“I Was Tracking Every Dollar and Still Losing Sleep.” Sound Familiar?

With tracking-based money apps, you know how much money you have. You also have no idea how much money you have. Both things are true.

You give a piercing gaze to your inflows, your outflows, your impulse Amazon buys at 2 a.m. You have a checking account and a savings account. You pay your credit card bill on time and even toss a little into retirement when you remember.

By all appearances, you’re a fully functional adult, responsibly… adulting. 

You’ve been paying attention. And still, somehow, it feels like you’re falling behind. Like no matter how closely you watch things, the money worry never really lets up.

If that sounds familiar, you’re not alone. I’ve been there. I see it all the time: people who are tuned into their money and still worried about it. People doing all the “right” things—and still losing sleep.

Because here’s the truth no one tells you:

Tracking your spending isn’t the same as feeling good about it.

(Say it again for the people in the back!)

All the inflows, outflows, and color-coded charts in the world can’t tell you what you actually need to know:

• Where’s my money really going?
• Why does it never feel like enough?
• And what should I do next?

Those inflows and outflows might tell you that you “spend too much” on fancy treats for your dog, but they won’t tell you why that matters—or what you’re really missing. At best, tracking shows you there’s a problem. But too often, it just reinforces the worry without offering clarity. And without clarity, the stress sticks around.

This is exactly where Jonathan was when he shared his story with our team. He wasn’t ignoring his money. He wasn’t careless or checked out. He was paying attention—closely.

And yet, the numbers kept moving in the wrong direction.

What changed everything wasn’t tracking harder. It was finally getting clear on what mattered most to him—and aligning his money with that.

Jonathan shared his story through the YNAB Stories Survey, and you can too!

Tracking the numbers, but still losing sleep

Jonathan and his future fiancé, Samie, moved into their first apartment together in 2020. It was the first time living out of their childhood homes for both of them! Like a lot of us, they saw it as a milestone, a sign they’d finally made it into adulthood.

That came with expectations.

We thought, "Now we are adults so we gotta buy all the consumer items we dreamed of."

They bought the things they’d put off for years. The blender. The Wacom Cintiq monitor. All the symbols of having arrived.

And Jonathan was watching the money.

Even though I was watching my money, the numbers were always going in the wrong direction.

No matter how closely he tracked things, the math didn’t improve.

I was on average spending $300 more each month than brought in from all sources.

Jonathan had even built up a cash buffer before the move, but month after month, it kept shrinking.

I knew this was unsustainable.

The worry wasn’t abstract. It showed up everywhere.

I was losing sleep… Somehow the daily commute to the office felt even worse because I knew every month no matter what I did I was still digging myself a financial hole.

This is the quiet kind of stress, the kind that follows you into bed, into your car, into moments that are supposed to feel normal. And for Jonathan, this went on for quite awhile. He may have still been there if a big financial goal hadn't forced him to make a change.

A wedding forces the question

In 2021, Jonathan and Samie got engaged. Like most couples, they were excited and then quickly overwhelmed.

Jonathan had one non-negotiable.

My only ‘Must Have’ was to have no debt... I refused to go into debt for a party. Why pretend to be rich?

But Samie had a detailed vision for their wedding, and it was going to cost some money! Nothing super extravagant, as Jonathan put it:

No helicopters or anything…

But when they added up the numbers, reality hit hard.

When she totaled up what she did want it was well over $40K CAD.

Samie and Jonathan wanted to get married. There was no doubt at all about that. But their non-negotiables about this wedding were in serious conflict. Samie wanted the wedding she dreamed of and Jonathan didn't want to use debt. In their current situation, making them both happy didn’t feel ambitious. It felt impossible.

This turned into a bitter argument…

And of course it did. They were two people who both wanted something reasonable and important. Samie wanted a wedding she’d dreamed about for years. Jonathan wanted to start their life together without debt hanging over them. 

Neither of their priorities was wrong. 

