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Earning to Sail, Sailing to Earn

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Many long-term cruisers save up a large pile of cash and then slowly spend it while sailing the world. Hooray for them! However, most of us life-long sea gypsies don’t have a large pile of cash – or even a modestly-sized one. We only have a small boat and large dream. Despite this, we manage to circumnavigate.

How? By working as we go.

This is neither easy nor quick but it can be fun. Believe it or not, there are actually advantages of being time-rich and penny-poor.

money and fun and contentment have little relationship to each other.

Many “speed circs” only take two years, which is barely enough time to explore the Caribbean let alone, Planet Ocean. Well-funded circumnavigators often own a lot of stuff “back home” and thus spend a lot of time servicing their money rather than enjoying it. With surplus money, you have many options perhaps, occasionally, too many. Plus, since you can do anything, you feel you should always be having a swell time despite the fact that money and fun and contentment have little relationship to each other. Also, there’s a tendency to return home so often that you never really leave it mentally, and your circ ends up an extended vacation from reality rather than your reality.

The Best Cruising Grounds On Earth

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Perhaps the worse aspect of a pre-funded circ is watching your pile of money shrink, shrink some more, and shrink further.

Oh, pity the poor yachtsman, no matter how well-heeled his Topsiders!

Contrast this with your average work-as-you-go circumnavigation. These frugal circumnavigators spend, on average, around seven years on their Big Fat Circle and are, by definition, forced to interact with the locals far more often. This is a huge advantage. Sailing offshore, as delightful as it is, is only half the story. The other half is the people you meet. Here, on a person-to-person level, the work-as-you-go skipper has the edge. It is easy to understand a culture when you’re breaking rocks with its sweating members less easy when you are merely hiring them to wash your clothes, drive your taxi, or remove your barnacles.

St. Augustine

We have “or want” nothing ashore.

Too frequent jet-travel isn’t merely bad for the environment; it’s bad for the cruise as well. Picture how proud Josh Slocum must have felt sailing Spray back into New Bedford and contrast that to how he’d feel if he’d returned to Boston every three months to “shake the money tree.”

The sea gypsy life is, at least as we Goodlanders practice it, pretty simple. We have nor want nothing ashore. Our only fixed bill is $250 per year for our Sailmail connection. (In the Med we were forced to get liability insurance for $350 per.) We started out our first circumnavigation with $5,000, and returned with zero. Knowing how easy earning money would be while undersail, we started our second circ with $4,000 and returned with $46,000.

That’s right. We saved $42,000 while circumnavigating the oceans of the world over the course of seven fun-filled, very eventful years and had more fun than most.

Megayachts Come Home for the Winter

The good news is that I can earn my living anywhere I go. the bad news is that I have to!

Was it easy? No, it was not. I wrestle with my pen 20 hours a week, and Carolyn wrestles with how to make money drip out of that same pen also for 20 hours per week. (Invoicing, photo-editing, book-formatting, etc.) Thus, we put in a 40 hour week aboard, 52 weeks a year.

This takes tremendous will power especially when my wayward friends are always buzzing by in their dinghies asking if I’d like to go diving for lobster, yacht racing, guitar playing, windsurfing, kite flying, or rum-guzzling.

The good news is that I can earn my living anywhere I go. The bad news is that I have to!

Part of the equation is, of course, living inexpensively. You have to be frugal. Forget “I deserve it.” Instead, embrace squeezing Abe Lincoln so hard he cries. This is relatively easy on a yacht in Chagos where we spent four months without spending a single penny, since there is nothing ashore. No government, no buildings, no people, no problems. None!

Inquiring Letters to the esteemed Fatty Goodlander

But, regardless of how little you spend, you have to earn some money along the way if you didn’t bring much in the first place.

One common method is chartering-as-you-go… The legality of which varies country-to-country. Many low-key, under-the-radar yachties in the Pacific just make sure they aren’t taking a local’s job and then proceed with caution. (Warning: a USCG captain’s license and various other pieces of paper are required on a US registered vessel whether on-or-off-the-books.)

Often, it isn’t the yachtie who makes the first move. They just sail into a small, remote island with a large resort and the resort owner asks them if they’d like to day-charter (as all the local boats are open fishing vessels).

If the skipper is wise and desires to stay awhile, he hires a popular local kid for a deck hand and jobs out the catering too so the locals win as well as the resort.

Everyone gets what they want, especially the customers. There are no losers only winners.

Does the yachtie make a fortune after paying his booking fee, his deckhand, and for the catering? No, but they replenish the cruising kitty to add another year or two onto their circ which is what it is all about, from the cruising sailor’s standpoint.

