nice, very nice;
Nice, nice, very nice;
Nice, nice very nice--
So many different people
In the same device.

We’re all tangled in an interdependent world that gives each individual a first-person view into a tiny fraction of the picture. With no one to stop us – I am never thinking inside your thoughts or experiences – each of us tends to wildly extrapolate our influence as if our trivial perspective were statistically relevant.

Let’s take a normal president. (This works for abnormal presidents, too, but I don’t want the current situation to distract you like algae in a swimming pool.) A president, just like my neighbor Charlie down the street, or you, probably, has a significant conversation with at most twenty people a day. You might have fewer or more, but hardly anybody directly influences more than about 20 in a day. It’s not a large number. Everybody influences a few people and like a game of telephone, your words and actions keep going out and out and out until they’re fully absorbed into the maelstrom. The Queen of England’s role is equal in biological significance to the sleeping drunkard in Central Park, or to Charlie, or to the president, or to you.

If asked who influenced your life most, you might include a few books, but that’s not true. A few people influenced your life the most, and they were folks who were in direct contact with you. We’re copy-cats. The world is a high-touch place, and jobs and roles are a high-touch business. AI may reign as an authority, but the humans around the machines are taking direction from a few humans and giving direction to a few more humans.

My role, which emerges at times as a productive strand in the grand species network, is not just determined for me – it also has no more weight than anyone else’s role. Vonnegut’s “device” might as well be a jigsaw puzzle: Each of us is a tiny die-cut shape, different from the ones next to me but like-sized and equal in value.

My interests are translated to me in thoughts. I’m just narrating as I go along. Mostly they’re about distinguishing self from other: relating what I sense around me to what I’ve said about things before. All of my daily experiences are fully organized on their own; I just pick some components out and make connections. What if consciousness and thought and writing and conversation are just the play of fascination?

Five Days to Better Writing through Self-Trust

Montana Writing Retreat with Neal Allen

September 20-25, 2026

CLICK HERE FOR MORE INFORMATION

In 1970 I’m a 15-year-old junior in suburban DC. Annie’s a 16-year-old senior in a San Francisco suburb. A continent apart, we share the same roster of heroes. We are reading the same books. It’s hard to believe, but culture had yet to fragment into tribal identities. All of our important teachers and professors, our peers, the book reviewers, and the style makers praised Updike and Baldwin, listened to Miles and Monk, caught the new Truffaut and admired Rauschenberg. Culture was still monolithic and thought to be a meritocracy. It would be close to a decade before the Eagles and Madonna, Spielberg and Lucas, and Bret Easton Ellis and Jay McInerney opened the door for facile, meretricious works to be labeled genius.

In 1970 Henry Miller — my personal hero — was winding down his life, holding salons at his porticoed home six blocks from a beach near Santa Monica. I completed Dashiell Hammett and moved onto Thomas Wolfe. Annie’s paragon, J.D. Salinger, had released his final public writing five years earlier. Next stop for Annie was Virginia Woolf, including all six volumes of her letters.

These were and are among our formative authors, as influential as Shakespeare and Austen and Dostoevsky would be in college. Then after college Bukowski, Beriault, Olds, Morrison, Portis, Calvino, and on and on.

We trained. Mostly by reading well. And suddenly in 1980, Annie and I were both ordained professional writers. That year my wife published her first novel a few days after her 26th birthday, and a daily newspaper printed my first story as a staff writer. A continent apart, we had shared the same exemplars and dreams, and hadn’t given up.

To me, with success might eventually come the glamor of Paris cafe society, the Algonquin Roundtable, and fireworks in the Hamptons with Gay Talese. Or the reverse glamor of the down-and-outs toughing it out in an blisteringly intense reality: Miller and Orwell in Paris and London, the Beats in Tangier, Exley and McGuane in the Keys. These were my visions.

Annie knew better. The child of a literary father, her family’s Marin County living room unveiled the drunken sloppiness, questionable morality, and sketchy brinksmanship that passed for salons of witty banter. The reality that irony and glamor prevent intimacy was exposed in her own house. And she could see that the average literary writer lived on hot dogs and Four Roses in shabby apartments. Glamor, no, Annie had no illusions. But respect and notice from the day’s literati? Yes, that was a substantial goal, and it required an East Coast stamp, from the New Yorker and the New York Times mainly. That was Annie’s vision.

Here our stories part. From the start, Annie was brave and I was chicken. If she was to be a famous writer, she must produce her first novel. As soon as material presented itself — her father’s brain tumor — the process began. Her father encouraged it, with the remark, “Why don’t we both record what happens to me?” His draft petered out quickly, as his cognition declined. Annie stuck with it, and her novel about a family in shock, titled Hard Laughter, put her on the map. And it would be hot dogs and Four Roses for a long time.

