When to Cut Your Losses
Sometimes the most expensive lesson is the one you refuse to learn after multiple opportunities.
Last year, I helped my girlfriend move to Costa Rica. She’d put down a deposit on a place she’d been referred to by a friend, with only pictures to have a sense of its condition. When we arrived, reality hit hard. For starters, to reach her intended new home, we had to cross a river that would become impassable during the rainy season. The place itself was only vaguely like the photos: mold growing in multiple areas, the smell of bleach in the air, water leaking dangerously close to electrical outlets, and an overall state that screamed “health hazard,” especially for someone with allergies.
My girlfriend was spiraling with anxiety, overwhelmed by the stress of being in a new country with what felt like no viable housing option. I suggested we step back, book an Airbnb for a night or two, and make the decision from a clearer headspace rather than from panic. There are always choices to be made if you zoom out enough.
That breathing room made all the difference. Away from the immediate pressure, we could think rationally. I found a better option through Reddit, and though it meant losing her deposit and paying more monthly, we both knew it was worth it for her peace of mind and quality of life. She’s still happily living there today.
Fast forward a couple months after that experience.
I drove two hours to Fort Pierce for a potential photoshoot and to visit the nearby nude beach. Trying to keep costs down, I booked what looked like a charming converted garage on Airbnb. The photos weren’t quite misleading, as they so often are, but I definitely didn’t fully appreciate how gloomy it would feel due to the lack of natural light. Then it started raining. And kept raining. To make matters worse, my photoshoot fell through due to work conflicts on the other person’s end.
After one night in that depressing garage and a morning spent walking around the small waterfront downtown area (which was actually lovely), I faced a choice. The rain was rolling in again, promising another afternoon and evening trapped in that dim space. I could stick it out because I’d already paid, or I could cut my losses and head home early.
The Costa Rica experience flashed through my mind. Sometimes the grown-up move isn’t stubbornly sticking to your original plan because of money already spent. Sometimes it’s recognizing when to fold and choosing your sanity over your sunk costs.
I packed up and drove home, eating the cost of the unused night. Sure, I was out the money, but I gained something more valuable: the reminder that I don’t have to endure misery just because I’ve paid for it. The irony wasn’t lost on me. In Costa Rica, I’d convinced my girlfriend to prioritize her wellbeing over a lost deposit. A few months later, I had to take my own advice.
Whether it’s travel, work, or life decisions, we often trap ourselves by trying to “make it work” after we’ve invested time, money, or energy. But cutting corners to save a few dollars frequently costs more in stress, discomfort, and lost opportunities than just paying for what we actually need from the start.
Sometimes the wisest investment is knowing when to walk away. Pay the extra for peace when you can. Make space for comfort and clarity. Your future self will thank you for choosing ease over stubbornness.
In the end, I focus more on the morning I spent exploring the downtown area, chatting with local artisans at a plant nursery and gem shop than on the accommodation I endured or the photoshoot that never happened. Ultimately, learning to trust my instincts about when to hold ’em and when to fold ’em made it a net positive.