Boat Maintenance: Pre- & Post-Covid

if you are cruising in the Third World where a billion people earn less than two dollars a day, well, food is cheap. It might not be the food you want but, if you are truly hungry, it is the food you need.

David Wegman sailed around the world on an engine-less schooner while spending only pennies. He sold paintings, traded molas (from San Blas), and even accomplished amazing feats of island-style construction to earn his way.

His motto is: “No one ever starved to death sailing around the world.”

That’s true. You might be hungry but if you are cruising in the Third World where a billion people earn less than two dollars a day, well, food is cheap. It might not be the food you want but, if you are truly hungry, it is the food you need.

I will take that statement a step further: I have never ever met anyone who was arrested for working or earning money in a foreign country who had not stopped immediately upon notification.

The South Atlantic Toddle

It is the scofflaws that get into trouble those pugnacious folks that sneer, “…this is a US government documented vessel, and you can’t tell me…”

Those are the guys who end up in jail for working in a foreign country as well they should. But if you just fold your tent and fade usually, nothing happens.

Don’t get me wrong. I am not advocating breaking the law. I am merely stating the facts, and the facts are that everyone has to put food on their table and, as crimes go, working for a living isn’t a particularly terrible one.

Of course, there’s no reason to ever go ashore. I’ve earned many freedom chips by working on other yachts: doing electrical installation, plumbing repair, and wood butchery.

Aren’t there marine electricians overseas? Absolutely! But not in Minerva or Beverage reefs and none who are willing to work for a pittance, like I am.

Some vessels have flippable canvas lifeline nameboards which have the boat name on one side, and “Jack-Tar-of-all-Trades” on the other.

One electronics expert in Sint Maarten told me, “People pay me $80 an hour to RTFM ”  (read the #&%@#%& manual) that came with their marine electronics. The answers are almost always there it just takes some time and literacy to drag them out. So, that’s what I do. I read the manual until it says, “the red wire connects to the positive side of the battery and everyone thinks I’m a genius.”

Carolyn makes Biminis and dodgers with her trusty Pfaff sewing machine as well as minor sail repairs. (She’s such a push-over I think she’s fixed as many sails for free as she’s charged for.)

Are you an expert at something? I’d never tell some nerd in Silicon Valley that I was a computer whiz because I am not. But I know how to install Quickbooks, defrag a disk-drive, and de-porn a clogged hard drive all of which are considered minor miracles in Fiji or Madagascar.

Often, a resort buys a Wifi router and can’t install it (mostly) because they can’t read the manual. If you can read English this, in-and-of-itself, is often a service worth paying for.

Am I recommending you pretend to be a brain surgeon because you can get away with it in the Third World? No, I am not.

What I am saying is that many people in Africa who can afford an iPhone5, can’t figure out how to Bluetooth or Wifi them to their corporate network and if you can, you’ve got something to sell.

There are lots of ways to earn money offshore.

During my first circ, 2000 to 2005, I produced a weekly radio show called the Circumnavigator’s Report that was broadcast via WVWI in the Caribbean.

How? By Fedexing back the tapes. Four times a year, Carolyn (yes, she’s a hard worker and stern master) would say, “Wednesday is radio day, Fatty!”

I’d groan, and make sure I was well rested.

Then she’d run 14 people/guests/friends through the boat for 40 minutes each, and hand me an index card with topics and suggested questions just prior to doing so. Thus, I’d do 14 radio shows in one day, and she’d spend another day editing and packaging up the tapes and we’d get a weekly paycheck deposited into our account 52 times a year. (Amazingly, I had the radio show for over 17 delightful years.) The station was sold twice. And when I finally came in to visit the corporate offices during my second circ, nobody knew who I was and kept insisting that I wasn’t there. “No, mon! Dat boy, he sailing de islands of de Pacific! Dat true! He gone, long gone, me son!”

Don’t miss the next installment as Fatty takes a look at even more creative ways of earning under sail in Earning to Sail, Sailing to Earn PART II

Cap’n Fatty Goodlander has lived aboard for 53 of his 60 years, and has circumnavigated twice. He is the author of Chasing The Horizon: The Life And Times Of A Modern Sea Gypsyand numerous other marine books. His latest, Buy, Outfit, Sail: How To Inexpensively and Safely Buy, Outfit, and Sail a Small Vessel Around the World is out now. Visit: fattygoodlander.com

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Cap'n Fatty Goodlander
Cap'n Fatty Goodlanderhttp://fattygoodlander.com/
Cap’n Fatty Goodlander has lived aboard for 53 of his 60 years, and has circumnavigated twice. He is the author of Chasing the Horizon and numerous other marine books. His latest, Buy, Outfit, and Sail is out now. Visit: fattygoodlander.com

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