Remote Work and Sail Life: How We Afford a Liveaboard Lifestyle

Wondering if it’s possible to live a liveaboard lifestyle and work remotely at the same time? It sure is!

Like many before us, we didn’t want to choose between careers and travel, between income and adventure, or between wealth and seeing the world while we were still young(ish). Instead, we’ve tried to combine the thrill of a life of travel with the security of a reliable income.

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Our skill sets and office-based work experience meant that we would be unlikely to earn money by busking or offering our services as handy people as we sailed from port to port. With this in mind, we set out to find remote work that aligned with our backgrounds and would be suitable for an on-the-go lifestyle.

Let’s be clear: the voyage to earning money while sailing isn’t easy; it certainly isn’t idyllic; it can be stressful, frustrating, and downright scary (ever tried to run a meeting from a boat in a gale?). But the payoff for us has been immeasurable. The freedom of waking up in a secluded bay, putting in a few hours of work before hoisting the anchor and setting sail for an island on the horizon, coupled with the security of knowing we can afford our lifestyle and save for the future, is a powerful recipe for satisfaction and fulfillment.

Hopefully, sharing what we know about building a profitable life at sea or while traveling can help you turn your dream of sailing the world into a sustainable lifestyle.

Our Journey to Working From a Boat

The day we finally stepped aboard our boat, the transition from land-based work to working from the sea was actually quite straightforward. We had been working and traveling in a van for four years before we bought a boat. Many things we learned transitioning from regular, office-based 9 – 5s to working from a van are directly relevant to working from a boat and laid the foundation for success when it came to working from our sailboat.

Finding Remote Work Compatible With Travel

Our journey to remote work while traveling began in 2018, well before the pandemic had really opened up the potential for remote work opportunities.

We had decided to quit our jobs, fly to Santiago de Chile, and buy a van. Our first year traveling South America while trying to find remote work was stressful.

When we set out, Kelli didn’t have a job, and I had just a few hours a week teaching online for less than $15 per hour working for the now-shuttered online Chinese school DadaABC. Classes were early in the morning and late at night. Our tiny van was not set up for work, and teaching for hours folded up in the front seat was uncomfortable.

We were both constantly searching for more remote work opportunities, but they were few and far between. When we did occasionally get an interview, the challenge of finding fast and reliable Wi-Fi or cell service and dressing up the van to not look like a van added more pressure. When the question of where we were in the world arose, panic would set in; pre-pandemic, most employers had a dim view of employees dialing in from the darkest Peru.

We were living off savings and had to adopt a strict budget. We were often stressed and frustrated, wondering if we had made a terrible mistake.

But little by little, our efforts began to pay off. Eventually, Kelli found freelancing work as an accountant, and that first opportunity led to more work. The networking she had been doing for months resulted in more contracting opportunities. I found a second job teaching English with better hours and better conditions. After a while, we had more work than we could handle, and we needed to cut back on work actually to travel.

Building Good Habits

During that first trip and over the following four years, as we worked while traveling, we learned a lot and developed the skills and habits required to work while living and traveling.

It was hard at the time, but the first year of strict budgeting paid incredible dividends. Previously, with paychecks arriving regularly, we hadn’t really considered the need to budget. During that first year, we learned the true value of a peso. We learned to track our spending habits down to the minutest detail and to derive satisfaction from living well within our means. Those habits we learned seem to have stuck with us.

Although our income has risen over the years, we still make a yearly budget and track our expenses religiously; this gives us a broad overview of how we’re doing financially and the detail that allows us to zero in on areas where we can trim the fat. We still get a kick out of saving a buck; and while people often smirk at the fact that we share a mobile phone, always take the red eye, and usually stay in poky Airbnbs when we think about how we’ve spent the money we saved, we feel like it has been a worthwhile trade-off.

We had to become self-disciplined to adapt to remote work. Without the structure of a 9 – 5 work day or the external motivation of a manager, we needed to motivate ourselves to roll up our sleeves and get stuck into a day’s work.

