Leaving The Land Of Coconut Cowboys

I’ve referred to SE Asia as the Land of Coconut Cowboys for a long while now.

The term itself is combination of two concepts I’d had long conversations about – Dan Andrews’ description of visiting the Philippines as “the Wild West” and James Schramko’s presentation at last year’s Dynamite Circle conference about the dangers of resting on “Coconut Cash.”

Having lived in SE Asia for just a short three years, I observed two very different types of entrepreneurs relocating their lives and businesses there:

  • The Pioneers – Like the settlers of the Wild West in the United States, they were visionaries, determined to make a huge front-end investment to get to a place ripe with potential. The trips were long and dangerous, so many died. The ones that made it, they would set up shop (most people in the Wild West were entrepreneurs, or in-training to be one; you don’t hear of many saloons or ranches that employed thirty minions) and were able to control their surroundings by leveraging these new finances. No longer needing the comforts and aesthetics that served as social markers for success in their East Coast existences, their money was reinvested and their legacies lasted for generations in the townships.
  • The Proselytes – Young men who read the yellow page stories of the Wild West adventures, and decided that they wanted in on that. With no plans, no money, and no idea they hopped railcars to attempt to recreate the success of others. They eventually made enough to live in a room over the whorehouse, maybe dated one of the courtesans, found ways to swindle or wheel and deal to make money for their next bottle of whiskey. This level of freedom was more than they ever would have in the workhouses of New York City. They died penniless (having maintained a lifestyle of zero-balance) but were probably happy enough.

(In reality, this is a cycle that continues much further back into the historical archives than the Westward Expansion of the US in the 1800’s, as I’m sure my irritated European friends will note (while rolling their eyes at the stupidity of Americans, thinking we are the first people to ever realize the concept of geoarbitrage.) I’m sure our Asian friends are doing the same, thinking how foolish Europeans are to believe that they are the only ones who ever fought wars for territory. Brave people exploring a developing world to discover opportunities and innovation are not exactly a novel concept.)

When I arrived in Chiang Mai earlier this year, after four months of bouncing around countries and cities aimlessly, I was adamant that I needed to find a place to settle down for a bit. I needed to focus on my own business, which was beginning to spin out of control with clients no matter how hard I was working to neglect it; I needed a space that I could escape, my introverted personality needs were being drained by the level of extroverted obligations; I needed to surround myself with people that were not just looking for the next vacation spot, but wanted to surround themselves as well to form a community.

I returned home to the States a few months later for my baby sister’s wedding, attend a few conferences and masterminds, and finally be able to have Skype calls with the majority of my clients and peers without having to schedule across a ten-twelve hour time zone difference.

The plan was always that I was going to return my Chiang Mai apartment in October, in time for a conference in Bangkok.

In August, I began to have the sinking feeling I had made a massive mistake. The Land of Coconut Cowboys was no longer calling to me as it had over the past three years. Like Wendy in Peter Pan, half the time I wanted to jump down into the lagoon and play Cowboys and Indians and half the time I wanted to stand on a rock with my hands on my hips and scream back at them “You all need a Mother!”

Throughout September, I procrastinated buying my flight with every excuse I could find. I’d just wait to see if the ticket price went down (I knew it wasn’t going to). Maybe a flight less than twenty-five hours would come up (of course it wasn’t going to). I still had some things I needed to finalize in the States for my business (that easily could have been taken care of with electronic signatures and a few phone calls). I didn’t know what day I wanted to return to Bangkok (so I should wait until I had that plan perfectly figured out).

Finally, one night, I sat with the nauseous reaction to fear in my stomach. The fear that swirls inside your heart and eventually reaches up with its sinewy fingers to trap your head; the fear that you dare not acknowledge but you know is there.

I was putting it all off because I simply did not want to go back.

As I sat at my laptop and filled out my decision-matrix (a spreadsheet I use to assign numeric values to the pros and cons of big life choices so that emotion cannot cloud the outcome) I found myself listing more lifestyle opportunities to the pros and more weight to the impact of the cons.

Even more simply, I was not happy in the Land of Coconut Cowboys.

That’s the thing with location independence.

You don’t have to live someplace that you don’t want to be, if it isn’t where you want to be.


  1. Tom Mullaly

    Terrific introspection and well-shared honesty Elisa. It’s critical to admit when places/people/jobs no longer fit us, to avoid having our present become some worn out monument to standards we’ve outgrown. No point in that.

    With location independence the doors never really close anyway, and #6334 will always be open for you.

    • Elisa Doucette

      So true! That’s the great thing with planes, they fly both ways. I’ll be back in #6334 and bugging you for lunch everyday before we know it. 😉

  2. Jake Schuster

    Beautifully said–so few have the guts to express this! Good for you for going (staying!) where you want. New England ain’t a bad place to be 🙂

    • Elisa Doucette

      Not a bad place at all! Though I’m only here through Christmas, then off to NYC for a bit. Even in the States I can’t REALLY stay still. 😉

  3. D.R. Fideler

    A great piece of writing.

    • Elisa Doucette


      • D.R. Fideler

        Elisa, here’s a two minute video I made that relates to the theme of Coconut Cowboys. Thought it might make you smile.


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