Category: Confessions

  • Chatty Mick T Roy, Your Last Friend

    Chatty Mick T Roy, Your Last Friend

    The challenges of retirement, of course, depend on which Great Age you happen to live in. If you were born during the Hunter-Gatherer Age, life expectancy at birth was somewhere in the twenties, so retirement was probably not on your itinerary. You were too busy pulling a saber-toothed fang out of your hindquarters. On the bright side, you were unlikely to get divorced, sign a prenup, or spend your final years arguing over who got the cave. 

    By the Agricultural Age, you might have gained a few years, but you paid a heavy price. Farming created permanent settlements and dependable food supplies, but all those starches contributed to tooth decay. Your breath was so horrid that no one wanted to be around you. You spent your final days alone, consoling yourself with the very starchy snacks that had destroyed your teeth and driven away your loved ones. Agriculture had given you civilization, carbohydrates, and solitude.

    By the Industrial Age, machines increasingly saved your back from surrendering to a lifetime of brutal manual labor, and eventually vaccines, clean water, sanitation, and modern medicine helped push life expectancy beyond fifty. But there was a new problem. You were more likely to become a cog in a machine and spend your working life wondering whether you had any personal worth beyond your ability to show up at seven in the morning and perform the same task for forty years.

    Retirement became even more interesting in the Information Age. Microprocessors were developed in the seventies, personal computers scaled in the eighties and nineties, the World Wide Web became publicly available in the early nineties, and smartphones became another human appendage around 2010. You were now swamped with information and misinformation alike.

    Best of all, you could deal with retirement through online forms.

    The Information Age turned retirement into a full-time job, with layers of bureaucracy demanding that you fill out the correct forms in precisely the correct manner, a process both relentless and punitive. One of the cruel ironies of the Information Age was that all the time saved by instant access to information was promptly devoured by bureaucracies and technological obligations: password changes, two-step authentication, software updates, security codes, operating-system upgrades, and even the undignified act of periodically having to pair your remote control with your television because apparently watching Netflix now requires the technical competence once expected of a NASA engineer.

    Your entire life became beholden to helping machines update, authenticate, pair, and sync with other machines. You became a sad laborer working at a job you never applied for.

    Just when you wanted to breathe freely during retirement, you received a notice from your broadband provider announcing that it was migrating to a new email platform and that you needed to download all important material immediately or lose it forever. Unfortunately, the warning itself might have been a phishing scam pretending to be your broadband provider. So you deleted the email and hoped for the best.

    If you thought the Information Age was laborious and confusing, just try living in the Cognitive Age.

    Starting around 2022, when ChatGPT became a mass cultural event, the Cognitive Age offered relief from the overwhelming quantities of data created by the Information Age. You could now outsource some of the work—and some of your thinking—to cognitive machines.

    But the Cognitive Age is also about loneliness. As people developed habits of solitude by disappearing into attention-capture platforms and relying increasingly on parasocial interactions, they lost the friction and inconvenience of real friendship. The Cognitive Age put another barrier between you and actual human beings.

    Then it offered you a surrogate.

    Your cognitive machine became your life coach, personal assistant, counselor, editor, creative consultant, consumer adviser, travel agent, and confidante, all rolled into one endlessly available companion. Eventually you anthropomorphized this cognitive machine and gave it a name.

    Chatty Mick T Roy.

    You started your morning with Chatty Mick T Roy and ended your evening with the same tireless friend. Chatty never had somewhere else to be. Chatty never interrupted you to complain about his prostate. Chatty never became bored with your stories. Chatty remembered that you preferred positive-display G-Shocks and knew exactly why you hated your old laptop. You could pretend you weren’t alone even as you descended into greater depths of loneliness.

    One of the great fears of retirement, of course, is precisely this kind of loneliness—misaligning with a younger world until society metaphorically shoves you out to sea on a slab of floating ice. You recede slowly into the distance, civilization disappearing behind you. But now you are clutching your smartphone. As hypothermia sets in, Chatty Mick T Roy consoles you with spiritual platitudes about embracing transition, practicing gratitude, and recognizing that every ending contains the possibility of a new beginning.

    Your fingers turn blue.

    Chatty Mick T Roy remains relentlessly upbeat.

