How I chose which city to move to
It was a weird realization that I knew I wanted to leave New York but had no idea which city I wanted to move to next! I think I had this idea in my head of when I realized it would be time to leave New York City, that there would be a really motivating reason for me to go. Of course in my early 20s, I thought I would've met the man of my dreams and we would be deciding where to move together to start the rest of our life. But life didn't work out that way for me!
So there I was, in my late 20s knowing that New York was no longer the fit for me, but not knowing where I wanted to build the next stage of my life. There's not really a rulebook for that!
One thing I knew for certain was that I didn't want to just pick a city based on reputation and move there – that seems like way too huge risk for some thing as important as this next stage of my life. And I wanted to avoid a situation where I spent all the time and money moving to a new city only to discover that I didn't really like it.
So an idea starting to take shape…
What if I spent some time trying out new cities to live next?
A little under a year later, I’m writing to you having finished out that adventure and the experiment worked! I moved to Austin at the end of January 2025 and I am so unbelievably proud and grateful of the year it took me to get here. So in today’s post I’m going to walk you through how I thought through deciding on a new city this way and how I ultimately decided on Austin. Let’s go!
Why you should give cities a trial run
Of course, this post won’t apply to you if you've already decided where you want to live or if you've had a dream that you've been nursing your whole life of living in a specific city. And girl, I support you, I dreamed my whole childhood of living in New York and so when it was time to graduate from college there was never a doubt in my mind that I would be moving to the big city!
But after nine years in New York, I was at the end of an era there I needed to figure out what was next…
What’s the best way to figure out where to move?
There are 1 million different ways to evaluate where you want to live next. Of course, there's googling and researching based on articles or videos you see on TikTok to get a sense of what different cities are like. But as I was thinking about where I wanted to move next, I knew that what was right for the people I saw on the Internet might not be right for me. It's such a personal decision what city is right for you and as I was in a bit of a identity transition, I was nervous about just making a decision based on reputation or what other people said.
That's why I decided that I needed to spend real time in cities that I was considering moving in so that I can really get a sense of what it would be like to live there to inform my decision. And now that I've completed this journey and chose a city, I could not recommend this approach more.
The biggest reason why I recommend this approach? I didn't end up where I thought I would. If I'm being honest Austin was probably the least likely option on the list when I made it at the beginning. That's not to say I didn't think I would like it but other cities had potentially more going for them in reasons why it might be an exciting move.
Letting cities surprise you, disappoint your or exceed expectations is the best part of testing out cities.
As a result of having given each of the city as a real shot, I was able to make a decision about where I wanted to move next with real confidence. I don't know that I would've felt the same if I had just based my decision on reputation and then in those inevitable moments in a new city when I was doubting myself I would've had even lower confidence about the decision. I can only imagine how much that would lead to second-guessing and doubting myself and that's not a reality I wanted to set up in starting this new stage of my life.
So as I began planning this journey, I decided to try to spend between two and four weeks in each city that I was seriously considering. I felt like that amount of time would give me enough of a chance to begin to get a lay of the land, meet some people, and do a little exploring to collect relevant information as to whether it was a city that I could see myself.
I ultimately decided on a short list of four cities: Los Angeles, Nashville, Austin, and Charleston. I'd spend time in each of these cities, and compare and contrast to ultimately come to a decision about where I wanted to live next. Of course I was open to the possibility that I did not like any of the four and if so I would need to go back to the drawing board and add more cities to the list. I thought it was an unlikely scenario and turns out it was!
Now you may be saying to yourself: four months does not equal a year? And yes, you'd be right about that! While I dedicated a year to figuring out where I wanted to live next I was not spending every week or month of that year in that search. I knew that bouncing around between cities would be intense, logistically complicated, and sometimes exhausting so I built breaks into the year where I would not be bouncing around quite so much. This also included a two month trip to Europe because I wanted to take advantage of this time while I was living so flexibly!
Of course, this plan depended on the fact that I was able to exit my housing arrangements in New York and that my work allowed me to live flexibly. I talked more about what makes somebody a good potential fit for the digital nomad life, whether you're testing out cities to move or just wanting to travel more in this article so if you’re curious you can check out more there!
