Tag: first time homebuyer mistakes

Think back on your most memorable road trip.

We signed a house contract at a used car lot—on our honeymoon road trip to Alaska.

My husband and I postponed our honeymoon for a year because we both dreamed of driving from Wisconsin to Alaska. At first, we planned to fly, but then he asked why we didn’t look up the driving logistics. I did, and it came out to about 60 continuous hours on the road.

“That doesn’t seem too bad,” I thought.

So we began planning a three-week road trip for June 2018. We bought a new Subaru Crosstrek, figured out the perfect gear and packing technique, and anxiously counted down the days.

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Trailer hitch

Rear mounted cargo hold

Cooler

Blackout Shades

The House That Hijacked Our Honeymoon
What we didn’t plan for happened the day before we left. We toured a beautiful house and property that was for sale by owner. We were actively looking, and this one appeared on the market that Monday. The day before departure, we put in an offer. The next morning, already packed and driving down the highway, we got the call: they accepted it. Then came the catch—they insisted we turn around, come back without a realtor, and negotiate the terms in person.

In hindsight, the red flags were glaring. At the time, we were just young and excited. We’d only made it to the next town over, so back we went to sit with them and work out an agreement that we later learned was heavily biased toward the seller.

The Used Car Lot “Realtor”
They had plenty of experience. They’d bought rental properties before, were about thirty years older than us, and had their real estate friend there “just to write up the paperwork.” We met them at his actual business building: a used car sales lot. Meanwhile, we had a suitcase in the backseat, a printed itinerary to Alaska, and a lot of naive trust that people were generally fair. We signed what they put in front of us, then handed the agreement to a lawyer we hired sight unseen because the deal needed to close before we returned from our trip— because this was the trip of a lifetime we’d already postponed once.

We told ourselves it was fine. We didn’t know enough yet to recognize just how stacked against us the whole setup really was.

Alaska via Internet Cafés
From Velva, North Dakota, we hired a real estate lawyer over the phone. From Saskatoon, Saskatchewan, we tracked down a home inspector willing to examine a property we hadn’t even emotionally committed to yet. From a restaurant with spotty Wi-Fi, we opened our email and read the lawyer’s first warning that the terms weren’t great. From Watson Lake, Yukon—somewhere between the Sign Post Forest and actual spruce forests—we began to grasp just how bad the terms really were. And from Anchorage, Alaska, with mountains filling the windows and our honeymoon dreams fading in the background, my husband was completely fed up and trying to convince me to walk away from the whole deal.

I pushed on anyway, stubborn and hopeful as ever. I hunted down internet cafés and libraries in small towns, asking clerks if they had a scanner I could borrow. I hunched over public computers, printing documents, signing them, re-scanning, and emailing everything back to the lawyer and sellers while other travelers casually checked weather reports or email. There’s a particular absurdity to signing legal addendums about well inspections with bear safety posters hanging on the wall behind you.

Honeymoon Highlights Amid the Chaos
The road trip itself was everything we’d dreamed of and nothing like we imagined. We drove long stretches of highway that seemed to belong to no one, met kind strangers at gas stations, and watched the sky turn light again at 3 am . We ate sandwiches in the car, argued about which way to turn, and pointed out every moose sighting like excited kids. But running underneath all the glaciers and mountain passes was this constant undercurrent of “Did that email go through?” “What did the lawyer say now?” “Are we making a huge mistake?”

What That House Meant to Us
Looking back, what makes this road trip so memorable isn’t just the honeymoon or the bad real estate decision. It was us—very early in our marriage—learning how each of us handles pressure. He was ready to cut our losses for the sake of peace. I was determined not to walk away from something we’d already invested so much in: time, money, emotion, and the dream of that house and property. We took turns being the calm one and the panicked one. We learned how to argue in a car without a door to slam and how to apologize at the next gas station.

In the end, the house did become ours, but not without real emotional and financial cost.

However, that property saw us bring home our first child, learn how to garden from scratch, fix a house that needed a lot of love, grade our first driveway, and bring home our very first chickens—the true beginning of our homesteading life. Five years later, we sold it. Not because we didn’t love it, but because we needed to move closer to family as we planned for our daughter.

The road from Wisconsin to Alaska became the backdrop for midnight phone calls, scanned signatures, and the slow realization that experience and age really do matter when you’re sitting across from someone at a negotiation table—or their used car lot “realtor.”

If I had it to do over, I’d bring a realtor, a lawyer, and a far more cautious pen. But that trip also forced us to grow up a little faster and see each other clearly, flaws, stubbornness, and all.

When I think of my most memorable road trip, I don’t just picture mountains or long stretches of Canadian highway. I see a young couple in an overstuffed Subaru, chasing one dream all the way to Alaska while fighting not to lose another one back home.

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