7 times boomers proved they’re completely out of touch with reality

Every generation thinks the one before it is a little out of step.

But sometimes, boomers don’t just miss the mark—they overshoot it by a mile.

I’m not talking about harmless quirks like still writing checks at the grocery store or printing out MapQuest directions. I mean those moments when their advice, beliefs, or decisions show they’re living in a world that doesn’t quite exist anymore.

If you’ve ever had a conversation where you thought, “We’re not even speaking the same language,” you know what I mean.

1. Telling people to “just buy a house”

I’ve lost count of how many conversations I’ve had where a boomer, usually with a fully paid-off home they bought for the cost of today’s down payment, tells me I “just need to stop eating out” if I want to buy property.

That advice might’ve made sense in 1975, when median home prices were roughly four times the average annual income. But today? In many U.S. cities, the ratio is closer to five or even six times income. And that’s before factoring in rent soaring, wages stalling, and student debt peaking.

NAR economist Lawrence Yun has bluntly stated: “Housing affordability is at its lowest level in decades.” But somehow, the avocado toast myth still lives on in their heads, like a bad pop song you can’t get rid of.

Here’s the reality: even if you cut every “luxury” purchase from your life, you’re not closing the gap on a $300,000–$500,000 home with $20 salads and cold brew coffee savings alone. Yet, that’s often how boomers frame the conversation—through a lens that hasn’t been updated since the Carter administration.

2. Thinking “entry-level” means you need zero experience

Here’s one that grinds my gears: boomers telling younger people that you can start from scratch in any field and work your way up with “hard work.”

They’re picturing a time when companies actually trained employees from the ground up. You’d start in the mailroom, prove yourself, and eventually move into management.

Today? Entry-level job postings regularly ask for two to five years of experience, specialized software skills, and sometimes a master’s degree.

I once had a friend apply for a junior role that required more experience than the senior role she was already in. She didn’t even make it past the first round. Try explaining that to a boomer who still believes you can walk into a place, shake the manager’s hand, and get hired.

The market’s changed. Jobs aren’t just about “paying your dues” anymore—they’re about already being overqualified for the position you want. And for a lot of younger workers, that’s not just discouraging, it’s absurd.

3. Acting like staying in one job for life is the goal

Many boomers see frequent job changes as a red flag. In their world, loyalty was rewarded with pensions, promotions, and job security.

But now? Stay too long in one place and you risk falling behind in pay, skills, and opportunities. Research from ADP shows people who switch jobs see, on average, higher wage growth than those who stay put.

I’ve mentioned this before in another post, but I once had a boomer mentor look horrified when I said I was leaving a company after three years. To him, that was barely a warm-up. To me, it was three years of stagnant growth, frozen salaries, and watching opportunities pass me by—time to move.

The “gold watch after 40 years of service” era is over. Today, adaptability is the new loyalty. And that’s something many boomers still struggle to wrap their heads around.

4. Believing college is the ultimate ticket to success

Boomers love the “go to college, get a good job” line. And to be fair, it was solid advice back when tuition was affordable and a degree practically guaranteed you a middle-class life.

Now, many grads are walking into the workforce saddled with five or six figures of debt and competing for jobs that either pay poorly or don’t require a degree at all.

As financial educator Anthony ONeal emphasizes, higher education “is not a scam, but pushing it without teaching financial literacy sets people up for failure.”

I’ve met people with master’s degrees who can’t get hired in their field but are too “overqualified” for entry-level roles outside it. Meanwhile, the cost of higher education has grown at more than twice the rate of inflation since the 1980s. That math just doesn’t add up—and yet, the advice hasn’t changed.

5. Treating mental health like a weakness

This is one of the biggest generational gaps I see.

Boomers grew up in a “tough it out” culture, where admitting to stress, anxiety, or depression was seen as oversharing—or worse, as being unstable. Many still default to advice like “just think positive” or “stop overreacting.”

I remember telling a boomer family friend I was feeling burnt out and considering therapy. She replied, “In my day, we just got on with it.” The irony? She later mentioned how many people “back then” drank too much, got divorced, or worked themselves into early health problems.

The science is clear: untreated mental health issues can impact physical health, career success, and relationships. Pretending they don’t exist doesn’t make them disappear—it just buries them deeper.

Experts like Dr. Kristen Lee—behavioral science educator and resilience researcher—argue that true resilience isn’t about powering through at all costs; it’s about finding sustainable ways to care for your mental and emotional well-being. That’s a message our generation is finally starting to take seriously.

6. Thinking the news is neutral and trustworthy

Many boomers still see traditional media as an impartial truth-teller. That made sense when there were a handful of major networks and newspapers, all competing to maintain credibility.

But the media landscape has shifted dramatically. Misinformation is rampant, outlets cater to specific political leanings, and the news cycle moves so fast that accuracy often takes a back seat to speed.

I once showed my dad how two major news sites covered the same story with completely opposite spins. He genuinely thought one must be lying—because in his mind, news wasn’t about framing; it was about facts.

The truth is, media literacy is now a survival skill. Younger generations have had to learn to cross-reference sources, check dates, and question the angle of every story. For many boomers, that level of skepticism feels foreign—because they grew up trusting the messenger without needing to question the message.

7. Believing retirement is a guaranteed chapter of life

Boomers were told that if you work hard, save steadily, and stick with your company, you’ll enjoy a comfortable retirement. And for many of them, that worked out.

But for millennials and Gen Z? Between the decline of pensions, rising healthcare costs, and the instability of the gig economy, retirement as they knew it is looking more like a luxury than a guarantee.

A 2023 Gallup survey reveals that 47% of non‑retirees don’t believe they'll receive Social Security when they retire—especially those aged 30 to 49, highlighting a deep-seated lack of trust in the system’s future.

And yet, I still hear boomers tell younger folks to “just save more” without acknowledging the structural changes that make their old playbook almost impossible to follow. It’s like telling someone to win a race without noticing the track is uphill and covered in hurdles.

The bottom line

Boomers didn’t create all these problems, but they did grow up in a reality that no longer exists.

When their advice ignores how much the world has shifted, it’s not just unhelpful—it can make younger people feel like they’re failing at life when they’re really just navigating a completely different game.

The truth is, we all have blind spots shaped by our era. The key is being willing to update our views instead of clinging to a world that’s long gone.