Money habits aren’t just about math—they’re about mindset. And let me tell you, the way my generation approached finances looks almost unrecognizable to many younger folks today.
We grew up in a world where buying a house in your twenties was doable, jobs came with pensions, and saving a little from every paycheck was just what you did—not something you had to fight for.
Now, I’m not saying we had it all figured out. Every generation has its blind spots. But as a boomer myself, I’ve noticed how some of the financial decisions we took for granted now seem baffling—or even impossible—to younger people.
And honestly, I get why. The economy has changed. Life has changed. But still, it’s worth taking a look at the choices we made—because they tell a story of a very different time, and they shed light on just how much the rules of money have shifted.
1. Buying a home almost straight out of college
When I was in my twenties, it felt natural to start planning for a house. A lot of my friends were doing the same, since housing prices back then were comparatively lower.
Many boomers felt homeownership was the gateway to security. In fact, I recall looking at real estate listings fresh out of school and thinking, “Well, this is the logical next step.”
It was the dream: a modest down payment, a bank that trusted you, and a stable job that covered the mortgage.
For younger generations, though, the stakes are much higher.
It’s not just higher home prices; it’s also large student loans, gig-economy salaries, and unpredictable housing markets.
If I mention to a millennial or Gen Z relative that I bought a house in my early twenties, they look at me like I’m describing a scene from a fantasy novel. That’s understandable, because student debt alone can limit that big first purchase for many of them.
It’s not that younger folks don’t want homes—they just aren’t finding the same financial conditions that many boomers relied on to make that dream happen.
2. Relying on a pension for retirement
Back then, our mindset was that if we stuck with our jobs long enough, we’d retire on a decent pension. I spent over three decades in the school system, and I saw coworkers retire with full pension benefits that let them transition quite comfortably into their later years.
That belief in a steady retirement check shaped a lot of our financial decisions.
Younger folks often don’t even know what a pension is—or if they do, they treat it like an urban legend. Few employers offer them nowadays, favoring 401(k)s and other contribution-based plans.
So while we boomers could rely on these programs to form the bedrock of our retirement plans, millennials and Gen Zers often patch together multiple income streams—from freelance gigs to creative online ventures—just to feel secure.
3. Paying for college without crippling debt
I realize this one might come across as a sore spot for a lot of younger readers. Back in my day—though college wasn’t necessarily cheap—it was still possible to work a summer job and pay a decent chunk of tuition.
Scholarships and grants were also more readily available in some places, and not every student felt forced to take on massive loans. Personally, I chipped away at my costs with a part-time teaching-assistant job and some tutoring gigs.
Today, student debt is a major hurdle. The figures are staggering. According to a recent NerdWallet study, the average 2025 high school graduate faces a whopping $40k in college student loans.
That shapes every financial decision, from postponing a house purchase to delaying marriage. It’s no surprise younger generations look at boomers’ college-era stories with a mix of envy and disbelief. And who can blame them?
4. Writing physical checks and doing all banking in person
When I first started teaching, I would breeze through the bank on Fridays to deposit my paycheck and catch up with the friendly teller about local happenings.
Writing checks was an everyday affair: rent checks, electric bill checks, even checks for groceries (yes, grocery stores used to accept them more readily).
With no online platforms or mobile apps in existence, physically going to the bank was just part of life, and it felt perfectly normal.
Nowadays, I have nieces and nephews who can’t remember the last time they entered a bank branch—if ever. They tap away on phone apps to deposit checks and transfer money. A few even manage everything through digital wallets without handling a single paper check all year.
While I’ve embraced some of these conveniences myself, a part of me fondly remembers chatting with real people and physically checking off my bankbook. It’s a quaint memory, but a younger colleague once told me it “sounds like something from the 1800s.”
5. Saving aggressively and focusing on an ‘emergency fund’
Boomers were taught to put aside money no matter what—to keep a “rainy day fund” that often amounted to several months’ worth of living expenses.
When I first started working, my mother drilled into me the idea that you don’t touch that emergency money unless absolutely necessary.
That habit of consistently building up savings has been an essential part of how many baby boomers define financial wellness.
In contrast, many younger people struggle to prioritize emergency funds because they’re contending with rent spikes, healthcare costs, and student loans.
While we boomers might pat ourselves on the back for having a sturdy safety net, younger folks often feel it’s next to impossible to build one to the same scale.
Dave Ramsey, a popular financial expert, famously says, “Saving must become a priority, not just a thought.”
Yet in the modern workforce, where job stability and wages can fluctuate wildly, setting aside significant emergency savings can feel more like a luxury than a step-by-step plan.
6. Sticking with one employer for decades
Growing up, I always heard the phrase, “Loyalty pays off.” You’d choose a company or institution, work diligently, and trust that they’d reward you with raises, bonuses, or at least a sense of security.
I spent the majority of my career teaching at the same school district. Sure, there were ups and downs, but the continuity felt normal.
Many of my friends who worked in corporate roles had similar experiences—some even retired from the same company that hired them out of college.
Younger generations, however, see the job market quite differently. They’re confronted with layoffs, contract work, and the concept of “job-hopping” as a strategic move to increase salary.
Work culture and technology change so rapidly now that it makes perfect sense for them to pivot roles every few years.
While that might seem strange to some boomers who value stability, younger folks can’t relate to the idea of pouring a lifetime into a single employer. And honestly, given how uncertain the market can be, I understand their mindset.
7. Trusting Social Security checks as a mainstay of “success in retirement”
Finally, we come to the Social Security checks—something my friends and I viewed almost like a guaranteed allowance from Uncle Sam once we turned the right age.
Growing up, everyone around me trusted that Social Security would provide a significant slice of their monthly income after retirement. With that promise in place, many boomers felt comfortable investing the rest of their money more conservatively.
Today, younger people face constant headlines about Social Security potentially running short or undergoing major reforms.
Whether that’s a worst-case scenario or a true risk, the uncertainty alone affects their financial planning. Many of them adopt a more self-reliant approach—starting an IRA, dabbling in stocks or real estate side hustles, and, in some cases, considering international options.
What was once the cornerstone of a boomer’s retirement plan now seems shaky to some younger folks. I guess you could say that while we felt success was partly guaranteed by government programs, they’re finding success in forging new paths on their own.
Wrapping up
These days, whenever I talk with my grandchildren about my “good old days,” I have to remind myself that the landscape we boomers navigated is entirely different from theirs.
Some of our strategies still work well—saving money and being mindful of our finances never goes out of style. But the specific decisions we made can feel downright impossible (or irrelevant) to someone starting out now.
We can’t turn back the clock, but we can learn from the past as we all figure out our next steps forward.
After all, retirement, stability, or whatever you call “success” can be redefined at any stage—no matter what choices came before.
Let me know what you think, and as I often say: it’s never too late to start defining success on your own terms.
