One of the great things about freelancing is being able to work from wherever you want. Of course that doesn’t mean blindfolding yourself, spinning, and pointing to a place on a map that you’ll call home. There are certain factors you take into consideration when deciding where to live. Cost of living and housing is a big one. When you become your own boss and are responsible for your own paycheck, you naturally become more cost conscious.  

Other important factors include education and schools, proximity to family, safety, lifestyle, major airports, transit, healthcare costs, and local industries and business opportunities. 

After learning more about the cities below, check out our new monthly city guide series featuring a Portland, New York and Brooklyn, and San Francisco and Oakland.

Where are freelancers from the CloudPeeps community based?

We wanted to know what cities freelancers prefer to call home beyond our own experiences and assumptions. So we looked at where our community of freelancing Peeps are located and compared that to data and research we found online. 

1) New York, NY

Photo by
Photo by Bicad Media

New York is home to the largest concentration of Peeps at 17%, compared to 8% living in our number two city, and includes Manhattan, Brooklyn, Bronx, etc.

Sure, New York is expensive as number 46 on Zenn99’s top 50 cities for independent workers with a median monthly housing cost of $1293 and income tax of 8.82%. But the opportunities are endless. A New York address adds to your credibility with access to some of the best businesses and leaders in nearly any industry, from fashion to tech; entertainment to e-commerce, and beyond. Then there’s the incredible creative community and unmistakable energy New York offers as well.

It may not be the most cost-effective city for a freelancer with a family. But for those only worried about taking care of their own self, it’s a great place to live. You can find deals on housing if you know where and how to look. Stores such as Trader Joe’s and farmers markets make every day meals affordable and healthy. And with sufficient public transit, you don’t have to worry about the cost of owning and maintaining a car.

2) San Francisco, CA

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Photo by Isaak Dury

San Francisco is another pricey but popular city for freelancers. With more startups hiring freelancers to help them scale their businesses, this comes as no surprise. It’s an exciting time to freelance for tech companies, and SF is the perfect place to do it.

Like New York, you’re going to pay a lot for housing with the median cost at $1640, income tax set at 13.3%. But with the higher cost of living comes higher pay and better access to the most innovative companies in the world.

Also like New York, the diversity of industries and cultures is vast in San Francisco. There’s a ton to see, eat, and do. Not to mention the healthy lifestyle SF allows. There’s plenty of bicyclists, running paths, stairs to climb, parks to explore. And with such close proximity to Big Sur, Santa Cruz, Tahoe, your weekends will never be boring.

3) Los Angeles, CA

Los Angeles
Photo by Matteo Paganelli

If you live in the Northeast, you’ve undoubtedly seen an exodus to LA. It seems like more and more creatives are calling the city home.

Housing cost apparently isn’t much of a concern to freelancers today. Zenn99’s data shows that LA is also a costly place to live with median housing cost at $1333 and income tax of 13.3%. But with LA’s vibrant arts scene, a variety of culture, perfect weather and abundance of sunshine, why wouldn’t freelancers flock there?

Nerdwallet listed LA as the number one best city for freelancers, saying “Because so many people do freelance work, there are a lot of outlets for freelancers to connect, including meetup groups and dozens of co-working spaces.”

4) Chicago, IL

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Photo from Sohohousechicago.com

Another large metro area making the top of the list. Chicago has a median housing cost of $1073 and income tax of 5% — putting it at number 34 on Zen99’s list. The windy city is often referred to as “like New York, but cleaner.” It has its own arts and culture scene, mixed with big city opportunities. The winters may be more brutal than the top three cities on the list, but mild summers and sunshine offer a pleasant environment.

5) Atlanta, GA

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Photo from artinstitutes.edu

We’ve seen Atlanta gain popularity among freelancers. That’s why we were surprised to see it at number 43 on Zen99’s list, likely because of its $1061 median housing cost. With nearly 10% of its population being self-employed, Atlanta is a great place to get a big city feel without as much congestion. It’s neighboring states of Florida and the Carolinas offer some excellent vacation options too!

6) Austin, TX

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Photo from siliconhillsnews.com

Who doesn’t love to keep things weird? Austin is a mecca for creatives with plenty of coffee shops, culture, art, music, and a booming tech and startup scene. As Austin’s popularity has increased so has its housing cost with a median of $1138. But it still boasts zero income tax and a vibrant city full of opportunity. And maybe you’ve heard of SXSW? A great chance to check the city out and see what it has to offer.

7) Portland, OR

Portland, OR

Portland’s bragging rights are many. Among them are its reasonable cost of living with a median housing cost of $1164 and an average rent of $960 per month. Portland is the hub for Freelancers Union, which makes sense considering about 15% of its population are freelancers. The city is extremely green and bike friendly with excellent food, tons of nature to explore and outdoor activities to take part in. According to Nerdwallet, freelancers in Portland are writers, web developers or work in other creative industries.

8) Seattle, WA

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Photo by Zhifei Zhou

If you were to take everyone’s favorite elements of San Francisco, New York and Portland, it’d likely be something like Seattle. There’s a big tech presence with Microsoft based there, as well as tons of smaller tech startups. But with all the nature surrounding the city, it doesn’t feel as tech-obsessed as NY or SF.

With zero income tax and a median housing cost of $1376, it’s an affordable place to live. The city has lots of coworking spaces and coffee shops with free wifi to accommodate the 14% of the population who freelance. 

9) Washington, DC

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Photo from dcnationalguard.com

Aside from it being a lovely city, we were surprised to see so many freelancers living in Washington. It’s not exactly cost friendly with median housing cost at $1477 and income tax of 8.5%. It was, however, ranked 6th for women-owned businesses in 2014. And it offers work-life balance with tons of museums and nice weather, as well as inspiration and energy from its large young professional population.

10) Boston, MA

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Photo from bostonrealestate.net

Boston didn’t make Zenn99’s list of best cities for freelancers. Only a small percentage of our Peeps live there, but enough to make the list, especially as a great city for work-life balance. It’s also a great place to work if you’re focused on the finance or education sectors.

Other cities to consider

If you’re looking to expand your horizons globally, among our Peeps’ favorite cities to live internationally are London (2.5%), Melbourne (2.5%) and Toronto (1.7%).

If you’re looking to stay in the states, other popular cities were San Diego, CA, Denver, CO and Philadelphia, PA.

Do you feel like your city or another one that hasn’t made this list is perfect for freelancers? Share your insights in the comments below — fellow freelancers would love to hear about your experiences!

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CloudPeeps Team
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