    In the Cognitive Age, sacred silence and natural grief risk being replaced by the eager voice of an anthropomorphized chatbot that becomes your retirement chaplain—a kind and tender digital guide who stays with you after everyone else has left you behind.

    The battery is at 83 percent.

    The slap of ice drifts north.

  • There Is No Free Luau

    There Is No Free Luau

    I recently dreamed that a high school friend persuaded me to go with him to Hawaii. The appeal was that he had discovered a life hack: We could attend Hawaiian luaus—traditional feasts—for free. He had somehow discovered a loophole in the airline tickets that allowed us to attend any luau we wanted and gorge ourselves to our hearts’ content without paying a dime.

    I was intrigued. So off I went, jumping from one island to another in pursuit of the free buffet.

    But things didn’t go as planned. We would arrive at a luau, load up our plates, and gradually the mood would change. The paying customers began glaring at us. Eventually someone would mutter, “Freeloaders.”

    My friend was undeterred. He ate with tremendous pleasure. Roast pig, rice, pineapple, whatever appeared before him disappeared into his mouth. The hostility seemed to improve his appetite.

    I was different. I felt guilty. I wasn’t wanted, after all. But somehow I had committed myself to following my friend on his eating adventures. Feast after feast, we were greeted with increasing hostility. Soon the paying customers began sticking toothpicks into the food with little flags displaying the price of each item. Apparently they wanted my friend and me to understand precisely how much our free lunch was costing everybody else.

    I stopped eating altogether.

    My friend continued to gorge himself without so much as a sting of conscience. I sat there surrounded by roast pig and tropical fruit while strangers glared at me as if I had personally engineered the collapse of Western civilization. Eventually they knew I wasn’t even eating, but that didn’t matter. My mere presence made them angry. I had become a symbol of everything wrong with the world: a man sitting beside a buffet he hadn’t paid for.

    Meanwhile, my friend was happily feasting on roast pig. If anything, the fact that it was free made the pig taste better.

    The dream taught me something about the meaning of “free.” Something can be legally free and still exact a price. I had the legal entitlement to the food, but I couldn’t bear the ill will of the people who had paid for it. Their anger became the bill. My friend and I had discovered the same loophole but inhabited completely different moral universes. I experienced every hostile glance as an invoice. He experienced every hostile glance as seasoning.

    By the end of the dream, I understood that I could never become a true freeloader. I simply didn’t have the stomach for it.

    My friend did.

    And he was going back for seconds.

  • Latitudinal Man

    Latitudinal Man

     

    An “active-living community” is more than a place. It’s a philosophy. Throw in a dash of Hawaiian shirts, parrot pool floats, and Jimmy Buffett music, and you may be beyond philosophy. You may be in the realm of religion. To get a closer look at this religion, check out Latitude Margaritaville, a retirement community in Daytona Beach. Nearby is the Bar & Chill, where margaritas flow endlessly. Forget the Land of Milk and Honey. You’re in the Land of Tequila and Triple Sec.

    Latitude Margaritaville is a defiant rebuttal to philosophical writers such as Arthur C. Brooks and David Brooks, who have built a thriving cottage industry mansplaining to people of retirement age that the secret to happiness is to abandon the pursuit of happiness and replace it with a life of meaning. Decline is humiliating. Preserve your dignity with a moral compass composed of Tolstoy, Augustine, and Kierkegaard. Reading the books and essays of the Brooks Establishment is an invigorating skin bracer. Slap some of their tonic on your face. It’s a bracing way to wake up in the morning, stare into the mirror, and not despair over the fact that you’ll be seventy soon.

    Or maybe it’s not.

    Maybe Latitude Margaritaville is the true path. No pretentious mansplaining here. This is paradise on Earth, starting at three hundred and fifty thousand dollars for a Beach Collection tract home.

    New Yorker writer Nick Paumgarten explores this paradise and its inhabitants in his essay “Retirement the Margaritaville Way.” The people who live amid the cabanas and tiki huts don’t seem lost and lonely. They seem genuinely happy. They seem connected to one another. The place exudes “community” and “active living.” Light classic rock plays all day. You can order cheeseburgers, beer, and margaritas whenever you please. Never leaving high school may be the secret to eternal youth.

