People who struggle financially their entire lives usually make these 8 money mistakes

I’ve noticed that many people I’ve met over the years—friends, family, acquaintances—have vastly different relationships with money.

Some thrive financially, while others seem forever stuck in a cycle of stress and worry. More often than not, this gap comes down to a handful of habits we develop and never question.

Whenever I scroll through social media, I see countless “hustle gurus” offering all sorts of quick-fix solutions. But real, lasting financial stability isn’t about chasing the latest trick; it’s more about avoiding the pitfalls that quietly drain our resources.

I’ve had to learn some of these lessons the hard way, especially back when I started my first small business in my late twenties.

In this post, I’d like to talk about eight key mistakes that tend to keep people trapped in ongoing money trouble. I’m speaking from personal experience and from what I’ve gathered researching entrepreneurs, but I believe these mistakes are universal enough that we can all learn from them.

1. They don’t have a clear plan

One of the most frequent errors I’ve seen—and one I’ve made myself—is not having a financial roadmap.

Without a plan, money slips through our fingers before we even notice. A rough budget might be scribbled on a sticky note or typed into a phone app, but that’s where it ends. No accountability, no monthly check-in, no real clarity.

I used to think, “I know approximately how much I spend each month. That’s good enough.” Turns out, an approximate idea isn’t the same as an intentional, detailed plan. Over the years, I’ve become more structured about setting targets, tracking expenses, and regularly revisiting my financial goals.

The funny thing is, having that plan doesn’t feel restrictive. It’s actually liberating. It takes away the dread of looking at my bank statement, because now it’s all mapped out and I can see how each choice aligns with my bigger picture.

Even if you’re not an obsessive numbers person, a simple spreadsheet or budgeting tool can make a world of difference.

2. They spend to impress

I’ve seen people go for pricey items—cars, gadgets, designer clothes—simply because they want to look successful on the outside.

A mentor once told me, “True wealth isn’t what you show off; it’s the stability you have when no one’s watching.” That stuck with me.

When I was younger, I felt pressure to appear more accomplished in my career. So, I bought a phone that was way above my price range and took on a monthly subscription fee just because it made me feel “legit.” It didn’t feel so great a few months later when I realized I was juggling a growing credit card bill.

This isn’t to say we can’t enjoy nice things. Life is about balance. But the drive to buy something just to impress others often leads down a rabbit hole of debt and financial stress.

The real goal, I think, should be about building a solid foundation first—being prepared for emergencies, investing in assets that bring long-term returns—before splurging on luxuries for the sake of appearances.

3. They ignore building an emergency cushion

If there’s one thing I’ve learned, it’s that life is wildly unpredictable.

An unexpected car repair, a medical bill, or a sudden drop in business revenue can throw off your finances in a flash. People who struggle financially often have little to no savings set aside for those curveballs.

I used to skip saving for emergencies because it seemed like an unnecessary sacrifice when I could be buying something fun or putting that money elsewhere.

Then life taught me otherwise. All it took was one big plumbing disaster at home—pipes bursting, water damage, the whole headache—to make me realize I needed a separate stash of “just-in-case” cash.

Having an emergency fund won’t solve all problems, but it prevents a temporary crisis from turning into a long-term financial headache. It doesn’t need to start big: even small contributions each month can grow significantly over time.

Think of it as a personal safety net—something that lets you handle life’s sudden hurdles without spiraling into debt or panic.

4. They try to wing it without learning about finances

I’ve heard people say, “I’m just not good with numbers,” or “Investing is for experts.”

Ironically, these same folks might spend hours figuring out complex video game strategies or memorizing sports stats. The truth is, if we put that same energy into learning about personal finance basics—saving, investing, interest rates, or how compound interest works—we’d be much better off.

For me, reading articles from sources like Farnam Street or Harvard Business Review introduced me to new ways of thinking about money. I started small: reading about different types of investment accounts, understanding mutual funds versus stocks, or learning why a high-interest savings account can be a game-changer.

By treating personal finance as a skill to be learned, rather than a chore to be avoided, we empower ourselves to make informed decisions. And you don’t need to be a math whiz to grasp these concepts. A little dedicated study goes a long way.

Over time, you’ll see how small choices made with knowledge can compound into major advantages down the road.

5. They believe credit is always a safety net

Credit cards have their perks—rewards points, convenience, and short-term liquidity. But relying too heavily on them, or thinking they’re a financial safety net, is a major setback for many.