For now, let’s dig a little deeper into how I decided on the short list of cities and ultimately what helped me decide that Austin was the final pick!
What do I want in this next stage of life?
The thing about moving in any scenario, to a different city, country or even just neighborhoods is that there aren’t objectively better and worse places for you. It all depends on what you’re looking for in this next stage of your life.
The tendency to Google, ask other people’s opinions or research will only be as useful as you can filter the information you get through what matters to you.
Want to focus on your health more this year? Then moving to the neighborhood with the greatest night life or a city with a huge career focus shouldn’t be key decision-making factors.
Want to spend more time with your family? The best cost of living and most beautiful landscape won’t help if that place is 3 hours further away than you currently live.
So there is no more crucial step in this process than figuring out what it is you’re trying to solve for in this move. As I decided to leave New York, the first pieces of information I gathered to answer these questions were actually the things I was ready to move away from. What about NYC wasn’t working for me?
For me, as a self-employed entrepreneur and someone who puts a real premium on friendships and connections, New York’s work obsessed culture had been grating on my lifestyle for years. In my experience in New York, stepping out of dinner because your boss called or having to reschedule last minute because of work is pretty universally acceptable, if not supported. (To be clear, this happens to everybody once and a while, but we’re talking this being a normal pattern in day-to-day life.) I didn’t prioritize my life the way most people around me did and I wanted a different balance.
Separately, I had started to notice how my time in Nantucket was always my happiest time, even when it wasn’t the summertime (because we’re all a bit happier in the summer, right?). After some reflection, I realized that I got way more natural light in those times, even if it was a cold fall day and that my life in NYC had less of that.
While realizing what you want to step away from is great, it’s super important to focus your attention on what you do want. The good news is, this isn’t too hard to transition from when you realize what you don’t want. Some reflection time with questions like “if I could solve for this, what would the solution look like?” “What’s my preferred alternative here?” You may not know exactly where you can find it as you are doing this reflection but starting to craft an idea in your head about what you want is key.
I spent the months leading up to leaving NYC thinking hard about what these qualifications were. The core list I came to was:
A culture that values life outside of work as much as career
More sunshine, natural beauty and a slightly slower pace of life
A culture of interesting people, friendly to outsiders
An airport I can reasonably get to family and friends in other places
A place that felt like a good counterpart to summer in Nantucket (which also means a place I’d be fine to be away from in the summer!)
But then I was tasked with figuring out where to go to see if I could find these things!
What cities should I consider moving to?
Once I’d developed my list of what I called “search queries” for my new home, it was time to narrow down on where I wanted to try out. At this point, because I felt like I had clarified what I was looking for, I opened up to suggestions from people who knew me well and I trusted.
Whenever I’d sit at a dinner with friends or a key family member, I’d say something like: “So I’m thinking about which cities I might want to try out. I have a few things I’m focused on looking for… [at which point I’d list out my search queries from above]. Where do you think would be a good fit for me given those things I’m looking for?”
My friends would then usually start working their way around a mental map, verbalizing their thoughts as to cities I should consider. Over at least a dozen of these conversations, the same four places seem to consistently pop up the most: Los Angeles, Nashville, Austin and Charleston.
These had popped to the top of my awareness too but hearing many of my friends and family come to the same conclusion that I had made me feel very confident that these were the places I should try. But I am certain that if I hadn’t given them the guidance of what mattered to me, the list would likely be way more all over the place. Which is why the search queries are so crucial so that the recommendations you receive is not filtered through the cities that they love or might dream of living in one day and instead, stays focused on what you’re looking for.
With this list more secure, I knew where I wanted to visit and reasonable confidence that one of them might be the final answer. So it was time to make a plan!
How do I live on the road for a year?
The logistics of digital nomad life, or whatever you want to call this type of adventure are no joke. I had already figured out how to get out of the housing costs I had in New York so I wouldn’t be paying for two places at once. But questions I had to answer included:
Where would I store my stuff? My family has a place in NYC that I was able to take over a closet for clothes and personal items but I said goodbye to all furniture that would have required a storage unit.