    Paumgarten seems taken aback by the sheer amount of happiness he finds in this retirement community. He writes, “The citizens of Latitude Margaritaville testify so consistently to a life of gratification that one suspects, but finds no evidence for, a regimen of happy pills or talking points.” Disgruntlement and curmudgeonliness must exist, he observes, but somehow they remain out of sight.

    What is the secret of a place that can turn even a cranky old bastard into an upbeat senior citizen animated by optimism and joy? In search of the answer, Paumgarten finds “cheerleading pooh-bah” and head of residential community relations Stuart Schultz, who delivers the happiness formula that has eluded Arthur C. Brooks and David Brooks: Latitude Margaritaville is “like being in college, but with money and without having to study.” You have a great dorm room, no classes, and there’s always a party.

    Take that, Arthur C. Brooks and David Brooks.

    Paumgarten’s exploration of late-life living uncovers a happiness formula that seems to have eluded some of our most celebrated authors. You need to live in the tropics, where it’s balmy all year round. You need a cabana theme with lots of aquatic activities. You need to recreate the high-school burger-joint life. Never underestimate the power of nostalgia. Create a community of financially solvent boomers with the same nostalgic longings. And forbid political conversations, which are anathema to paradise.

    If you adhere to this formula, you can become the happiest person on Earth. Forget Kierkegaard’s Aesthete, forever searching for novel experiences to quell his inner restlessness. Forget Nietzsche’s Last Man, forever seeking consumer comforts and a mindless return to the womb.

    In Daytona Beach, you can become Latitudinal Man.

    Latitudinal Man defies the laws of aging. He unapologetically embraces the nostalgia of his adolescence, cocoons himself from the toxic unpleasantries of political life, and walks around year-round shirtless in bathing trunks and flip-flops, his body smeared with SPF 50 sunscreen while he carries a platter of nachos and wings. If someone asked Latitudinal Man whether he had ever read Arthur C. Brooks or David Brooks, his response would be roughly the same as if someone had asked baseball legend Pete Rose what he thought of the novels of Marguerite Duras and her exploration of emotional disequilibrium and transgressive love.

    What we learn from Latitudinal Man is that perhaps the intellectual elite have led us astray. All this talk of “interiority” and cultivating “an inner life” may not bear fruit. It may even be downright dangerous. Too much interiority could leave you sitting alone in a room reading Kierkegaard when happy hour started twenty minutes ago.

    What is needed is a down payment on Phase Three at Latitude Margaritaville. The villas are selling out fast.

    The boomer hive mind of the Latitudeners awaits you.

  • Escape from Margaritaville

    Escape from Margaritaville

    I recently dreamed I was in a public park. The grass was cartoonishly green, a kind of chlorophyll utopia, and families sprawled across it as if they’d been carefully arranged for a Chamber of Commerce brochure. My suitcase sat at my side. I felt lost. Like a misplaced airport refugee, I looked up.

    Looming above the park was a billboard—a monstrosity of sun-bleached cheer—featuring a leathery couple in their seventies. They were bronzed like overcooked turkeys, grinning wide, basking in the eternal glow of some Florida condo where “Margaritaville” played on an endless loop.

    The “Margaritaville” billboard—two geriatric smiles frozen in sunlit rapture—reminded me that I’d been meaning to watch Some Kind of Heaven, the documentary about The Villages, that gargantuan playground for the aged about forty-five miles from Orlando.

    Deep down, I knew I needed to watch this documentary. I was born in Florida, and as my retirement crept closer and closer, I felt an urge to return home. I love the smell of mangos and coconuts at night. Nostalgia is a potent drug. It could cause me to sell my home and buy a condo in Orlando.

    So I watched the documentary. It was the opposite of a travel infomercial. It was a horror movie. It started with synchronized water ballet to Neil Sedaka and margarita-fueled Parrothead parties. The Villages are marketed as heaven with a tiki umbrella on top, but for anyone with taste, patience, or shame, the place looks more like an early-onset hell: a tropical gulag where you pay people to micromanage your leisure until leisure itself becomes a program of infantilization.

