For many people, a career in law represents the pinnacle of success: stability, prestige and financial security. Janeen Blake had all of that, but the long hours and a culture obsessed with billable hours left her exhausted and unfulfilled. Within that high-pressure environment, something unexpected happened though. The same career that left her feeling burnt out also introduced her to international travel, and a completely different vision for how life could look.
After a carefully long-planned exit built on financial management and remote income streams, Janeen walked away from corporate life entirely. At 42, she relocated her family to Portugal, where she now spends her time building her own businesses and exploring a slower, more travel-led way of life. This is her story.
Life inside Big Law
Janeen’s early career was defined by intensity. She found herself working unfathomably long hours, often in the office until 9pm.
“It was all about your billable hour,” she explains. Every year she had to log a minimum 2,000 hours just on client work, not including the countless emails, prep and other tasks that don’t appear on the billable clock.
“I just worked endless hours and took abuse from more senior associates. Sitting at my laptop nonstop, eating lunch in front of my screen, and then doing that day after day, only thinking about work and productivity and not really making time for taking care of myself outside of work, was completely unfulfilling.
“I could not believe that this could be it for the rest of my life.”
How travel changed the paradigm
While the daily experience of a legal career mainly served to wear Janeen down, it did bring something new and transformative into her life: travel.
“I literally did not have a passport before working at the law firm,” she says. “Then I got a passport and was whisked off to London, Hong Kong, Macau, and all of these different places I had only ever seen on screens.”
After moving on from that first law firm to become the in-house counsel at a pharmaceutical company, she continued to embrace travel as much as possible, making her way to South Africa, Japan, Greece, Australia, New Zealand, and many countries across Europe.
Through these experiences she was able to see beyond the meetings and business dealings into a world of new cultures, languages and changing environments. And with every trip came a growing realisation. Returning home felt heavier, more restrictive and less aligned with how she wanted to live.
“International travel became a priority because of the way it made me feel and the things I learned, and that really set the tone for our move to Portugal,” she says.
An exit plan 15 years in the making
It’s said that the best things in life are worth waiting for, and Janeen’s story is testament to that. Her transition away from corporate life took years of planning, sacrifice and persistence.
The combination of $230,000 of law school debt and deep dissatisfaction with her job pushed her to take action about her money situation and long-term security. She began educating herself on financial literacy, investing early and consistently. Over time, she layered in additional income streams that could eventually support an independent and more deliberate lifestyle for her and her family.
“The biggest strategy for me was just doing tons of research, committing my energy to it in the pockets of time I had, and then getting smart about building systems around what I was doing.”
This meant using whatever time was available to her while balancing a full-time career and raising two young children. Evenings, commutes, weekends and lunch breaks were dedicated towards achieving the goal.
At 40, Janeen launched an Etsy shop using a print-on-demand model, allowing her to build a business that could run from anywhere. Combined with 15 years of careful investing, that gave her the foundation she needed to step away entirely.
Embracing a new life in Portugal
In 2024, Janeen finally made the move that had been years in the making, relocating her family to Portugal in search of a slower, safer and freer life. One huge and immediate benefit was how it allowed her to be present for her children during their most formative years.
“The lifestyle change of being able to spend more time with my kids while they’re little has been fantastic,” she says.
Instead of commuting and sitting behind a desk for 12+ hours a day, her life is now centred around family, flexibility and the local community in Lisbon.
“We don’t have cars anymore, and now that I live in a walkable city, I walk everywhere I can.”
Janeen has also prioritised giving her children an upbringing connected to culture, language and environment. As she explains: “My daughter started daycare when we moved at two and a half, and she now speaks Portuguese. My son goes to an international school and is learning Portuguese too. That was something I really wanted, for them to learn the language and feel like they were part of the culture.”
Travel is a core part of their lifestyle, but it is now woven into everyday life rather than squeezed into limited annual leave. And the family makes the most of time off to explore. They are currently planning a month-long family trip in August.
“During school breaks, we travel around Portugal or Europe as much as we can.”
Building a different relationship with work
After years in a system where output was measured in hours and productivity, Janeen now operates on her own terms, growing her Etsy business in a way that aligns with her lifestyle.
“Work today is something I enjoy doing, so it doesn’t really feel like work. I don’t even love calling it that,” she says.
Through her blog, Love Eat Travel Repeat, Janeen shares insights on building a portable income and documenting life in Portugal, helping others to explore similar paths. “Now I know I can work on things I enjoy, work much less, and still live the life I want, in a way that is abundant, joyful, healthy, and rested.”
The challenge of slowing down
After years in a high-pressure environment, stepping away from that mindset isn’t immediate, and the transition has taken time for Janeen to adjust to.
“Emotionally, it has been harder than I thought,” she admits. “I still have a little bit of that survivor mentality where I feel like I just need to keep going. I don’t yet fully know how to just sit and enjoy without doing something.”
Even without the demands of a corporate job, there’s still a lingering instinct to stay productive, and to keep building, improving and achieving.
“I need to actually and intentionally make time to enjoy this new life.”
“Patience and a plan”
Janeen’s long journey has taken her from huge law-school debt and a demanding career to a lifestyle-rich world of financial and location independence. There was no sudden leap or single defining moment. But at the root of everything was a mindset.
“You can change your circumstances if you are not happy,” she says. “It is not easy, and it takes patience and a plan, but if you are craving something different, you should explore it. People in high-pressure careers are incredibly smart and got to where they are for a reason.”
You can read more inspiring stories in our travel sabbatical series. To start planning your own sabbatical guide, check out our ultimate guide to taking a travel career break.
Do you have a story to tell about a travel and work lifestyle change? Get in touch to share your tales of travel sabbaticals, workations, and how they have inspired lifestyle changes.
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