Send us Fan Mail

A 66-year-old baby boomer, up late with a drink and a cigar on a South Florida patio, asks the question sitting under a lot of family dinners and comment sections: why do so many younger adults seem to resent boomers so intensely? We don’t tiptoe around it. We get into the raw emotions behind generational conflict, the fear that retirement programs like Social Security and Medicare could become political targets, and what it feels like to watch your entire generation turned into a meme-shaped villain online.

From there, the conversation drills into the usual charges: boomers won’t babysit, boomers chased cruises and comfort, boomers fueled consumerism, and boomers “stole” affordable housing. We challenge the clean narratives and talk about incentives, responsibility, and the long arc of homeownership. We also talk about lifestyle choices that are more common now such as renting longer, traveling more, delaying marriage and kids and how those choices can be joyful and valid while still changing the math on buying a home in a high-rent, high-down-payment market.

We also wrestle with culture shifts that are harder to quantify: the decline of the nuclear family, changing expectations of commitment, and what gets gained or lost when stability stops being the default goal. And we end with one place where boomers may genuinely share the blame: pushing college as the only path, helping create a student loan debt crisis while too many grads struggle to connect degrees to income.

If you’ve ever argued about boomers vs Gen Z, housing affordability, student debt, or the meaning of “paying your dues,” this one will spark a reaction. Subscribe for more, share this with someone who’ll disagree, and leave a review with your take: what do older and younger generations realistically owe each other?

Support the show

Send us Fan Mail

Support the show

Send us Fan Mail

Support the show