NewsMaking It In San Diego


Military spouses take on career that can move with them

Devin Drake
Posted at 6:12 PM, Apr 18, 2022

SAN DIEGO (KGTV) — When duty calls, military families often pick up and move at a moment's notice. For working spouses, that can mean having to start their careers all over again in a new place.

A growing number are Making it in San Diego and wherever they go- by taking on a profession that's as mobile as they are.

“I’m going to include some peanut butter for you to put on your fruit,” said Amy Hensley as she shot a video of herself putting together a care package for her Navy husband Matt. He's currently deployed in the Western Pacific with the USS Ronald Reagan.

She's also tending to her own profession.

“I was looking for something that I could take with me,” Hensley said. “And be able to keep my career and not change jobs every, one, two, three years.”

With military families so often on the move, Hensley found a company called Boldly which matches qualified executive assistants with those who need them.

“One of my clients I manage their email, their scheduling, all of their calendar," she said. “Any meetings that need to be scheduled go through me.”

Across the country, Devin Drake can relate.

“For one moment, I'm working for somebody in cyber security, and the next moment, I'm working in life coaching,” said Drake from an office with a Boldly logo behind her.

But as ABC 10 News found out, this too, was right from home.

“People ask me that all the time because I do have the Boldly sign behind me. But this is my home office,” she said.

Drake went from executive assistant to Recruitment Manager for Boldly. She's also a military wife who lived with her family in San Diego until her husband was transferred to North Carolina.

She's now focused on getting other military spouses on board for remote careers.

“We cannot keep up with our client demand. There is just so much of a need for remote executive assistants,” said Drake.

She also found a career ahead of the curve when it came to dealing with the pandemic.

“I didn't predict the pandemic coming but it worked out because I've been working remotely since 2018 and it's been just a blessing for me and my family,” said Drake.

Drake and Hensley both say the big advantage is flexibility; not only can remote assistants take their jobs with them, but they say it's easier day to day, to shift work around other needs.

“If have that doctor's appointment, or that dentist appointment, I can usually flex my schedule a little bit," Hensley said. "Work later in the evening or earlier in the morning.”

The office decor — especially just off-camera — can take on a very personal touch, Drake points out with a smile.

“What you can't see behind the screen, is the rabbit cage there that I'm looking at,” she said.

Drake says Chewy Bun Bun appreciates the company, and that some remote assistants choose the career to stay close to their pets.

Drake says Boldly executive assistants start at $23 an hour and Boldly is looking for a range of talents, including writers, project managers, and those with experience in marketing and social media.

Boldly is one of many remote office support companies looking for assistants. The pay ranges from $35 to $85 thousand a year.