The Long Boomer Farewell

This will not be a clean handoff. It will be an extended interregnum.

This is part 3 of a series on transitioning to a post-boomer world.
- Part 1 - The boomer reckoning no one’s ready for
- Part 2 - Boomer caregiving will wreck our politics
- Part 3 - The long boomer farewell (this essay)

I wasn’t going to write about boomers again. But then Dan Grossman died.

I got the news on New Year’s Day. It felt like a curtain dropping before the year had even started. The symbolism was unmistakable: the long boomer farewell was underway.

Dan was a longtime friend and mentor, the man I used to jokingly call my “Jewish dad.” At 81, he was the same age as my parents and on the outer edge of the boomer generation.

I met Dan in my early twenties at a political event in Washington, D.C. Over countless lunches, he mentored me as I built my first business, coached me into becoming a disciplined Boglehead investor, and offered Yoda-like guidance as I navigated personal and professional decisions. As the decades passed, our lunch tradition continued, always with dessert. We served on two nonprofit boards together. In 2024, I attended his 80th birthday party at Anderson House in Washington, D.C. A couple months ago, I sat at his table at a New York City gala as he received a lifetime award for his service to dozens of libertarian organizations.

A few days before Christmas, Dan and I met for lunch one last time, at his usual restaurant, at his usual table in the back. We joked, caught up, and he commented on my latest Substack essays, which he always read. I asked his advice about a personal issue. Then he asked for mine.

“How do I get people to stop nagging me about my health?” he asked.

Little did I know that would be our last conversation.

Or maybe, deep down, I did.

Looking back on my writing over the past year, a pattern is obvious. Again and again, I found myself circling the same theme: a long, uneasy goodbye to the boomer generation. Two of my most-read essays touched on it directly, one on reckoning and another on caregiving. I honored my aunt when she turned eighty. I wrote letters to men of different generations, including one to “Boomer Man.” At the think tank I founded, we half-jokingly framed our mission as “building a post-boomer America.” The phrase stuck because it felt true.

I also found myself reckoning with my own aging and mortality, alongside a sense we’re living through a civilizational transition.

I see now that I’ve been processing what I’m calling the Long Boomer Farewell. I toned down the boomer jokes. I tucked away my Gen X resentments. I became a caregiver. And I realized this transition was beyond any one person or family. It was a macro force.

As 2026 begins, I want to name it and go deeper.

The Long Boomer Farewell is the roughly twenty-year period from now through the mid-2050s, during which the boomer generation will pass from dominance into history. The timing is not arbitrary. The oldest boomers are turning eighty this year.¹ Over the next twenty years, the number of boomer Americans will drop from roughly 65 million today to a small remnant.² That same demographic arc is playing out across the developed world, from Japan to Germany and beyond.³

If you are in midlife, you can already feel this. It shows up in aging parents and prolonged caregiving. In national politics, where leaders like Biden and Trump remain central figures well past what once felt normal.⁴ In popular culture, where Harrison Ford is still carrying franchises. In the spread of 55-plus communities and the growth of healthcare services built around longevity. Even if you don’t yet have a name for it, you are already living inside the Long Boomer Farewell.

The Long Boomer Farewell will not be a clean handoff. It will be an extended interregnum — an awkward time between orders, when the old governs but the new has not arrived.

I remember the collective farewell to the World War II generation in the 1990s. They were canonized as a heroic cohort shaped by depression, war, and national purpose. Popular culture gave their passing a kind of closure. Tom Brokaw memorialized them as The Greatest Generation. Steven Spielberg did the same in Saving Private Ryan, with scenes that still make me tear up.

That transition felt relatively straightforward, rooted in broad emotional consensus. As that generation exited the stage, post-war institutions were still solid, younger leaders were waiting in the wings, and America retained a more cohesive sense of self. Tributes were made. Entitlements were paid. Authority moved on. It was a transition, not epochal rupture.

The Long Boomer Farewell will not be like that.

It will be slower, noisier, and more emotionally complicated. No single narrative will neatly canonize boomers or tie a bow around their time on earth. Whether they deserve it is beside the point. The conditions for closure no longer exist. They are wealthier and healthier than any generation before them, deeply embedded in political, economic, and cultural power, and often (understandably) reluctant to step aside. Their senior years are unfolding not in a confident, triumphant “end of history” America, but in a fragmented, strained, less trusting society already struggling to renew itself.

The farewell to the Greatest Generation had closure. The Long Boomer Farewell will drag for decades.

Longevity is one reason why. Even as the boomer population shrinks, people are living longer than ever. Over the next two decades, the number of people living into their nineties and hundreds will quadruple.⁵

What makes the Long Boomer Farewell epochal is timing. A massive generational exit is colliding with failing entitlement assumptions, fraying geopolitics, and a technological revolution moving faster than institutions can absorb. Social Security, Medicare, and public budgets were built for a younger, growing society, locking governments into preserving the present at the expense of the future. Liberal democracies increasingly operate in maintenance mode rather than renewal.

Meanwhile, the postwar order is breaking down as great-power competition returns, just as artificial intelligence and automation begin to reprogram the economy itself. America and much of the developed world face a choice: managed decline or deliberate renewal.

The Long Boomer Farewell is not a normal generational turnover. It is a succession crisis unfolding inside a broader civilizational shift, full of risk and opportunity, with no script for navigating it.

If Dan were looking down from above, he’d probably joke that he timed his exit well. I’d tell him that wasn’t funny. He’d smile anyway. Then he’d ask what I thought we should do about it.

The Long Boomer Farewell isn’t something we can skip. It’s already here. I feel the heaviness of grief I know is coming, the frustration of institutions that don’t move, and the fear of global rupture. But I also sense an opening — for renewal, advancement, and paying closer attention to the people in my own life while there’s still time. This, I suppose, is what an interregnum feels like.

Dan taught me to value sound economics, human freedom, and forward-looking pragmatism. Those principles are as good a guide as any for navigating the Long Boomer Farewell. I will miss him.

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Related Essays

• The boomer reckoning no one’s ready for

• Boomer caregiving will wreck our politics

• The virtue and private sorrow of Boomer Man

Theme Song

1. See Pew report.

2. Ibid.

3. Check out this Madison Trust Company report.

4. 24 members of Congress are 80 and older. See NBC article.

5. See Pew report.