My decision to go out on my own began as many do — with a seed.
I had felt for a while that my journalism career was being dictated by external forces. In five years at daily newspapers, I repeatedly fought for raises and responsibility tweaks only to be told to wait. That direction kept me in eternal limbo, drained by the feeling that if I just stayed long enough or just worked hard enough, something might change.
I eventually realized that it wouldn’t. Like many newspaper journalists, I was weary after a boom-and-bust cycle of trumpeting out new hires only to follow them with pay cuts and layoffs.
Yet I couldn’t find a palatable escape. Even the thought of applying for other journalism jobs filled me with dread. It is an industry problem. I wasn’t convinced that anywhere else would be better.
What I wanted was to be empowered mentally and financially. What I wanted was to pitch stories that mattered to me and to — get this — actually write them. What I wanted was to work for editors that had time for me, that wanted to discuss story ideas and finesse my work to make it as good as it could possibly be. What I wanted was to grow and to expand, not to shrink to fill whatever professional space I was lucky enough to be given.
It was stumbling upon Jenni Gritters’ Medium article that first made me think there was another way. The headline begged to be clicked — “How I made $120,000 in my first year as a freelance writer.” The number alone made my eyes pop out like a cartoon character. That was nearly three times my salary. I didn’t even know six figures and the word writer fit in the same sentence.
After a coaching session with Gritters, who co-leads freelance writer podcast and group The Writers’ Co-op, my path began to look clearer. I started to envision a different kind of world, one where I chose the assignments I took on and the money I made. I made important mindset shifts — I would not be freelancing but, instead, starting my own writing business. I had to take myself seriously as not just a writer but a professional.
The first month was scary. I struggled with how to announce my transition, because I didn’t have a lot of examples to follow. I waited almost a month after leaving my job to note the change publicly because I was terrified. Who was I without my title? How dare I tell the world that I was enough of a writer and journalist on my own with no news organization backing me up?
I’m now nine months along this journey. It’s the best decision I’ve ever made. I try not to hawk freelancing like an eager salesperson, because I realize that my experience is not necessarily a reflection of everyone’s. But I do think there’s a myth that needs to be debunked, that freelancing is a tenuous career path that yields half the money for double the time. That mantra keeps too many people in unfulfilling jobs that make them wildly unhappy or, worse yet, numb. This is a viable alternative.
First, it really is possible to make more money — Gritters wasn’t exaggerating. I earned more in six months on my own than in the entirety of last year at a full-time job. And I’m on track to more than double my total income this year.
I’ve seen that the main limiter of my aspirations is me. I’ve written for publications not even on my radar because I assumed they were far out of my league, and I’ve pitched dream stories only to have them accepted. (Reader, this does not happen all the time.)
By going out on my own, I’ve come into my own. I’ve started to realize who I am and who I want to be as a writer and a professional. I have a better sense of my strengths and weaknesses. And I feel stimulated by my work because there is always a glimmering sense of possibility.
I wake up and wonder: What could happen today?
* * *
I’m not the only person who decided to make a big life change — professional or otherwise — in 2020.
20% of Americans are considering freelancing, according to surveys by freelance site Upwork between June and July of 2021. More than 50% of those surveyed who planned to quit said they would consider freelancing. A large percentage said the ability to work remotely or flexibly would be a factor.
Even before the pandemic, self-employed people made up more than a third of the U.S. labor force — 35%, according to a 2019 study from Upwork and the Freelancers Union. 57 million Americans freelanced that year, an increase from 53 million in 2014. But only 60% of those 57 million said they started freelancing by choice.
In perhaps the least surprising finding, age plays a role in willingness to freelance. Roughly 53% of Gen Z workers and 40% of millennial workers said they had freelanced versus only 29% of baby boomers.
And for those who choose to freelance and stay, many of them are happy. 51% of freelancers said no amount of money would cause them to take a traditional job.
For those in the media industry, freelancing is often either a siren call or a safety net. Sometimes, it can be both.
