Am I Doing It Right? Learning to Trust Yourself With Money

When a woman tells me she isn't good with money, I listen for what's beneath that statement. Usually, it isn't a lack of knowledge. She's read the books, taken the course, and may have followed three different money experts over as many years. What she's missing is trust in her own judgment about what fits her life, especially as that life has grown more complex than the systems she built for an earlier version of it. I've come to believe that learning to trust yourself with money is the skill underlying all the others.

You may have every bill on autopay and a spreadsheet that would impress your accountant, yet still wonder whether you're doing it right. That's usually a sign you've gotten too far into the weeds and can no longer see the big picture. That question can also feel like proof you're failing. I see it differently, though. I see it as a skill no one ever taught you, and skills can be learned.

The Question Running Underneath Everything

A woman I worked with recently left a corporate career to build her own creative business. She'd made that leap with real courage, and her income now fluctuated month to month in ways her old paycheck never had. Her expenses were lean, and many of her decisions were genuinely smart. She'd built a spreadsheet listing every bill, due date, and account. She'd set up autopay so nothing slipped, and she'd paid off her phone early to switch to a cheaper plan.

What she hadn't done yet was step back, look at the big picture of her new life circumstances, and ask whether the underlying structure still met the needs of the life she was living now. She had no high-yield savings account as a cushion and no rhythm for paying herself from the business. Her previous savings had done exactly what savings are for and carried her through the leap, but nothing had been designed to refill them. When we got to what was really weighing on her, she named it in a single question: "Am I doing it right?" That question had sent her through different circles of financial education, each promising to be the thing that finally made everything click. Every new framework and tactic meant a new tab on the spreadsheet, and each new tab raised the same question again.

When Dave Ramsey's Method Doesn't Fit Your Life

Years earlier, during her marriage, she and her then-husband took Dave Ramsey's course and tried his zero-based budgeting method, giving every dollar a job each month. She committed fully and got so deep into the weeds that it began to strain her relationship with herself and her spouse. She started to feel like she was policing every dollar instead of living her life. It also led to the classic case of not being able to see the forest for the trees. When you track every small detail, the bigger picture slips out of view, and you stop focusing on what actually moves the needle in your finances.

In her marriage, as in so many others, she didn't have the full financial picture, especially when it came to her spouse's finances. Many women know this experience well. She was meticulously tending to the trees she could see while part of the forest stayed out of sight. No method, however rigorous, can make up for numbers you can't see.

Many people find their footing with Dave Ramsey, and that deserves respect. But a method designed for one set of circumstances isn't a verdict on you when it doesn't fit yours. When a system stops working, it's easy to conclude that you're the problem rather than the fit. The lessons she actually took from those years were wise: keep it as simple as possible and be aware of everything you can. Simple enough to see the forest, and aware enough to know what's in it. Those are her rules, written from experience, and they suit her life better than anything she borrowed.

Trust Yourself With Money, Even When Your Values Differ From Your Family's

Outside experts aren't the only voices we measure ourselves against. Many women in an older generation value well-made furnishings that last and often want to pass those pieces down through the family. The generations after them may have different values, though. That dining table, set of silverware, or china might not fit how a younger woman lives now, and the question of who will keep it can carry a lot of weight on both sides.

My client felt torn and struggled to navigate the situation. The most challenging and important part is understanding where each person is coming from and recognizing that each person is entitled to their own values. A grandparent or parent might feel their values are being judged as wrong if you choose different values. Communicating that you're not judging them or thinking they're wrong lets you hold your values while validating theirs.

This matters for money because much of what we call "doing it right" comes from our parents and grandparents. Many of us grew up in families where money was something you kept quiet about, and those messages follow us into adulthood. As I've written before, inherited money is never just money, and the same is true of inherited money rules. Honoring where you came from doesn't require running your life by someone else's values.

From "Am I Doing It Right?" to "Am I Doing What's Right for Me?"

In Positive Intelligence, which I bring into my coaching, the part of us that insists there's one correct answer is called the Stickler. Its strength is order, and its false promise is that if you get it exactly right, you'll be safe. The Stickler is present in my life and in my clients' lives. With this client, the Stickler was traced back to math class, where an answer was either right or wrong, and wrong was bad. Your accounts don't work like math class. They hold no right-or-wrong answers, only information to get curious about.

We changed the framing from "Am I doing it right?" to "Am I doing what's right for me?" That shift changes what it means to trust yourself with money. For her, it meant trading a weekly finance date that kept getting pushed back for a short daily check-in she could maintain. It meant validating her need to work in a loud environment, because her brain needs noise to focus, rather than going somewhere quiet, which other people's brains might need. It also meant deciding how and when her business pays her, so her personal accounts receive a predictable paycheck even when her income fluctuates.

None of those steps came from a new framework. They came from paying attention to how her life and brain actually work, then building structure to match. That's what I mean by ADHD-informed systems and habits: the system fits you, not the other way around, whether or not you've ever received a diagnosis.

If your life has become more complex than the money systems you built for it and you keep searching for the right way, please know that nothing is wrong with you. You've likely been working within a structure designed for an earlier version of your life and measured against someone else's values. Learning to trust yourself with money is a skill that grows stronger with practice and guidance from someone who knows the terrain.

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If you're carrying more complexity than your money systems were designed to handle and find yourself second-guessing every financial decision, I invite you to schedule a free Money Conversation. We'll start with what's right for you and build from there.

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Financial Coach Sabrina

Insight Financial Coaching

Know Yourself. Know Your Money. Claim Your Financial Agency

Serving high-earning midlife women carrying the financial load on their own

in Austin, TX, and nationwide via Zoom