When my family and I set off on what we thought would be a two-year sailing sabbatical in 2018, we didn’t have any plans of working along the way. We were not the exception; almost all our fellow cruisers seemed to be on a work hiatus. We spent time blissfully unaware of what day of the week it was and rarely looked at emails. However, after 12 months of Caribbean cruising our funds had dwindled.

I decided to use my newfound freedom to design a career that would allow my family and I to travel. I always thought I’d make a good entrepreneur; I just never had the time or courage to make it happen. Now I had endless time and nothing to lose. Friends and family encouraged me to try my hand at writing. I wasn’t a writer, I was (and still am) a terrible speller, but I did have experience in interviewing and that, combined with curiosity and determination, has led me to interview some of the biggest names in cruising and have dozens of articles published around the world.

In 2019 I started my own PR agency (roamgeneration.com), my very first client being SV Delos. Fast forward four years and our sabbatical has turned into our full-time way of life. I work from the aft cabin of our Moody 47, and now it seems almost everyone we meet on the water is also working along the way, so I asked eight cruisers for inspiration and advice:

1 Office work in the cloud

Cally Duncan (CAN/AUS), bookkeeper, sailing 38ft Ericson Tala

As an ex-accountant, my speciality is in cloud accounting software. Due to covid, I started my own business as a Canadian cloud bookkeeping expert (approvedbookkeeping.ca) and have maintained a few favourite clients now that I live on my boat. I also maintain a YouTube channel (shestheskipper.com).

As a solo sailor, any space on board can be allocated as I see fit, so the main saloon table and settee is my home office. I use what I already had (laptop, second monitor, keyboard and mouse) with the addition of a 12V charger for my laptop which helps save battery.

I need to plan my sailing around deadlines, such as biweekly payroll or tax season. Sleep, social life and being a tourist are often sacrificed.

The biggest challenge is probably noise. A Zoom meeting on a windy day will have halyards clanging on the mast and worse still is when the anchor alarm goes off during a meeting.

My advice is to start a side hustle, see if it’s for you and see if it’s sustainable. Get a base level of clients, so you feel confident giving up the reliable income stream of full-time employment and then go for it!

2 Work in marine services

Johan Mulder (NED), furling boom maker, sailing Lagoon 410 S2 Adore

My family and I started cruising in September 2021, later than anticipated due to covid. Adore is our first boat and we chose this lifestyle because my wife and I were at risk of burning out on land.

We started a company in 2020 that produces furling booms for sailing yachts, called Made Engineered (furlingboom.com). My wife and I ran companies before we started cruising, so those skills have helped us a lot. My biggest hurdle to overcome was working less than I was used to – after all, what’s the point of cruising if I’m working all the time? However, I can focus far better on a boat, so I’m more productive.

Depending on the weather, I work at either the saloon or cockpit table. However, I really miss having a desk and comfortable chair. I have an Ultimaker 3D printer and Wacom drawing boards on the boat and we use Microsoft Office 365 tools to communicate with our employees. Up until now, we’ve used local 3G/4G networks, but we’re waiting for Starlink to be operational so we have coverage around the world.

As we’re starting to produce a new type of furling boom, I need to fly back to the Netherlands every five weeks. My biggest challenge is the fact that I’m designing and producing things without seeing the parts myself. This is why we have the 3D printer onboard, plus we use video calling and review a lot of photos of the parts we’re making.

3 Make your boat your business

Nim Hirschhorn (ISR/USA), charter yacht owner/operator, sailing Lagoon 450S Luna

I’m a US Coast Guard-certified captain and an experienced PADI Divemaster. I’ve sailed extensively throughout the Caribbean and Mediterranean. My wife Fabiola grew up sailing. After years of working in jobs that didn’t fulfil us, we came up with the idea of using our skills to create a business.

We’re in the all-inclusive, crewed-yacht charter business, Sail Luna (sailluna.com), and a typical charter runs for seven nights. We have always loved hosting, travelling, and sailing, so thought: “why not do this full time?” We sold our first boat, upgraded to a new Lagoon 45 and decked her out with all the luxury fittings. Many of our past skills helped us – for example, project management, accounting, IT, along with marketing and sales.

The boat is our business, so it has to be impeccably maintained. It’s also vital to always have good internet connectivity. Since we cruise near the islands most of the time, we mainly use a cellular data connection – but we also have access to a SAT linkup when needed. We have a small office setup onboard, including a Network Area Server that is constantly syncing our data to the cloud.

Our advice is do what you love to do, and you will make it work. Jump and the net will appear!

4 Multi-lingual? Translation on the go

Megan Bott (USA) interpreter and translator, sailing 62ft gaff schooner Inanna

We own a 62ft gaff-rigged schooner that we are fixing up while we live on our 38ft Morgan Sloop. We currently cruise Lake Ponchartrain and the Gulf Coast of the US.
I’m a freelance interpreter and translator fluent in Spanish, Russian, and French (in addition to English, my native tongue).

I can do translation and editing from anywhere. When it comes to interpreting, I sit at a table in the main cabin. Depending on the video call and client needs, I may put a sheet up behind me to hide any distracting background.