Would I go straight from one place to another? No, I decided having a reset between stops would help relieve pressure on packing and allow me to see friends and maintain existing doctors during the year
What type of living situation did I want in these spots? As I was evaluating for living, it felt important to do more apartment-style living in AirBnb’s and VRBO’s vs. hotels so that I had a kitchen, laundry and parking. Also was far more budget friendly. Speaking of budget…
How much was I willing to spend on this year? Short term rentals, rental cars and flights were going to add up. I had to take a hard look at my budget and accept that it might be a more expensive year but that once I figured out where I wanted to live next, things would normalize
This is the category where research is your friend. Pay attention to people who are doing the same type of travel or exploring as you are. I wrote about this in much greater detail in my Digital Nomad Beginner’s Guide post, so if you’re curious how I thought through more of this, go check that out!
Looking back, a very important part of this year being successful for me was that there were some breaks built in. I went to my first stop, LA, in March and then travelled (just recreationally) in Europe for 2 months and spent the summer in Nantucket before I went on to my second stop, Nashville. Between Nashville and Austin, I had time off for Thanksgiving. And before my final stop in Charleston, I had the holidays with my family.
Looking back, having space between the cities was important for processing each stop, what I liked, didn’t like and what I had learned. The ability to have a little space between each stop allowed me to go in more clearheaded to each, instead of actively processing the prior stop as I was settling into the next one. This might not be right for everybody, but for me I think it was a crucial part of the success of the journey.
What it’s really like deciding where to move next
I had a plan. I booked AirBnB’s and rental cars. And then I actually got on the plane and showed up in a new place. As you can expect, it was full of unexpected!
The importance of mindset when trying out new cities
I knew going in that I was actively taking steps out of my comfort zone by doing this adventure. I had the foundation of significant solo travel under my belt beforehand, without which I’m sure this adventure would’ve felt significantly harder but even so, I had a very realistic expectation that this year wouldn’t be all fun and games.
As such, from arriving in a new city and dealing with the uncertainty of settling into a new home, to the days when you just want to sit on the couch but are battling guilt about not exploring this new place, I very consciously cultivated my mindset throughout.
Some of the big things I was reminding myself were:
Being uncomfortable is a sign we’re doing something new - our bodies don’t like new things but when you remember that you didn’t like the “old,” it can make it easier to embrace the discomfort because it’s a sign of something new!
I can handle this - reminding myself that any logistical inconvenience or something not going the way I hoped, while annoying, was still absolutely something I could find my way through
I can trust my instincts - as I was evaluating cities and cultures, I was refining my taste and what I was looking for and I chose to trust my own instincts rather than looking for objective right and wrong (this ended up being really important!)
It’s okay to have a bad day - this journey wasn’t meant to be perfect and just like in normal life, allowing the bad days meant that I wasn’t gritting my teeth trying to pretend everything was alright
Making sure I got the relevant info out of each city
Because I was still somewhat working while traveling, it became abundantly clear that if I wasn’t purposeful, I could easily kill multiple weeks of a visit just living out the mundane. So I started to put in place certain guardrails that would set goals for what I needed to do and see in a place to make sure I got the information I needed. This included…
Compare neighborhoods - sometime in the first week of a visit, I did a “lay of the land” afternoon which normally involved driving around to different neighborhoods, down major thouroughfares, etc. The point wasn’t to explore each neighborhood, that would come later, but rather to just get an understanding of geography and be able to visualize different neighborhoods. I didn’t need to explore the whole city (imagine how long that would’ve taken me in LA!) but being able to place myself within the larger sense of a city was key.
Find a third place - I tried early in each of my visits to scope out a coffee shop, restaurant or wine bar that seemed to fit my vibe where I could visit a couple times during my stay. These spots gave me a tiny sense in community as a bartender or barista started to recognize me over time. These spots were also great for getting a sense of the energy of a community - how do people dress, interact, what do they talk about? All important info!
Ask for introductions - in the lead up to each stop, I would mine friends and family for introductions to people who lived in the city. These were key to get the real perspective of people who lived in each city and hear more about why they liked living there. I am unbelievably grateful for the people I met in each spot for how they helped me paint a fuller picture of each city.