Me? I went for a steady income, and landed a reporting job at an upstate New York daily with an annual salary of $12,500, almost double what Annie lived on. Within a few years I was making $45,000 as a publisher for a chain, then back down to $25,000 as a reporter again, rising to nearly $40,000 for a large Jersey daily. I bought a house, supported a wife who was trying to make it in the New York art world, and figured I would get around to novels at some point.

From my first days in newspapers, forty years sped past before I took novel writing seriously. Meanwhile, Annie built her literary reputation with a series of novels, interrupting them with two remarkable nonfiction books, Operating Instructions and Bird by Bird, that brought her real fame and money. Her dream had come true. And there was proof of her acceptance into the literary tribe. Until she tired of it, she traveled as a regular on the writing retreat circuit, hobnobbing with the day’s literary dons as a made member. She was a single mother, so her little boy Sam came along. Her memories aren’t of witty repartee, but kind men and their wives helping out with Sam. Kurt Vonnegut, Peter Matthiessen, Frank McCourt, and Evan Connell were just guys entertaining her five-year-old.

When we met nearly ten years ago, I was completing my first book, a description of a small corner of spirituality, which I wrote as if by accident in homage to a former teacher. Annie had just finished her 17th book, all of them written at her own instigation and for no other reason than that she believed they weren’t already out there. If the writing retreat circuit could be called glamorous, she had left fame and glamor behind years before we met. No writing retreats, no hanging out with famous men. Annie liked staying home and participating in the lives of old friends, few of whom were writers, and her tightknit family. She corresponded by text with near-strangers, friends of friends who found their way to her, usually because they were dying or drowning in the wake of a nearby alcoholic, never about publishing. Our days gravitated around a quiet living room that engaged in little snark other than that aimed at the Trump regime. (We fell in love two months before the 2016 election.)

Early on, Annie tied a red Buddhist string around my right wrist and prayed aloud, “May a writer’s life come to you.” She knew my history — reporting and editing, publishing, corporate communications, PR, a dozen years of strategy and product management, landing finally in executive and spiritual coaching. And a steady complaint that I hadn’t yet chased my dream. Yes, a lot of writing in there, but a hack like me was filling in the blanks for others. By “a writer’s life” Annie meant writing for myself for once.

Like in everything else in life, you do what you can. If you can write persuasive sentences, you probably trained your eye on that skill, and might well be a writer. It’s what you can do. But just because I was confident I could write well didn’t mean I was courageous in life. That’s a whole other thing.

Annie showed her courage at 19, dropping out of college because it was getting in the way of her ambition. I showed my cowardice by settling for newspapering and a regular paycheck. Straitjacketed within a format that didn’t suit my drawl, the spark in my writing style went out. I revived it briefly — quit my job, got divorced, sold the house, rented a cabin in the woods, and taught myself fiction in 1988 and 1989 — and then snuffed it for a corporate career and magnificent paychecks in the Nineties and on.

Slowly, with Annie’s encouragement, I adopted the writer’s life. Over the first year of Covid I published my spiritual book and wrote a second, this one my own. That was Better Days: Tame Your Inner Critic, based on techniques I had refined with private clients over the prior few years. As soon as it was published, I started a third book, which turned into Good Writing: 36 Ways to Improve Your Sentences, co-authored by Annie. That one got me the imprimatur of a major publishing house and the cred of making it onto the New York Times bestseller list. No glamor arrived, and my daily life didn’t change: inner critic clients, gardening, watching TV with Annie, some exercise outdoors, and a little writing.

Oh, by the way, I wrote a novel that I got into shape this year and is being pitched by my agent as you read this. Too bad Gay Talese isn’t still around. Apparently I got into the game too late to taste the glamorous life of a novelist. And besides, it has been five months and no publisher has picked it up. Maybe it sucks.

Hemingway advised writers to state what is rather than what is not. Like all rules, this one deserves to be broken at times. Despite all my 15-year-old self’s hopes, writing turned out to not be a path to glamor. So why do I still do it, and why am I finally writing novels? That’s another essay.

Five Days to Better Writing through Self-Trust

Montana Writing Retreat with Neal Allen

September 20-25, 2026

CLICK HERE FOR MORE INFORMATION

Hey kids, I’ve got an app that accompanies the book Good Writing: 36 Ways to Improve Your Sentences, co-authored by my wife, the fabulous Anne Lamott

TRY OUT THE APP