East Bay, California-based audio producer Adwoa Gyimah-Brempong continually found herself lured back to freelancing. She took full-time jobs only when she needed, as she put it, “someone else to pay my insurance and a steady check.”
“I am someone who really likes being freelance,” she said. “It makes me really happy.”
There are so many aspects of freelancing that work for her. She loves doing her taxes, so much so that she calculates across three systems to find the best return. She understands how to set her own schedule. She enjoys the expansiveness.
But it took COVID-19 — literally — for Gyimah-Brempong, 35, to step away from her most recent full-time job. She had worked for three years as a producer for a public radio station. When she contracted COVID-19 before it was a prominent disease in the U.S. and then spent the following summer nauseous for months at a time, she hit her breaking point. The stress of the job was no longer worth the sickness. So she quit.
“The lack of opportunity and high turnover of women of color made it clear that I wasn’t going to grow in my career unless I left the station, and the microaggressions and lack of respect from management were the other incentives,” Gyimah-Brempong said. “Ultimately, I was like if I were to die tomorrow, is this how I want the end of my life to look? And it wasn’t, so I made a change.”
Now firmly on the other side, Gyimah-Brempong offers audio production, editing and sensitivity listening for clients. In the past year, she’s reported her first feature, reported and hosted her first podcast episode, was a member of an editing fellowship cohort and is currently working on a narrative podcast.
Despite her history in public radio, she prefers to work with clients rather than on journalistic or donor-driven nonprofit pieces.
“I care about telling a clear and focused story,” she said. “I find that donor work is kind of, ‘Congratulate us for how great we are.’ And journalism is, ‘We have to look at both sides of this burning building.’ And client work is really, ‘We want a good product. Can you make this good product for us? Cool, go make it.’”
With each client, Gyimah-Brempong has a sweet spot in mind — a long-term contract, which is standard for audio production. Rather than work on one-off pieces, she prefers projects that offer consistency and a clear-cut schedule and payment structure.
Her success proves that part of being a freelancer is intentionality. If something isn’t working, the only person who can change it is you. That’s why knowing when to say no is just as important as knowing when to say yes.
Gyimah-Brempong recalls advice from an old boss: Figure out why you’re taking your next job. She keeps that in mind as she considers each project.
“Go into this thing knowing what you’re getting out of it and making sure it’s enough,” she said.
Others, like Tampa-based photojournalist Octavio Jones, took the leap to permanently freelance because of external circumstances. As a full-time staffer at the Tampa Bay Times, he had prepared to go independent. Rounds of layoffs and the turmoil of the industry left him wondering when he would be next.
Jones got the phone call on an early March 2020 day, shortly before COVID-19 would take over the world. His time was up.
“I wasn’t angry. My time there was the best. I thoroughly enjoyed being at the Tampa Bay Times. I really loved my job. It was the best thing,” Jones said. “If it weren’t for those 10 years being at the Times, I don’t think I would be able to be where I am when it comes to freelance.”
At first, Jones wasn’t sure which direction his career would go. It took months before another call jogged him back into place. It was his former editor at the Poynter-owned Tampa Bay Times (also my most recent full-time employer), asking him to cover a protest in Tampa following George Floyd’s murder by police.
“When he called me and said, ‘I think I might need you,’ I didn’t even think twice about it,” Jones said. “I said, ‘Let’s do it.’”
He got enough material for the day and thought he was finished. But a colleague soon called. There was another protest at a local university, he said. Jones hesitated until he learned that part of a major road was shut down. He was struck by the massive scale of the protest. That’s when the realization hit.
“It’s not over for me as a photojournalist,” he said.
If anything, Jones has experienced a renaissance. He’s photographed for The New York Times, The Wall Street Journal, The Washington Post, Reuters, Getty Images, GQ and Elle, among many others. He called me from Haiti for this story, where he documented the aftereffects of the earthquake for NPR.
But working as a visual freelancer — especially coming off of a staff job — yields some unique obstacles. As a staff photojournalist, Jones’ equipment belonged to the Tampa Bay Times. When he was laid off, he had barely any gear — something that can cost as much as $10,000 to replenish. An initial non-journalism gig paid him just enough to invest in the tools necessary to stay in photojournalism.