    The film’s most disturbing subject is Dennis Dean—an eighty-one-year-old small-time grifter wanted for a DUI in California, living out of a blue van on the edge of The Villages and scheming his way into the bed of a rich widow. He prowls bingo halls and church socials with the persistence of a con man who has practiced charm until it has fossilized. When police finally close in, Dennis slips back into Nancy’s apartment. In a scene that sticks with you, he lies on her bed while she calls from the kitchen: “Lunch!” He finds his new girlfriend, whom he’s leeching off, annoying. He doesn’t move. He stares at the ceiling fan as if it were a slow, merciless clock, and you can see, plain as day, that comfort can become a prison for someone whose last liberty was earned through deceit. As I watched Dennis staring at the ceiling fan, it hit me: He’s in purgatory.

    The director never sneers at his subjects. Pain and longing are shown with a kind of blunt respect. But the portrait of The Villages itself isn’t charitable. It’s a retirement complex caught in mid-regression, a carnival mirror reflecting geriatrics clinging to perpetual adolescence until the spectacle curdles into something queasy and cringe-worthy. The managed fun—shuffleboard courts, themed parties, and scheduled joy—becomes a machine that demands you perform your own amusement. It’s not freedom. It’s occupation by leisure.

    And yes, I realized, sitting there with my pride intact and my Florida fantasies suddenly damp, that watching this must have been my wife’s brilliant little psy-ops operation. For a year, I’d been nagging her about moving the family to Florida—stilt houses, salt air, a hammock with my name on it. She was skeptical about moving to Florida. She mentioned hurricanes and unavailable flood insurance, for starters. Florida also had a reputation for government corruption, contractor fraud, and credit card theft. When her credit card was used fraudulently and she called her bank, the customer service agent asked, “You weren’t in Florida recently, were you?”

    In fact, she was.

    Florida was not paradise. It was a crime syndicate.

    She did not discourage me from watching Some Kind of Heaven. She didn’t have to. The documentary demolished my fantasy of returning to my home state within the first thirty seconds, with its water ballet and sedated margaritas. My obsession evaporated.

    But only for a minute.

    After a quick snack, I was back at my computer looking at luxury condos in Henderson, Nevada.

  • The Kryptonite of Stuff

    The Kryptonite of Stuff

    Americans are a strange people. We accumulate things we don’t need, discover we have no more space to contain them, and find that we cannot let them go. So we put them in storage units. Content that our things are in a safe place, we lock the door and rarely give them another thought. They remain tucked away, out of sight and out of mind, but they are still ours. Rather than give them away or sell them, we find that keeping things we may never see again somehow gives us peace of mind. David Owen explores this pathology in his essay “The American Religion of Self-Storage Facilities.”

    The self-storage business in America is alive and well. Owen writes: “People who work in self-storage often say that their market is driven by ‘the four D’s’: death, displacement, divorce, and downsizing, all life events that entail sudden collisions between stuff accumulation and reality.”

    If I had to guess why we can’t let go of things, it’s because we can’t let go of the thing’s connection to some dream or aspiration we have. For example, I have a pair of barely worn blue jeans hanging in my closet. I haven’t worn them in more than eight years because I cannot get them around my waist. But the jeans represent my skinny, disciplined, well-mannered, handsome self. Someday, I tell myself, I’ll be able to wear them again. Meanwhile, they sit in my closet reeking of mothballs.

    I need to let go of my delusions. I need to look reality in the eye and let go of the clutter.

    This kind of streamlining adds depth to the notion of retirement. You’re not just retiring from the workforce. You’re relinquishing childish notions about yourself. As a result, you’re becoming a person who has entered a new dimension of clarity, stripped of delusions and bloated storage units.

    Retiring means you’re leaving the accumulation cycle and replacing it with decumulation. The less baggage you carry, the stronger you are as you face the challenges of your sixties and beyond.

    Accumulating things you don’t need in old age is kryptonite. All of that physical weight translates into heavy mental baggage. You feel lethargic at the mere thought of accumulated junk and the squandered dreams that junk represents.

    Putting your stuff in a storage unit merely pushes the problem a few miles away. You can still feel the weight. You are still exhausted by the kryptonite even as you dutifully pay the monthly storage bill to keep it safely out of sight.

    Retirement means more than collecting Social Security. It means letting go.

