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How to tell your career story when you are bouncing from job to job

October 2, 2026
in News
How to tell your career story when you are bouncing from job to job

The playbook of how to build a career in the gig economy is still being written.

There are no straightforward steps like in the days when a diligent worker could land a job at a good company, work hard to get promoted and hope to climb the corporate ladder.

A significant share of the U.S. workforce — nearly 7 million people in 2023 — is engaged in what the Bureau of Labor Statistics classifies as “contingent and alternative employment arrangements.” That could mean working a freelance job, picking up gig work or finding short-term contracts.

I’m one of those workers. I’ve been freelancing since 2024. And I know it can be scary.

People may worry about where the next job will come from and how much it will help pay the bills. They may also struggle with how to establish themselves in a field as they jump from job to job, from boss to boss, from client to client, having to prove themselves over and over again.

A lot of the work that goes into gig work can feel invisible, and the financial inconsistency can take a toll on someone’s self-esteem.

“Gig work can be really tough to build a career, especially for someone who doesn’t already have connections or a decent nest egg to weather dry spells,” said Shelly Steward, chief research officer at the Workers Lab. “People are concerned about building a career where you grow in benefits and wages, where you do better and better.”

Career coaches and recruiters agree: Whether a worker is working gigs by choice or by circumstance, the narrative they craft for future employers is vital.

Future hiring managers may review such a worker’s résumé and question the candidate’s ability to lead teams or settle into a full-time job environment, said Victoria McLean, CEO and founder of Hanover Talent Solutions.

She recommends that workers get ahead of that by underlining the skills they’ve honed from years of freelance and gig work — like the ability to take initiative on self-started projects, build client relationships and work across various industries.

“Position it as an upside, not a downside,” she said. “You’re agile, you’re flexible and you can hit the ground running.”

Eliana Goldstein, a career and success coach based in New York, suggests that freelancers and gig workers envision themselves at the center of a “career web” rather than standing at the bottom of the proverbial career ladder.

The ladder image inherently implies a hierarchy with some people on top, some people at the bottom. A career web instead positions a single worker’s goals, skills and story at the center of the web, with opportunities shooting out from all directions.

“In a lot of ways, the resilience you build freelancing and the slew of situations you find yourself in is really powerful,” she said. “If you can communicate that in the right way, it can be tremendously helpful.”

The post How to tell your career story when you are bouncing from job to job appeared first on Washington Post.

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