Mythology of Retirement
Why Boomers Remain a Steadfast Enemy of the Generations
The mythology of retirement as sold to the Boomers and passed like gospel to subsequent generations sits at the heart of our bloated entitlement systems and the slow rot of intergenerational trust.
It’s commonly observed that Boomers are an ardently selfish generation. Recent polling confirms what many younger people feel anecdotally: their top concerns aren’t the environment, income inequality, or long-term social stability.1 They care, primarily and almost exclusively, about two things: Medicare and Social Security. It strains me, as a natural contrarian, to say this, but the Zillennial affectation of “hating Boomers” is justified. If nothing else, it’s understandable. No other generation clings so tightly to what they believe is theirs, or shows such indifference to the consequences of keeping it.
So why are they like this?
I’m not here to build an airtight sociological thesis. We won’t isolate every variable behind this particular brand of cussedness. But I do want to suggest one key explanation: the mythology of retirement: a distinctly modern, distinctly post-war construct has been imprinted on Boomers like an intaglio etching, and they will not let it go.
For most of human history, people worked until they died. Morbid, yes. But this wasn’t up for debate. It was the human condition. Retirement, as we know it, is a freakishly new idea. A luxury born not of progress alone, but of a specific historical moment. After World War II, with the rise of American prosperity, labor unions, pensions, and the modern welfare state, a powerful new narrative took shape: you work hard, pay your dues, and one day you’ll rest. The golden years. A reward at the terminus.
To the Boomers, that story wasn’t just comforting…it became foundational. Not a dream, but a promise. Retirement wasn’t a possibility, it was a rite of passage. To question it now is to violate something sacred. Tell a Boomer they might need to work a few more years or take a modest cut to their benefits, and you’ll be met with righteous fury: “I paid in. I earned this.” Never mind that what they paid in doesn’t match what they’ll take out. Never mind that I will also pay in and almost certainly not be paid out. Never mind that the system was always designed with demographic assumptions: lifespan, workforce size, birth rate—that no longer hold. The mythology remains intact.
At least for the Boomers, the mythology remains intact. But for every generation that followed, it has either faded into skepticism or been immolated outright.
Gen X ever the ambivalent middle child, stood too close to the myth to fully reject it, yet never quite believed in it either. They clocked in, rolled their eyes, and learned to navigate the system with a quiet, ironic detachment.
The Millennials, by contrast, are the true tragic inheritors. They were raised on the retirement myth—taught that if they studied hard, worked harder, and played by the rules, they'd one day earn their spot on the golden shores. For decades, they carried that belief like a torch through student debt, unpaid internships, and the wreckage of two economic crises. Eventually, it dimmed. They made halting attempts at rebellion: Occupy Wall Street, the Bernie Sanders wave, but the system was too calcified. Now even the supposed reformers: the Warrens and AOCs of our time—speak of retirement with vague gestures and platitudes, as if it were a quaint relic rather than a burning crisis.
The Zoomers? They never believed at all. They’ve only known stagnating wages, inflationary wealth reaping, and a job landscape defined by hustle, burnout, and algorithmic precarity. For them, retirement is as fantastical as a pensioned unicorn.
I can only shudder for Gen Alpha.
I used to believe in it too. I even did the math once my projected payout versus what I’ll pay in, and LOL’d. Not out of bitterness, but because I knew the only way I’d ever actually retire was by brute-forcing it. Thanks to some good investing, high IQ, and my triple-job stacking and business ownership of the Tortuga Society, I’ll be one of the rare few my age who does retire.2 But that’s enough of a tangent.
That mythology of retirement, more than any spreadsheet or actuarial projection, is what makes entitlement reform politically radioactive. It’s not the math that is incomprehensible…it’s the betrayal. The mythology of retirement promised that the fruits of labor would be neatly harvested at 65, ideally on a beach with a cocktail in hand. That this was a historical anomaly, afforded by a one-time explosion of post-war wealth and rising birthrates never registered. To the Boomers, it's simply how things are supposed to & always will be.
And so they vote accordingly. Not out of malice, necessarily, but out of a conviction that history owes them what was promised. The problem is, that promise was a lie, or at least a short-term experiment masquerading as a permanent fixture. Now, the younger generations are left holding the bag: paying in more, starting later, inheriting less. The ship is sinking, and the people who built their lives on the upper deck are refusing to move.
