How My Biggest Regret of My 20s Became the Greatest Adventure of my 30s

Jennifer DeSimone
January 16, 2024

I am about to board a plane with a one way ticket.

How many times have you heard that line? This story isn't what you're already thinking about though. 

It's 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 20s, I focused on my career

Study abroad, grad school, my first big job, followed by a promotion - it was the life I had so carefully planned for and actually had wanted.

I travelled extensively both for work and for play, but every time someone I knew moved abroad, I felt a pull in heart.

I pushed it aside, seemingly satisfied by travel on my own time in between my career.

It was the biggest regret of my life

And maybe it would have remained so had the universe not conspired to provide an opportunity I never saw coming.

This part of the story starts like how so many stories start, I met a guy, fell in love...

And then proceeded to have the second quarter-life crisis in less than 3 years.

Then, one random day (it's 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.

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The original gang

What the f*ck were you thinking? 

This was my first thought.

The excitement, the allure, the potential – all of it was already gone. 

Reality began to settle in: 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.

Then I turned my biggest regret into the greatest adventure of my life

The day I got a parasite

In these past twenty-two months 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), spent 5 weeks in Iceland, became the Chief of Community for U30X, attended a Tony Robbins event, and became a life coach.

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.

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This crew....going to miss them

A friend once told me to go seek a new adventure 

It's a simple idea but a revolutionary action – and it's a mantra I've lived since that day.

So while this is goodbye to Costa Rica for now, it's not a door closing. Instead, it's a sweet ending to one adventure and the beginning 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.

Jennifer DeSimone
Currently based in Austin, Jennifer is the Chief of Community for U30X. She has a passion for creating connections, community, and opportunities for more empathy. In her spare time you can find her on her yoga mat, whipping up something yummy in the kitchen, or reading a good book.


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