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, my 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 my darkest days, I could hardly even look in the mirror.  I had uprooted my family and moved to an economically depressed island only to be pinching pennies.  Believe me, it’s no fun to live in “paradise” if you’re flat broke.  At the end of the year, it was hard to point to anything positive.  All my savings and trading accounts were down and my carefully laid out plans had gone up in smoke.

redefining the dream

Once I grew tired of wallowing in shame and self-pity, I tried to snap out of my funk 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 I wanted and needed the money, I knew I’d be miserable and unsatisfied before long.

I had about 9 months before I 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 my boys when they were ready to find work.  After about 3 months of relentless learning, applying, and bidding, I landed my first client, though at an admittedly low hourly rate.  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 was needed.

end of year assessment

Now, looking back over 2017, it’s like the mirror image of 2016.  My trading accounts are up huge and I am as “location independent” as any digital nomad.  As long as I have an internet connection, I can work.

Beyond having the finances taken care of, I can enjoy an amazing quality of life that would not be possible 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.  I regularly attend yoga classes to the sound of waves and a view of Desecheo Island.  I never even did 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 me experiences I 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.  However, on our darkest days of 2016 I must admit that my 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 I hadn’t hit rock bottom, I don’t think I would’ve been desperate and hungry enough to do the work necessary to redefine my “dream” lifestyle and basically make it happen.  I am perhaps living closer to my ideal lifestyle than at any other time in my life.  Further, since lifestyle design is a journey, not a destination, I look forward to the many twists and turns that undoubtedly lie ahead!

I hope my story inspires those of you not already living your best life.  Life’s much too short to settle.  Sometimes you have a take a flying leap and fall flat on your face like I did before you discover an uncharted path forward.  Happy 2018!