How 3 Essential Life Lessons from My Late Father Improved My Travels

On a lazy Sunday morning with clear blue skies, my 2 miniature Schnauzers and I leisurely strolled down to Mamitas Beach in Mexico.   Unceremoniously I released a small bag of my father’s ashes into the Carribean Sea.  I had long since mourned his death but hadn’t made time to bid the final farewell.  As I watched the black ashes coalesce with the turquoise waters, I thanked him. My current cushy life I owed in part to some valuable lessons from my late father.

Some guidance he imparted through positive examples.  For instance, he showed me the merits of unconditional love and perseverance.  On the other hand, he also conveyed wisdom through misfortune.  My dad spared me a lot of hardship by failing himself, and consequently showing me what not to do.  Often personal growth flourishes more after failure rather than following success.  He took some hard knocks so I didn’t have to.

How 3 Essential Life Lessons from My Late Father Can Improve Your Travels

Life Lessons from My Late Father. My parents in Venice, Italy in 2006.
Life Lessons from My Late Father. My parents in Venice, Italy in 2006.

1 – Don’t be Afraid to Meet New People

My dad was a master at meeting new people.  However, he sometimes lacked the tact and grace required.  So in this example, life lessons from my late father manifested themselves in both positive and negative scenarios.

My dad knew more people and had more friends than I think I’ll ever realize. 

He wasn’t afraid of rejection or making a mistake.  His jovial attitude was invaluable especially on the road.  Case in point, we had probably the best meal of our trip in Barcelona, Spain at Accés because of recommendations from a group of law students he chatted up on Las Ramblas.

Nonetheless my dad’s friendliness could sometimes make me uncomfortable.

To illustrate, at a supermarket in Boston he started speaking Japanese to a stranger who turned out to be Korean.  Personally I saw this as a bit offensive and racist.  Just because someone looks Asian does not mean they are from a specific country or speak a certain language.   In another case, an unknown Italian woman fled a grocery store in Mexico after my father abruptly approached her and recited some pleasantries we learned in Rome.

My father meant well but his delivery needed work.  There are limits to what we should say and how.  Discussions on heritage should be saved for good friends (or avoided entirely) depending on the length and strength of the friendship.

Regardless of making faux pas, I make it a priority to meet new people thanks to my dad.

We can learn an infinite amount from others.  As proof on a recent trip to Galway, Ireland my mother and I started chatting with a lovely couple from Seattle, WA who were also world travelers.  They not only gave us some wonderful recommendations on where to dine, we agreed to meet up with them next time we are in Washington state.  Now we have some local experts to show us the ropes when we’re in the Pacific Northwest.

Lessons from my late father. My parents with me and friends Monique and Janet in Merida, Mexico. We took this road trip about 2 years after having moved to Playa del Carmen.
Lessons from my late father. My parents with me and friends Monique and Janet in Valladolid, Mexico. We took this road trip about 2 years after having moved to Playa del Carmen.

2 – Life is short. Make the most of your years.

I watched my father slowly deteriorate from lung disease over a period of 3 years.  The last trip we took was with my mother and Allan to Paris in 2015.  Even though he struggled to keep up with us, I’m thankful he went.  Sadly after that trip, the doctor forbid him from flying due to the risks of contracting a cold on an airplane.

So traveling, the one thing he loved most in this world, was the one think he could not do.

When it came time to have them visit me at home in Playa del Carmen the next year, they couldn’t.  Instead I left the 80 degree weather in Mexico and visited them in the 30 degree cold in Boston.

Travel before it’s too late.  Plan that vacation you’ve been thinking about.  Don’t wait till next year as it’s not guaranteed.  Have fun today while always remembering to plan for tomorrow.  Life is short.  Thrive rather than survive.

Life Lessons from My Late Father. This is a photo of me and my parents before my junior prom in high school. This may have been the last time I ever wore a tux!
Life Lessons from My Late Father. This is a photo of me and my parents before my junior prom in high school. This may have been the last time I ever wore a tux!

3 – Take risks but make sure they are calculated and researched.

My Dad took some risks that in retrospect weren’t wise decisions.  One in particular was especially alarming.  When I was in middle school my parents invested $100,000 USD in buying a second home in Maine.  They took out a second mortgage in the hopes of having a vacation rental property near the ski slopes of Sunday River.  Sadly the crook developer ensconced with the money, taking his family to Australia and then suddenly filed for bankruptcy.

What could have turned into a frequent travel spot for my family turned into a catalyst for them filing for bankruptcy.

My parents took a risk but it was not researched or calculated.  They didn’t ensure the developer owned the land or was financially stable.  This could have been discovered by a title search and asking for copies of his bank statements.  Also they should have asked around for his reputation (which was not good).

On the positive side I learned from the blunder.

When it came time for my partner and I to take a huge risk, we made sure to do all our research beforehand.  In 2008 we wanted to quit our jobs, sell everything we owned, and move to Playa del Carmen, Mexico (“Playa”) to start a property management company.

However before doing so we thoroughly investigated the idea, interviewing anyone who might have insight – from real estate developers to other property managers.  We surveyed the market in Playa to determine the necessity and viability of our dream.  In the end, within 3 months of our brainstorm, we drove from Boston to Mexico with nothing other than our dogs and anything that could fit into our SUV.

Lessons From My Late Father. My parents in Starda, Spain in 2008. Starda is my favorite city in all of Spain. It's must-see.
Lessons From My Late Father. My parents in Girona, Spain in 2008. Girona is my favorite city in all of Spain. It’s must-see.

Now 10 years later we have a thriving company with 30 employees.

And we work in shorts and sandals in the Carribean. Even though there were no guarantees of success, our hard work, a bit of luck and our flawless researched all helped.  Thankfully now the business provides us with the structure to travel 4 months a year.

Getting ahead in life is difficult if you don’t take risks.

But don’t just jump on any idea because you like or trust the person who suggests it.  Do your homework first.  It can make the difference between make or break, literally.

What are some life lessons you learned from your parents?  How have they helped your travels?

Let me know in the comments!

Happy travels,

Matt Weatherbee

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Matt Weatherbee
Matt Weatherbee

Hi, I’m Matt.  In 2008 I quit my job, sold everything and drove from Boston to Mexico to start a business.  Now I live and work in the Carribean, and spend my free time traveling the globe.  Learn more.

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2 Comments

  1. Marge
    June 21, 2018 / 7:38 pm

    My parents taught me to not own a lot of stuff and not to be overly attached to it all. Life is about people and experiences, not possessions. Upon retirement that translated for me into “sell it all and move to Mexico”. Shortly followed by joining home exchange, where you swap homes, as an economical way to travel. GO!

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