Mistakes I Made Working Remotely From The Boat | Become A Cruiser
Mistakes I made Working Remotely From The Boa

Mistakes I Made Working Remotely From The Boat

When we first moved onto the boat we were trying to wrap up the transfer of our business to a partner.

I naively thought that it would be dead simple to work remotely from the boat while sailing in the Caribbean.

Our new partner had bought into the business about a year previously with the understanding that Nic and I would be going cruising. He was highly competent and over the past six months or so I had slowly been sliding more and more responsibilities his way.

The sale of our business was structured as follows. Our new partner had bought fifty percent of the business when he joined with the intention of acquiring the remaining fifty percent of the shares one and a half years in. I would remain, president, and retain control until the transaction was complete.

Our business should have been simple to run from the boat. It was an easy to manage product distribution business. Distributing electrical components to mostly local customers. We had grown to a reasonable size and up to the point of acquiring our partner, we had run the business alone for three years.

All of the products we distributed were drop-shipped from a variety of manufacturers directly to our customers.

The plan was that our partner would handle the customer and logistics side of things on land and that we would work with our suppliers remotely from the boat.

For the two years leading up to us moving onto the boat, we had focussed on tech solutions that would enable us to run our business remotely. We had no staff members, only an accounting service that took care of the final accounting each year.

We built out a customer order system and integrated it with a shipping and logistics platform. Our customers could order on our website, and the shipping instructions would be sent directly to our suppliers. Everything integrated with our online accounting system.

In the five years, we had had the business it had grown organically, at a steady clip. Most of our customers were small businesses, and new customers mostly came to us by word of mouth.

All that left was for our partner to do was to make sure our customers were all happy and to slowly grow the business.

Mistakes I made working remotely from the boat
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Our First Mistake Working Remotely From the Boat

We transitioned to working remotely and living on the boat at the same time. In hindsight, this was a bad idea. Both are big transitions, and combining the two was sure to cause problems.

The first real issue we had was that our partner came from a multinational corporate environment and loved meetings. He lived for them. We had slowly weaned him off them. But he still wanted a daily wrap up session each day at 5 pm his time, via skype. We agreed we would do these for a few months, but they had to stop.

The frustrating part for me was that the entire content of these meetings had already been discussed during the day, on the phone, or via email. Still, he needed the meetings as a safety blanket.

The problem was our business was on the West Coast, and we were sitting in the Caribbean. So 8 pm is a very inconvenient time to have a meeting.

As new cruisers, we were flooded with sundowner invitations that we didn’t want to decline. But, one of us needed to hold off on the cocktails and go and chat with our partner every evening. The bigger problem was the internet was really bad on the boat. So we had to dinghy over a mile to a restaurant bar onshore which was the only place with internet for miles.

Mistakes I made working from the boat
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We had been using the bar for the internet for a few hours a day. At 8 pm this was impossible. The bar was loud, and there wasn’t a table to be had. The last thing the restaurant wanted was someone with a laptop, hogging a table.

Within weeks our partner was irritated, and I started to feel animosity towards him for needing what I saw as a completely unnecessary waste of time each day.

During the day was not practical for meetings, as he needed to be available to answer phone calls. First thing in the morning was as much of an issue as at night because the only restaurant in the bay with internet available didn’t open until 10 am.

Moving the boat to another bay wasn’t an option for a few weeks as we were waiting for back-ordered spares to be shipped from Volvo in Belgium to repair a broken saildrive.

We tried quick phone calls during the day. But his personality molded by twenty-five years in a corporate environment wasn’t satisfied without a structured meeting. The relationship started to suffer.

Going Big

Ultimately in the not too distant future, this would have been our partner’s business if everything went according to plan.

Feeling frustrated at the lack of structure and communications, he began to run it as such. That should have been a good thing. It’s what we wanted, for him to take more control. The sooner he was comfortable taking control from us the better. Except he transformed the business model. He started seeking out major customers. Multinationals.

He began using his days building intricate PowerPoint sales pitches. And holding drawn-out sales presentations and expensive lunch meetings wooing prospective major clients. None came. Our competitors were much bigger and could offer better pricing.

Our business model was taking care of the little guy really well. Something the big guys couldn’t do. And now the little guys were being neglected.

Soon, my phone was ringing off the hook with unhappy calls from our customers. They weren’t getting the attention they were used to. I tried to patch things up. But, I wasn’t as attentive as I used to be back in my office.

We were new to the boat and there were tons of boat issues. I was spending my days upside down fixing things. When the phone rang I’d answer with dirty hands and wasn’t in a mindset to service them.

Mentally I had checked out. In my mind, I never intended to work permanently from the boat. It was a temporary thing. Six months max, until the sale was completed. And after four months of working remotely, I felt as if the transition should nearly have been completed. This wasn’t a good situation.

We were bleeding customers. We discussed the prospect of shelving the idea of working remotely from the boat and moving back home.

