The Best Way to Master Flexibility as a Sailing Digital Nomad

Stacy at the helm

If you have or plan to choose a life aboard a sailboat–for any length of time–then you have probably already abandoned a structured, comfortable land life.

It is no surprise that living on a boat requires a certain frame of mind and attitude. But what does it really take to thrive on the high seas, especially for so many cruisers embracing digital nomadism? 

This article will show you the best ways to master flexibility and an open mind if you dream of becoming a sailing digital nomad.

Why More People Are Ditching Land Life to Take to the High Seas

Most boaters we have met love spontaneity, adventure, and constant movement. They have dreamed about traveling, meeting like-minded people, and embracing different cultures instead of taking a once or twice-a-year vacation with the family.

For those who buy a sailboat, like us, it’s the allure of seeing a place on a very intimate level that allows us to squash the minor (or major) fears about life on the water. 

Cruisers have also taken actionable steps towards achieving their dream; they crave new environments that offer a higher quality of life and a major bonus–crystal clear water in different locations throughout a region, country, or continent.

When a cruiser first starts out on a boat, there is so much to learn and practice that it’s easy to forget the most important ingredient: flexibility.

This mindset requires the casual cruiser, the live-aboard sailor, and the digital nomad who prays to Neptune that stable work can occur. In an onboard environment, there are many different factors to consider.

Santa Cruz Island, the Channel Islands

This brings me to the most important considerations about maintaining a flexible attitude on the water:

1) Living on a sailboat may be a great way to see and explore the world, but it requires one to shake off rigid expectations about what life aboard is like. After all, a cruiser must abide by weather patterns that dictate things like route planning, arrivals into new ports of call, and even a good Internet connection. 

Since the ocean operates on its own schedule, checking the weather will dictate your entire life. When our cruising friends who traveled full time for 20 years by sailboat decided to call it quits, they said, “If we have to check our weather apps one more time in a given day–or for another hurricane season–we will surely go mad!” They loved their nomadic lifestyle but decided to take to the road where things were a bit more predictable. 

Our First Lesson In Flexibility

My husband and I learned the hard way in our first season that having family members fly into one region to go on a sailing adventure with us meant that we had to sail to that area despite the nasty conditions we faced along the way.

We had built in enough time for our kids’ arrival in Mexico in December. But we could have avoided 25-35 knots of wind, strong currents, and 6 to 10 foot swell during our 230 nautical miles across the Sea of Cortez.

It wasn’t that we did not check weather forecasts; it’s that we were not familiar enough with the regional weather patterns fondly referred to as the “Northers.” So we simply traveled in the wrong direction at the wrong time of year.

Digital Nomad Lifestyle at Sea

2) Flexibility also means discovering what onboard life looks like. Especially for digital nomads trying to balance work with having fun exploring. The work-life balance means the growing trend of remote workers, like me, must navigate life behind a laptop.

Rolly conditions at sea, often being heeled over in windy conditions, working down below in the salon with your stomach doing cartwheels: these are the realities of boat life which look nothing like land life. Not to mention, working during the day means fellow crew are out meeting new people. Or hiking toward panoramic views above a pristine anchorage without you.

Living aboard a boat, even if only one person is working part-time, means finding a quiet place for meetings or to get other work responsibilities done. This can be challenging if someone is prone to seasickness or does not have a room with privacy.

I consider myself fortunate to be on an Amel Super Maramu, where the large cockpit can comfortably seat up to 6 people. We also have two berths (bedrooms) where I can Zoom with a student in private.

But my peace of mind about working remotely with other crew aboard means that everyone works together to honor each other’s limited space.

Flexibility Means Handling Interpersonal Conflicts Quickly

3) Flexibility in a confined space 24/7 means getting out of your comfort zone and resolving interpersonal conflicts effectively. As an introvert living and interacting with an extrovert, I can tell you this is no easy feat.

Many cruisers talk about how you might go a little crazy when you can’t get away from your loved one, even at anchor, when times are tough. Even though my husband and I make a great team the majority of the time, both of us have been surprised by how often and how thoroughly we need to manage our expectations. About the boat and about each other.

