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The First Time I Felt Like I Was Winning With Money

Posted on May 7, 2025April 19, 2025 by Harper

For a long time, money just felt like something that happened to me. The paycheck hit, the bills took their slice, the rest vanished in a blur of groceries, MetroCards, and random purchases I couldn’t even remember making. I was always broke, always stressed, and always trying to figure out how the hell people were affording brunch and Sephora hauls like it was nothing. I wasn’t lazy. I wasn’t irresponsible. I was just always behind.

So when I started trying to get out of debt, I had no idea what a win was supposed to look like. I thought it would be something big and flashy—like paying off an entire credit card in one go, or finally hitting a savings goal that let me breathe. But that’s not how it went.

My first real win was so small I almost missed it.

I was sitting on my couch one Saturday morning, looking through my bank transactions like I’d promised myself I would. (Back in the day, I avoided my banking app like it had a virus.) I was tracking my spending for the week, trying to stay honest with myself about where my money was actually going. And something caught my eye—there was still $86 in my checking account, just sitting there, untouched.

Now, that might sound like nothing. But for me? That was huge. I used to be the kind of person who ran out of money by Thursday. The idea that I could go through a whole week and not hit zero was wild. Even better, I hadn’t deprived myself of anything major. I’d meal-prepped, skipped takeout, made my own coffee, and said no to a couple of things that didn’t really matter. That $86 wasn’t leftover because I got lucky—it was leftover because I was finally being intentional.

I sat there staring at it like it was gold. Not because I was going to do anything exciting with it, but because it felt like proof that I wasn’t doomed. That maybe I could do this.

That weekend, I transferred $50 of it to my smallest credit card balance and kept the rest in checking as a mini buffer. It wasn’t a lot, but it felt powerful. It felt like control.

That small moment changed the way I looked at the whole process. I stopped waiting for the dramatic milestones to feel good. I started celebrating every time I stayed under budget, every time I packed lunch instead of grabbing something on the go, every time I said no to a purchase and didn’t regret it later. Those tiny decisions weren’t glamorous, but they were building a foundation. Every time I chose differently, I was rewiring my relationship with money.

And let me be real: some weeks I didn’t have anything left over. Some weeks were tight and discouraging. But once I had that first taste of a win, I kept chasing that feeling—not in a toxic hustle way, but in a I-deserve-to-feel-stable kind of way.

The most surprising part? As I got better at managing my money, I started feeling better in general. Not instantly, not dramatically—but steadily. There was something about knowing exactly where my dollars were going that gave me a sense of control I hadn’t had in years. I wasn’t constantly guessing or hoping I’d make it to payday. I was choosing. That felt like freedom.

If you’re in the early days of your debt-free journey and it all feels slow or frustrating, I want you to know that the small wins matter. They count. Don’t wait for the credit card to hit zero to celebrate. Celebrate the first time you check your balance without dread. Celebrate the moment you say no to something that used to be an automatic yes. Celebrate that extra $20 you didn’t spend, because that’s the beginning of momentum.

I’m still in the thick of it. Still chipping away. Still making trade-offs. But I know what it feels like to win now—even if it’s just a little at a time. And I’ve learned that consistency, not perfection, is what gets you to the other side.

Your wins might not look like mine. That’s okay. The point is to notice them. To claim them. To remind yourself that progress is happening, even when it feels invisible.

Because one day, you’ll look back and realize that all those little wins added up to a life you built—on purpose.

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