Remote Work Guide 2022: How to Choose Your Next Host City

By now, you have likely heard the term “The Great Resignation” being tossed out in conversations and headlines. Millions of workers have quit their jobs and have opted for a remote work lifestyle. While there is no shortage of opinions, as well as conflicting statistics as to why this is, many workers have cited one reason quite frequently: The ability to work from home or remotely.

What is Behind “The Great Resignation?”

Poor working conditions, lack of decent pay and benefits, and hostile management were also popular reasons for why workers were seeking other options, especially those in the service and hospitality industries. The Great Resignation looks like it is here to stay. 

For office workers though, they got a taste of the “work from home” lifestyle when the pandemic shook the world in March 2020, and they’ve made clear they don’t want to go back to business as usual. According to the Harvard Business Review, nearly 80% of U.S employees want to work from home at least one day per week. And according to PwC in an August 2021 report, 41% of workers want to stay fully remote!

This may not come as a surprise to veteran remote workers, who before the pandemic had been labeled everything from lazy to unproductive. Veteran remote workers understood the advantages of geoarbitrage and the positive financial and lifestyle impacts remote work has on their The Big Three of household expenses. They figured out how amazing it was to work from home. No more traffic-clogged commutes, ripoff parking prices, stuffy cubicles, or uncomfortable attire. 

On top of that, they could be so much more flexible. No more sneaking into the phone booth at work to schedule a dental appointment, or having to take a half-day of vacation so you could be home when your washing machine arrives (if it even gets off a ship these days). 

The Many Benefits of Remote Work 

Those who choose remote work can take their pets for a quick walk, tend to their child’s homework needs between sessions, run a load of laundry during a break, or take virtual training from the kitchen while unloading the dishwasher. You don’t have to keep a seat warm just to prove your worth as an employee. Workers have proven that they are just as productive, if not more, from home as they are in the office, and often much happier. 

But what about those who are truly untethered? For workers that don’t have to be near the office for any reason, or who don’t really have anything tying them to one location? Many workers, especially millennials, have taken this luxury of “work from anywhere” and taken off across the country. 

Now, I’m not here to write about #vanlife and how amazing it might be to work from a National Park. Many are turning to the digital nomad way of life as a full-time employee, not just as a bucket list item. 

Choosing the Right City for Remote Work

So how should you choose your host city as a digital nomad? How do your friends who have moved across coasts this year do it, and what makes one city better than the other? As someone who has lived in 6 cities between this year and last, I can share with you what goes into my decision-making process.

Finding cities with the best cost of living 

This is clearly the biggest one. We know that housing is generally a person’s biggest monthly expense. But poor assumptions about housing costs can limit our ability to make the best choice for us.

Just because you move to a major city versus a smaller one, doesn’t mean it will be more expensive. While Atlanta might be more fun and exciting than Pensacola, it doesn’t necessarily mean it’s more expensive. There are more housing, vacation rentals, and hotels available. So, you have more options.

In addition, you most likely won’t be signing a lease if you plan to remote work around multiple cities. That being said, you can find people looking to get out of their lease, or furnished apartments on sites like Craigslist and Sublet.com. Airbnb Sublets and Furnished Finder are also options I have used, as you can find furnished places that include things you may not want to lug around like dishes, kitchen appliances, and office supplies. 

After you find cities you want to visit that are within your budget, be sure to look at other costs. While you most likely won’t pay for utilities, you still might pay for things like eating out, healthcare, and gas. The cost of living in Austin is higher than in Amarillo, but as we’ll see below there’s more to the story of how to pick your next host city. 

Consider the Tax Rates of Each State On Your List 

*Disclaimer* talk to a tax advisor about your particular case! If you plan to become a resident of a city and state, which some claim is living there more than 30 days, then you’ll want to make sure you are taxed in the state you work in. 

While there are many variables, in order to be a resident you typically need things like  Driver’s License, deed, lease agreement, or utility bill to prove that you are indeed a resident. If you’re going to move to Tennessee for 7 months, then it’s likely you’ll be able to legally become a resident for the time being, as well as make it worth your time. That way, you won’t have to pay taxes on your salary if you choose to live in one of the 9 states that don’t tax it. 

Keep in mind that it’s not just income taxes, but others as well. Some states have lower sales taxes, lodging taxes, and city/local taxes. You’ll want to pay particular attention to lodging taxes as if you are staying in a hotel or Airbnb sublet, you may have to pay those taxes unless the laws waive them if you are there for more than 30 days. 

Make Sure Your Remote Work City Choice Has Enough Infrastructure 

If you are wanting to find the right place to be a digital nomad, you’ll probably want to explore the city that you’re considering. Otherwise, you’d just stay in one place! Does the place you’re moving to have lots of parks, trails, and bike lanes? Does it have free entertainment options such as museums and movies in the park? Is it centrally located to things of interest to you such as hiking and art?  

Most of the time, larger cities have a lot of infrastructure, but this isn’t always the case and even if the city does tout vast infrastructure, it doesn’t mean it is in the best condition. The nicest library I’ve been to is the one in Ketchum, (Sun Valley) Idaho. When you need free wifi and don’t want to hog the corner in a coffee shop, libraries are a quiet oasis with lots of interesting and meaningful distractions. 

How Accessible is Your “Work from Home” City of Choice? 

Remember, it might be cheaper to live in a smaller town or suburb, but you are likely going to spend more time driving. If you fly around during your nomad travels, this might end up costing a lot in rideshare usage. Ideally, you select a location where you can get around or explore on foot, by public transit, or by bike. 

You also may end up spending more to get to your next city if you’re not near a regional airport. You don’t have to choose a downtown location or limit your cities to ones that have expansive subway systems, but think about where you want to be. In the middle of the action, or in a quiet spot overlooking the trees and mountains? 

Staying Happier and More Productive Outside of the Office

One thing I did when I was looking for what part of town to stay in, was zooming in on sublets/hotels I found and looking for the little bus/train icon or the green line on Google Maps that signaled a pedestrian/bike trail. Not only were the green lines useful to find places walkable/bikeable to attractions, but I also found some incredible running trails!

Overall, remote work is the wave of the future. If you want to get started today, be sure to explore the best places to work from home. You may discover just how truly productive, happier, and fulfilled you become. 

By Gary Grewal.

Gary is a Certified Financial Planner, entrepreneur, and car aficionado. He writes at financialfives.com and is the author of Financial Fives: The Top 325 Ways to Save, Earn, and Thrive to Retire Before 65.