The problem was that all they really had to go on were the numbers they were tracking. They could see what things cost, but they couldn’t see a clear path forward. Without a way to decide what mattered most, every conversation felt stuck, and every option felt like a compromise someone would have to lose.

I gulped wondering how we'd save that with our monthly budget at the time feeling suspiciously like quicksand.

At that point, money had stopped being a simple line item and had started complicating a decision they both wanted to feel good about. They could see the costs, but they couldn’t see a clear next step.

YNAB Together can give you a system for shared visibility and goal-planning.

The difference between tracking and clarity

The turning point came unexpectedly.

Luckily in 2023 I happened to turn our TV to a YNAB beginner video.

What surprised Jonathan most wasn’t just the video, it was Samie’s reaction.

Samie was instantly intrigued. She loves logic and numbers and software so she was really curious to try YNAB the app.

Jonathan had tried to pitch YNAB before. Gently.

I tepidly asked Samie if she wanted to try YNAB but she was like ‘Pay money every month for a spreadsheet? No Way.

Maybe it was because they had a clear goal ahead of them. Maybe it was because of something in the video! But this time was different.

She took to YNAB like a duck to water. In fact, she became more passionate than I was!

Instead of just tracking what had already happened, they started seeing what their money needed to do next.

We broke down the wedding into categories. We set a wedding date and now both of us could see how much we had to save TODAY to make our dream wedding happen.

For the first time, the future wasn’t a vague source of stress. It was something they could actually see.

When the numbers finally start to feel good

Within a few months, things began to shift.

Finally after 3 months of YNAB I got my spending under control, started saving intently for True Expenses.

Then came the moment Jonathan had been waiting for.

May 2023 was Samie and my first cash flow positive months in years. I was up $426.58 and it was so humbling in a good way.

The changes weren’t flashy, but they were intentional.

Every expense was questioned. Every dollar was assigned.

Subscriptions, canceled. Takeout, cut back. Even things Jonathan cared deeply about were reconsidered.

I cancelled a personal trainer coach I recently signed up for. That was something I was really passionate about but now knew wasn't as big a priority as other stuff.

This is what I love about Jonathan and Samie's story. They weren't just cutting spending for its own sake. But Jonathan and Samie had a kick-butt reason behind every decision! They were getting married and were determined to throw a great party to celebrate!

Cutting back on spending for no reason is drudgery. No one wants to make sacrifices without a reward. But now they had a way to see that their sacrifices were worth it. They had a clear goal they were going after and, with YNAB, they could see the evidence of their progress.

But the real proof of progress wasn't even in this one big savings goal. It was in how Jonathan *felt* every day:

It's such a relief. I'm sleeping better now. Our arguments about money have magically evaporated. And my commute is nice now. I feel like I'm making progress every day and I can connect doing a good job at work with a potential raise in the future and even more freedom.

Clarity Changes How Life Feels

Jonathan’s story is such a powerful reminder of something we see again and again: tracking your spending isn’t the same as feeling good about it.

Worry thrives in uncertainty. It grows when priorities are fuzzy and the future feels unknowable. But when you can see what matters—and what it will take to get there—the anxiety starts to loosen its grip. It’s like finally turning on the lights in a room full of financial monsters. They’re still there, but now they look like what they are, some totally manageable piles of laundry. 

Jonathan and Samie are still saving for their wedding. They’re also saving for a future Disney trip. The difference now is how it feels.

I feel like I'm making progress every day.

And that feeling matters.

I’m here to remind you that money worry doesn’t have to be accepted as some sad side effect of growing up. You can have what you need and get what you want without the daily existential money crisis.

If you’re watching your money closely but still losing sleep, Jonathan’s story is a reminder that it's not because of a character flaw or a lack of effort. It’s a lack of clarity. When you can clearly see what matters most, and exactly what it will take to get there, the money worry starts to fade. Who knows? You might actually get some sleep for once.

Clarity is exactly what YNAB can bring you. If you're worried about money, you're not alone. Get YNAB, get good with money. And never worry about money again.