Starting Over in Our 50s: Why We Sold Our Dream Home for a Ski-In Cabin

When people ask why we sold our house and started over in our 50’s, we tell them the truth: time and opportunity.

That usually gets a pause, because it’s not the answer people expect. They are waiting to hear about a crisis; a layoff, a health scare, a marriage that needed saving. But that wasn’t our story. Our story was simpler and more deliberate than that.

We were 53 and 55. It was 2022 and we’d just finished a three-year DIY renovation on our dream home: the kitchen we’d always wanted, anchored by the Lacanche range I’d dreamed about for years, his and her walk-in closets, and a vegetable garden I’d spent seasons building up from nothing. The house was beautiful. I loved it.

But once it was finished, a voice in my head started asking whether this was the life I truly wanted anymore.

The housing market was at a high, and we were certain our house could sell. We had a significant amount of capital sitting in those walls. And if we were willing to move, it could buy us something we couldn’t get any other way.

Time. And possibly opportunity.

Something else that weighed into our decision was that 15 years prior, we had purchased a small ski-in cabin on Mt. Hood. To us, the decision was becoming obvious.

Why We Started Over in Our 50s: Time and Opportunity

Our parents were aging. Mine were nearby in Oregon, but Bob’s were more than 1,000 miles away in Colorado. We wanted to be available in a way that a demanding job and the ongoing overhead of a larger home don’t really allow for. We didn’t want to “try to get there”; we wanted to be able to drop everything and go if something came up.

We knew there could come a time when Bob would need to be in Colorado more often. When you start thinking about your parents being in their 80s, the need for that kind of flexibility becomes reality.

At the time, we didn’t know what “opportunity” would look like. However, we knew that selling would free up capital, cut our monthly costs, and put us in a position to be ready when opportunities arose (more on that later!).

We Had a Cabin in the Mountains

We had something that made this choice a lot more feasible. We had owned a ski-in cabin on Mt. Hood for almost 15 years. In winter, our road closes. We park at the snow park by the highway and ski from our car to the cabin, about a mile and a half through the forest.

It was a family getaway we enjoyed year-round. The air up here is crisp and clean. We had hiking, biking, and cross-country skiing right out the front door. When we visited, we never wanted to leave. “I’m not going back” was a running joke for a long time. And now it’s our reality.

What We Left Behind

Once the decision was made, I was fully committed. But I’d be lying if I said I didn’t have doubts before we got there. And even after, there was sadness. We loved our house and where we lived. We still miss parts of it.

The Kitchen

My kitchen was the hardest thing to leave. I had spent hours poring over the layout to fit just the way I cook. We had built the cabinets and thoughtfully chosen the appliances, including the Lacanche I had saved for and waited on for years! I never thought I would leave that thing on purpose. But I’ve come to appreciate my little, hardworking cabin kitchen. It’s taken some time, but I’ve started to figure out systems that I can work with.

The Garden

I miss homegrown fruits and vegetables. I was so spoiled. Almost anything can grow in the Willamette Valley. We had tomatoes, cucumbers, berries, and more. I’ve tried to grow tomatoes at the cabin, but have never gotten more than one or two ripe ones. The mountain doesn’t cooperate with my garden ambitions! Thankfully, my parents have a garden and keep us well supplied with homegrown produce whenever we see them. But it’s not the same as walking out your back door. I really feel this loss. But we do have wild huckleberries to forage, and we can forage mushrooms from spring through fall, so that’s something!

The Convenience of City Life

Bob and I used to run out for last-minute Saturday night movie snacks and think nothing of it. Now our grocery runs are 45 miles away (plus a 3-mile round sled and ski trip in winter) and happen every two or three weeks. I miss the library, which we would walk to once a week, and all the restaurants on Main Street. I miss easy hair appointments. I miss being able to grab a quick lunch with friends. Simple living in the woods sounds romantic, but you don’t always picture the part where you can’t just run out for cream.

