Untethered Productivity — My Experience with Workbreaker

Whitney Durmick
6 min readJan 5, 2020


I am living the millennial dream. I work for an established, dynamic tech giant that also happens to be a proponent of remote work. My team is distributed around the world, and many of us have chosen not to be beholden to physical offices. We’re a group of high performers who have proven that we deliver quality work regardless of our location.

To maximize this dream scenario, I went nomad. I spent the first half of 2019 on the road, literally. I packed my car with the essentials and drove across the United States, planting myself in various locations for a week or a month at a time, leveraging the modern amenities that enable this lifestyle — WiFi hotspots, Zoom, Slack, and AirBnb.

I planned about 2 weeks in advance, moving around the country to spots that piqued my interest, letting AirBnbs entice me to the next location. Following that lead, I spent a week in a yurt in Topanga Canyon, and two weeks at a condo on the beach. For a few days I settled into a cabin on a mountain farm, where emus would stop by the porch to investigate me and my laptop. I watched a meteor shower from a casita in Santa Fe and embarked on sunrise hikes in Sedona, fitting in adventures around my workday.

A sample workspace. (Not pictured: curious emus)

The freedom was exhilarating, but it did get lonely. Even after connecting digitally with coworkers during the day and chatting with locals whenever I could, I still felt like a hummingbird flitting across the surface of a pond. I started to crave something deeper.

A friend told me about a program that she’d seen on LinkedIn, an opportunity for professionals like me to experience work and life in inspiring cities. The first session was coming up in Lisbon, Portugal, a place that had enticed me from my Instagram feed with its mosaic-paved streets and red-roof skyline. After months of subsisting on truck stop beef jerky and flying by the seat of my SUV, a trip abroad felt like a logical and very grown-up next step.

Workbreaker — a program for professionals

Investigating Workbreaker, I instantly understood that this program was catered to people like me who work hard but prefer to live outside the cubicle. It didn’t seem to carry a party vibe like some similar programs I’d seen, and I appreciated that I needed to apply, because it made me feel reassured that it was not some Internet cash grab. The application was simple but robust — it didn’t take me long but it did make me think.

I sent it off and hoped for the best, already starting to dream of sunsets over the Atlantic.

Brightly colored buildings abound in Lisbon.

I got good news from Workbreaker’s founder Dan Phan within a few days, and we started planning my trip. From the very beginning, Dan took time to understand my goals and expectations for my time in Lisbon. He was sincere, insightful, and clearly passionate about his company and adopted hometown.

Workbreaker was an opportunity to spend time in a new city while staying grounded in my work. Lisbon is busy, welcoming, and beautiful with incredible weather and delicious food. It’s also surprisingly affordable (at least for now). I enjoyed pretty much everything about my time with Workbreaker, but these are the highlights.

Focus + flexibility

When I travel, I tend to vet my AirBnbs exhaustively to curate the perfect experience for myself. Dan was happy to let me coordinate my own accommodations, offering insider knowledge to guide my decision. I ended up with a stunning apartment with panoramic views in the peaceful but accessible Estrela neighborhood. The back-and-forth with Dan empowered me to make the trip my own (a consistent occurrence with Workbreaker — this trip is very much yours to maximize).

A view of the Basilica from my apartment at sunset.

I arrived in Lisbon on a Sunday, and met up with the group in a busy plaza to embark on a walking tour of the city. We sampled local fare and enjoyed the sunshine while Dan shared the history of the city he had come to call home. At the end of the day, we’d logged an impressive 20,000 steps, fueled by Lisbon’s famous pastéis de nata and espresso. By the time I hiked back to my apartment, which was perched on the top of one of Lisbon’s famous hills, I was pleasantly exhausted and ready to start the workweek.

Making ourselves at Home

The next day we settled into our workspace. Second Home Lisboa is a bright and bustling co-working space located above a popular market. All manner of professionals, entrepreneurs, and side hustlers frequent the plant-filled office, which also has its own delightful café with coffee and lunch specials. I can’t say enough about the quality of people I interacted with at Second Home. Everyone was warm and passionate about what they do.

The program officially kicked off with a session led by Dan, in which he shared insights from his tenure in corporate retail. It became clear that he was not just an expert on the city of Lisbon, but a dynamic speaker and thought leader as well.

Stopping to admire the street art on the walking tour of Lisbon.

Doing the work

Together, we outlined our goals for the week, then broke out to work. This is what made the biggest difference for me — I didn’t have to take time off from my “real” job to make time for the program. I was able to settle into a new city, meet new people, explore new parts of my own profession while rooted in my day-to-day responsibilities. I had an adventure, but skipped the guilt, the “Sunday scaries,” and apologizing to the boss.

In fact, my boss encouraged the trip, recognizing that our global team would benefit from letting me expand my worldview. Plus, the time zones work out beautifully. Getting up early in Lisbon gave me plenty of time before my inbox started filling up with messages from the United States.

Breaking out of the routine

My favorite day: exploring monastery ruins near Sintra.

While the major appeal of Workbreaker was exploring a new place while staying tuned in to my normal day-to-day, my absolute favorite part of the experience was the trip out of Lisbon. We took a train to the coastal town of Sintra and spent the day exploring palaces, ruins, and dramatic sea cliffs. This day was the very welcome “breaker” aspect of Workbreaker.

Looking back

The week passed quickly, with each day balanced between work responsibilities, Workbreaker sessions, Second Home programming, and exploring the city.

Leaving Lisbon was logistically easy but emotionally difficult. I traveled on to Paris, London, and Barcelona, and while those cities were beautiful in their own right, my heart ached for the crystal blue skies, golden light, serene atmosphere, and vibrant energy of Lisbon.

The location alone makes Workbreaker worth it, but the program also offers well-constructed curriculum, personalized coaching, and cultural experiences. It’s a truly unique and worthwhile adventure for people who want to break out of their routine and gain some fresh perspective with like-minded professionals.

You can learn more about Workbreaker on their website.



Whitney Durmick

Mostly writing about travel.