How We Decided Where to Live, and Chose An Unexpected Place

If you don’t want to read the story behind this personal decision, here’s a TL;DR version. 

These five steps are how we decided where to live. Maybe this framework will work for you, too.

• Identify what you need in your next town, plus what you’d like to have
• Create a spreadsheet matrix that assigns values to those needs and wants (examples below)
• Add your dream towns to the matrix and see how they score
• Visit towns that score well on your matrix
• Pick one and move there, even if you’re not sure. You will never be sure.

In search of the perfect place to live

My husband Ben and I have spent many weekends and vacations visiting small towns for their hiking trails. 

Places like Halls Gap in Australia for the Grampians; Luray in Virginia for the Shenandoah; Te Anau in New Zealand for the Kepler Track; and El Cercado on La Gomera, in the Canary Islands.

Each time, we’d look around at the mountains and the quaintness of the town and say to each other, I wonder what it’s like to live here.

It was just a fantasy during our first few years together. We wouldn’t actually move to a small town in the mountains. We were used to cities and their amenities, having access to diverse restaurants and yoga studios and tech scenes. And we both needed to be self-employed, or at least have the freedom to work remotely, to live in a smaller town without worrying about finding a job there.

But over the last couple of years, we started to get serious about giving ourselves better access to mountains. We wanted to hike and bike and run on trails in our daily life, not just during vacations.

Our desire became more acute when we moved to Saint Petersburg, Florida, so I could help grow a company there. While St. Pete has lots going for it — beaches, warm weather, family-friendly, hip restaurants — it was about as far away from the mountains as we could get. Between two all-encompassing full-time jobs and two kids under three years old, our trips to the woods were few and far between. We desperately missed that terrain and the outdoor adventures it brings.

We began to scheme on a move that would take us closer to the outdoors. We planned to stay in Florida for at least another year or two, so it was a slow exploration, no urgency. But as my husband’s business grew, we became more excited by the prospect, so we made a spreadsheet to evaluate our options. 

Yes, a spreadsheet. I’m married to a Google Developer Expert who specializes in Google Sheets, so our entire life is organized there. 

Here’s what happened next.

How to answer the question, Where should I live?

Once we started looking for the “perfect place,” I realized this was a search a lot of other people were doing as well. Friends shared that they, too, were looking for the ideal town to get settled or raise their kids. Vox even launched a podcast, Nice Try, dedicated to the topic.

I wondered whether this was the phase of life we were in, with young kids, or because we’d lived in cities full of professional transplants, or maybe because my generation is rarely satisfied, always looking for the next best thing.

The challenging part — or perhaps the fun part — about this question is there’s no one right answer. The answer is different depending on what you want from your life. Everyone has their own idea of what the perfect place looks and feels like. 

So you can ask all your friends and family and the Internet late at night where you should move, and it’s quite possible none of them will give you the right answer. 

We relied heavily on online lists for ideas: lists of best outdoor towns, best cities for outdoor enthusiasts and most liveable hiking towns.

But get this: the place where we ended up was not suggested by a single person or list.

I can’t remember whether it was Ben or me who threw this small town into the running, but it was the spreadsheet that helped us realize it was truly worth considering.

How a spreadsheet helped us decide where to live

Those “best of” lists did, however, help us populate our spreadsheet.

We built a simple matrix in Google Sheets that included all the things we wanted in our next home: 

• Walkable to hiking and biking trails
• Walkable to restaurants
• Walk/bike to school
• Walk/bike to coworking space
• Startup scene (for networking and learning opportunities)
• Warm weather (well, this was my wish. Ben likes cold)
• Affordable housing costs
• Good public schools (we’ve got two kids)
• Close to an airport (to easily visit family overseas)
• Nearby university (for the learning atmosphere)

Then we assigned a possible total value to each of those items based on how important it was to us. The more vital it was to our lifestyle, the more points it could earn. 

For example, housing costs had a possible score of 15, while warm weather could earn up to five points. If a town was less than 30 minutes from an airport, it got 10 points; less than 60 minutes, five points; or less than 90 minutes, 1 point.

This scoring system was not mathematically sound. It was entirely made up by us, and yet it was incredibly helpful in making this big decision.

We added a bunch of cities and towns to our list, mostly pulled from those “best of” lists. Here are a few of the places that were on our list:

• Boulder, CO
• Charlottesville, VA
• Arlington, VA
• Boone, NC
• Flagstaff, AZ
• Boise, ID
• Park City, UT
• Asheville, NC

We went through each category for each town and assigned a score as best we could without visiting, leaning on online research and what we’d heard from friends. Then we added up those scores to get a total score for each place.

Here’s what our spreadsheet looked like:

Our No. 1 criteria was easy access to hiking and biking, and in an ideal world, that meant not having to drive to hit the trails. We wanted to be able to walk to trails from our house.

The hard part, though, is that we also wanted to walk from our house to restaurants and shops or some sort of town center. This combination, we realized pretty quickly, was a lot to ask. In fact, there was a period when I wasn’t sure that unicorn of a place even existed.

Once we had our totals, we used those scores to decide which towns to visit.

First up was Asheville, North Carolina.

Should we move to Asheville?

We get together with my extended family for a week every summer, and that summer the destination happened to be an hour from Asheville… so we drove to the city one day to visit. Asheville ranked high according to our matrix, and we also had friends living there who had picked it after going through a similar process.

During our short visit, we saw Asheville as a nice town, but it didn’t hit us as the right place for our family. It felt too suburban, and we couldn’t picture ourselves there.