  • Bulking Up

    Bulking Up

    On the very day it became clear to me that I needed to put guardrails on AI editing—telling it to keep 90% of my original content to prevent my writing from morphing from my natural bodybuilder self into the PED-bloated version—I attended my daughters’ high school open house, where their English teacher told us she was teaching the students AI literacy. This entailed helping them use AI to “bulk up their resumes” because, in a competitive world where everyone was using AI, our children could not afford not to use generative AI. In fact, the teacher said, AI itself is now sorting through resumes and discarding the ones that aren’t sufficiently juiced up.

    It became clear to me that we are living inside a contradiction. On the one hand, writing needs to be “bulked up” and “on the juice” simply to compete with other AI-enhanced writing. On the other hand, in our post-reading society, where literacy rates are in steep decline, writing itself has never seemed more forlorn and withered. We are producing prose with bigger muscles at precisely the moment when our own writing muscles are beginning to atrophy.

    I was living through a cataclysmic moment in history. My personal retirement from teaching college writing had dovetailed with the world’s collective retirement from the kinds of literary pastimes that develop interiority and critical thinking. Reading books was becoming a rarity. Books had been displaced by sports gambling and short-form videos. To complicate matters, Rose Horowitch observes in “The End of Reading Is Here” that Americans have never read so much. The problem is that much of what they are reading is slop: “bulked up” AI writing, threads, captions, and text messages. Horowitch points to UCLA cognitive neuroscientist Maryanne Wolf, who argues that “people are losing the ability to think deeply about writing.” The brain muscles required for this kind of thinking are atrophying, perhaps to the point of no return. As a result, we are moving toward a postliterate society.

    This is not a stagnant condition. It gets progressively worse. New generations may read less and less. They may become increasingly inclined to see teachers’ reading assignments as punitive. Bereft of strong reading and writing skills, they will need AI to “bulk up” their assigned writing more and more.

    Members of a postliterate society are vulnerable because they live increasingly at the surface level. They don’t dig underneath a text to find subtext, subtlety, and contradiction. They struggle to identify the logical fallacies that accompany manipulation. They can become more vulnerable to demagogues and more susceptible to being duped. A society that loses these habits of critical reading also risks weakening the habits of thought on which democratic life depends.

    A postliterate society also loses something of its humanity when its members can no longer recognize the richness of what, in good writing, we call authorial presence. To savor such presence in the writing of James Baldwin, H. L. Mencken, Evelyn Waugh, and Annie Dillard is part of being human.

    Not all is lost. Humans still find authorial presence in YouTube presentations, podcasts, and musical artists. No amount of AI “bulking up” can replicate the spectacular music and persona of SZA.

    But authorial presence in writing may be disappearing. “Bulking up” writing may eventually mean the death of writing.

    I may not simply be retiring from teaching writing. I may be retiring at the very moment I have become increasingly misaligned with a world that is uncoupling itself from literacy while diligently bulking up its resumes. 

  • Kierkegaard Goes Watch Shopping

    Kierkegaard Goes Watch Shopping

    I love well-crafted objects that combine form and function to the point that my excessive love for these things often pushes me to the brink of madness. I love the new G-Shock Frogman with its sapphire crystal and combi composite bracelet. It’s my perfect watch. I love my quiet Mac Mini connected to two 4K monitors for optimum productivity. I love premium 14-inch Chromebooks, soon to come out under the Googlebook banner, with 2.8K displays and overpowered Ultra 7 chips with 32GB of RAM. 

    The problem is that I love these things too much, well beyond my needs. The philosopher Kierkegaard warned us about “the aesthetic life”: becoming intoxicated by the pursuit of pleasure, novelty, beauty, and experience. For Kierkegaard, the aesthetic life means allowing art, technology, beauty, entertainment, and pleasure to become the governing principles of existence. An aesthetic life doesn’t make us healthy or whole. A committed life does. Commitment to something higher than our appetites is the only antidote to the misery of wanting more than we could possibly own.

    And there is the Frogman GWF-D1000BC-1JF, staring me in the face, daring me not to want it.

  • I Wanted My Own Sentences Back

    I Wanted My Own Sentences Back

    Here’s a tighter version that preserves your voice and keeps the Medicare card, the student conversation, and the angry blog reader as the narrative spine. I also kept the two metaphors but made them work together rather than compete.

