The future is freelance: 4 things to know before going out on your own

Photo by Kennieth Holmes
Kim Lawson at her home office. This photo has been altered to remove sensitive information.
Photo by Kennieth Holmes Kim Lawson at her home office. This photo has been altered to remove sensitive information.

In 2015, I left my longtime staff position at a Charlotte media company to freelance as a writer full time. I wasn’t happy with the direction the owner was taking the newspaper, and thought, ‘Surely working for myself would be better than this.’

It was — though it took me a while to realize that.

According to a 2018 study commissioned by Upwork and the Freelancers Union, 3.7 million more people (myself included) started freelancing between 2014 and 2018. That means, according to this research, more than 56 million Americans have chosen to work on a contract basis for (potentially) multiple clients, rather than stick with one employer. A large segment of that population, unsurprisingly, are millennials.

Experts say that if current trends continue, the majority of Americans will be freelancers by 2027.

If you’re considering making the jump from traditional employment to working for yourself, here are four things to know:

(1) Many people just won’t get what you do for a living—and that’s OK.

Despite the growing number of people going into business for themselves, the idea of freelancing is still difficult for many — such as my mom — to wrap their heads around. A lot of our parents and grandparents worked for “the man” and punched timecards. If they started their own businesses, there was something concrete and tangible to show for it: a storefront, for example.

Today, however, modern technology gives freelancers the ability to sell our skills from the comfort of our couches.

“Being in business for yourself is as much about mindset as it is about skill,” said Angela Haigler, marketing strategist and the founder of One Boss Writer, Writing, Editing, Coaching & Consulting. She started her business in January 2018. “I have to give myself a pep talk every day, telling myself that ‘Yes, I can do this.’ Because I, like most of us, have been trained to get jobs and keep jobs.

Courtesy of Angela Haigler Uzzie T. Cannon

“I’m in the minority in a lot of my networks, including my home environment,” she said. “For example, my mother is incredibly worried about me and still can’t quite understand why I don’t just go out and get a job.”

2. You have to treat freelancing like a business. Because it is.

When I launched my freelancing business, one of the first things I did was create my own website. I needed a place online to call “home” so that potential clients could find me. A designer friend crafted my logo, another friend who works in user experience design reviewed my site, and then I had business cards made.

But there’s so much more to the business side of freelancing that I wasn’t aware of then. How do you track your client work and the amount of time you invest in each project? How do you attract clients? How do I set my hourly rate? Taxes, what taxes?

These are questions Jodi Helmer, a local freelance writer with work in Sierra, Entrepreneur, NPR and other national publications, geeks out about. “I am a business owner first and writing is my product,” said Helmer, who has been freelancing since 2002. “Having those business skills and really treating it like a business has been far more important to my success than being a really stellar writer.”

Courtesy of Jodi Helmer<br/>Jodi Helmer

Examples of those business skills include marketing, networking and researching your client base, she said. “At the end of the day, I am writing far less than I am doing any of those other things. Also, I think you need to be really smart about setting your hourly rate and knowing your worth.”

“If you want to suffer for your art, there are plenty of places that would be happy to have your writing,” she said. “If you want to pay for health insurance and rent and food, you have to approach it differently.”

(3) Working for yourself can get lonely, so be sure to find your tribe.

Aside from client meetings, it’s possible to go a whole day without speaking out loud to another human being. (I recently moved my two dogs’ beds into my home office to help mitigate some of the loneliness I was feeling being on my own for hours. It’s great — until I’m on a phone interview and my chihuahua starts barking because she hears the mailman driving by.)

Having others who can relate to how isolating life as a freelancer can be is not only good for your spirit, but it can also be motivating for your business. Haigler, for example, is a member of an informal group of Charlotte-based freelancers. “It’s a totally supportive environment,” she says. “We encourage each other and hold monthly ‘pitch parties’ where we practice our pitches to publications and share resources and tips.”

(4) Freelancing can be unpredictable, so be nimble.

That’s Beth Howard’s advice. She’s a Charlotte-based freelance writer and editor who’s penned stories for a host of publications, including Good Housekeeping, Cosmopolitan, Prevention and others. She wrote her very first piece at the age of 19 for Charlotte Magazine and has been freelancing full time for almost 18 years.

Courtesy of Beth Howard<br/>Beth Howard

“I entered publishing about the time the Web was invented and, sadly, the industry has been in decline my entire career,” Howard said. “During the Great Recession, markets I’d written for for a decade went under, and it took several years to revive my career. I’ve transitioned to other writing venues by staying flexible — and humble. My career looks nothing like it did when I started, but I still love what I do.”

For me, a big part of ensuring I make my financial goals — which, to be honest, I don’t always make — was being open to trying new things, including diversifying my client base. I’m a writer, but I also edit and manage social media.

As Howard pointed out, “Freelancing is a balancing act.”