Stories

The 5 Biggest Shocks of Moving From Staffer to Freelancer

By Amy Klein August 31st, 2016

When I was a full-time newspaper reporter, I imagined all the wonderful ways I’d be spending my time if I were a freelancer.

To be free from the confines of one particular publication, office, and subject sounded like editorial heaven. I could work in my pajamas and only pursue interesting stories!

Well, after my editors and I mutually decided I was not passionate enough about my beat (religion) to keep writing about it exclusively, my dreams came true.

Or did they?

Moving from the coddled, cozy cocoon of a staffer to the often callous, cold world of freelancing turned out to be quite the transition. I’m not an exception either. I spoke to a number of former staffers who made the jump, and it turns out there some shocks almost everyone experiences.

1. You miss the office

I never thought I would miss the 7 a.m. alarms, rush-hour traffic, or banal water-cooler conversation. But once I found myself with all the free time in the world, I started to wonder what everyone else was doing and talking about.

Some people find they need that chatter around them. “I miss the newsroom—the relationships, the collegial atmosphere,” said Ben Davies, who preferred to not give his real name. Davies worked at a major newspaper for 10 years before leaving to work on a book. “I miss sitting around and talking with people all day about my stories. It’s just a way to get your mind working. When you’re a freelancer, you’re doing it in a vacuum.”

Laura Shin, who has gone between staff jobs and freelancing over the years, agreed: “My favorite things are story meetings where you bounce ideas around. … There’s a sense of camaraderie and fun where you’re part of something bigger. You’re working as a team.”

2. You don’t have the inside track anymore

Karen Goldman worked as an editor and writer at for eight years before leaving to raise kids. A few years ago, she returned to the industry as a freelancer.

While the whole pajamas stereotype appeals to her—“The dress code was terrible. It was a particularly conservative work environment where we were expected to wear business attire”—she misses the insider knowledge she had from, well, being on the inside.

“Being on staff, you know the ins and outs of how the place works, which you don’t know when you’re a freelancer,” she said. “If you’re on staff, you know who the readership is, what kind of content they’re looking for, what their editorial calendar is. As a freelancer, you’ll have to intuit that [for every] publication you’re trying to pitch. There’s a lot of guesswork involved.”

3. Time takes on a new meaning

I love falling down the Google rabbit hole as much as the next person, spending days researching my story (and watching dancing baby videos, of course). I could afford to do that as a staffer, but now time is money. My money.

When he was on staff, Davies could just walk into his editor’s office and say, “’I want to work on this.” Even if his boss wasn’t sure about it, Davies could explore it. “I don’t have that luxury anymore,” he said, noting that now he has to invest time and effort into pitching. “You’re basically working on spec.”

“There’s a different kind of time management that’s required,” Goldman said. “I think part of being successful is really trying to figure out how to maximize your efficiency, calculating ‘Is this article worth doing for the return I’m going to get?,’ especially in this market, where a lot of publications are not paying what they should.”

4. You realize you run a business now

It’s not only the loss of a steady paycheck. One of the hardest parts about moving from staff to freelance is all the bureaucracy that comes with it, like finding health insurance and filing your own taxes quarterly. Put simply: Your work becomes a small business, with all the headaches that come with it.

The first time Shin was a freelancer, she struggled financially. “Your own ability to manage your money is going to be hugely helpful,” she said. “If you set a budget in order, have some savings, save for retirement, plan how you’re going to take vacations … [you have to] try to be your own employer.”

This time around she’s been much more successful, in part because she knows how to manage her finances. “You have to run your own business. There’s a lot of administration,” she said.

5. The separation between work and life is harder to see

I used to dream of all I would do instead of commuting and sitting in pointless meetings. And I was very efficient when I first started freelancing. But then life and work started to get all mixed up since I was doing both of them in the same place.

Other staffers-turned-freelancers have found that separating work and life isn’t easy.

“I always wonder if two hours going down some path—is that work?” Davies said. When he was on staff, “You enter the building, eat lunch, and leave the building. There’s still tangible evidence you were working. But when you’re freelancing at home, you don’t have that structure. You lose track of what is work.”

While Goldman deplored her 80-minute commute and the face time she had to put in at a staff job, “There’s a lot to be said for showing up to work, and when you leave you don’t have to take your work home with you,” she said. “When I left, it was pretty much understood I wasn’t working, and there was something really nice about being able to distinguish between work time and personal time.”

But there are still plenty of advantages

Luckily, everyone I’d talked to—myself included—has found ways to adapt to the shocks. And even with the financial pressures, the lack of structure, and minimal camaraderie, there are plenty of advantages that, so far, have kept these freelancers from going back to the staff life.

“You’re not beholden to a story you’d rather not be doing,” Davies said.

While many successful freelancers find it more efficient to focus on one or two areas (Shin, for example, is an expert on Bitcoin and Blockchain), what exhilarates Davies about freelancing is following his passion wherever it takes him, from sports to culture to entertainment to business.

“There’s this world or area or subculture I had been wondering about for a long time and had no idea it existed,” he said. He loves pursuing it. “If I’m not interested, it’s very hard for me to fake it.”

Image by Getty Images
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