This Is What It Takes To Get A Regular Job After Giving Up On Self-Employment

Four ex-“solopreneurs” share why they went back and what it took to land job offers.

This Is What It Takes To Get A Regular Job After Giving Up On Self-Employment
[Photo: Thomas Barwick/Getty Images]

Osvaldo Ruiz has no trouble recalling how “cutthroat” the mortgage industry was in 2005, and how many “dubious people” were out there hawking mortgages nobody could afford. That’s because it was the year he quit his full-time job in construction “with hopes of becoming a real estate mogul,” a dream that Ruiz sounds glad didn’t pan out in retrospect.


Around a year before the U.S. housing market cratered, dragging the economy down with it, Ruiz moved to Denver “to start over” in software development. Now Shutterstock’s director of engineering, he’s one of countless people in today’s workforce with stretches of self-employment on their resumes–some failed “solopreneurs,” some fed up with the contractor and freelance slog, others wooed by onetime clients–who’ve returned to full-time positions. So Fast Company spoke with several to find out why they ditched their solo gigs and what it took to get hired again.

Show You Can Deliver

“Successful freelancers know how to get shit done and how to convey results,” says Sandra Rand, now vice president of marketing at OrionCKB, a social media advertising firm. “That’s how their work is judged and their pay is justified.”

Rand went solo in November 2010 “to escape a terrible boss” and freelanced for the next five years. In that time she had two children, and before long the freedom that self-employment had earlier seemed to promise began eluding her. “I found the administrative elements [like] invoicing, taxes, time tracking, drafting proposals . . . to be time-consuming and stressful while I was juggling my growing family,” Rand reflects.

“I was only making money if I was sitting in front of a computer producing work,” she points out. “Though I loved my clients and was making great money, the hustle required to be successful equated to time away from my kids and husband.” So she joined OrionCKB full-time in February 2015–and credits that “hustle” with landing her the offer.

“I think any employer who finds freelance work to be a strength knows that, in order to be successful working on your own, you have solid time-management skills, you’re resourceful, have great communication skills, and can prioritize multiple projects and deadlines at once.” Rand adds, “I wouldn’t have been a very good freelancer if I couldn’t produce the results my clients were looking for.”


Solopreneurship Can Be An Asset

Rand says she didn’t have much trouble demonstrating those skills to her now-employer, but it’s hard to know how typical that might be. Last week, one former recruiter who’d left the industry after more than a decade told Fast Company there’s a widespread belief in the talent world that “if you’re self-employed, it’s because you can’t get full-time work.” She even advised former solo workers to “downplay how much you took on in terms of risk or innovation or ability,” warning that hiring managers may see that as a liability.

None of the four ex-solopreneurs who shared their views for this article said they encountered that bias. Rand acknowledges that freelancers may still face a stigma left over from the Great Recession, “when a lot of people who were laid off pursued independent work because they were underemployed,” but this wasn’t her experience.

It wasn’t Matthew Kirk’s either. An author and machine-learning expert who’s alternated between four full-time positions and four stretches as a solo worker over the past decade, Kirk says that “the companies I have worked for full-time value my entrepreneurial spirit.”

By now, many hiring managers themselves have periods of self-employment on their resumes just like Ruiz, Rand, and Kirk do, so they aren’t likely to blink when they see the same on others’. “Just because I don’t have fond memories of the time I worked for myself doesn’t mean others didn’t have positive experiences and successes when they ventured off on their own,” Ruiz points out.

When he’s making hires now, he say, he looks for “self-starters and problem-solvers, and entrepreneurial-minded people can match up well with those norms and expectations.”


Turn Clients Into Employers

Indeed, there’s little reason to believe former solo workers are any less loyal than people who’ve only ever held full-time jobs. Average job tenures these days are tough to measure but generally thought to be around two to three years, and plenty of freelancers hang onto clients for just as long.

Many of Rand’s clients kept her on for years, so she had no trouble “emphasizing their longevity” while interviewing for full-time roles, in order to “[show] that they were happy with my output and my dynamic within their team,” she explains. “In fact, it was my clients who recommended me to others, so their endorsement of my work positioned me as a strong candidate. I even had one client pursue me for an in-house position while I was still happily freelancing.”

When the same thing happened to Sandi Harari, she took the job. Now executive vice president and creative director at the ad agency Barker, Harari said she was never actively looking for full-time positions. She’d worked for Barker for a few months before the company offered her a role as a creative director, which she accepted in 2006.

“Some of that may have been how I framed what I was doing,” she explains. “I worked for various companies–but I called them clients–under the name ‘Sandi Harari Design,’ and treated it like a firm. It was a choice I made to go solo and start my own thing.” Fast Company contributor Suzan Bond regularly advises independent workers to do the same, and even suggests avoiding the term “freelancer,” which may unwittingly invite mistreatment from clients. “To me it was a business venture, definitely not freelance work,” Harari adds.

After four years on her own and a portfolio of work for big agencies, she was surprised by “how refreshing joining a small firm was . . . It was a classic Goldilocks moment in my life where I found the right-sized agency that was also in line with my creative vision.”


Not everyone who returns to corporate life finds their sweet spot. Kirk accepted his most recent full-time job last year, in part “to get health insurance and have some sort of stability in my life during an extremely testing time.” His father had died suddenly in a car accident and Kirk was being treated for cancer, so he’d thought of the position as “just a place to recoup and reflect.” But this year he decided to “go back to what I enjoy the most, which is being a solopreneur.”

“Every time I’ve taken a full-time job after being solo, minus the first time, I have found the job to not be entirely to my liking,” he explains. Having written two books on machine learning and built up a following through his blog, consulting services, and training programs, Kirk says it’s clear to him now where he really belongs. “I seem to do best doing this.”

About the author

Rich Bellis was previously the Associate Editor of Fast Company's Leadership section.