I worked two jobs to fund my dream vacation — here’s one mistake I’ll never make again

I thought the hard part was the hustle.

For six months, I lived on a loop: café shifts at dawn, laptop at night, tips tucked into a jam jar on my counter like little boat sails.

I sold half my closet, learned twelve ways to cook beans, and watched my “Dream Trip” fund inch upward — slow as ivy, steady as breath.

When the number finally clicked, I celebrated the only way a travel-obsessed person knows how: I booked Florence, closed my laptop like a curtain call, and braced for the opening scene — gelato at sunset, sandals on cobblestones, a cinema of golden light.

Except the montage didn’t arrive on cue.

Florence was luminous. I was gray around the edges. My itinerary read like a dare, not a trip — four cities in eight days, sunrise trains, twilight tastings, lines I’d “beat” with willpower.

I’d picked the cheapest connections with the most transfers because I was still living in “stretch every euro” mode. Saving forty bucks meant a 5:40 a.m. bus to a regional train to a shuttle to a tram.

I arrived everywhere vibrating instead of arriving. The city kept handing me beauty and I kept trying to optimize it, like a person eating a peach with a calculator.

That’s when the quiet truth slipped in like a draft under a door: I’d planned for money; I hadn’t planned for the body that would spend it.

The mistake you don’t see until you’re in it

Here’s the part I wish someone had told me: you can be excellent at budgeting cash and terrible at budgeting capacity.

I tallied euros, hunted off-peak fares, bought museum tickets in bundles, and patted myself on the back for getting a “deal.” What I didn’t account for was the cost of arriving after months of double shifts with a nervous system like burnt toast. Hustle had rewired me.

On the ground, that looked like rationing joy and auditioning for the role of “person who does everything.”

The early warnings were small and therefore easy to ignore. I skipped a tiny museum because the entry fee felt “unnecessary,” then spent the same amount on three forgettable snacks because I refused to sit for lunch.

I chose a lattice of transfers over a taxi when I was already running on fumes.

Decision fatigue set up its campsite in my skull: “Left or right?” felt like a midterm exam. In a sun-splashed piazza, surrounded by a city begging to be experienced, I froze—not out of fear, but out of depletion.

I kept thinking, I worked two jobs to get here; how dare I rest? But rest wasn’t indulgence. It was infrastructure.

Treating a vacation like a finish line turned it into another shift to clock. That’s the mistake I’ll never make again.

Church steps, new gospel: one anchor, ease on purpose, room to breathe

On day three, I sat on the cool steps of a church and wrote rules on the back of a crumpled receipt — nothing dramatic, just a different blueprint for the next twenty-four hours.

If the trip was going to survive me, it needed new math.

1) One anchor, not five.

Each day got a single thing I’d be thrilled to remember: a morning with a painting, a long lunch with a view, a neighborhood walk at golden hour.

If I had juice for extras, great. If not, I’d already “won.”

No more cramming four highlights into a single afternoon like socks into an overfull carry-on. One anchor gave the day a center of gravity. Everything else could orbit or fade.

2) Convenience is a line item.

I set a small daily “ease fund” I could only spend on reducing friction: a timed ticket to skip a serpent of a line, a taxi when transfers looked like a puzzle, the café next door with shade and a clean bathroom.

Not splurges—energy investments with wild ROI.

When I bought time or comfort on purpose, my trip stopped charging interest in the form of headaches, hangry sighs, and missed trains.

3) Build margins like a civil engineer.

Travel days became half-days, not “squeeze three more things in” days. I padded train times, booked lodgings with laundry so I wasn’t doing sink acrobatics with hotel shampoo, and ended afternoons with the four most luxurious words I know: “That’s enough for today.”

I protected mornings like a treasure because they decide the tempo of everything after. This wasn’t quitting ambition; it was right-sizing it.

The first night I honored those rules, my sleep stitched itself back together. My appetite returned and tomatoes tasted like they remembered the sun.

I lingered under an arcade while a storm rinsed the city and, for the first time since landing, my shoulders actually dropped.

Beauty was there all along — I’d finally made space to feel it.

The grind I loved, the story I changed

I have to admit something humbling: a part of me adored the grind. It made me feel competent and necessary.

“Two jobs! The dream!” is a story with applause built in, and I’d been performing it for months.

That part didn’t vanish when I boarded the plane — it put on a new costume—an aggressive itinerary, a fear of “wasting” the money I’d earned, a habit of turning every minute into proof that I deserved to be there.

Naming that part helped. I started talking to it like a slightly overcaffeinated friend: I hear you. We’re safe. We can go slow.

I paid for small luxuries in advance so my depleted evening brain didn’t debate them on the sidewalk—one beautiful dinner, one guided walk with a local I actually wanted to talk to, one seat with a view.

I moved from “How much can I squeeze in?” to “What’s the simplest way to meet the day well?” And then something clicked.

Compliments from strangers shifted from “Where’d you get that?” to “You look happy.”

That’s the metric I trust now.

Not the list of sights checked, but the way my face softens when I’m not proving anything.

I also learned to treat the weeks before departure as part of the trip.

No last-minute stack of extra shifts. One day off to pack without panic. One day on return to land without whiplash.

Fewer cities, more nights. A decision threshold (no more than three choices after 6 p.m.). A small envelope labeled “Delight” that

I spend shamelessly — good gelato, a locally made object I’ll touch every week for years. The past version of me didn’t work all those hours for a blur of transfers and receipts; she worked for a handful of moments that make the work make sense.

If you’re hustling for a ticket right now, read this before you board

I’m cheering for you — truly. Working two jobs to fund a dream is brave.

Just budget for your future energy with the same ferocity you bring to your spreadsheet.

Add buffers on both ends of the trip. Prepay a few ease-makers so you’re not negotiating with a tired brain. Pick one anchor per day and let everything else be a consequence of being present.

Remember that convenience, when well-placed, is not decadence — it’s protection for the human who earned the ticket.

Most of all, refuse the lie that you must empty yourself to deserve joy.

The best souvenir isn’t the perfect itinerary — it’s wanting to do it again—arriving as a person, not a husk.

When your pace matches your pulse, a trip stops being content and becomes a memory that keeps paying rent in your life. The montage won’t always roll on time. That’s okay. You get to write new scenes.