Generational Divides with Nick Gillespie
Journalists from three generations (Baby Boomers, Gen X, and Gen Z) have a lively, debate-y conversation on intergenerational wealth.
Topics: Culture, Finance & Economics
Release Date: November 14, 2025
Are Grandma’s Social Security benefits imperiling Junior’s future? Is owning a home still a defining part of the American Dream, or a relic of a bygone era? When we look back on the 1950s, do we see a golden age, or are we simply indulging in nostalgia? And how large is the gap between different age groups on whether intergenerational wealth is still achievable?
In the inaugural episode of a new Open to Debate series, “Generational Divides,” Reason’s editor-at-large Nick Gillespie brings together three debaters from three generations — Baby Boomers, Gen X, and Gen Z — to unpack how age, experience, and economics shape our ideas of prosperity, opportunity, and freedom. It’s a lively, cross-generational debate on whether the promises of the past still hold up in a rapidly changing America.
Featured Debate Topics:
Are Grandma’s Social Security Benefits Imperiling Junior’s Future?
Is Homeownership Still A Defining Attribute of the American Dream?
What Are People Really Nostalgic for About the 1950s—and Was the Economy Actually Better Then?
Our Guests:
For Baby Boomers: Joe Nocera, Deputy Managing Editor at The Free Press
For Gen X: Stacey Vanek Smith, Journalist and Reporter; Co-host of “Everybody’s Business” at Bloomberg Business
For Gen Z: Kyla Scanlon, Financial Content Creator, Economic Commentator and Author of “In This Economy?”
Nick Gillespie, Editor-at-Large at Reason, is the guest moderator.
About Generational Divides:
Smart, contrarian, and funny, Generational Divides with Nick Gillespie embodies Open to Debate’s commitment to lively, nuanced discourse in an age of echo chambers. With provocative prompts, generationally diverse guests, and Gillespie’s trademark wit guiding the way, the series invites listeners to question their assumptions and join a conversation that’s as entertaining as it is enlightening.
Special thanks to Liberty Ears Foundation who made this series possible.
This was such a refreshing format — not just “who’s right,” but how different starting points shape what each generation even hears as possible.
What struck me most was how Gen X often ends up as the hinge: old enough to remember stability as a lived reality, young enough to feel how quickly it eroded — and to be quietly carrying both directions at once (kids on one side, parents on the other).
The debate around homeownership and Social Security felt less like nostalgia vs. progress and more like a mismatch of timelines and assumptions. Same words, radically different math underneath them.
More of this, please. Cross-generational conversations that don’t flatten experience into slogans are exactly what’s missing right now. 💛Kelly
Why no millennial? Not that Kayla isn’t capable of arguing or perspective as well.