James Carter
Have you ever found yourself hesitating to invest in something new because it feels “too risky,” even if that risk might pay off big time? Or maybe you’ve felt guilty spending on experiences—like traveling—because it’s not “practical”?
If so, you’re not alone. Many of us millennials grew up with parents who had certain generational beliefs about money. And while these beliefs might have served them well at one point, times have changed—and so have our financial realities.
So how do you know if you’ve inadvertently inherited these views?
Let’s dive into five telling signs.
1. You believe a steady, traditional job is the only path to financial security
When I was in my early 20s, I remember telling my parents I wanted to become an entrepreneur someday. They panicked. From their perspective, job-hopping or launching a startup was a one-way ticket to financial doom.
You see, many people from the baby boomer generation grew up in an era where a stable corporate job at a reputable company was the gold standard. You’d put in 40 years, get the pension, and call it a day. In their eyes, the path to financial security was linear—anything else was borderline irresponsible.
But let’s be honest: the modern workforce doesn’t look like that anymore. A single company rarely offers cradle-to-retirement job security. The gig economy, remote work, and the rise of technology-based careers have opened countless avenues to earn a living.
If you do your research, weigh your options, and move forward with clarity, you might find that “risky” actually opens doors to bigger rewards.
2. You’d rather collect assets (like a house) than experiences
Let me be clear: I’m not saying investing in property isn’t a bad move. Real estate can be a powerful way to build wealth. The question is: do you believe that home ownership (or similar assets) is the one and only sign of success?
If the older folks in your life constantly told you “Renting is throwing money down the drain,” there’s a chance you’ve absorbed the idea that every cent should be funneled into tangible assets like a house, a car, or even certain collectibles.
You might feel guilty about “frivolous” spending—like taking a sabbatical, traveling around Asia for a couple of months, or even enrolling in a pricey online course that doesn’t give you a “thing” you can hold.
However, the truth is that experiences can pay dividends in a different way. They can expand your worldview, enhance your skill set, and open up new creative or professional paths.
In my opinion, the best balance is a mix of both. There’s nothing wrong with owning property, but if you find yourself scoffing at the idea of a gap year or at spending money to learn a new skill, it might be a clue that you’re stuck in an older generational mindset about the “right” ways to use your money.
3. You feel uncomfortable talking about money—and see it as taboo
The classic boomer script around money? Don’t talk about it.
It’s almost like politics or religion at the dinner table. Money was personal, private, and, in many households, somewhat shameful to discuss openly.
I’ll admit, I sometimes catch myself hesitating to speak candidly about my financial situation with friends or peers—worried I’ll come off as bragging or complaining. But transparency can be incredibly powerful. By comparing notes on salaries, investments, or budgeting tips, we can learn from each other’s experiences.
4. You equate frugality with morality
Have you ever felt a strange sense of pride for getting the cheapest option—even when you could afford better? Or maybe you’ve caught yourself judging someone (even just a little) for spending “too much” on something you’d never splurge on?
In my experience, this kind of thinking—where spending less is seen as morally superior—is deeply rooted in a middle-class, Boomer-influenced mindset. Many of us were raised with phrases like “A penny saved is a penny earned” drilled into our heads.
While being intentional with your money is a smart move, it’s important to recognize when saving becomes performative or rooted in guilt. Sometimes, it makes more sense to pay for convenience, quality, or even joy. That doesn’t make you irresponsible—it makes you human.
The goal isn’t to spend recklessly, but to question whether your tight grip on your wallet is really about financial strategy—or about an ingrained belief that spending is inherently “bad.” Money is a tool, not a moral compass. Use it in ways that align with your values, not your inherited guilt.
5. You believe hard work equals success
This one hits deep because it’s so deeply ingrained. Many of us were raised to believe that if you just work hard enough, success will follow. Period. End of story.
It’s the classic middle-class Boomer belief: put in your hours, and eventually you’ll be rewarded. And while that mindset might’ve worked in an economy where upward mobility was more accessible, it doesn’t always track in today’s world.
Let’s be honest—plenty of people work incredibly hard and still struggle to pay rent, afford healthcare, or build wealth. Meanwhile, others leverage connections, luck, or timing and skyrocket ahead. It’s not always fair. It’s not always merit-based. And it definitely isn’t always about how many hours you clock.
That doesn’t mean hard work is meaningless—but believing it’s everything can be toxic. It can lead to burnout, self-blame, and a warped sense of worth when things don’t go according to plan. Worse, it can stop you from looking for smarter, more sustainable paths—like collaboration, investing, or building scalable income—because you’re too busy grinding it out solo.
Here’s the truth: success today is about more than effort. It’s about strategy, relationships, access, timing, and sometimes rest. If you’re killing yourself trying to “earn” a life that constantly feels out of reach, it might be time to question the equation—not your value.
Final words
Breaking out of old-school beliefs about money isn’t about discarding everything our parents taught us. Many of the above beliefs have a lot of merit.
But it’s worth questioning the blueprint we inherited. Are we clinging to a formula that worked decades ago but doesn’t align with how the world works now? Or are we proactively shaping our own financial identities?
By examining which beliefs serve us and which ones hold us back, we can become more strategic, more open, and ultimately, more successful with our finances.
So take a moment to reflect: which of these signs resonate with you? Do you find yourself hesitating because “that’s just how it’s done,” or are you forging your own path?
Whatever your answer, remember you have the power to write your own story.