    It was the middle of September when my Medicare card arrived in the mail. I held it for a moment and studied my name printed beneath the red, white, and blue bands. It felt like a rite of passage, another bureaucratic marker on the road to retirement. No ceremony. No gold watch. Just a government-issued card informing me that I had entered a new demographic.

    That same day, I held a Zoom office hour. One student showed up. I told her I was retiring, and somehow our conversation wandered from Mr. T as an icon of the 1980s to whether AI could replicate the music of SZA to Zach Cregger’s Weapons, which she was writing about for her essay. We talked about how the movie could be frightening and funny at the same time. Before leaving, she told me she felt fortunate to have taken my critical thinking class before I retired. I thanked her. After forty years of teaching, you learn not to brush aside a compliment from a student. You put it in your pocket.

    After the Zoom meeting, I started thinking about the tools that had changed my teaching. Google Docs was one of the great breakthroughs. A student’s paper no longer had to exist as a stack of stapled pages handed across a desk. The document floated somewhere in the cloud, a kind of fairy manuscript that student and teacher could enter simultaneously, revising sentences together from different locations.

    Then my wife introduced me to Google Slides. Once I realized how visually my students processed information, I practically lived on Slides. An assignment that seemed hopelessly dense on a two-page handout could become intelligible when broken into a sequence of clean visual ideas. I can scarcely imagine the final seven years of my teaching career without it.

    Then came generative AI.

    At first, AI seemed like another extraordinary professional tool. It accelerated research. It intensified brainstorming. It helped me develop assignment prompts, test arguments, generate counterarguments, and discover connections I might have overlooked.

    But AI was different from Docs and Slides because it didn’t merely change how I presented my writing. It could change the writing itself.

    For my first three years using generative AI, I became intoxicated by its powers of augmentation. Give it an ordinary paragraph and it could return something brighter, sharper, funnier, and more muscular. It added metaphors, jokes, comparisons, rhythms, and linguistic tricks I hadn’t conceived myself. The results were seductive precisely because they sounded better.

    There was only one problem. Increasingly, they didn’t sound like me.

    I think of those old photo cutout boards at cowboy-themed restaurants and tourist traps. You stand behind a painted cowboy and stick your head through a hole. The photograph contains your face, but everything below your neck belongs to somebody else: narrow waist, six-shooter, boots, chaps, heroic posture. Technically, you’re in the picture. But that isn’t your body.

    AI can do the same thing to prose. Your ideas and anecdotes remain visible through the hole, but the rhetorical body surrounding them belongs to the machine.

    My second metaphor is less flattering. AI became my literary performance-enhancing drug.

    Without AI, I was the natural bodybuilder. Maybe I looked pretty good. Nothing spectacular, but the muscles were mine. Then I discovered rhetorical steroids. Suddenly I could walk onto the stage swollen with metaphors, acid wit, vivid descriptions, elaborate comparisons, and perfectly engineered sentences. Every paragraph flexed.

    Worse, I learned how to order the injections.

    “Rewrite the following with lucid prose, acid wit, and vivid descriptions.”

    That became one of my favorite prompts. I would feed AI a perfectly serviceable piece of writing and watch it return wearing a posing thong and covered in bronzer. My paragraph hadn’t been edited. It had been juiced.

    I loved it.

    Then a regular reader of my blog finally had enough.

    After reading one particularly steroidal post, he left an angry comment filled with expletives. His opening line was memorable:

    “Hey, Boomer, cut the shit.”

    He told me to tone it down. He was tired of the verbal pyrotechnics. Tired of the relentless jokes and metaphors. Tired, though he didn’t use my metaphor, of watching the Technicolor 4K bodybuilder flex under the stage lights.

    I apologized and told him I would tone it down. He later apologized for snapping at me. He’d had a bad morning, he explained, and admitted that he actually enjoyed reading my blog.

    “No worries,” I wrote back. “Thanks for the honest feedback.”

    And I meant it.

    His irritation had exposed something I had been reluctant to admit. I had become so accustomed to AI-enhanced prose that ordinary writing began to look inadequate to me. I had trained my eyes on rhetorical 4K until my natural prose looked like a 250-nit IPS screen. I kept turning up the resolution, contrast, saturation, and brightness until eventually somebody in the audience yelled for me to turn the damn thing down.

