Empowering women, one itinerary at a time: Milliman's Alyssa Johnson takes solo globetrotting to the next level

It was four days before the world stopped, and Alyssa Johnson had no idea that her favorite hobby, world travel, was about to suffer an abrupt and extended delay.

Alyssa, a senior operations specialist for Milliman’s MedInsight practice, was living her best life in a city she loves, traipsing around London in March 2020. Then everything changed for everyone.

“I came back before the border closed, and that was it for three years,” Alyssa says. “So I had all that time to think about travel and reflect on things I’ve learned."

Once travel opened back up, Alyssa decided to take a cruise from Barcelona to London. While on the ship, she had a conversation with a fellow traveler and an idea was born.

“The person is a travel agent that books trips for friends and family,” Alyssa says. “And I thought about the fact that I’ve been a career admin for 20 years, booking travel in the corporate space, and at the time I really wanted people to get out traveling because I had gotten so much from it.”

Alyssa began booking travel for friends and family and realized that she was hearing from a lot of women like herself who wanted to get out there and see the world but might have been a bit hesitant to do so because of things they’d read and stories they’d heard.

“As a woman, you don’t necessarily feel safe doing things alone,” Alyssa says. “So I thought about how I could help women feel safe and comfortable as solo travelers, and I grew an audience from that group.”

She started building a social media presence that includes a popular TikTok channel and Instagram account, and it evolved into Fearless Freedom Travel, a travel business that allows Alyssa to visit the far-flung locales she wants to explore while organizing itineraries for others. On the business website, Alyssa offers a free solo travel guide with tips on avoiding loneliness, safety, saving money, and more.

Then, prior to departure, Alyssa arranges for the traveling groups to connect on a WhatsApp chat, where they can get to know each other and talk about issues and concerns.

“I get women from different age groups, from late 20s to late 60s, but one thing that a lot of them share is that relationships have recently ended and they want to get out there and see the world,” Alyssa says.

"And for some of them, it can be challenging to travel by themselves. Women who are older than me born with traditional gender roles and expectations, it takes a lot to break out of those. I’m happy to help them do it.”

She’s happy globetrotting, too. Alyssa went to 21 countries in 2022 and 24 total in the last two and a half years. She’s done six group trips under the Fearless Freedom banner, with many more to come. She’s got the full support from the MedInsight leadership, and with long holiday weekends, PTO, and the occasional remote-work day from a cruise ship or international port of call, she makes it work with her Milliman work.

But the best part of this adventure, she says, is getting constructive and often inspiring feedback after the trips have ended.

“It’s amazing the number of women who have said these trips have changed their lives,” Alyssa says. “There have been women who went from having never left the country to going on 12-day international trips by themselves. And they tell me they would never have done it without my involvement.

“To hear that, it’s kind of wild, and it’s also very rewarding.”