top of page

Untethered Productivity - My Experience with Workbreaker

Written by 2019 Workbreaker participant, Whitney Durmick

I am living the millennial dream. I work for a an established, dynamic tech giant that is also a proponent of remote work. My team is distributed around the world, and while some take advantage of office locations, many have chosen to break from being beholden to a physical office. We’re a team of high performers who have proven that we deliver high quality work regardless of location.

To take advantage of 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 at a mountain farm, where emus would stop by the porch to investigate me and my laptop. I watched meteor showers from a casita in Santa Fe and embarked on sunrise hikes in Sedona, fitting adventures in around my workday.

The freedom was exhilarating, but it could get lonely. Even after connecting digitally with work during the day and chatting with locals when 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 heard about 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

Brightly colored buildings abound in Lisbon

Investigating Workbreaker, I instantly understood that this program was catered to people like me who work hard but prefer life 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 re-assured me that this was likely 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.

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.

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

Focus + flexibility

When I travel, I tend to vet my AirBnbs exhaustively to curate the perfect vibe. Dan was happy to let me coordinate my own accommodations, offering insider knowledge to help me decide. I ended up with a stunning apartment with incredible views in the peaceful but accessible Estrela neighborhood. The back-and-forth with Dan empowered me to make the trip my own (a consistent experience 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 Workbreaker 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 and sampled some of 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 on top of 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.

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

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 do our 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 this program. I was able to experience a new city, meet new people, explore new parts of my own profession while rooted in my day-to-day responsibilities. Adventure, but skip the guilt, the “Sunday scaries,” and apologizing to the boss.

On the contrary, my boss encouraged the trip, recognizing that our global team could only benefit from letting me expand my worldview. Plus, the time zones work out beautifully. Getting up early in Lisbon gives you plenty of time before your inbox starts filling up with messages from the United States.

Breaking the routine

My favorite day: exploring monastery ruins near Sintra

While the major appeal of Workbreaker was being able to learn and explore a new place while staying tuned in to my normal day-to-day, my absolute favorite part of the experience was the day trip. We took a train to the coastal town of Sintra, where we spent a day exploring palaces, ruins, rocky cliffs, and charming small towns. This day was the very welcome “breaker” aspect of the Workbreaker experience.

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 and vibrant, 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 enriching cultural experiences. It’s a truly unique and worthwhile adventure for professionals who care to expand their worldview.

This piece was written and republished with permission by Whitney Durmick. Her original post can be found HERE.

203 views0 comments

Recent Posts

See All


bottom of page