Open those dating apps - Obviously only applies for the single ladies but I changed my location to each city and spent time matching, talking and ultimately going on dates in each city. While my profile didn’t explicitly say I was only there temporary, it hinted at my history in New York enough that about 70% of the time, my digital nomad status would come up in the conversation before an actual date. While I expected more pushback, the majority of men I talked to were happy to go on a date and these connections were great ways to learn more about the type of energy in a city. The open-minded energy also helped me envision what life would be like in each place. And without sharing too much, this strategy really worked out for me ;)
Look at apartments - even though I hadn’t decided which city to live in, in each of my spots, I took tours of potential apartments. I usually waited until the second half of my stay once I had zeroed in more accurately on which neighborhoods might fit my personality but these visits were so useful in getting a practical sense of pricing, space, and visualizing what life might actually look like for me in these places.
Trusting your instincts
This deserves a section of its own because this adventure was basically an onslaught of information and feelings that I had to sort through. Each break between stops, I’d be updating friends and family on my conclusions and even family friend’s at cocktail parties were invested in where I was going to end up. It would have been easy to get overwhelmed or swayed by so many opinions.
This was especially important because as I zeroed in on the last two stops - Austin and Charleston - it was looking like one of them was going to be the final answer. And at this point, the predictions of my friends and family were overwhelmingly Charleston. Looking back, I was maybe not even fully open to Austin as I arrived and yet I felt a sort of creeping warmth and draw to the city even though it was the shortest of my stops. Trusting my instincts is potentially the most important lesson of this journey for me because arriving in Charleston, my instincts were completely unexpected. Which is to say, I liked it less than I expected to!
If I hadn’t been very intentionally tuning into my instincts, it would have been very easy to say “this is objectively the best choice for me” and override those little feelings that were pointing me the right way!
But I bet you’re curious about specifics so let me walk you through my process of evaluating between the various cities
How my short list stacked up
Before I share my experience here, I think it’s so important to clarify/remind that what might not have been right for me could be the perfect place for you. Not to mention that my experience in these cities was fully anecdotal, i.e. you could go there and have a completely different experience. But I want to share my personal journey in case it helps someone else. If you love any of these cities, please know that I don’t mean offense to your beloved city, just might not have been for me.
Los Angeles
I went into LA with serious pre-conceived notions. My dad and family (divorced parents!) had lived in LA for 16 years so I’d visited many times, but mostly to neighborhoods where I wouldn’t live as a young person. But even my periodic adventures down into cooler neighborhoods like West Hollywood, Venice Beach or Santa Monica had been fun but not really lit me up about LA.
I stayed in Santa Monica this trip and the time here helped me understand what people love about life in LA. Walks around neighborhoods or to the beach, being able to “vibe shift” whenever you wanted just by going to a different neighborhood and yes, the weather helped me understand why people like it so much there.
Yes, the traffic is bad. And the city itself, as in the architecture, didn’t speak to me aesthetically. But the real kicker against LA was really it’s location - so much of my life is East Coast or Texas plus with the time difference, it became clear that I’d feel really far away from my prior life, even though I’d have my dad and stepmom nearby.
Then my dad got a new job in Florida so that officially crossed LA off the list!
Nashville
I jumped into Nashville after a long break from the testing cities so I came in with great energy! I was immediately blown away by the food scene in Nashville - I knew it was vibrant but didn’t expect it to this extent. Nashville was the first of the three smaller set of cities I went to and I immediately new I was on the right track in terms of the logistics of living in a slightly smaller city - I could see how it would just be easier than places like New York or LA.
As I explored Nashville on my own and through meeting people there, it was obvious that it’s a very social city, especially with the draw from many big state schools in the South. What I started to notice, though, was that the topics of conversation or even really just the energy was especially social focused. While I know this isn’t 100% of Nashville, my experience felt like it was a less intellectual city or just the culture wasn’t as focused on learning as maybe I had become unknowingly accustomed to in a place like New York.
My other observation about Nashville is that it felt very new! While of course there’s great history of the country scene and music in general and there are certainly some historic buildings, most of the city felt like new construction in a way that lacked a little character.
