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Jennifer Jackson on finding security and financial freedom in freelance work

by | Nov 20, 2023

Jennifer Jackson, freelance campaign marketer
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For years, marketing executive Jennifer Jackson often crossed paths with freelancers at the office. She admired their grit—which she assumed they had in great supply. How else could you maintain a life of unsteady employment and probably low-paying work?

Then came the pandemic of 2020. Within months, DRUM Marketing, the company where Jennifer was a group marketing director, closed its doors. Suddenly, she was without a job in the midst of one of the most brutal job markets in recent history.

A few months later, she got a call from Katie Elliott, the head of sales strategy and operations at We Are Rosie. Katie had been the person who connected Jennifer with freelancers when DRUM needed them. Now Katie had a question: Would Jennifer consider being a Rosie herself?

Jennifer, who’s based in Atlanta, accepted the offer. But she had a caveat. She’d take temporary work to get income in the door until the world opened up again. As soon as it did, though, she would return to a company as a full-time staff member.

She liked security. She liked a steady paycheck. She liked traditional work, with its traditional perks.

“Three years later, I’m still contracting,” Jennifer says, laughing. “And it’s the best decision I’ve ever made.”

Right out of the gate as a freelancer, Jennifer was hired for higher-level, better-paying jobs. The contracts she signed were with major national companies, where she met industry leaders and forged valuable connections she’d previously never dreamed of making.

“We Are Rosie helped me realize my worth,” Jennifer says. “Even with the first gig, I started making six figures. I came in as a program manager and with my degrees and my experience, I would never have thought I’d make that much.”

Three-month projects got extended to six months, and then longer. And when a contract did come to an end, We Are Rosie would set her up for an interview with another top-shelf company. Every interview she’s had has led to a lucrative work opportunity. Her latest one, for a leading telecom company, has been going for over a year now, with no end in sight.

Loving her job again

And the work’s been fulfilling, too. Jennifer describes a recent campaign called “Codes of Connection,” which was an outreach to the Hispanic community in Houston, Phoenix, and Los Angeles.

“The idea is that everybody is connected to their area code,” she says.

Latin American communities tend to be close knit, and people living in certain neighborhoods all have the same area code. It’s a connection to your people. So Jennifer worked on a campaign promoting the idea that the telecom company would let you keep your number (with your old area code) even if you moved out of state.

“Anyone from L.A. who sees your 323 area code knows that you are from a particular area,” she says. “Being able to keep that area code keeps you grounded.”

The marketing department promoted this idea on social media and through the big Hispanic radio stations in these cities. As program manager, Jennifer played a leading role in integrating the message throughout all departments. Using prior experience she’d picked up at another consulting job, she helped the whole enterprise to onboard the project management software Workfront.

“All the departments are using the same tool now,” she says. “So the next time we’re doing a campaign across departments, there’s documentation.” And the software has already eliminated inefficiencies in the company.

The joy of financial freedom

Of course, Jennifer’s ambition was potent long before she became a freelancer. She’s always been mindful that her grandmother only received a sixth grade education—while she herself was the first in her family to finish college and grad school.

But with her entry into consulting and project-based work—and the six-figure salary that accompanied it—she was able to reach a new milestone: She could afford to build her own home. This was also a family first. “My parents had always rented,” she says.

In December of 2021, when Jennifer received her first approval on a loan, “I called my mom crying,” she says. “I never thought I’d be able to do that. There are some days I still can’t believe I’m a homeowner.”

The day she closed on the house happened to be her grandmother’s birthday, and her mother recorded the proceedings. (“I want your grandma to see it,” she explained.) Jennifer remembers that when it was over, she grabbed her house keys, called her grandmother (who lives in the Midwest), and said, “I did this for you.”

“She’s coming out here in April of next year,” Jennifer says.”She wants to see my house!”

No regrets

Like many people, Jennifer learned some big lessons in the last three years. For one thing, full-time, in-house work isn’t always the best path to security.

“I never wanted to have the stress of not knowing where my next gig would come from,” she says. “But in this [post-pandemic] environment, you have those same issues working full-time. The company could be here today and gone tomorrow.”

Ironically, the freelancer life has given her a greater sense of security, boosting her confidence in her own abilities and resting in the knowledge that she can always find career opportunities. She says she’s happy where she is right now. “But if I wasn’t, I could call We Are Rosie, and they would work to find me something else.”

Jennifer Graham Kizer is a features writer and content creator who provides editorial services to print and digital publications, schools, churches, companies and individuals. Her work has appeared in over a dozen national magazines, including Good Housekeeping, Health, TV Guide, Parenting, and others. Find samples of her writing at She can also be found on LinkedIn.

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