And what of our political class? They’ve done nothing. Less than nothing, really. Because to do nothing implies negligence—this is closer to cowardice. Our leaders, right and left, have spent decades tiptoeing around the retirement crisis not because it’s unsolvable, but because it’s untouchable. There is no incentive to confront the sacred cow. No glory in telling Boomers the truth. And certainly no votes in telling Millennials and Zoomers the bad news; that the money’s gone, and no one’s coming to save them.
These aren’t statesmen. They are managers—risk-averse careerists clinging to ten-point leads and donor goodwill. The idea that elected office might carry a higher calling, a kind of noblesse oblige to steward the future: that idea is dead. Our modern political class doesn’t think in generations. They think in quarters, like investors, chasing short-term returns and memetic clout.
The left, to its credit, has flirted with rebellion. Occupy Wall Street was a real movement, born of righteous fury and economic disillusionment. The Democratic Socialists under Bernie Sanders gave voice to a generation that saw the rot for what it was. But both were subverted-first by internal disorganization, then by party absorption. That anger, once aimed at the economic order, was cleverly rerouted into endless cultural scuffles. It’s easier to argue about identity, language, or TikTok bans than to confront the fiscal trap we’re all in. The left chose the path of least resistance and now mouths platitudes about “dignified aging” while knowing full well the math doesn’t add up.
The right, too, had its moment. The Tea Party began as a visceral response to bloat and insolvency. Ron Paul spoke directly to the economic anxieties of younger conservatives; warned them about central banks, endless wars, entitlement cliffs. But like the left, the right couldn’t hold the thread. That populist energy was hijacked, commodified, and eventually swallowed whole by the culture war machine. Now we get sloganeering about “cutting waste” and cynical stunts like the DOGE initiative, more spite than substance. Let’s be clear: I have no love for administrative excess. But pretending that slashing funding for these bloated agencies will somehow balance the books while our FICA entitlements consume a third of the budget is unserious bordering on delusional.3
It’s a dog and pony show and a simulacrum of responsibility. The public gets a headline. Congress gets a talking point. And the structural collapse continues unchecked.
The most chilling part of this crisis isn’t just the numbers, but the silence and tacit acceptance. It’s rare for a political issue this dire to receive this little serious attention. Rarer still for both parties to agree, implicitly, to look the other way.
And so the Boomers remain, not just an older generation clinging to comfort, but a kind of mythological remnant; custodians of a dream no longer possible, yet still politically dominant. Their belief in the retirement covenant has calcified into dogma, and anyone who dares to question it becomes a heretic. This is why they are not just frustrating, but structurally antagonistic to the generations that follow. They are the last true believers in a central tenant of the post-war social contract that’s been all but voided for their successors, and they will burn the ledger before they admit it.
Pluribus Inservimus!
—First Mate, Theon Ultima
From a retired worker, after decades of work: you’re a flaming asshole. You, too, will get old. You will need - and will deserve - to spend your older years living with dignity, and with healthcare. Not “access to healthcare.” And all of this is more than possible. This country pisses away over a trillion dollars a year on war. Our private medical system saddles us with the highest cost for piss-poor results, especially when compared to other advanced countries and even many lower income nations. Wealth inequality is reaching Gilded Age levels. The ability to pay for secure retirements and national health care (for all ages, you twit) is there: just look at the insane billions in the hands of a tiny sliver of the population. And even with your brief hat tip toward leftists who have struggled for these things, you wind up doing the bidding of the 0.1%, pretending this is a generational rip off perpetrated by “Boomers” and not by the capitalist class. Extract head from ass, and figure out who has benefited in the past three or four decades, and aim your fire accordingly. Sheesh!
This article is not criticizing all Boomers, only successful Boomers who did not value the future. That said, a lot of the resentment stems from cultural, rather than purely economic reasons. A certain portion of the Boomer generation is blamed for having inherited an extremely successful American way of life, and then rejecting it for a path of hedonic individualism. In particular, this segment of boomers can be held responsible for not having enough children to keep the American social system afloat. I bear no ill will to the Boomers who stuck to the old American philosophy.