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The “Regret-Free” Approach to Choosing Where to Live

By May 14, 2014 One Comment
By Ben Sands – For additional insights, tools, and leadership resources, click here

After 8 years of living and working in Washington, DC my wife and I relocated to Charleston, South Carolina.

Today, we couldn’t be happier. In fact, it feels as if the move to Charleston was the most easy and obvious decision we’ve ever made.

That could not be further from the truth.

In fact, our move was the culmination of a nearly year-long process of reflection – about our values, our work, our family and the life that we want to live.

The journey – and it was, both literally and figuratively – was an extraordinary rewarding process. In addition, we took special care to craft our approach to picking our new city in a way that would be consistent with the “regret-free” philosophy that guides the rest of our life.

For that reason, I call it the “Regret-Free City Search” approach. Here’s what it looks like.


As in all things regret-free, I want to first start by describing the foundational assumptions/beliefs that underpin the specific approach we adopted:

Assumption #1: Where to live is one of the most important decisions we make in our lives.

The reason? Because, according to a mountain of new research on the subject, where we live – the state, city, community – has the single greatest impact on one’s overall well-being.

In his book, “Well-Being: The Five Essential Elements,” author Tom Rath describes well-being as:

“…the interaction between physical health, finding your daily work and experiences fulfilling, having strong social relationships and access to the resources you need, feeling financially secure, and being a part of a true community.”

The Gallup Organization (for whom Rath used to work) defines the five essential elements as:

Social: Having supportive relationships and love in your life

Financial: Managing your economic life to reduce stress and increase security

Community: Liking where you live, feeling safe and having pride in your community

Physical: Having good health and enough energy to get things done

Purpose: Liking what you do each day and being motivated to achieve your goals

In the 2013 Gallup-Healthways “State of American Well Being” report, levels of “well-being” vary dramatically among states – and can even vary dramatically among communities within the same state.

This robust data confirms my own personal experience. I have lived in a variety of places in my life, including: Connecticut, Raleigh-Durham, NC; New York City; Aspen, CO; Nantucket, MA; and Washington, DC and can say, with confidence, that no factor affected my personal sense of well-being MORE than where I was living.

Assumption #2: That where you live is a CHOICE. It should be made consciously.

I recently heard this startlingly (albeit unverified) statistic: 80% of people who move to New York City and remain there for 5 or more years, will likely spend the rest of their life in the greater New York Metro area.

Current US Census Bureau data would seem to support that. Between 2012 and 2013, only 1Screen Shot 2014-05-14 at 10.45.23 AM1.7% of Americans changed residences – one of the lowest numbers since the government began tracking those numbers in the 1940s. Of those that moved, over 40% moved less than 50 miles.

There is nothing wrong with living in New York City (in fact, I agree with the adage that everyone should do it once!) but I believe strongly that we must not let job or family obligations overwhelmingly influence where we live our lives.

According to the Gallup Well-Being metrics, our job and our family are a foundational part of our sense of wellness, but together they represent on 2 of the 5 key factors.

Where you live is a choice. More importantly it should be your choice. Not a choice made for you by your parents when they decided to settle down in Schenectady 40 years ago – or when your company decided to save money by relocating to Topeka.

Assumption #3: Moving is hard. But not moving and suffering is miserable.

No one “likes” to move. We all know it’s miserable. But, as far as I am concerned, the opportunity to wake up every morning in a location that energizes and excites you is well worth it. Sure, moving is hard – but “inertia” is a poor excuse for living a sub-optimal life.

Where you live is a choice. More importantly it should be your choice. Not a choice made for you by your parents when they decided to settle down in Schenectady 40 years ago

Assumption #4: If you are going to move, you must be confident that your well-being will improve, not get worse.

Who hasn’t fallen victim, at some point in their life, to a “grass is going to be greener” assumption? Common examples include:

If I end this relationship, I’ll be happier…

If I take this new job, I’ll be more fulfilled…

If I go to grad school, I’ll have more professional options…

Certainly, in many cases this is absolutely true. But when we are making any big decision – moving included – we have be conscious of our natural tendency to be overly-optimistic about what will happen when we make this big change.

The “Regret-free City Search” approach is structured in such a way so that we can “test” our assumptions about what life will be like in our new city – before we actually move there.

Those are the beliefs that underpin the Regret-Free City Search approach.


Guided by these core beliefs, here is the specific approach my wife and I used to identify the next city in which we would live.

Step 1: Put together a list of “dream” cities.

The question we asked ourselves was simple: Where would we live…if we could live anywhere in the world?

That’s the first question we asked ourselves. And using that as our guide we put together a comprehensive list of all of our favorite towns, cities, vacation destinations…no restrictions.

During this brainstorming phase we had to consciously suppress the little voices in the back of our head saying things like:

“that’s too far away from our family”

“that’s too expensive”

“that’s too remote”

“I won’t be able to find work there”

Eventually we would take those considerations into account, but at the start it was important that we let ourselves really dream big.

To spur our thinking, we used pre-compiled “Best Places To Live” lists from trusted sources. Here’s a few of our favorites: Outside Magazine, Gallup, Money Magazine and Travel + Leisure Magazine.

