That’s the question Arestia Rosenberg, of Southern California, grappled with for years. She’d conquered Hollywood as a young producer, won awards for her videos as a content creator in Boston, and became a creative director at a major media brand in New York by the time she was just 30 years old. Then, at 31, she gave it all up to go “remote.”

Rosenberg left her job, apartment, and nine-to-five existence eight months ago for a new journey as a digital nomad, travelling to a new destination each month. She’s currently living by the beach in Split, along Croatia’s Dalmatian Coast, while working as a freelance video and content producer.

Rosenberg is part of a new generation of workers who can work remotely from anywhere on Earth, leveraging worldwide travel not only to live life to the fullest, but also to achieve their best productivity. Travelling together with a group of 75 other digital nomads, the young professional has become part of a roving community of like-minded millenials who seek to broaden their horizons and learn new skill sets through an international work experience.

The 31-year-old says the decision to completely uproot her life wasn’t easy. In fact, it was one of the hardest things she’s ever done.

“I always knew there were these guys in start-ups who could work from everywhere in the world, but I had never really internalized that as a lifestyle or something I could do,” she says. Then she found herself working remotely in California a few years back and realized that becoming a digital nomad might not be such a far-fetched dream. After all, living the life of a producer on the road had already prepared her for the unpredictability of a nomadic existence.

So, she took a big leap into the unknown.

“Something inside me said I had to do this or I’d always regret it,” she recalls. After four months in South America, and another four in Europe, she says that fateful decision has made her think twice about going back to owning things such as an apartment. “I don’t have that burden right now,” she explains.

Rosenberg is the first to admit that there was a steep learning curve in making this drastic lifestyle change. “It can be so easy to be pulled in all sorts of different directions when you are living on the road,” she says. “But you have to remember to really do what you set out to do and not get swayed by what might look shiny in the moment.”

The first few weeks were filled with myriad obstacles, such as how to figure out scheduling, conduct client calls and structure her day. But she says every month has brought new perspective, “and I feel like I’m a different person now.”

Rosenberg believes freeing herself from the office and all of its trappings has made her a much more creative person. “I have more ideas for stories and opportunities,” she says, adding, “the flexibility allows for more innovation.”

Rosenberg is currently planning for her next destination, Malaysia. She plans to wrap up her world tour Down Under in Australia and New Zealand before doing some domestic nomading back in the US. She’ll travel around America sharing her skills in content strategy and the digital nomad lifestyle in exchange for office space. Where the American storyteller goes after that, however, remains very much up in the air.