During those first years, we learned some valuable lessons while working remotely. We learned how to manage our time effectively and become reliable remote workers. We learned how to structure our day for productivity, set hours for calls, meetings, and classes, and be reliably available to employers, colleagues, and clients in different time zones.

We also had to learn that work-life balance is still important. We had to learn to close the computer and take advantage of our surroundings. We also discovered that burnout still exists even when you are working from a beach.

Diversifying Income Streams

Our lifestyle has inspired us and allowed us to pursue other projects while we travel. In 2018, we started a blog and began to learn about writing and SEO. In time, we started to generate income from affiliate marketing.

We also had the opportunity to learn the pain of hitching your wagon to a single horse when a devastating Google algorithmic update wiped out all the traffic on our blog.

That setback led us to diversify our content creation strategy, to be less exposed to the whims of a single algorithm. We started a vlog and a suite of new travel websites.

By keeping expenses low on the boat and without the ongoing expenses of a more stationary lifestyle, such as car payments, rent, or home maintenance, we have been able to save pretty aggressively and start investing that money into passive income sources.

By continuing to diversify, save, and invest, we hope that we can better limit our exposure to the less predictable nature of remote work and self-employment.

Adjust to Working From the Boat

When we moved onto a boat, we were pretty confident about working and traveling; we just had to fine-tune our skills for living on a boat.

We found that staying online and connected was easy from the boat, at least when sailing close to shore. Where van life had often taken us into the remote wilderness beyond the reach of reliable mobile coverage, sail life often enjoys great network coverage from the shore.

Recent developments in technology and wider access to satellite internet mean that now even sailors looking to get far off-shore can access fast, reliable internet.

While many people need to adjust to more confined spaces when moving onto a boat, we personally found that we had plenty of space to work from. Coming from a van, a boat set up with multiple cabins and a large central table was a luxury.

The thing that we really had to get our heads around was trying to work in poor weather when the swell makes us nauseous and the wind is roaring. Nights spent trying to take meetings while silently panicking that our boat was going to drag its anchor at any point are tense, to say the least. Taking precautions such as being extra careful about nasty weather and staying in marinas when we have important meetings has helped us reduce some of the stress of working from the boat.

On the whole, our adjustment to working from a boat was less dramatic than we thought it might have been, and many things were easier than we predicted.

The Benefits of Remote Work for Sailing, Travelling, and Life

While we may not always live on a boat, our travel habits may change or we may settle down, remote work gives us so many options and benefits I don’t know if we could ever give it up.

• We can decide when and how we want to work.
• We can spend our work days with each other on our boat (or anywhere else).
• It gives us total location independence, such that we can move countries, continents, or hemispheres at a moment’s notice.
• It gives us the flexibility to fit our work around our lives rather than the other way around.

Ultimately, it gives us the freedom, flexibility, confidence, and resources to live life on our own terms.

The Downsides of Remote Work While Sailing and Travelling

It’s not all beer and skittles. Working from a boat has its challenges.

• Traveling in different time zones from colleagues and clients can create less than ideal work hours.
• Working from a boat can be less comfortable than working from a dedicated office.
• Poor weather can add undue stress to our workday.
• There is no office full of colleagues to escape to.
• Working where you live can make it difficult to separate work from leisure and compartmentalize work stress.
• It is harder to find salaried jobs and security when fully remote.

There’s no doubt that sailing while working adds an extra layer of complexity to an ordinary workday.

Lessons Learned Working and Travelling

In the end, the key lessons we have learned working remotely from a sailboat and while traveling can are

• You don’t need to choose career and income OR sailing and traveling.
• It takes a lot of work and often time to build a successful career compatible with sailing life and travel.
• Careful planning and budgeting is essential.
• Being disciplined and managing your time is critical.
• Work-life balance is still important.
• The time to start diversifying was yesterday.
• The benefits of building location independent work or income are priceless.

Hopefully, our journey to working while living on a boat has helped answer some of your questions regarding working remotely and sail life, but if you have more, let us know below!