Sometimes the biggest career shifts aren't planned.
For freelance writer Rose Cryan, the move from corporate marketing to freelancing wasn't something she'd mapped out years in advance. When her in-house role unexpectedly came to an end, she found herself at a crossroads familiar to many marketing professionals: search for another traditional job or embrace a different way of working.
She chose freelancing.
Today, Rose works with organizations across multiple industries, helping brands communicate clearly through thoughtful, audience-focused writing. What began as an unexpected career pivot has become an opportunity to focus on the kind of work she enjoys most while collaborating with a wide range of clients.
Bringing Corporate Experience into Freelancing
Before going freelance, Rose worked as a copywriter and communications manager for a consumer retail brand, contributing to everything from product descriptions and email campaigns to video scripts, advertising copy, and in-store signage.
That breadth of experience became one of her biggest advantages as an independent writer. Years of adapting messaging for different audiences and channels, and balancing competing priorities, prepared her for the fast pace of freelance work.
The Surprise Wasn't the Freedom—It Was the Focus
People often imagine freelancing as trading meetings for flexibility.
For Rose, the biggest surprise was something else entirely.
"What surprised me most was how much I enjoy the focus. Instead of juggling competing internal priorities, I can go deep on a single project and think carefully about the audience, the message, and how the piece will be used."
That focus extends to the kinds of work she finds most rewarding. In her Wripple Talent Spotlight, Rose shared that she's energized by projects requiring creativity and insight—whether that means shaping campaign messaging or translating complex topics into engaging, accessible content. She especially enjoys collaborating with teams who value thoughtful storytelling and are willing to iterate until the work is right.
The Skills That Matter Most
While strong writing is essential, Rose says the skills that keep freelancers successful aren't always the ones people expect.
"Time management and hitting deadlines, without question. In a corporate role, those are expected. As a freelancer, they're what keep the work coming."
She also credits her ability to shift tone and messaging depending on the audience—a skill she developed working across different sectors, channels, and teams.
For clients, those skills translate into something invaluable: a freelancer who can step into a project quickly, understand the audience, and deliver work with minimal ramp-up.
The Work Beyond the Work
Rose says one of the biggest adjustments to freelancing is what happens between projects.
"The time it takes to find your next assignment, including reaching out, following up, and staying visible, is something people often underestimate."
Freelancing offers flexibility, but it also requires consistently managing the business side of your career.
That balance has shaped the way Rose approaches her work.
"I'm often switching between clients, industries, and formats, so I've gotten more comfortable adjusting my voice and approach quickly. It's also reinforced how important collaboration is—getting feedback, asking the right questions, and making sure the work actually meets the need."
Advice for Anyone Considering Freelancing
Rose doesn't romanticize the freelance life.
Instead, she encourages people to understand both the opportunities and the responsibilities.
"Freelancing has real upsides, but it's not as simple as trading structure for freedom. You do get flexibility and the chance to work on a range of projects, but you're also responsible for finding work and managing the uncertainty that comes with it."
For Rose, what began as an unexpected career pivot has become an opportunity to deepen her craft, work across a variety of industries, and build a career on her own terms.
Sometimes the path forward isn't the one you planned. But with the right experience, adaptability, and willingness to embrace change, it can lead somewhere even more rewarding.
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