We decided the business was too far gone and that this was a route we didn’t want to go. We called up our partner and informed him we wanted out. He still had his eye on the prize of getting some big accounts and was extremely happy to take over our remaining fifty percent for no additional money.

Within six months he had found an executive position at a large company and shut the business down.

Mistakes I made working remotely from the boat
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Lessons Learned When Transitioning to Working Remotely

Start Working Remotely From Home First

If you plan on working remotely from your boat. Start from home for a few months before moving onto the boat. This will give you time to figure out if the tools that you have work. You can try out new tools, while you still have unlimited internet to download software to experiment with it.

You will get an idea of what sort of routine is needed for working remotely. You can then start trying to modify your workday, to live as you would on the boat. Maybe waking up a couple of hours earlier and getting all your tasks done so that you can have the afternoon off.

You will want this type of schedule on the boat as that will most likely be the time you’ll set aside for activities such as snorkeling or visiting a new town. I would strongly advise you to make sure that whatever type of schedule you choose, you make sure you are done by 5 pm each day.

Even if you are not going to be going to sundowners with other cruisers every night (Socializing and meeting new people are a massive part of the cruising experience). In many parts of the world by five, anchorages start getting noisy as beach bars turn up the volume. Trying to disguise the fact that you are working on a boat or trying to maintain a professional appearance becomes impossible.

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Have Days That Are Completely Work Free

You need to build your routine that you can take a minimum of one or two days off per week. You’ll need these days for sailing to new anchorages or going on full-day hikes. And no, saving the weekends to sail to new islands doesn’t always work. The weather isn’t something you can schedule.

Make sure that on sailing days, your attention is focused on safely sailing your boat. You don’t want to be disturbed by an important phone call when trying to reef or anchor in a busy anchorage.

Part of being out here cruising and working remotely from your boat is so that you can enjoy simply being out cruising. Make sure you don’t just relocate your crazy busy land life to working remotely on a boat.

Make some changes. Without the distractions you get in an office, you will be able to work more efficiently. This means that you should be able to put in fewer, yet more productive, hours each day to do what needs doing.

Plan to Work When You Have Internet

Even with the best cell phone internet plan, you will encounter anchorages with little to no signal. Other times you will be in anchorages with excellent free or low-cost wifi. Plan your work for the times when you are in these anchorages. Join the Facebook cruisers group for the areas you will be sailing to, and ask before arriving what kind of internet service to expect.

If it’s a new country these Facebook groups can tell you which cell phone company has the best data rates. In the Caribbean, there are wifi providers dedicated to exclusively serving cruisers in various anchorages with high-speed data at very attractive rates. Ask if such services exist where you are going.

Set Expectations With Your Crew

We have two school-aged kids who require attention during school hours. Outside of those hours, we have set some rules. Such as work hours. Day’s we will take off. Who will make lunch? And setting adult alone time.

If you have an important call or project that needs to be completed, share that with your crew. This may involve staying longer in an anchorage with good internet and missing a weather window to the next island. Manage expectations to make sure everyone is on the same page.

Make Sure You Do Not Forget Why You Are Out Cruising

Make sure you maintain a good work balance. It’s easy to get distracted by work. Recently we were in Bora Bora for a month, I was writing articles for this site. We had two weeks of bad weather and great internet so we got down to work.

Solid work. We enjoy writing these articles to share what we’ve learned with future cruisers. But it’s easy to spend twelve to fourteen hours working. Between school, and writing the day is gone without realizing you’ve been at it for so long.

One day after the bad weather had passed, I looked across the pristine lagoon at the high peak on the island and thought to myself, “Shit I’m in Bora Bora! Why haven’t I noticed it for days?”

We have learned what it takes to work remotely from a boat. Watch out for my next article, where I’ll cover exactly what you need, to successfully work remotely from a boat.


Hi, I’m Nic! Our Family of four have been out cruising since 2016. We have sailed about 15,000nm, almost halfway around the world. We sold everything, took the leap of faith, and bought a 10-year-old Lagoon 380 ex-charter catamaran. We’ve fixed every system on the boat, often more than once. Cruising has been such a wonderful, positive experience for our family that I want to share my tips to help you Become a Cruiser.

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2 thoughts on “Mistakes I Made Working Remotely From The Boat”

  1. Shannon Hostetler

    Amazing post!!! Do you happen to have a list of wi-fi providers that cater to cruisers in the Caribbean?

    1. Hi Shannon,
      Thanks for the feedback. When we were in the Caribbean 2 years ago Digicel was the best provider. We were able to sign up for an annual plan using the address of the chandlery on our check-in paperwork in Martinique. The plan covered most Caribbean islands. When we left for Colombia I gave them written notice and a copy of my boat departure paperwork and they canceled the plan. They have different packages so you may want to look at their website to see which one works for you. https://www.digicelgroup.com/mq/fr/bundles.html if you search in chrome it will translate the page.

      As for Wi-Fi only providers. These tend to be more local on a country by country even anchorage by anchorage basis.

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