Some of the conflict simply exists because there has to be one captain on a boat. If an egalitarian relationship for you and a partner exists on land, then imagine being quiet when your husband or wife shouts a command like, “Jump off and grab the cleat!” And all you can think, coming alongside a dock, is yelling back, “Hell no, I’m not doing that!” 

Communication between crew, especially couples, generally means that situations like docking or anchoring require briefs and then de-briefs after the task is completed. I have been in no other living environment where daily life mandates such constant negotiation and tolerance for others’ quirks and moods.

Flexibility Related to the Boat's Many Systems

4) No ocean adventure is complete without flexibility related to a boat’s mechanical and operational systems. Water conservation, energy consumption, and maintaining redundant systems in case something breaks require you to constantly monitor yourself and the boat.

Every sink on our boat, for instance, has a valve for turning off the water when washing up. We have a 250 gallon water tank on our boat, but we still conserve when we can.

We also manage energy consumption when we use our Spacex Starlink system for high-speed Internet. Starlink has given us complete freedom in checking our daily weather, allowing me to do Zoom calls with students, and enabling us to stay in touch with friends and family at home.

However, we do not rely solely on Starlink. We have an Iridium Go package that, despite the extra cost, also allows us to download weather;  plan our sailing route; and keep in touch with family and other cruisers in case our Starlink system fails in some way. One tool is not superior to another tool. It’s simply a redundant system in case one fails.

Mindfulness is Everything

5) Finally, mindfulness and dealing with uncertainty represent the most important things about flexibility while cruising. Constant movement, watching developing wind and/or waves, dealing with queasiness, and interacting with others in a confined space affect your own state of mind.

On my first night passage aboard our friend’s new catamaran, my shift happened to occur as we rounded Point Conception, a notoriously dangerous point where wind and current from the entire northern part of the California coast funnel into the southern half of the coast, around and toward Santa Barbara. 

I remember being terrified by the black inky canvas which looked like a drape just beyond the perimeter of the boat. I couldn’t see anything. With my eyes trained on the B&G radar, I had to suspend my fears and allow my other senses to take over.

I sat at the helm under two blankets, shivering in the cold, and practiced deep breathing. I felt gratitude about having learned yoga as I counted backward with my breathing. It took a bit of time, but eventually, I acquired a new level of interacting with my own fears; and, honestly, I lucked out with the flat water and calm conditions that night.

Yoga stretches at sea

Flexibility Means a Better Work-Life Balance

I now do yoga regularly on the boat, both to stay limber and to practice meditation. I’m not saying I have forever quelled my fears because this would be a lie. But I have embraced the discomfort, knowing that it’s part of the adventure and has something to teach me.

Besides, the great thing about remote working away from a home base is the distinct lack of a standard routine. With cruising, we never know what we will encounter. Most days, my digital nomad lifestyle means I wake up with my french-pressed coffee in hand, answer emails, and sometimes grade up to six hours.

My breaks, though, consist of jumping on my standup paddleboard and going for a brisk row across an anchorage; or jumping in the water for a few laps around the boat. After these activities, my hunger matches my productive drive to finish my work day.

paddle boarding after work

Flexible Doesn't Mean Unproductive

I understand that different industries currently frown on remote work, especially now, in Fall of 2023. Many recent articles demonstrate CEOs’ displeasure of employees being too far from the office. But the future of remote work, with an increasing number of digital nomad jobs, means that employees must demonstrate extra commitment.

For me, this means ensuring I attend every Zoom meeting and taking on responsibilities that allow for an online presence. Even when it seems like every sailor around me is having a margarita or discovering a new sea cave to explore.

Flexibility Equals a New Perspective

Overall, being flexible on a boat means that settled routines take second place to uncertainty. Much like land or air travel, cruising by sailboat can be simultaneously exhilarating and intimidating. However, the rewards of a peacefully quiet anchorage, with an open sky lit like wildfire, make the adventure worth embracing.

sunset in Puerto Escondido mooring field.

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