The biggest challenge is connectivity. I need to have a solid connection to maintain the interpreting calls. Any lapse in connection can cause severe issues with misinterpretation. I have to coordinate my interpreting assignments around when the rest of the crew is off the boat. I legally cannot have anyone listening as I interpret sensitive and personal information.

Clients are spread across time zones from Europe to Senegal to all over the US, so hours vary. Language work is flexible, which makes it ideal for the cruising lifestyle.

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5 Copy and content

James Howard (GBR), freelance writer, sailing 27ft Trapper 500 Alcyone

I’ve been sailing for just over two years. I started late and didn’t have any prior experience coming into this lifestyle. I cruise the Solent and the south coast of England, and have lived on river pontoons, anchorages, and moorings, while gradually gaining confidence in my abilities.

I work aboard as a freelance content writer, email marketer, and copywriter. This gives me enough income to sustain my lifestyle while continuing to cruise on a budget. I find most of my clients through online freelance marketplaces and via my website (jamescopy.com).

I instantly found I was much more passionate about working for myself than I had been while working for a company. This resulted in a higher standard of work for my clients. I love the freedom and flexibility this lifestyle affords me and that I can take my work with me wherever I go. My work doesn’t need a great deal of equipment: a laptop, a phone, an internet connection and that’s about it – which is perfect considering the size of the boat!

The main challenge is power, especially in the winter months. Solar is fantastic, but I only have 320W of solar to power a house bank of 240Ah. This isn’t always enough to keep the batteries topped up, especially if there’s no sun for days on end. That’s when it’s time to row into town and plug in wherever there’s a power socket.

6 Trading stocks

Patrick Schulte (USA), stock trader and mentor, sailing 42ft Grand Banks, 35ft Wildcat Catamaran and 43ft Spindrift Bumfuzzle

I circumnavigated via Panama and Suez canals in a 35ft cat, cruised Mexico in a 43ft monohull, and am currently cruising the Caribbean in a 42ft trawler. I’ve been a trader (commodities and stocks) for over 20 years, first in the actual trading pits, and then once out cruising, on the computer. I traded this way for about 10 years. Then I wrote a book, Live on the Margin, about travelling and trading.

People who read the book wanted to learn more, so I started a mentoring group, teaching others. That eventually grew into Wanderer Financial (wandererfinancial.com), a roadmap where I not only teach trading and investing but also share the travel side of wandering and working remotely. Our daily live chat has become a great place for adventurous self-starters interested in a more remote lifestyle.

My business has allowed me to connect with like-minded people all over the world, making trading from a keyboard much more interesting day-to-day. The only things I need to work are a laptop and an internet connection, which usually comes from a local cell service for a hotspot.

7 Wellness and vlogging

Laura Colledge (GBR), online fitness and wellness, sailing Bavaria 42 Holly Blue

We sold up and left the UK bound for the Med with our two young boys in the early part of 2019. We’ve been sailing and documenting our sailing adventures ever since.

We operate two businesses from Holly Blue. One provides travel and sailing content on YouTube via Sailing Holly Blue. The other is our online fitness, nutrition and wellness website BoatFit (sailinghollyblue.com/boatfit), an area for both sailors and land folk to find educational health and fitness content.

A solution-driven mindset is essential in this lifestyle. We have to be self-motivated and work together to create new fitness and educational content ideas. Filming our sailing episodes requires picking up the camera for every special, exciting or unique moment, and Ross spends around 30-plus hours a week on editing each episode while I am responsible for all social media management and marketing.

For anyone running a business aboard, you need to be constantly open to the potential of change and happy to resign yourself to ‘let go’ when things aren’t happening as fast or as organised as you might hope. Work hard in the moments when life/Mother Nature allows, and be sure to remember to enjoy the reason you are there – savour every sunrise and sunset and make sure certain moments remain sacred.

8 Teach what you love

Timothy Geisler (USA) CEO of a sailing school, sailing Lagoon 400 S2 Never Say Never

I learned to sail 21 years ago, did many charters around the world, and started a sailing school 12 years ago. Since then, I spend almost half of each year on sailboats in Mexico, the Caribbean, Tahiti or the Mediterranean, teaching sailing courses on large cruising boats (40-55ft). Two years ago, my wife, kids, and I took a six-month sabbatical and cruised the Caribbean on our 40ft catamaran.

When I lost my corporate job and had a chance to reinvent myself, I knew I wanted to have a job that incorporated sailing and travel. We created Nautilus Sailing (nautilussailing.com) to introduce others to this amazing sport

It’s interesting how your life experiences can set you up to succeed later in life. For eight years after university, I was an elementary school teacher in Los Angeles, helped develop education programs, and train new teachers. This experience, combined with a five-year stint running a non-profit, helped prepare me to run a sailing school.

I can work anywhere in the world, as long as I have some internet connectivity. The Iridium Go messaging capability has been a lifesaver for staying in touch when offshore. However, we have a physical office in Colorado that handles the day to day operations.

The biggest thing to keep in mind is life is too short to not pursue your passions now! If you can figure out a way to live on a boat, whether you are working in the sailing industry or have a remote job that pays the bills, then you owe it to yourself to give it a shot.

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