I Thought I Was Good With Money. I Was Wrong.

I thought I was good with money. But boy was I wrong. 

I tracked everything in a paper ledger I bought at Kmart. I paid my bills on time. I even set up automatic transfers to savings—because that’s what responsible adults do, right?

But no matter how careful I was, money still felt stressful.

Car insurance threw me off every six months. A single unexpected expense could wreck my plans. I made it work, but it never felt easy. I assumed that money worry was just part of adulthood. Maybe everyone else was quietly doing the same mental gymnastics I was—trying to stretch each paycheck far enough, fast enough.

At the time, I was a public school teacher managing a modest income, and I truly believed I was doing the best I could. But when I look back now, I can see I wasn’t connected to my money. I was organizing it, but I didn’t understand what I needed it to do.

I wasn’t planning, I was reacting.

Everything changed when I found YNAB. I started asking better questions. I gave every dollar a job. I made intentional choices that helped me move forward instead of constantly treading water. Those habits stuck, and eventually, they led me to a new career: teaching others how to get good with money.

This is the story of the five questions that changed everything for me. The ones that turned worry into clarity and gave my money (and my choices) real purpose. I finally got good with money. And you can, too.

I kept a paper ledger for my monthly bills… but expenses still surprised me.

Each page of my paper ledger represented a single month. I wrote each monthly bill on a row of its own. I kept track of the name of the bill, the due date, and the amount I owed.

Look at me! So good a with money! I was SO organized and on top of things. 

But still… stuff would sneak up on me, like car insurance. I paid that every six months, and it was a crisis every time. Actually, the car was a huge source of stress—repairs, gas, registration—none of that had a home in my paper ledger.

Even so…

I paid my bills on time, but money was a constant source of stress.

Responsible adults pay their bills on time, and I wanted to be a responsible adult. So no matter what, I found a way to never pay late.

But it was hard! Sure, I paid my bills on time, but often it was at the expense of other important things. I lived through super tight periods, not because I didn’t have enough income, but because something unexpected popped up and ruined my plan.

About once a year, I’d calculate my cash flow incorrectly and end up over-drafting my checking account. We didn’t really have online banking back then, so the way I found out was when the credit union sent me a notice in the mail.

Nothing made me feel worse than getting an overdraft notice. I would literally feel sick to my stomach. This is what happens when you’re bad with money—and I was supposed to be good with money!

So I looked for ways to be even better. 

I borrowed money in order to build credit, but it took away my options.

I was taught that it was very important to build good credit, because if you want something expensive, borrowing is the only way to get it. I knew I’d eventually want to buy a house, so I set out early to build credit.

In my early twenties, I took out a loan for a digital piano. I still have it to this day—it’s a Yamaha Clavinova. As I mentioned, I was teaching music at the time, and since I was also renting, I needed a keyboard for lesson prep that wouldn’t drive my neighbors up a wall. I could plug headphones into the digital piano.

I took out a loan for $2,000 at my local credit union. I remember feeling so proud that I qualified for a loan. Look at me! I’m building credit! And it was the only way to get that kind of keyboard. No one has money like that!

I also used my credit card for big things, but only when there was a real emergency like a car repair.

But then I had to make payments, and those payments made everything feel even tighter than I had imagined. 

Still, I was trying to save. 

I transferred money to my savings account every paycheck, but it never stayed there.

"You’re supposed to save," they say, and I knew that. And you’re supposed to automate your savings! So I set up an automatic transfer at the bank to move $50 from checking to savings every two weeks when I got paid.

The thing is… I couldn’t make it stick. Sure, the money moved to savings, but I was constantly running out of money before the next paycheck arrived. That $50 moved over, but $40 moved back.

There was no intention behind what I was doing, no purpose behind my hard-earned dollars. As a result, I struggled to save. Automating savings seemed to automate me right out of the equation. 

If I was good with money, why did it feel so bad?

It’s so interesting when I think back on it—I thought I was good with money, but I didn’t feel good with money. And somehow, I accepted that contradiction as normal.

I never paused to ask, “Shouldn’t being good with money feel good?” 

I just figured stress and worry were part of the deal. That no matter how well I played by the rules, I’d still always be second-guessing, always bracing for something to go wrong. I think back then, I just assumed everyone had money stress. Everyone worried about money.

Money was something you managed, endured, tried to stay ahead of—but never something that gave you peace or confidence or clarity. That part didn’t even seem like a possibility.

What finally made me try a new way?

What finally forced me to face that contradiction was credit card debt… yet again.

I’d been debt-free except for a mortgage, and I really thought I’d moved past the credit card debt chapter of my financial life. But then I bought a house that needed major renovations, and without YNAB, I just did what felt reasonable: I spent some of the leftover money from the sale of my previous home.

“I’m good with money,” I told myself. “I don’t need to worry.”

But worry found its way back in. The money ran out faster than I expected, so I did what I had to do—I put the rest on a credit card. It happened so fast. Within six months, I’d gone from zero debt to nearly $8,000 on a card. And I was right back in the place I’d worked so hard to escape.

That was the breaking point. For the first time, I started to wonder if being “good with money” needed to mean something entirely different.

Asking better money questions changed everything.

