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Working While Cruising Full-Time: How We Actually Balance Boat Life and Income

  • Jaclyn Jeffrey
  • 1 day ago
  • 5 min read

The Myth of “Working From the Beach”

People often think we spend our days lounging on the beach, collecting coconuts, or surfing. While that is not entirely untrue, it is far from the full picture.


It is no secret that we are not trust fund babies or magically independently wealthy from selling feet pictures. We work. For most people, that still sounds like the dream, and in many ways it is. But we are not working from a beachside bar or tucked under a palm tree with a cocktail in hand like most people imagine.


This is how we actually spend our time working while cruising full time.


Spoiler alert: We never work like this.
Spoiler alert: We never work like this.


Why Balance Matters More Than Income at Sea


It is not just about money. Making money at sea and living the digital nomad lifestyle gets most of the attention, but the balance it takes to sustain that lifestyle is often overlooked. For us, that balance has been one of the hardest parts.


Last summer, income was the priority and it took over everything. We chose not to actively sail and stayed in one place so we could focus on work. Financially, it worked. But now that we are actively cruising again and have plans that keep us moving more often, we are trying to find a better rhythm.


Boat life adds layers that did not exist on land. Weather dictates our plans, not work calendars. Maintenance does not care about deadlines. Being struck by lightning and dealing with unexpected major repairs does not pause client expectations. Work and cruising are both non-negotiable, but something always has to give.

Our income keeps us afloat financially. Balance is what keeps us going.


How We Structure Our Workdays (Loosely)


We are not incredibly organized or rigidly structured, although one of us leans that way more than the other. What we do have is a routine that usually works, if conditions are ideal. That routine also looks very different depending on whether we are at anchor or underway.


Most days at anchor start early. Sunrise comes early, and mornings are typically the calmest part of the day. It is cooler, and once the day gets going, social plans or boat chores tend to get in the way of focused work. Starting early also means we can fit in quick exercise for both us and the dogs before work begins.


Mark is the structured one. His days usually include a dedicated block of time for work and education, with afternoons left open for whatever comes up. With very few meetings and mostly deadline-based work, I have more flexibility. That means I can structure my day around conditions. If the waves are good, I can sneak in a quick surf before settling into contracts and editing.


Underway days are different. Passages usually mean no work unless it cannot be avoided. At best, we can handle small tasks or a short meeting, but nothing that requires long stretches at the laptop.


The biggest lesson we have learned is that productivity comes in waves, and it looks different for each of us.


My day usually starts like this.
My day usually starts like this.


Cruising Plans vs Deadlines (Who Usually Wins)


One of the hardest adjustments we have made is accepting that cruising plans do not always come first. We have stayed in places longer than expected, looking at you El Salvador, simply because the working conditions were good.


On the flip side, weather can shut work down completely. A recent storm meant closing laptops to help a boat that was dragging, followed by hours of anchor watch to make sure we did not drag ourselves.


We now plan passages around both weather windows and work commitments. That often means staying somewhere longer than planned or occasionally leaving sooner than we expected.



The Tools That Make Balance Possible (and the Ones That Don’t)


Starlink gets most of the attention, and for good reason. Reliable internet has completely changed what is possible for working cruisers. Thanks to it, we can work almost anywhere, even underway when absolutely necessary. That said, it is not perfect, which is why we also rely on backup cellular data. Cell plans are affordable in Mexico, so having redundancy has been essential.


What is often overlooked is the power required to support remote work. Laptops, external screens, phones, tablets, internet equipment, and yes, the espresso machine all add up. We rely on a large battery bank and solar, but during the winter months there is not always enough sun to keep up. When needed, we top things off with the generator.


Then there is the workspace itself. This is one of the hardest parts on a boat. We do not have comfortable desks. We rotate between the nav desk, the cockpit, and a lap table on the settees. Occasionally, we will work from shore, but most of the time we make do with what we have.


Making the cockpit work as an office.
Making the cockpit work as an office.


The Hardest Part Is Saying No


The hardest part of balancing work and cruising is not the internet. It is saying no.

Saying no to surfing when there is a meeting. Saying no to sundowners when a contract needs editing. Saying no to spontaneous plans because studying still needs to be done.


The cruising community is full of retirees, seasonal workers, and people with far more free time than we have. Days can stretch into endless playtime if you let them. We have learned that sometimes saying no in the moment is what allows us to say yes to staying out here longer.


It’s hard to say no to a group of friends and a beach BBQ.
It’s hard to say no to a group of friends and a beach BBQ.


What’s Working for Us Right Now (and What Isn’t)


Honestly, balance looks pretty imperfect right now.


The last three months were spent moving the boat from El Salvador into Mexico and up to our winter cruising grounds of Tenacatita and Barra de Navidad. It was roughly 1,100 miles with little wind and plenty of counter current, broken up into multiple two-day passages. Work life balance was minimal. We moved when we could, stopped to catch up on work, and then moved again. Being struck by lightning along the way meant we were operating in less-than-ideal conditions.


Non-essential work fell away quickly. Blogging, studying, and social media maintenance nearly disappeared. Contracts and editing were kept to the bare minimum. The passages were tiring, and it has taken time sitting still, or making short hops, to recover and find a better balance again.


This season requires flexibility. What worked last summer does not work now, so we reassess constantly and adjust as we go.


Balance has been tricky, but we always try to make time to go to the beach.
Balance has been tricky, but we always try to make time to go to the beach.


Balance Is a Moving Target at Sea


Working while cruising full time is not about perfect routines or mastering productivity. It is about staying adaptable when conditions change, plans fall apart, or priorities shift.


Some days we have complete freedom. Some days we barely see daylight while we work inside the boat. Most days fall somewhere in between.


We choose this life because we like it. For now, we are still choosing it, and we are still making it work.

2 Comments


Guest
8 hours ago

Hello Jaclyn,

Always enjoy reading your write ups and always curious what the life of full time sailors entails. The work life balance imperfections of your current lifestyle is what makes it perfect. Most people would trade the rigidity of a 4 x 4 cubicle, literally and figuratively, for a chance to live without borders as you have. Sure there are still routines and set of responsibilities but they are yours rather than dictated to restrict you.


Safe travels!


cheers,

Chris Go

Edited
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Kathryn Beyea
a day ago

Hey Jaclyn:

Great write up on sailing and maintaining a work balance. You and Mark are an amazing and awesome team!

Love all your blogs! Interesting and informative.

Please writing about your adventures and experiences. Truly a great read!

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We’d love to have you along for the ride!

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