Our experience in Asheville taught us a valuable lesson: no matter how good a place looks in a matrix, it takes a visit to really feel the vibe and figure out whether it’s what you’re looking for. A spreadsheet can provide insight, but what feels right trumps all the numbers.

So we moved on. Next up, our spreadsheet told us, was Boulder, Colorado.  

Should we move to Boulder?

My parents stayed with our kids so we could turn the long weekend into a mini-holiday. 

And oh my goodness, we LOVED Boulder.

We loved the views, we loved the hikes, we loved the walkable downtown, we loved the outdoor vibe, we loved the tech scene. We could absolutely see ourselves living there.

But then we looked closely at the housing market. And the prices were crazy high. Higher than DC. In the part of town that was walkable to hikes, a home that was big enough to comfortably house our family and offices (because we envisioned both of us working from home) would’ve easily cost $1.2 million. 

That wasn’t the commitment we wanted to make when I was hoping to work less for a while. We did consider more affordable areas outside of Boulder, but that would’ve gotten us away from the walkable item on our checklist.

Boulder got tagged with a maybe. And then we kept looking.

Should we move to Charlottesville?

Next we tried Charlottesville, Virginia. Going into the trip, Ben was certain Charlottesville was the place for us. According to our spreadsheet, it ticked all our boxes.

But in the end we had a similar experience as Asheville: we liked the city as visitors, but it didn’t feel right as our home. The layout of the city, with trails circling it, made it difficult to visualize how we’d find a neighborhood that allowed us to walk both to those trails and to restaurants. 

Then we tried a town that wasn’t on any of the “best of” lists, one that felt like more of a gamble than the others.

How Harpers Ferry, WV, made it onto our list

We’d visited Harpers Ferry, West Virginia, a few times when we lived in Washington, D.C. It’s just an hour and 15 minutes from the city, and we’d gone there for hiking and biking.

We’d enjoyed the quaintness of the town, but we’d never considered moving there. Why? Because it’s tiny. Just 280 people.

When I mentioned that to a friend, she said, “you mean 280 thousand, right?”

Nope. 280. 

But I added it to our spreadsheet anyway, just to see the tally. It scored high, one of the highest on our list.

It had lots of hiking and biking accessible from town, some homes were walkable to restaurants, it was less than an hour from an airport, and an hour from a city. As a bonus, the Appalachian Trail headquarters was based there, which brought lots of thru-hikers to the town.

So I flew there for a long weekend, leaving Ben with the kids. If nothing else, it was an opportunity to visit with family that lived in D.C.

Our approach whenever we visited a town on our list was to go beyond what we might do there as a tourist, and explore it with liveability in mind. That’s what I did in Harpers Ferry, scouring the area for grocery stores, preschools, co-working spaces and yoga studios, all the pieces we’d need to create a life.

It turned out that while Harpers Ferry proper was tiny, several other towns are nearby, and altogether they offered all the amenities we needed. It’s at the junction of West Virginia, Virginia and Maryland, and the Shenandoah and Potomac rivers. It’s surrounded by park land, yet also has a train to D.C. 

I hiked the trail the town was known for, and it was magical: the woods, the snow flurries, the deer, the views, the quiet.

I returned to Florida feeling refreshed, but not sure Harpers Ferry was the place for us. So much about it called to me, but living there would also mean more driving, colder weather, and fewer poke bowls. It would be a huge lifestyle change.

Lucky for us, we didn’t have to make a decision right away. We were still planning to stay in Florida for the foreseeable future.

Then, just a few weeks after my Harpers Ferry trip, something unexpected happened: my company made changes that opened the door for my graceful exit. 

Ben and I realized this was our chance. Our chance to live in a place that offered mountains and trails at our doorstep. But we still didn’t know exactly where that would be.

How we chose where to live

That night we pulled out a whiteboard, and did a pros and cons list, pitting Boulder against Harpers Ferry.

Both towns offered hiking, but beyond that they were so different. Boulder was a far bigger town with a tech scene. Harpers Ferry was a historic community with a more affordable cost of living and proximity to my family on the East Coast.

We could picture ourselves in both places. But the image of us in Boulder included stress and unease about the cost of living. After a few years of growing babies and companies at the same time, we both knew we didn’t want that pressure. We wanted our next phase of life to be as stress-free as possible.

So we decided on Harpers Ferry. We moved a few short months later, and while we felt good about the decision, I can’t say either of us felt certain we’d made the right choice. We’d spent so little time in Harpers Ferry that we didn’t really know what it would be like to live there. Making a big life change was scary, especially with two toddlers in tow.

Yet eight months later, I almost can’t believe how lucky we were to choose this place. It is a better fit for us than we ever could have imagined. 

It didn’t happen overnight, but we have built a new life, one that includes hiking a few times a week before we start our workday.

Sometimes when I’m on my own on the trails, I think about what would’ve happened if we hadn’t taken the chance to pursue this dream. Would we still be in Florida? Somewhere city that felt like a safer bet? Would we still be visiting towns on our list, looking for the perfect place?

I never envisioned myself living in West Virginia, but I’m happy it’s home.

A framework for making your own decision on where to live

If you’re trying to figure out where to live, here’s one way of doing it.

1. Identify what you need in your next town, plus what you’d like to have
2. Create a spreadsheet matrix that assigns values to those needs and wants
3. Add your dream towns to the matrix and see how they score
4. Visit towns that score well on your matrix
5. Pick one and move there, even if you’re not sure. You will never be sure.

The last part is the most important: You will never be sure. You will never be ready.

You will never be ready, and you should make a choice anyhow.

The easiest way to make a big change in your life is to take small steps in that direction. You never know where those small steps might lead.