When I started using YNAB, I didn’t instantly understand what I was doing differently, I just knew it felt different. It felt good.

For the first time, I wasn’t reacting to money problems after they happened. I was asking questions before I spent any money. And not just any questions. Questions that gave structure to my decisions and helped me pay attention in a way I hadn’t before.

These five questions ended up solving every one of those old problems I thought were just part of being an adult.

What does this money need to do before I’m paid again?

This one took what I was doing—working paycheck to paycheck—and leveled things up significantly. 

It made me look beyond the regular monthly bills I had written in my old paper ledger and ask, what else needed to be covered? Gas. Groceries. That birthday party this weekend. Suddenly, I wasn’t scrambling or second-guessing. I could see what the money needed to do, and I could give my dollars jobs (on purpose).

What larger, less frequent spending do I need to prepare for?

Goodbye, surprise car insurance. Goodbye, popup registration fees and holiday panic. These things weren’t actually emergencies, they were just unplanned. This question made me name them and set aside money gradually, so when those expenses showed up, instead of reaching for credit, I had the money and was ready. 

This is how I first learned to really save money. Instead of automating blindly, I learned to name what I’m saving for. Saving for specific, real expenses made me much less likely to pull money out of savings randomly.

For the first time, my savings were actually tied to something tangible. If I pulled money out of my savings account, I was giving up something real. 

Prefer to watch? Sarah explains how to plan for non-monthly expenses in the new Money 101 series on TikTok!

What can I set aside for next month’s spending?

This question helped me finally break the paycheck to paycheck cycle. I used to feel like I was starting from zero every time I got paid—just trying to make the money stretch far enough, fast enough. But this question nudged me to look ahead. Even setting aside a little gave me space. A little breathing room. A little peace. I wasn’t scrambling to make it to the next paycheck anymore—I was building margin.

It took me about a year, but eventually I got to a place I didn’t think was possible: I woke up on the first of the month with the entire month funded. Instead of a pile of bills waiting for money to arrive, I had a pile of money waiting for the bills to arrive. I wasn’t just surviving between paychecks anymore. I was finally ahead.

What goals, large or small, do I want to prioritize?

I used to think goals were things I’d tackle “someday” when everything else was handled. But this question brought them into the present. It gave me permission to fund my future, even in small amounts, and feel good about it.

Setting goals by creating categories in YNAB gave me permission to save for the things I wanted, not just the things I needed. I proved to myself that if I saved intentionally, and all my regular bills are covered, I could spend on those things not only without worry, but actually with a lot of joy.

Not sure where to start with goal-setting in YNAB? Try a ready-made template.

What changes do I need to make?

This question gave me permission to be human. It helped me realize you just can’t see everything coming and making adjustments aren’t just normal— they’re smart. Flexibility isn’t failure, it’s actually a critical tool.

Plans change. Priorities shift. Life happens. I could move money, adjust, try again—and not feel like I’d messed up. That was huge!

These five questions didn’t just fix my money problems. They fixed the feeling of never being sure. They gave me a framework that made everything clearer, calmer, and more purposeful. I didn’t have to guess anymore. I could just… decide.

How to tell if you’re “bad with money” (even if you think you’re not)

For a long time, I thought being bad with money meant you were careless or irresponsible. But here’s what I’ve learned—both from my own experience and from teaching thousands of YNABers:

Being “bad with money” doesn’t mean you’re bad at life.

It just means no one ever taught you how to do money in a way that actually works. You might be in a situation just like I was, thinking money stress was just part of being a grown up.

Being bad with money is not a character flaw. It’s a missing skill. And the good news? You can learn it. You just need a method that makes sense for real life—one that helps you feel clear, confident, and in control.

Here are a few signs you might need a better system (not more willpower):

• You save money one paycheck… then pull it right back out the next.
  
• You’ve said, “I make good money, so why does it still feel like I’m always behind?”
  
• You feel a wave of dread every time your car makes a weird noise.
  
• You’ve used your credit card for emergencies more times than you can count.
  
• You’re doing everything “right,” but money still feels hard and unpredictable.
• Stressing about money and mentally transferring money between accounts keeps you up at night.
• Money talks with your partner end up feeling like money fights.

If any of this sounds familiar, you’re not alone. And you’re not broken. You’re just ready for a different way.

Connection, clarity and confidence

Before YNAB, I felt disconnected from my money. It was an external thing to be managed. I was doing all the “right” things—tracking bills, paying on time, trying to save—but none of it felt personal or grounded. I didn’t have a clear sense of where my money was really going. It felt like I was following a script someone else had written, and it wasn’t working.

YNAB gave me connection: connection to my money and as result, connection to myself. And with that came clarity: a full picture of my money, not just what was due today, but what I was planning for tomorrow. 

I could finally make decisions with confidence instead of crossing my fingers and hoping I’d guessed right. Money still had its ups and downs, but the constant anxiety? That was gone. I went from reacting and worrying to deciding and trusting. 

And for the first time, I was just doing things that made me “good with money,” but I felt like I was good with money. Because finally, I really was.

Ever worried about money? You’re not alone. I did too—even when I thought I was doing everything "right." YNAB taught me how to get good with money, and it changed everything. Try it free for 34 days and never worry about money again.