Talking to Boomers
Every generation inherits a set of assumptions about how the world works.
Boomers inherited assumptions that were often perfectly rational for the world they lived in:
- Work hard and you'll get ahead
- Buy a house as soon as possible
- Stay with one employer
- Go to college
- Save for retirement
- Trust institutions
- America will generally become more prosperous over time
The question isn't whether those assumptions were right or wrong.
The question is: Are they still true?
About the Segment
Talking to Boomers is a recurring 10-15 minute segment on The New Reality podcast. Each episode features a conversation with a Boomer about one of the old recommendations — exploring how it holds up in today's world.
These are not debates. They're not exercises in blame. They're honest inquiries: what did you believe, why did it make sense then, and what would you tell someone starting out today?
Why This Matters
A surprising amount of the anxiety people feel comes from following advice that no longer applies. The advice wasn't bad — it was time-bound. And when conditions change, old advice becomes new risk.
The point isn't to discard everything the previous generation believed. It's to sort: which assumptions still serve us, and which ones are quietly making things worse?
Episodes Explore Questions Like
- If "work hard and get ahead" was true in 1975, is it still true in 2026?
- What did housing actually cost relative to income when Boomers were buying?
- What happened to the employers that rewarded loyalty?
- Did college deliver what was promised — and for whom?
- When Boomers say "save for retirement," what assumptions about returns, pensions, and Social Security are baked in?
The Deeper Point
Talking to Boomers isn't really about Boomers. It's about inherited thinking — the assumptions we absorb from our environment without ever examining them.
Every generation hands down a mental model of how the world works. And every generation living through a transition has to decide: which parts still fit, and which parts need to be rebuilt?
This segment is an exercise in that decision-making. One assumption at a time.