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How flex work helps military spouse Jennifer Riddle balance career, family, and service

by | Nov 11, 2022

How flex work helps military spouse Jennifer Riddle balance career, family, and service.
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There are lots of reasons why marketers choose to go independent these days.

For their families.

For their mental health.

Because they need more free time.

For long-time Rosie Jennifer Riddle? It was all of the above and so much more.

As a military spouse, parent, and caregiver, Jennifer sought to build a career that would honor and provide space for all the roles of her life.

She found that in freelance work.


The journey from agency director to independent marketer

Jennifer’s career was thriving. She’d worked her way up in the agency world, becoming a media director with experience on big-name accounts across many industries. But when her husband, Major Robert Riddle, was deployed to Afghanistan in 2017, full-time work fell out of sync with the rest of her reality. She was suddenly thrust into existence as a single parent, while carrying the emotional weight of having a loved one deployed.

“The stress was just too much,” Jennifer recalls, explaining that it was sometimes challenging to focus her energy on advertising work while her husband was in harm’s way. “During my full-time job, there were several times where I broke down because I just couldn’t balance all the emotions that I had.”

She wanted and needed to continue working. The flexibility of freelance was appealing, but support was also essential in this season of Jennifer’s life and career.

“Finding freelance positions on your own is taxing,” she explains. “It also usually means that you don’t have the infrastructure that can support some larger campaigns, so the amount of money that you can make is really limited on your own.”

That led her to adopt yet another title: Rosie.

“Partnering with We Are Rosie allows me to take my expertise and plug in immediately at a company that had all the infrastructure I needed to do the job,” Jennifer says.

“It gave me the opportunity to step back in responsibility a little bit, but still stay in the game, still work and bring in some income.”


The ripple effects of remote and flexible work

Flexible work allowed Jennifer to continue her career on her own terms—something many military spouses don’t get to do. For years, the unemployment rate among active duty military spouses has been more than 20 percent, resulting in a significant loss of income for their families.

Part of the challenge, Jennifer explains, is that active duty members typically move every few years, making it harder to find and keep work that’s not flexible or remote.

As a member of the Oklahoma National Guard, Robert is able to maintain his home base in Texas, where he and Jennifer live. But he’s also away from home often, and when he is, the flexible nature of Jennifer’s work is a game-changer for their family.

Sometimes, it means that they can simply spend more time together, like when Robert travels for training and Jennifer is able to join him while working remotely.

Or, that Jennifer can help out with all the preparations that go into a deployment or special project, which can come at a moment’s notice.

But sometimes, the impacts are even bigger than that.

“There aren’t weekends when you’re deployed, when you’re on a special project,” Jennifer explains. “So, to allow me the flexibility to take care of things at home means Robert doesn’t have to think about them while he’s gone. He can focus on the obvious—staying alive. That’s a very real risk that everybody kind of forgets about.”

Flexibility for a new season of life

These days, Jennifer and Robert are adapting to life as empty nesters, after their youngest child graduated from high school in May. But that doesn’t mean that full-time, 9-to-5 in-office work fits life any better than it used to.

“In the beginning of the year, I was working for an agency again, working really long hours,” Jennifer recalls. “My dad had just gotten out of the hospital and I was still working at eight o’clock at night on a Friday. And I was thinking, ‘What am I doing? I need to put the focus on my family.’ I decided to resign and immediately contacted We Are Rosie and said ‘Okay, I’m ready to get back to work.’”

Well, almost ready.

Jennifer has come to appreciate how flex work makes it easier to take time off, so she’s enjoyed hitting pause for a month or two before diving into new projects as a Rosie.

“You really need to get your game back up, remind yourself what’s important, and revitalize your energy to bring it to a new position,” she says.

As for the future of work, Jennifer believes that flexibility is here to stay. As more employers recognize the human side of work, more people will be able to craft the careers and lives that they want, just as she has.


Looking to build your marketing career in a way that works for you? We Are Rosie connects you to flexible, remote work opportunities and all the support you need to thrive. Join our community of marketing experts today.

Written by We Are Rosie

Welcome to The Write-Up, a space for conversations about the future of work and flexible careers.

Whether you’re a CMO or an independent marketer (or both), we’re here to bring you bold perspectives, inspiring stories, and helpful advice from We Are Rosie's community of experts and thought leaders. Together, we're building a more inclusive, human future of work.

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