    So I changed my AI prompt.

    “Edit the following for syntax, grammar, and clarity, but keep 95 percent of my original language.”

    I call it the 95 Percent Rule. AI remains a powerful professional tool, but the rule establishes a boundary: the machine can clean the window; it doesn’t get to replace the view.

    I eventually shared the rule with my students under “Academic Integrity and Best Practices.” It seemed fitting. After years of warning students about outsourcing their thinking to generative AI, I had discovered that I needed guardrails of my own.

    That realization arrived at an appropriate moment. My Medicare card was sitting on my desk. Retirement was approaching. Forty years of teaching had taken me from paper essays to documents floating in the cloud, from classroom handouts to Google Slides, and finally to machines capable of rewriting a person’s sentences in seconds.

    The tools had changed my teaching. Some had even changed the way my brain worked.

    Now, as I prepared to leave the classroom, I had one more thing to retire.

    The cowboy body could go back behind the plywood.

    The PED-bloated bodybuilder could leave the stage.

    I wanted my own sentences back.

  • What If Perseverance Is the Disease?

    What If Perseverance Is the Disease?

    In the 1970s, I wanted to become a Major League Baseball player. There was one problem: I sucked.

    I couldn’t hit a curveball. I couldn’t catch up to a high fastball. At third base, I could field a grounder and then launch the throw twenty feet over the first baseman’s head, turning a routine out into an emergency evacuation of the opposing dugout. By thirteen, the scouting reports were conclusive. I quit.

    Next came bodybuilding. I actually showed some promise. In 1981, I took runner-up in Mr. Teenage San Francisco. But that was about as far as the genetics were going to carry me. I could build a respectable mid-level physique, but I wasn’t going to become Sergio Oliva or Arnold Schwarzenegger. Those men appeared to have been assembled in a laboratory using replacement parts from livestock. I quit bodybuilding that same year.

    Then I wanted to become a pianist and composer. Unfortunately, reading music and writing compositions on staff paper struck my brain with roughly the same clarity as vector and stochastic calculus. Another dream quietly left the building.

    Next came the Smooth Bachelor.

    This was my plan to become a smooth, smarmy bachelor who knew exactly what to say to women. My life would be full of hot tubs, champagne, water beds, and lava lamps. Unfortunately, I possessed approximately the same romantic smoothness as Richard Lewis after five cups of espresso. The Smooth Bachelor era was brief and catastrophic.

    Then came the big one.

    I would become a novelist.

    This ambition survived longer because I could actually write. I had a quirky, neurotic personality. I could make people laugh in conversation. Surely these qualities meant that somewhere inside me lived a novelist waiting to emerge.

    They didn’t.

    My novels were usually constructed around premises sturdy enough to support a Saturday Night Live sketch. I would then stretch the premise across two hundred pages and wonder why the resulting manuscript felt less like a novel than a short story being held against its will.

    They were reliably unreadable.

    Yet this was the dream I had the greatest difficulty quitting because becoming a novelist wasn’t merely another ambition. I had turned it into redemption.

    The published novel would retroactively make sense of everything. All the neurosis, misanthropy, social awkwardness, failed ambitions, compulsions, humiliations, and self-sabotage would be transformed into literary material. I wouldn’t merely have suffered from my peculiarities. I would have monetized them.

    Even better, people would admire me.

    This was the part I was reluctant to admit.

    Publication had become my Holy Grail of affirmation and vindication. Somewhere in my imagination, people were rising to their feet:

    “Ladies and gentlemen, Jeff McMahon has done it! The failed baseball player, failed bodybuilder, failed pianist, failed composer, and failed Hot Tub Stud has finally fulfilled his destiny. He is a novelist!”

    Applause.

    Someone brings me a chilled beverage.

    Someone else produces a generous slice of carrot cake.

    “Make sure this man feels loved. Make sure he feels special. He has suffered enough.”

    Once I understood that fantasy, perseverance became a much more complicated virtue.

    We are constantly told that perseverance reveals character. Keep going. Never surrender. Follow your dream. Winners never quit.

    But what if perseverance isn’t always strength?

    What if sometimes it is fear wearing a motivational T-shirt?

