I was still clearing the cobwebs from my brain with my first cup of coffee as I opened my inbox. Among unread newsletters, random special offers, and a daily digest of what my neighbors were arguing about on NextDoor, something caught my eye: a Delta trip confirmation.
At the time, I had a high-stress job that involved non-stop travel; every day was a blur of interchangeable hotel rooms and nondescript rental cars. Every night was spent alone at a table for one in some random city. Nothing was memorable because it was a real-life adaptation of the movie Groundhog Day—the same day every day, with slight changes.
But what was this?
It came back to me with a jolt: Scrolling through my phone late at night before bed and encountering an unbelievable deal offering roundtrip flights to Rome for just under $300. Lonely, bored, and desperately missing my kids, I had impulsively booked a trip to Italy for the three of us…to leave in three weeks.
Morning Me, who is an entirely different and far more manageable person than Late Night Me, immediately panicked. What was I thinking? There wasn’t enough time to plan, there wasn’t enough money, this was irresponsible, this could ruin me. Thank goodness I had 24 hours to cancel.
Rome would be amazing, but this is just not the sort of thing one does within three weeks.
Rome would be amazing, and one day I’d deserve a trip like that but not now.
Rome would be amazing.
What if I could do this? I checked YNAB. All of the overtime from that soul-sucking job had made it possible to stick extra money in a generic “Vacation” category. I checked how many hotel points I’d accrued while on the road. I checked how many hotel points it would take to spend 12 days in Rome. I booked a room. I emailed our HR department to tell them I was taking all of my PTO. I texted my sons to tell them we were going to Rome in three weeks and that I would have no time to plan before then but we would figure it out when we got there.
Was it a crazy thing to do? Absolutely.
It was also the trip of a lifetime; a formative experience for all three of us and a treasured memory now. We learned art, history, train travel, and pasta. We experienced the joy of getting lost on purpose and the adventure of exploring without a plan. We did deserve a trip like that—not one day but right then. And it was possible not just because I had the resources (which was no small feat), but because that money was already earmarked for travel—there was no sense of guilt, no shame, no vague fear that the money was needed for something else.
My methods may have been unconventional, but it wasn’t irresponsible. It wasn’t going to ruin me.
My Money Never Felt Right
There’s a segment of the population who doesn’t feel like they’re bad with money, but doesn’t necessarily feel good with money either. I know because I was one of them. In the past, even when I made plenty of money, my bills were paid on time, and I could buy things I wanted, I still never felt confident about what I could really afford and couldn’t quite figure out how to get ahead. I often felt guilty or confused about my finances and experienced a slight twinge of shame with every purchase.
I didn’t feel like I was bad with money but money made me feel bad.
Money is a finite resource but it felt like an abstract concept to me. I blamed it on a strong aversion to math but it turns out that hypothesis was wrong. I’m still bad at math (and so grateful that my third grade teacher was wrong about the likelihood of having a calculator on me at all times as an adult) but now I am good with money.
The actual problem was that I was disorganized and overwhelmed—in all aspects of life, if we’re being honest—but definitely when it came to my finances. Not for lack of trying, either. I tracked my spending (in the most passive way possible) with Mint. I made spreadsheets of my monthly bills. I tried couponing, made DIY cleaning products, and attempted meal planning. But that was all actually just more stuff that felt boring, overwhelming, and suspiciously related to math. My commitment to any of it was sporadic, at best. I also wasn’t seeing any real progress.
It took a lot of little treats to get me through these trying times. A new lip gloss, a bottle of nail polish, a fancy coffee drink—just a small something here and there so that it felt like there was some reward for working. I deserve this, I would tell myself, but I would always feel guilty and anxious about unnecessary spending, no matter the cost and regardless of how much money I made at the time. The spending felt good for a minute, but ultimately, this behavior just added to the clutter in my life and in my head.
A New View on Money
When I came across YNAB, it was the promise of a new process that lured me in at first. Following four rules felt easy enough and I knew I was in need of some strategy and structure when it came to my finances. Giving every dollar a job and having my expense categories so nicely defined made me feel so organized and in control. Seeing all of my financial information in one place gave me a reference point that made my money feel more “real” to me.
But the real tipping point? The guilt, shame, and fear began to disappear. I knew, with confidence, when and if I could really afford something because the money was already in that category waiting to be spent. I no longer had to justify purchases by telling myself I deserved it, because I’d actually earned it. Spending money on what I wanted brought me joy instead of regret.
“I no longer had to justify purchases by telling myself I deserved it, because I’d actually earned it.”
Eventually, I didn’t “need” as many little treats, despite knowing for sure that I could afford them now. That little dash of dopamine wasn’t as appealing if the $10 I was about to spend on lip balm could help fund a vacation instead. Once I could see that money accruing in my travel category, I understood the trade-offs I had been unconsciously making and it was easier to stay committed to my different savings goals.
And that’s how I ended up accidentally taking an unplanned trip to Italy without guilt or stress. Organizing my finances provided opportunities that new lip gloss could never offer. It gave me freedom, confidence, and security—it also meant less mental math at the cash register, and we know how I feel about math.
That’s what I actually deserved: a general sense of well-being and the comfort that came with feeling like I was in control of my finances. It’s better than any treat you can buy.
(But a trip to Italy is up there, for sure.)
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