living the dream in puerto rico - david with tiki (cat)

living the dream in puerto rico

The end of each year provides an excellent opportunity to stop and assess where you’ve been and the direction your life is heading, so you can make any necessary adjustments for the coming year.  Last year, our end of year assessment wasn’t good.  I moved my family to Puerto Rico in the summer of 2015 with high hopes.  I quit my good-paying corporate job and naively felt I could make ends meet by day-trading with an Act 22 decree.  By September of last year, with bills mounting and my main trading account cut in half, I had no choice but to admit my plans had failed.

On our darkest days, Holly couldn’t even speak to me.  She was understandably furious that I had uprooted our family and moved us to this economically depressed island only to be pinching pennies.  Believe me, it’s no fun to live in “paradise” if you’re broke.  At the end of the year, it was hard to point to anything positive.  All our savings and trading accounts were down and my carefully laid out plans had gone up in smoke.

redefining the dream

Obviously, wallowing in shame and self-pity is not a productive use of time and energy, so I tried to snap out of my funk as soon as possible and conjure up a new plan.  My initial reflex was to revert back to what I’d done in the past and apply for another corporate job.  Lockheed Martin, HP and Honeywell all have campuses in Aguadilla with positions similar to the one I left.  However, as much as we wanted and needed the money, I knew I’d be miserable and unsatisfied before long.

We had about 9 months before we would be completely out of money, so I decided to use that time to try to break into the mythical lifestyle of the “digital nomad” and find work that could be done remotely.  Not only would I be happier long-term, but I also figured this knowledge would be invaluable to pass on to our boys when they were ready to find work.  After about 3 months of constant and relentless learning, applying and bidding, I landed my first client.  I realize this sounds pretty fast, but let me assure you, it felt like an eternity at the time.  After that, it took an additional 4 months or so before I was really making as much as we needed.

end of year assessment

Now, looking back over 2017, it’s like the mirror image of 2016.  Our trading accounts are up huge and I told Holly the other day that we are officially as “location independent” as any digital nomad.  Both of us work online and can therefore work wherever there is an internet connection (which is a bit iffy in Puerto Rico at the moment!).

Beyond having our finances taken care of, we enjoy an amazing quality of life that would not be possible for us in the states .  Probably 8 months of the year, the boys and I walk down to the beautiful Black and Gold Coast in front of our condo to go surfing or body boarding.  The rest of the year we take our paddleboards or snorkeling gear down.  The boys go to a wonderful school across the street from a great surfing beach.  Holly and I attend a yoga class on Sunday mornings to the sound of waves and a view of Desecheo Island at a beach front inn in Rincón.  I had never even done yoga in the states!

Even Hurricane Maria, which initially seemed to mar an otherwise perfect year, may turn out to be a net positive if the infrastructure is rebuilt to be more resilient.  If nothing else, the storm gave us experiences we will never forget as well as unscheduled, extended time with family.

living the dream in puerto rico

An old friend of mine once told me “it’s always darkest before dawn.”  The saying has stuck with me and really helps keep life’s lows in perspective.  On our darkest days of 2016, however, I must admit that our confidence in the truth of this saying wavered.  Only now, with the benefit of hindsight, is it clear that 2016 laid the groundwork for 2017.  If we hadn’t hit rock bottom, I don’t think I would’ve been desperate and hungry enough to do the work necessary to redefine our “dream” lifestyle and basically make it happen.  We are perhaps living closer to our ideal lifestyle than we have our whole lives.  Further, since lifestyle design is a journey not a destination, we look forward to the many twists and turns that undoubtedly lie ahead!

I hope our story inspires those of you not already living your version of “the dream”.  Life’s much too short to settle.  Sometimes you have a take a flying leap and fall flat on your face like we did, before you discover an uncharted path forward.  Happy 2018!


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