If you could live anywhere, where would that be? You must’ve thought about it, given that most freelancers say freedom and flexibility are their greatest motivations for pursuing a 1099 life. Getting out of the big, expensive city you’re currently in sounds particularly good after the ongoing nightmare of 2020. According to UpWork, “7 in 10 freelancers are interested in moving somewhere other than a large city, if opportunities were the same.” With so many of the lifestyle advantages of cities like NYC or SF off limits, what’s the point of living there? And with the recession expected to last for years, every dollar counts. There’s more to think about than square footage though. According to Jon Younger from Forbes, “internet speed, co-working spaces, quantity of start-ups, migrant acceptance, apartment rent, cafes with free Wi-FI, green space, cost of beer, and annual sunshine” are all part of the decision of where to hang your hoodie. As you start tallying your pros and cons, you should take the following into account:


If you’re going to relocate, live somewhere cheaper than wherever you are right now. Not only will you get more space for less, but your entire life will be cheaper (from groceries to gas to gym memberships and date night). Your overhead has the greatest impact on your potential profits, so the less you need to spend to break even, the sooner you’re “in the black” each month. For freelancers, that overhead is mostly your rent, especially now that we’re all working from home. Keeping your overhead low makes it easier to build your business. You can charge less than the competition, who are still shelling out the big bucks to live in a big city. Your client doesn’t care if you’re in San Francisco, California, or Dickshooter, Idaho (not kidding, look it up) if the price is right and the work is great. Lower overhead means more profit. Plus, you get to live in a town called, “Dickshooter.” Win-Win.


Be realistic about the value of your local network in growing your business. Chances are, most networking is virtual these days, like everything else in the new normal. The exceptions are in certain industries, which are historically based in specific cities. If you’ve already put your time in and established a network, maybe you can leave L.A. and still get work in the entertainment industry or move to Montana and maintain your graphic design work with New York ad agencies. But certain career paths are famously contingent on contacts and connections. The biggest mistake would be to just assume that you’ll be fine and make a dramatic move. Better to test it out with a short-term rental outside your city and see if being away for a few months has a negative impact. If you’re not reliant at all on local networking, you can live anywhere, but most freelancers benefit from being connected, professionally, to their own community. If nothing else, freelancing can be very isolating. Even if you’re not finding clients, networking/socializing with other freelancers can be very valuable, especially when starting out. Prioritize potential locations with an established freelance culture that you can tap into. Looking at the percentage of self-employed individuals in an area can tell you a lot. If there’s no one there doing what you do, they’re probably living elsewhere for a reason.


Be honest about where you’re happiest (or at least where you’re not happy). For many of us, the weather is truly important. Maybe you need the seasons, or maybe traveling to see family for a white Christmas is enough snow to check that box. Or maybe you’re passionate about a specific lifestyle that’s best in parts of the country and absent altogether in others. If you’re into surfing or skiing, start there. It’s easier to compromise on other things when you know you’ll get to spend more time doing what you love. If you’re single and want to date, check out the talent in prospective cities or towns by changing the location on your favorite dating app. If you’re making a lifestyle change to chill out or clean up your act, there are plenty of places that shut down at 8pm. If you like to party, a sleepy little town will bum you out. Once you’ve done a reasonable amount of consideration and research yourself, ask people you know and trust if they think the new location is a good fit for you. Then go stay there for a week. Live your life in that new spot, making sure the things that matter are available to you (from sushi to Soulcycle), and really get a sense of the best neighborhoods. Use the trip to lock down an apartment, check out the scene, maybe even meet people. It’ll make the move much easier, a few weeks later.

Moving is a big decision. Like all of us, you’ve had nothing but time in 2020 to think about it. If it’s more than a passing thought, get serious about the process and make it happen. No place is perfect but working through this information will better inform your decision, give you confidence that it’s the best option, and reassure you that you’re going for the right reasons.  Things can only get better than wherever you are now, right?