How My Biggest Regret of My 20’s Became the Greatest Adventure of my 30’s (To Date)

Jennifer DeSimone
Aug 28, 2017 · 4 min read

On August 31, I will board a plane on a one way ticket.

How many times have you heard that line? This story isn’t what you’re already thinking about though. Its about my biggest regret, the biggest risk I’ve ever taken, and the greatest adventure of my life thus far.

See, my one way ticket is from Costa Rica back to the US, back to home, to settle in and grow.

In my 20’s I focused on my career, job promotions, and some travel.

What I never accomplished in my 20’s was my dream to live aboard. Sure I had studied abroad and travelled abroad — but living abroad always seemed elusive.

It was the biggest regret of my life — and it was about to become the biggest risk of my life.

And then, like how so many stories start, I met a guy, fell in love…… and had my second quarter-life crisis in less than 3 years.

One random day (its always those random days) a call came in to my now husband, asking him to move down to Costa Rica. Within weeks I left a job I loved, packed up our life that we loved in Raleigh, and sobbed my way through goodbyes.

I still remember the night we arrived in our new apartment.

The original gang

“What the f*ck were you thinking?” was my first thought.

The excitement, the allure, all of it was already gone. I had no job, no friends, no clue of what to do next — just my fiancé and a suitcase.

I cried myself to sleep that night….and for several others after.

In the 22 months since then, I turned my biggest regret into the greatest adventure of my life.

The day I got a parasite

In the almost 2 years since we moved, I didn’t just live abroad — I dug deep into myself to create the life I want for myself.

In the process I married my best friend, backpacked through Southeast Asia (my second biggest regret of my 20’s — check), spent 5 weeks in Iceland, became the Chief of Community for U30X, attended a Tony Robbins event, became a life coach — and so much more.

It wasn’t easy.

There were tough days. Don’t believe me? Call my best friend and ask her.

There was a snake bite incident, and a parasite. The death of a dear friend. And missing out on moments back at home.

Stepping way out of my comfort zone

But there was an awakening, a facing of so many fears, and a confidence that grew within me that I never had.

But, would I do it all again knowing what I do now?

In a heartbeat.

These sunsets still amaze me

My biggest regret of my life right now?

I can honestly say none.

Ok, maybe not taking Photography 101 in college.

But as I begin to pack up my life here in Costa Rica to start a new chapter in Austin, TX, I’m beginning to feel a little emotional.

I will miss the sunsets, and the calming sea that I get to see almost every single day. I will miss our office and the people who fill it every single day. I will miss the pura vida lifestyle.

I also have fears and anxiety over moving to Austin. As an East Coast girl with roots in NYC, I refuse to start wearing cowgirl boots.

This crew….going to miss them

In 2012, a friend of mine told me to go out an find my next adventure. Its a mantra I’ve lived since that day.

So while this is goodbye to Costa Rica for now, its not a door closing. Its a sweet ending to one adventure and a new start of the next.

Austin, I am coming for you!

Until next trip…..Pura Vida!
Photo Credit: Luis Alvarenga

Interested in traveling to Costa Rica? Join us in Manuel Antonio, in the rainforest, or join us on a 9 day trip across both locations.

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Jennifer DeSimone

Written by

Jennifer is a traveler, lifestyle coach, and vegan foodie who seeks to live her most radiant life. Follow the adventure on Instagram @theartofintentions_.

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