My grandmother volunteers at the food bank every Saturday. She’s been doing it for years, rain or shine, even though she’s well into her eighties.

When I asked her why she doesn’t slow down and enjoy retirement like the magazines promised, she laughed. “Those magazines never mentioned I’d need to work until 70 just to afford my medications.”

That conversation stuck with me. The boomers were sold a dream of retirement that looks nothing like reality. They did everything right, or at least everything they were told was right.

Yet here we are, watching an entire generation discover that many of the promises they built their lives around were, well, lies.

1) Your company pension will take care of you

Remember when companies actually valued loyalty? When I was reviewing indie bands in the early 2000s, I interviewed a drummer whose dad had just lost his pension after 30 years with the same company. The firm went bankrupt, and decades of promised security vanished overnight.

This wasn’t an isolated incident. Companies shifted from defined benefit plans to 401(k)s, essentially saying “good luck, you’re on your own now.” The safety net that boomers counted on? It got pulled out from under them while they were already mid-air.

The psychological impact of this betrayal runs deep. Research into the psychology of control loss shows that when people perceive a loss of control or their expected safety is removed, the stress-response systems (like cortisol release) are triggered in the same way as physical threats.

No wonder so many boomers feel constantly on edge about money.

2) Social Security will be enough

Here’s a fun fact that isn’t actually fun: the average Social Security payment is about $1,827 per month. Try living on that in California. Try living on that anywhere, really.

Boomers were told Social Security would be a comfortable safety net. Instead, it’s more like a frayed rope that might hold your weight if you don’t move too much. The cost of living has skyrocketed while benefits have crawled forward at a snail’s pace.

What really gets me is how this impacts daily choices. I see it at the farmers market every weekend. Older folks carefully counting change, putting items back, making impossible decisions between fresh produce and prescription refills. This isn’t the golden years anyone signed up for.

3) Healthcare will be affordable in retirement

Medicare was supposed to solve everything, right? Except nobody mentioned the gaps. The supplements. The things it doesn’t cover. The medications that somehow cost more than a car payment.

A friend’s parents recently had to sell their house because of medical debt. They did everything “right” – saved, invested, had insurance. But one unexpected illness wiped out forty years of careful planning. The American healthcare system doesn’t care about your retirement dreams.

Studies show medical expenses are often a major contributor to bankruptcy filings. For example, a national survey found that illness- or medical-bill-related problems contributed to about 66.5% of U.S. bankruptcy cases between 2013 and 2016.

That’s not a bug in the system; it’s a feature. The promise of affordable healthcare in retirement was always more marketing than reality.

4) You can retire at 65

Sixty-five used to be the magic number. The finish line. The moment you could finally rest.

Now? I know more people working into their seventies than not. Some because they have to, others because retirement without purpose feels like slow death. But mostly because they have to.

The retirement age keeps creeping up while the ability to maintain employment gets harder. Age discrimination is real, even if nobody admits it. You’re too old to hire but too young to retire. It’s a special kind of limbo that nobody prepared boomers for.

5) Your home will be your biggest asset

“Buy a house,” they said. “It’s the best investment you’ll ever make,” they said.

Then 2008 happened.

Even those who recovered from the housing crash face a different problem now. Property taxes that never stop climbing. Maintenance costs that would make your head spin. The inability to downsize because smaller homes somehow cost just as much.

Your home becomes a prison disguised as an asset. You’re house-rich and cash-poor, unable to access your wealth without losing your shelter. Some investment strategy that turned out to be.

6) Retirement means relaxation and leisure

Can we talk about the retirement industrial complex for a second? All those ads showing silver-haired couples walking on beaches, playing golf, living their best lives?

Reality check: most retirees are stressed about money, worried about health, and dealing with existential questions nobody prepared them for. Who are you when your career no longer defines you?

I’ve mentioned this before, but purpose doesn’t retire when you do. The human need for meaning and contribution doesn’t disappear at 65. Yet we built an entire mythology around retirement being about doing nothing. Turns out, doing nothing is its own kind of hell.

7) Your kids will be financially independent

Here’s something the retirement planners didn’t factor in: your kids might never leave. Or they’ll leave and come back. Or they’ll need help with their kids. Or their student loans. Or their everything.

The sandwich generation became the club sandwich generation – taking care of parents, kids, and grandkids simultaneously. That retirement fund you carefully built? It’s now the family emergency fund.

Economic mobility has stalled. Wages haven’t kept up with costs. Your kids face challenges you never imagined. So much for empty nest syndrome when the nest stays perpetually full.

8) Investment returns will be steady and predictable

“Just put it in the market and get your 7% annual return.”

If only it were that simple.

Market volatility, black swan events, global pandemics – the steady returns boomers were promised look more like a roller coaster designed by someone who hates you. One bad year at the wrong time can derail decades of planning.

The financial industry sold predictability while building products designed for complexity. Hidden fees, complicated structures, conflicts of interest. By the time you figure out you’ve been played, it’s too late to start over.

Conclusion

The lies weren’t always intentional. Some were optimistic projections that didn’t pan out. Others were systems that changed while boomers were already locked in. But intentional or not, the impact is the same.

What strikes me most is the resilience I see. My grandmother, who raised four kids on a teacher’s salary and now volunteers instead of relaxing on a beach somewhere, doesn’t complain. She adapts. They all do.

Maybe that’s the real lesson here. Not that we should expect promises to be kept – systems change, economies shift, life happens. But that flexibility and community matter more than any retirement account.

The boomers who seem happiest aren’t the ones with the biggest portfolios. They’re the ones who built networks instead of just nest eggs. Who found purpose beyond paychecks. Who learned that security isn’t about money alone.

For those of us watching this unfold, taking notes for our own futures, perhaps the biggest takeaway is this: don’t believe the promises. Question everything, build multiple safety nets, and remember that the only guarantee is that there are no guarantees.

At least my grandmother’s weekly food bank shifts give her something the retirement brochures never mentioned – a reason to get up in the morning that has nothing to do with money. Maybe that’s worth more than any pension could ever be.

 

If You Were a Healing Herb, Which Would You Be?

Each herb holds a unique kind of magic — soothing, awakening, grounding, or clarifying.
This 9-question quiz reveals the healing plant that mirrors your energy right now and what it says about your natural rhythm.

✨ Instant results. Deeply insightful.