Sometimes, the biggest leaps take place in the smallest moments. Mine came one September afternoon when I found myself clutching a glossy real estate flyer, staring at a historic New England property that was as weathered and enigmatic as my love life at the time. Was I truly about to leave a perfectly stable job, sell off my safety net in the form of a too-comfortable Boston apartment, and sink my savings into a centuries-old eyesore? Reader, I was. But let me back up a bit.

The House That (Almost) Broke Me

To understand why this wasn’t just about shingles and floorboards, you need to know a little about me. I was born with salt in my veins. Growing up in Kennebunkport, I spent my summers crabbing on docks and daydreaming under the shadow of weatherworn lighthouses. But as I entered adulthood, that oceanic comfort zone began to feel more like an anchor. Sure, I cherished my tight-knit community and its postcard-worthy scenery, but where was my spark? My leap of faith?

Then came the house. A sagging, Captain-Ahab-meets-HGTV “opportunity” nestled amid the pines. It wasn’t just a project; it was a lifestyle change. A full return to a slower, more deliberate way of living—and more importantly—loving. Because truth be told, I wasn’t just looking for a physical home. I was trying to rebuild my sense of self and redefine what I wanted in relationships after a string of romantic near-misses.

Here’s what they don’t tell you about throwing caution to the wind: it’s terrifying. And yet, much like a hastily written love note, there’s power in taking that leap. My story may involve a dilapidated house, but I promise you, it’s about so much more.

Commitment Issues (Yes, Even with Wallpaper)

Renovating a centuries-old property is not for the romantically faint of heart. For one, there are the surprises. Did I picture myself crying over the realization that restoring crown molding cost more than my entire English degree? No. Did I think I'd end up brushing insulation out of my hair like I was starring in the least glamorous episode of Fixer Upper? Also no.

But here’s where my metaphorical drywall cracks into personal epiphany territory: the process taught me everything I needed to know about commitment—relationships included. Often, we idealize the finished product (be it the “perfect” partner, a dream home, or even a flawless Thanksgiving turkey). We trick ourselves into thinking anything worth having should come easy. Spoiler alert: it rarely does.

  • Lesson One: Say “yes,” even if you’re scared. No, especially if you’re scared. I hemmed and hawed over signing my name to that house contract the way someone deliberates over a lukewarm Hinge match. But you can’t grow without taking risks, and in hindsight, that moment of terror was the first stone in rebuilding myself into someone stronger, braver, and more imaginative.
  • Lesson Two: Love the process, not the potential. Sure, the house would eventually become a place of clapboards and soft linens and airy ocean breezes, but first, it had to get ugly. Just like relationships, there were stormy moments when messiness revealed everything vulnerable and true.

The Midnight Plaster Crisis of ’22

Because no leap of faith is complete without a moment where you question all your life choices, mine came at approximately 1:17 a.m. on a Tuesday. I had been sanding down some rogue patch of plaster when, possibly due to exhaustion, I began to cry—bawling over missed deadlines, dwindling finances, and the unholy betrayal of whomever invented lead paint. I could’ve left, tossed in the metaphorical towel, and fled back to a life of safe, non-splintery predictability.

But I didn’t. And here’s why: one small victory is often all it takes to rebuild courage. For me, it was replacing a broken windowpane and running my fingers along the smooth, clear glass afterward—the satisfaction was electric. It reminded me of something my grandmother used to say: “Small steps get you to the top of the lighthouse.”

When you're in a relationship—or healing from one—it’s the same rule of thumb. There are nights when you’re so deep in the “plaster” of arguments, misunderstandings, or personal doubts that it feels like you’re walking away with nothing but dust. But sometimes, holding out a little longer reveals a clarity you never saw coming.

Risks Come with Rewards (Even if They’re Humble Ones)

Did the house remodel turn me into some picturesque Pinterest success story? Not entirely—and that’s okay. The reward for taking wild leaps isn’t always perfection; it’s perspective. By making one brave, borderline-reckless choice, I rediscovered who I was at my core: someone strong enough to wade through uncertainty with both grace and gumption.

When I think of the biggest risk we take in love or in life, it’s not the grand gestures—it’s the decision to show up boldly, flaws and all. Whether that’s risking heartbreak with a new partner or practically bankrupting yourself for antique heart-pine flooring, what matters is how the experience stretches you. If I hadn’t taken that chance, I’d still be staring out my safe city window, dreaming of a hypothetical “someday.”

A Takeaway for You, Brave Reader

Life, love, and fixer-uppers are all complicated, messy, and inconveniently timed. But the best relationships—whether with people, places, or even yourself—are always worth the risk. Remember:

  • Perfection is a myth. Whether you’re staring at peeling paint or unpacking emotional baggage, lean into the imperfections. They’re where the magic happens.
  • Risk-taking isn’t about the outcome; it’s about the process. The house didn’t instantaneously transform me, but it taught me patience and faith in my own resilience.
  • And if all else fails? Well, lobster rolls and Milky Way views help heal even the deepest mistakes.

So, whatever leap you’re staring down today, take it. What’s waiting on the other side may surprise you. At the very least, you’ll have a great story to tell—and who doesn’t love one of those?