Now I schedule appointments on grocery days. Kindle and the Libby Library App have become my friends. And in the winter, it’s only about a four-mile ski trip to Charlie’s Mountainview and back if I need to pick up a package! What’s fun is that now, instead of grabbing a bite, our friends will come stay a night or two at the cabin. We almost see more of them.

Moving to the cabin was the right decision, even though we still miss the house and the convenience of living in town sometimes.

Four Winters Into Cabin Life

Opportunity Knocks

Last summer, after 3 years up here, two properties near the cabin came on the market. Because we’d made that financial move when we did, we were in a position to help our son Hayden purchase one of them. After 7 years out of state, our son is moving home! I had honestly resigned myself to the idea that my sons would never live close to me again. Now he and his wife are moving back in a couple of months to start renovations. They are going to live within walking distance of us! And we purchased the lot next door for a future project. I’m excited!

The Physical Reality

In the summer we are busy sourcing, cutting, splitting and stacking wood. It’s relentless. I’ll tell you about my trigger finger experience someday. In the winter, we ski 1.5 miles to reach our car. I take a sled with me on my grocery runs so I can haul them in.

Bob and I are both healthier and more fit than we were when we moved here. I’m really thankful for that. Friends thought we were a little nuts when we told them we were moving here full-time. I kind of wondered that too. But I love it here because it is hard sometimes. It makes me feel capable and accomplished.

The Practical Side of Living in the Mountains

Because we only get to the store every two to three weeks, I’ve adapted an ingredient-based kitchen. I cook almost everything from scratch, and we live out of our pantry much of the winter.

We know all seven of our neighbors. Life in the mountains is smaller in some ways and larger in others.

We can forage, hike, mountain bike, cross-country ski, and snowshoe right from our front door. That never gets old. I honestly can’t believe it sometimes when I am out walking Cooper on the trails near our place. I often think to myself, I GET to live here.

The Unexpected Part

We’re not off-grid. We’re not survivalists. We have Wi-Fi. But life has definitely shifted. Unexpected is the change of pace, the purpose, and the peace I feel living here. We chose this life deliberately, rather than coasting with how we thought we were supposed to live. After four years here, our ordinary days still feel full of adventure: skiing to the car, hiking the trails every day with Cooper, and trying not to fall asleep as soon as it gets dark.

This Is What Changed

Some people get hung up on the decision, the old paralysis by analysis. We did too, for a while. The indecision, the what-ifs, the thought of giving things up. It turned out our worries were bigger than any problems we encountered. I am so glad we made the decision. But we’ve always kind of been that way. We hem and haw, but when we finally make a decision, things move very quickly!

What matters most to me now is filling my time with things I value. Learning new things. Sharing this life. Building something. Connecting with people who are asking the same questions we were asking four years ago.

We did it at 53 and 55. Not at 35, not at 45, not after some divine moment of certainty. We did it in the middle of everything: parents aging, a demanding job, and celebrating the accomplishment of finishing our home. We figured out what we were missing and what truly mattered to us. It turned out to be time and opportunity. We intentionally arranged our lives so we wouldn’t miss them.

Who This Is For

Since we made the move, I’ve been surprised by how many people will ask the same question: how did you actually do it? Not because they want to live in a ski-in cabin on Mt. Hood. But because they are starting to wonder what their own next chapter could look like.

If you’re somewhere in your 50s and the question “what do I do now” has started getting louder, this is for you. If the kids have grown and left and you’re standing in a quiet house wondering what an empty nest is actually supposed to feel like, this is for you. If you’ve ever driven somewhere and not wanted to come back, and you’ve been calling it a fantasy instead of a signal, this is for you.

Starting over in your 50s doesn’t usually happen because everything is perfect. It happens because you look at your life honestly and realize that time is moving whether you make changes or not.

If you’re asking yourself what comes next, or whether it’s too late to change direction, I understand that feeling.

Starting over in our 50s wasn’t perfect timing, but it was the right decision.
This is what life looks like now.

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Thanks for reading-