“Philippe and I are leaving San Francisco, but I want to continue working for WaterSmart.” My boss laughed, cocked her head to the side, and asked, “where, exactly, are you and Philippe planning to go?”
I had met my husband, Philippe, four years earlier. Eighteen months after we started dating, we purchased a sailboat with a plan to opt-out of the expensive San Francisco housing market and simplify our lives. We sold most of our possessions, moved aboard, and named our boat Untangled.
“We’re going to sail down the coast of Mexico,” I told my boss. It was now summer 2017. The timing was right for our sailing adventure, but I also loved my job. After a few fitful nights of sleep and several long discussions with Philippe, I scheduled a meeting with my boss and proposed a unique arrangement: I would continue working in my existing role, but would do so from wherever the winds blew Untangled.
I am fortunate that my employer, WaterSmart Software, has a flexible work-from-home policy. Even so, my proposal was unique. WaterSmart, which provides powerful cloud-based tools to help water utility managers analyze data and engage customers, had never considered this type of arrangement before. As the Associate Director of Customer Success, I work with WaterSmart’s utility partners to ensure that they are trained to be experts in our software and have extremely successful programs. In theory, I could do my job from anywhere with reliable internet. In practice, everyone on my immediate team was based in San Francisco.
At this point, I’ve been sailing and working remotely for six months. As I make friends along the way, people regularly tell me that they wish they could propose something similar, that I’m “living the dream”. As a result, I’ve reflected on some of the things that made my proposal, and subsequently my remote work arrangement, successful.
For starters, I spent my first five years at WaterSmart working really, really hard. I took on strategic projects and ensured I produced high-quality work. At the three-year mark, I started working from home at least one day per week. This allowed me to refine my remote skills, and demonstrated my ability to work effectively outside the office. An employer may perceive any deviation from a traditional work structure, especially if it involves modified duties, as risky. Cementing your role as a critical contributor can give your proposal an advantage, however, particularly when the alternative is the uncertainty of a new hire.
As our trip drew closer, I connected with others who worked remotely, especially from small towns in other countries. I asked how each person approached remote work and what tools were critical to their success. Most importantly, I asked what their biggest challenges were. A few themes emerged, including:
- Preserving a healthy work/life balance, especially when working in a different time zone
- Maintaining strong social relationships with colleagues
- Effectively leading or participating in meetings when the rest of the team is on-site
- Finding reliable phone and internet coverage, especially during a weather event that damages local infrastructure
I took copious notes, and considered ways in which their experiences might translate to my position. I used these insights to write a comprehensive remote work plan. The plan included expected benefits, potential challenges and mitigations, required tools and resources, a tentative travel timeline, and detailed logistics. My boss and I reviewed and adjusted the plan together. For example, we set explicit expectations of how many visits I should make to the office each year and who should pay for the travel costs. The document has no signatures and is not binding, but it was critical to demonstrating our commitment to the success of a shared vision.
Philippe and I left San Francisco in early-October. During our sail down the coast, we’ve spent time in 4 US and 11 Mexican cities, seven marinas, and 13 anchorages. Soon we head to Central America. Seven days a week, I wake up on a sailboat in paradise. Five days a week, I forego daytime trips to the beach and lunchtime cocktails with cruising friends. Instead, I pull out my laptop, scout out a café or negotiate a day-rate for a hotel room, and settle in for eight hours of work. To remain close to WiFi and cell service, we meticulously schedule our relocation sails for weekends or holidays.
Working gives my days structure and purpose. It brings a source of income and benefits, including health insurance. I recognize, though, that I am fortunate to have a career that I love. I am a firm believer that someone who doesn’t love their existing career would not be a good candidate for a lifestyle that so delicately balances full-time travel and full-time work.
Sailing Untangled while working remotely has been one of the most rewarding experiences of my life. I continue to contribute to a cause for which I care deeply, while pursuing a personal dream with my new husband. In the past six months, I have launched WaterSmart’s first international customer, contributed to our strategy for hiring additional team members, and traveled to nine US and UK cities for work. I have also chased my dog on a solitary beach after a tiring multi-day sailing passage, gone skinny dipping in a sea of cerulean bioluminescence, and eaten countless carne asada tacos from street carts in small, dusty towns full of energy, color, and kindness. I am learning to speak a new language, fix a diesel engine, and identify whales as they breach against auburn sunrises. People are right when they say that I’m living the dream.