That job was the first of many that have given Jones a financial lift. Working full-time at the newspaper, he said he struggled to make ends meet. Some weeks he borrowed money in a cash advance because he didn’t have enough to buy groceries.
“Even though I loved being at the daily paper, financially, I was struggling,” Jones said. “I was almost living paycheck to paycheck. That was a dark time. It was something I didn’t really enjoy.”
He’s now able to pay himself a decent wage every week. He has enough for bills and a profit margin to spare. And yet that income has to be doled out in increments, adjusted for the fact that assignments aren’t evenly spaced out and one month can return five figures while another might bring in only a couple thousand.
“You really have to stick to a budget,” he said. “A lot of your clients are going to have their own funding, yes, but you have to have that operating budget to be able to move.”
Would he return to a full-time role if the opportunity arose? He says he still considers that.
“Being an entrepreneur is a good feeling. It’s financial freedom — you know how much you are going to save,” he said. “It would be tough, but it depends on who it is. It would have to really be somewhere that I had always desired to work for.”
Dallas-based writer Claire Ballor had her own circuitous path to freelancing, one that took her to Florence, Italy, before returning to Texas. She spent most of her early career as a breaking news reporter at The Dallas Morning News before taking a real estate job at the nearby Dallas Business Journal.
“I knew real estate was probably not a beat I’d cover forever,” she said. “But I’ve always been interested in freelancing. So I figured, ‘OK, this is a great job, I’m going to do this knowing that at some point I might leave and go into the freelancing world.’”
Ballor was also balancing another interest on top of her work — a deep affection for food. When the opportunity came up to attend a culinary program in Florence, she jumped. She didn’t know quite how it would affect her career at the time, but she wanted the opportunity to try.
“I love food and I love writing and other people have food writing careers, but I realized that I wasn’t pursuing that because I just wasn’t working at publications that had a need for that,” she said. “If you wait for a beat to open for you, it’s just often not going to happen.”
Living in Italy was restorative and educational. Ballor learned how to “set writing aside and just live.” She completely immersed herself in the world of food and came out a better writer for it.
The idea that a journalism career had to be linear was ingrained in her. She didn’t take lightly the decision to leave and eventually freelance. She worried that she would hurt her prospects by jumping ship.
“I had absolutely no idea how it would work out,” Ballor said. “I didn’t necessarily go into this thinking, ‘Well, I’m just going to freelance for the rest of my life.’ I just knew at the time that I needed a change and it felt like, ‘Why not now?’”
Much of Ballor’s freelance journalism work is centered at The Dallas Morning News, her former employer. The consistency means she worries less about a regular paycheck — at least for now — because she knows she’ll always have some work. There, she’s carved out a niche for herself, the one she always wanted as a food reporter.
After more than a year and half as a freelancer, starting shortly before the beginning of COVID-19, Ballor misses the energy and buzz of a newsroom. Even if she does go back to a full-time journalism job, she knows she’ll never be the same because she freelanced.
“I’m open to going back to a newsroom, but my thinking will forever be changed by having freelanced,” she said. “If I could find an on-staff journalism job that would allow me to do the kind of important reporting and stories that I’d like to do in a way that I think is a little healthier than a lot of jobs can be in our industry, that would be the ideal.”
* * *
At a dinner party a few years ago, a family friend asked for my 5-year career goal.
The answer should have been easy. It’s a classic interview question, after all. I listed off a few high-profile outlets I hoped to be working at by then.
He countered. But what do you want to be writing about? I was stumped. What did I want to be writing about? I had spent so much of my life framing my career goals in terms of prestige — work at this place to go to this place to reach this level, that I had never stopped to think how I actually wanted to fill all that time.
Perhaps that is where my freelancing journey really started. That was where I realized that a truly fulfilling career cannot be made up of titles. It must be made up of something bigger — a path led not by names but by meaning.
Correction: Adwoa Gyimah-Brempong worked for a public radio station for three years.
