A recent Wall Street Journal article titled “They’re in the Top 10% of Earners. They Still Don’t Feel Rich.” struck a chord with me—not just professionally, but personally. As a financial planner, I hear this sentiment often, especially from people who are objectively doing well on paper. But I also hear it from friends, family, and if I’m being honest, sometimes from myself.
So what’s going on here? Why do people with high incomes still feel stretched or uneasy about their finances? Part of the answer is simple: fixed costs have gone up. Between housing, childcare, insurance, and other essentials, a growing portion of income is spoken for before we even get to discretionary spending. When you add in variable expenses, like groceries and dining out, and episodic expenses, like vacations and unexpected home repairs, it’s easy to feel like there’s never quite enough.
That’s why one of the most important questions I ask clients is: Do you have a clear picture of what expenses are fixed, which ones are flexible, and which just pop up from time to time?
It’s important to be on top of your cash flow—because even small purchases add up over time. Tracking your spending isn’t about restriction; it’s about awareness. When you understand where your money is going, you can decide whether it’s aligned with what actually matters to you.
But even with that clarity, it’s still easy to feel like it’s not enough. That’s because there’s often something deeper going on: the constant desire for more. In the U.S., success is often measured by what we have—our homes, cars, vacations, and how seamlessly we can keep up with it all. There’s an unspoken pressure that if you can afford more, you should get more. But at what cost?
I recently bought a brand new car. It was something I needed and had planned for. The numbers worked. It was all in alignment with my financial plan. And yet—almost immediately—I felt guilty. It felt excessive. Maybe that’s the nature of being a financial planner, but it still caught me off guard. I had to remind myself multiple times: You can afford this. You made this decision intentionally. It’s okay to spend money on something you value.
While some (myself included) may always feel some sort of guilt for large purchases, it gets easier when you have a plan. When you’ve thought it through, run the numbers, and know it aligns with your bigger goals, it shifts the feeling from impulsive to intentional. You can remind yourself: this isn’t reckless—it’s something I prepared for. That peace of mind doesn’t erase the guilt entirely, but it definitely quiets it.
That guilt—that uneasiness—is something I see come up again and again. Often, we’re not spending on things that actually bring us joy or match our values; we’re spending to match a version of success we think we’re supposed to strive for.
If you’ve ever felt like your income should stretch further than it does, or questioned your spending even when you’re not overspending, you’re not alone. The key is to get clear on what matters to you. Align your “things” with your values. It’s not about spending less or never enjoying what you’ve worked for—it’s about spending intentionally.
So let me leave you with a few questions to think about:
- Have you taken the time to track what expenses are fixed, what expenses fluctuate from month to month, and what expenses are less frequent but still matter?
- How often do you have expenses that surprise you?
- What are you spending on that doesn’t actually bring you joy?
- Do you know what parts of your spending are on autopilot versus the ones you can adjust?
- Are your financial decisions reflecting your current season of life—or are they tied to an old version of success?
- Do you feel in control of your money, or is it controlling you?
You don’t need all the answers right away—but getting curious is often the first step toward building a financial life that feels good, not just looks good.