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Digital Nomad: Working from our Sailboat in the US and Bahamas Month One

It was a beastly thing to leave our jobs in the summer of 2016. We both had great, steady jobs at a university with all the fixings: I had great coworkers, 4 weeks of vacation, paid holidays, health care, matched retirement plan, the whole enchilada. I knew that once we closed that door and walked away, we would never be that lucky again. We'd be reduced to taco crumbs.

Over the last 20 months, we have lived the life we wanted. Sure, sometimes (see: 50 knots and dragging!) living the dream is an unqualified nightmare. Sometimes we joke that it's time to sell the boat and buy an RV. (see: anything to do with our saildrives). Sometimes we even research AirBnBs in Georgia, the country. (see: that time our propellor seized in the Gulf Stream).

The majority of cruisers we meet are older and are comfortably retired after a lifetime of wise planning. The "young" people fall into two camps: those who are on a short-term sabbatical with plans to return to land-based work, and those who work from the boat.

I've always been intrigued by the second camp, however, no amount of rum or prodding has been able to produce an actionable answer as to what, exactly, these lucky bastards do. It's "marketing" or "managing" or "my own business". Yes, yes, but what do you manage, and what is your business? I just want to be like you!

A land-based life of driving around and wearing shoes and breaking photocopiers beckons. We are feverishly slaving away trying to squeeze ourselves into the "lucky bastards camp".

Our first month "back at work" has been the best month of work I've ever had! No commuting, a dog-friendly office, and no shoes! I've been teaching classes with VIPKID, Forbes #1 rated work from home job for 2018. VIPKID connects American teachers with Chinese students who practice their English speaking skills via video conferencing. 
The hours (4AM-8:30AM) are perfect.  I was even able to teach a few classes the day we crossed to the Bahamas! You can find out more about VIPKID by clicking here.


Matt has been getting freelance photography and graphic design contracts through Upwork, including one to shoot photos and test recipes for an Irish recipe book. We drank Irish coffee and ate bangers and mash for a few good days. Not bad for a day's work from our floating office!
Irish Coffee
Bangers and Mash
On January 31 at 9AM we closed the books on the month. For the first time in 20 months, our income exceeds our expenditures....by $33, the exact cost of two cheeseburgers with fries and two "Wrecker" rum punches. Those bygone days of the whole enchilada? Boring and dry. Bring on the days of the cheeseburger in paradise!
Cheeseburger in Paradise!

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8 comments

  1. Sounds like things are working out very well! I'd like a job where I get paid to drink Irish coffees and have bangers and mash. Sounds delicious.

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    1. The real problem is the desire to have Irish coffees every day! And why are you up at 3AM?!

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  2. Geez! Not only am I craving a huge cheeseburger in paradise now, I could kill a couple of beef sausages. Thanks a lot, guys! ;-)

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    1. I guess we all picked a bad week to be vegetarian! :-)

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  3. Retired? Sure. Older? Most definitely. A lifetime of wise planning? Hahahaha!

    Congrats on your new and enjoyable jobs!

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    1. Hahaha indeed! And...thank you! It's all fun and games while it lasts!

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  4. I love this post! It is so inspiring to read how you have both managed to “change camps” after such a short time! An awesome way to celebrate with that yummy meal and the drinks! Tropical life and cruising long-term does sound good at times. :-)

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    1. Thank you! Life can be so good.....we've got to try and enjoy the good times when we can!

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