I’ve watched friends buy things they couldn’t afford, rationalizing it with “I’ll pay it back next month.” But “next month” comes, and they’re stuck with a hefty bill plus interest.

This habit can become a slippery slope. The more you rely on borrowed money to patch monthly gaps, the bigger those debts become. High-interest rates, late fees, and penalties can pile up fast, locking people into a cycle of payments that leave them with even less disposable income.

Early in my business journey, I fell into the trap of using personal credit cards to fund certain operational costs without a solid repayment strategy. The outcome? A mountain of stress and a crash course in why mixing personal and business finances can be dangerous.

The better approach: treat credit as a tool, not a financial crutch. If used wisely and paid off regularly, it can help. But if you’re leaning on it every month just to survive, it’s a red flag that your overall plan needs a serious reboot.

6. They don’t adapt to changing circumstances

If there’s one thing I’ve learned from both my personal life and my work with startups, it’s that you have to stay adaptable.

People get used to a certain way of living or spending and stubbornly stick to it, even when their income shrinks or their expenses spike. That’s a recipe for long-term financial headaches.

Let’s say you’re used to dining out four times a week because you have a well-paying job. Then you switch careers or launch a small business, and suddenly your income fluctuates.

But you keep up your old lifestyle, telling yourself, “I deserve this, I’m used to it.” Before you know it, you’re relying on credit cards or dipping into your savings just to keep up appearances.

Financially stable individuals—be they wealthy business moguls or savvy freelancers—often emphasize being flexible. Simon Sinek once said something along the lines of, “We’re not good at everything, we’re not good by ourselves. Our strength lies in finding how to succeed in the face of change.”

While he spoke about teamwork, the idea still applies to money management. Embracing change, adjusting budgets, and recalibrating priorities are crucial to preventing financial struggles from becoming permanent.

7. They avoid talking about money altogether

I get it. Conversations about money can be awkward, especially if you grew up hearing things like “It’s rude to talk about finances,” or “Money talk is taboo.” But avoiding those chats means we end up in the dark about potential opportunities or pitfalls.

A while back, I almost made a costly mistake while purchasing a car because I trusted the dealership’s financing pitch without consulting anyone. Luckily, a friend who’s more knowledgeable about loans and interest rates stepped in, gave me some suggestions, and saved me from a not-so-great deal.

Sometimes, we just need a second opinion—whether it’s from a friend, a financial advisor, or an online community of entrepreneurs. Many successful people I’ve interviewed say they’ve learned as much from open, honest conversations about financial failures as they have from reading books.

Sharing personal finance stories, comparing strategies, and seeking guidance can help us dodge hidden fees, negotiate better deals, and discover overlooked opportunities. Silence only keeps us trapped in ignorance.

8. They never set long-term goals

One of the biggest oversights is failing to think beyond the immediate horizon.

When I started my first small business, my only goal was “make it profitable.” I didn’t think about how I wanted to reinvest earnings, what kind of lifestyle I aimed for, or how I’d handle retirement savings. Everything was about the short term—just trying to put out one fire after another.

But as years passed, I realized how crucial it is to have long-term targets, even if they’re flexible. I set milestones for business growth, personal savings, and even big family goals (like funding my kids’ education).

Having these targets in mind influenced my day-to-day decisions. It became easier to say “no” to impulse buys because they didn’t align with the bigger picture.

Adam Grant once noted that successful people often strike a healthy balance between present enjoyment and future gain. They’re willing to invest time or resources now, knowing those efforts will compound and pay off later.

Without a vision for the future, it’s easy to get stuck in a loop of short-term decisions that never add up to real progress.

Wrapping up

All of us have made at least one or two of these mistakes—I know I’ve been guilty of a few. The good news is that nothing here is set in stone.

With a shift in approach and a willingness to learn, it’s possible to move out of old spending patterns and into better financial habits.

I always remind myself that true financial security isn’t a one-time achievement. It’s an ongoing practice that we refine as we go, adjusting to new jobs, family needs, market changes, and personal goals.

We don’t need to go from zero to perfect overnight. Small, consistent steps—like reading up on personal finance, building modest savings, cutting back on unnecessary expenses—can gradually transform our money situation.

Most importantly, a calmer, more informed approach to money tends to spill over into other parts of life. When you’re not in constant financial stress, you think more clearly, you’re able to invest in meaningful experiences, and you have the headspace to plan for a future that excites you.

It’s never too late to get started on that path.