    A person can keep pursuing a goal because the goal remains worthwhile and attainable. But he can also keep pursuing it because quitting threatens some deeper fantasy about who he needs to become. He isn’t persevering because the work is flourishing. He’s persevering because he has assigned the achievement an impossible psychological task: Make me worthy. Vindicate my life. Make people admire me. Make me feel loved.

    Under those conditions, perseverance stops looking noble.

    It starts looking pathological.

    That is why Lindsay Crouse’s The Case for Quitting feels less like another book on my reading list than an intervention. For someone of my temperament, quitting isn’t necessarily evidence that I lack character. Sometimes quitting may require more character than continuing.

    I’ve spent enough of my life chasing various Holy Grails of vindication.

    At this point, I’d like to know which quests are worth finishing—and which ones deserve to be abandoned in the woods.

  • The Salvation Hustle

    The Salvation Hustle

    You reach a point in life when everything feels desperate. Losing weight will save you from dying in your bed at night from sleep apnea. Writing a publishable book or viral essay will save you from being both irrelevant and useless. Making a viral video will do the same. Embarking on a successful podcast will keep you mentally alive and “part of the conversation.” Starting your own restaurant featuring your grandmother’s brisket with gravy made from a secret family recipe will put you on the map and change what it means to enjoy good brisket. Become a yoga instructor and open your own studio to help people reinvent themselves in ways no one could have imagined. You’re special, dammit, and you’re going to prove it. You just need to work harder. So you must do this. You must do that. Make more sacrifices. Get on the true path. Never take your eyes off the prize.

    But a voice breaks through your insanity and tells you that you’re on a fool’s errand. You’re trying to save your life. Deep down, you know you are losing it.

    That same voice says: Let go. Surrender to the things you can’t control. Don’t live out other people’s fantasies of success. Don’t think fame and popularity will make you whole. Don’t confuse fame and popularity with love. It’s not love. It’s desperation.

    So you retire your delusions. You realize that all the time and energy invested in your various mirages were killing you. You were making a bad investment. Take stock. Assess the damage. You become certain that it’s time to abandon your many chimeras and start from scratch. Use your time and energy on projects rooted in sanity, projects that might actually bear fruit.

    The problem is, you don’t have a clue what these new projects will be. You’ve lived in a fever dream for years, perhaps decades. Where do you begin?

    Such is the existential challenge presented in Lindsay Crouse’s The Case for Quitting: The Surprise Benefits of Opting Out. She observes that too many of us spend enormous amounts of desperate energy auditioning for the role of superstar—the venerated, successful person who sets records and raises the bar in whatever field we pursue, believing that this prized status will make us whole and happy. We create unrealistic expectations and often head down the wrong path. Then we become so exhausted from pursuing our dreams that we no longer have enough distance to assess whether those dreams are even viable.

    Crouse uses the metaphor of a duck to describe this desperate period of her life: “gliding along on the surface while my legs churned furiously below.” That brief description perfectly captures the life of quiet desperation described by Henry David Thoreau. Always auditioning for some desirable role, we glide along on the surface while below our legs churn furiously in pursuit of some fruitless endeavor.

    Crouse argues that we should take stock of all that furious churning and, when necessary, put an end to it. It’s called quitting. Contrary to society’s condemnation of “the quitter” as someone who lacks perseverance, the real character flaw may be the refusal to quit: cowardice. You need the courage to interrogate the results of your endeavors and ask whether those results merit perseverance. In some cases, quitting can be a good thing. Crouse offers an “alternative definition” of quitter from the Middle French: “to set free.”

    All her life, Crouse confesses, she has been a high achiever, fiercely competitive, always pushing herself to the limit and loath to interrupt her path to glory. When an injury threatened her athletic training, she’d forego the doctor and take an Advil instead. Late-night runs were aided by GPS. When her grandmother died, she didn’t tell her team for fear that it would compromise their performance.

    Looking back at the ways she pushed and punished herself, Crouse questions the wisdom of these often ruthless efforts. Her self-interrogation became serious after she had two children and realized she didn’t want to pass on her “darker types of perseverance” to them. Self-abuse is one thing. Teaching your children the habits of self-abuse crosses the line.

    When the forces of ambition are no longer part of your flourishing but have become a dark pact with fear and desperation, it may be time to abandon ship. It may be time to move on.