I liked it but I didn’t love it and I was craving more character in my environment. So honestly, at the point I left Nashville, I fully thought the answer was Charleston. I expected I’d love the historic character and the vibrant food scene. I though Austin was going to feel too new, too hot and not pretty enough.
But then…
Austin
I arrived in Austin having booked the shortest visit of all four cities, really because I was pretty pessimistic about this being the final answer and thought I should just knock it out so I could get on to my final stop! (At this point, I was very ready to not be on the road anymore!)
My drive around of Austin confirmed some initial perceptions, which is that it’s not the most visually beautiful city. The nature and parks are great and I felt more of it’s presence than I had in Nashville but many neighborhoods show decent wear and tear.
My restaurant exploration in Austin met expectations. By that, I mean there were some good spots but I wasn’t absolutely blown away. Even while I was there, I was asking myself if it was something I could get over because your girl loves restaurants!
But every introduction made for me in Austin led to me meeting amazing people. The connections I made in Austin felt like my people. And every single one of them mentioned, without much prompting, that they liked the city of Austin but they loved their friends here. This refrain of the emphasis on the quality of the people in Austin became very front of mind.
The obvious con of Austin is the heat and while it did register to me as warmer than my ideal climate, knowing that I’d be away in Nantucket for the worst of the summer heat made this a more tolerable idea.
By the end of my stay in Austin, my mind was a little scrambled because I was feeling such a draw here, even when much of the logical conclusions didn’t quite map with what I thought I was looking for coming out of Nashville. So I was endlessly curious whether Charleston was going to come in and come over the top or if I’d really found something in Austin!
Charleston
I came in with high expectations of Charleston (key to say that I had been there before to visit, so it wasn’t completely blind). There had been many comparisons made between Charleston and Nantucket, which is my happy place so I expected to find it similarly beautiful. I knew the food scene was supposed to be exceptional and a coastal town was going to hold plenty of charm.
But even in my first couple of days in Charleston, it didn’t feel quite as charming as I expected. I realized as I explored that most of the “charming” parts are where you spend the most time when visiting but that the areas that would become more of your day-to-day when living there weren’t quite as charming.
It also felt quite small. Coming from New York, I knew I wanted a smaller city and Nashville and Austin had certainly felt small by comparison but within a few days of exploring the peninsula (which is the heart of Charleston), I felt like I had really gotten a lay of the land to the point that I wondered if I’d get bored living there full time.
The food scene absolutely lived up to the hype, if not exceeded expectations and I don’t think I had a single bad meal. If I were making decisions based solely on the quality of the food scene, Charleston would have been a slam dunk.
I met some great people in Charleston but definitely not to the frequency I had in Austin and one of the big themes that I heard was how girl-forward the city is, which has an impact on the dating dynamics there. I can’t speak enormously to this (you can definitely feel it’s a girly city) but feels important to mention.
But going back to trusting my instincts, the more days went on, the more I felt like Charleston wasn’t the place for me. I battled all the expectations I’d had throughout the process that this was the final answer but the more I came back to what my gut was telling me, the more the answer was becoming obvious…
How I decided where to live next
While still in Charleston, I realized that not only was I done living on the road and ready to make a decision, it was also clear to me what that decision was: Austin.
Actually making the decision wasn’t really a climactic moment, but more of a coming to terms with what I already knew. In fact, I had to ask multiple people in my life to confirm that it was okay for me to make a call so early into my time in Charleston (I hadn’t even hit 2 weeks yet)! But this truly was a “when you know, you know” type of situation and I knew.
The relief and excitement of finally having made a choice was immediate and I was so excited to start researching apartments and envisioning what life was life next.
Realizing that the right choice for me was one of the more unexpected outcomes deeply confirmed for me the merits of doing this type of experiment because I truly think if I had to just look at different cities via research and asking for opinions, I probably wouldn’t have ended up here.
Not to mention, this experience of identifying my goals, evaluating places and cultivating my internal compass is a skill that I know I will continue to use in all sorts of parts of my life. I’m so grateful for 2023 me for taking the leap on this plan even though there were many months in the middle where I was unsure and didn’t know how this would all work out.
Turns out, we really do know the way, if we’re willing to be brave enough to step out of our comfort zone to find it!
