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.
Cinemorphosis 
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