Here’s a snippet of the list that we came up with:

> Park City, UT

> Paris, France

> Aspen, CO

> Boulder, CO

> San Diego, CA-area

> San Francisco, CA-area

> Austin, TX

> Charlottesville, VA

> Charleston, SC

> Telluride, CO

> London, UK

> Portland, OR

> Seattle, WA

> Jackson Hole, WY

> Miami, FL

> New York City

> Sun Valley, ID

+ approximately 20 more….

Step 2: Prioritize your life (i.e. decide what matters MOST to you)

With an exhaustive starter list of “dream” cities established, we had to start the pruning process. But how?

Recognizing that the goal of this entire process was to improve our well-being, we used the Gallup Organization’s five essential elements of well-being to create an simple way to evaluate each city on our list.

As described above, the five elements are:

> Social: Having supportive relationships and love in your life

> Financial: Managing your economic life to reduce stress and increase security

> Community: Liking where you live, feeling safe and having pride in your community

> Physical: Having good health and enough energy to get things done

> Purpose: Liking what you do each day and being motivated to achieve your goals

Having five factors on which to assess each city was helpful,  but we quickly realized that there was NO PERFECT CITY (i.e. a city that could meet all of these needs equally at a very high level).

Given that, we had to prioritize. In other words, which of these components of well-being were MOST important (in what order) to us as we began the next phase of our life?

This was the hardest – and most rewarding part – of this whole process.

Sarah and I spent many days and nights talking through what we wanted our life to look like, feel like, be like…and used those conversations to help create a prioritized list of factors by which we would evaluate each city/place on our list.

Here’s the prioritized list we came up with…and a little bit of the rationale behind each choice:

1. Purpose. As far as Sarah and I are concerned, nothing is more important than being able to wake up, every day, energized and excited by the work we are doing. The number one factor guiding where we live is that we MUST be able to continue to do the work we love.

2. Financial. In my most recent book, Regret-Free Personal Finance, I talk a lot about the correlation between money and being able to do work you love. All other things being equal, we wanted to move to a location with a lower cost of living including both housing and education (we are expecting our first child in September of this year).

3. Physical. At first we struggled picking “Physical” over “Social” given how dear our family and friends are to us. But, upon further reflection, the choice was clear: we wanted to live somewhere beautiful; where it was easy to access the outdoors, exercise and maintain a healthy lifestyle. The reason? Because that is where our energy comes from. Without it, we can’t do the work we want to – at the level we want to. We wanted to live in a place where it is as easy as possible to feel energized, inspired and vital…every day.

4. Social. My wife and I have all been blessed with incredible friends and family and we wanted to stay close enough to them to allow us to physically see them at least a few times/year. The implication was that we had to pick a city in which we could get in and out of easily – either by car or plane (i.e. we’re not moving to Sydney…).

5. Community. We prioritized this last among the five essential elements of well-being simply because of our belief that, all other things being equal, we were committed to investing in our new home, city, location in such a way that the feeling of connection and community would follow – wherever we landed.

Again, this prioritization process wasn’t easy – but it was incredibly powerful. In addition to helping us make a better decision about where to live, it also allowed us to reconnect and recommit to the vision of the life that we wanted to live together.

Step 3: Filter your list of “dream” cities into a list of the Top 5

We used our prioritized list of characteristics as a filter with which we evaluated all of the “dream” cities on our list.

Slowly but surely we were able to distill the large list into a “Top 5” – the five locations with the highest probability of meeting your prioritized well-being needs.

Our Top 5:

> Park City, UT

> Boulder, CO

> Charleston, SC

> Austin, TX

> Charlottesville, VA

Step 4: Test and validate your assumptions about each of your finalist cities

With our Top 5 list developed, we began the final (and most fun!) part of the process: testing.

As mentioned above, the only way to be truly confident that a move to a new city will enhance your well-being is to live there. Given that we only wanted to move once, we decided to “test” each city – to move there for a short period of time to experience, first-hand, what life would be like.

In order to do this on the cheap (tip of the hat to The Lean Startup), we used the website Home Exchange to trade our condo in Washington, DC for a place to live in each of our test cities. Depending on how much time we had spent in each city previously, we spent between 2-9 days “living” in each.

To be clear, we explicitly didn’t treat these trips as a vacation, but attempted to recreate our “normal” routine as best we could. Doing so, we were able to test and validate our assumptions about each city – and develop our own unvarnished perspective about what life would really be like living there.

Of course, you already know how this story ends up. In the end, we chose Charleston, SC. I am, however, 100% convinced that had it not been for our “test” of Charleston we would have never ended up moving here.

Prior to our trip, I had heard (and was concerned) that the city might be “too small,” “too insular,” or “too Southern,” to be a good fit for us. But after a week of testing, we were able to draw our own conclusions and ultimately felt more comfortable in Charleston than in any other city in our Top 5.


When Sarah and I first got married, we knew that, at some point in the next 3-5 years we wanted to leave Washington DC, the city where we met.

Given that, we quickly began the process of creating “geographically-independent” professional lives (i.e. careers in which we could work from anywhere). It was, ultimately, the first step in this entire process.

If you don’t currently have a job that offers geographic independence, don’t lose heart/hope – this city search process can still work for you.

When it comes time to do your testing however, be sure to use that time in each city to better understand the job/business environment in the area – as well as to make some initial inquiries.

While there’s no guarantee that a job will emerge, I have long believed in what Alchemist author Paulo Coehlo writes: “when you know what you want, the universe conspires to support you.”

Have you consciously chosen your hometown today? If so, how did you choose? If not, what’s holding you back from making a move?

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