How One Simple Challenge Spontaneously Landed Me in Cuba

As you know, each quarter Yellow has focused on one overarching theme to see how it inspires, shapes, and challenges us. Not only do we explore themes like Pioneer, Wander, and Tension here on the blog, but our Yellow Collective members spend time diving into them together! Each quarter, all of the members take on a challenge together - each woman interpreting it in her own way, but all held accountable to each other. In our Spring series, Wander, the Collective challenge was:

Go to a place you’ve never been before. Have no plans. None. Let yourself explore and reflect.

Some members wandered around their neighborhoods. Others, a nearby city. But for Ashley Marie Taylor, she took the challenge all the way to Cuba. Read on as she shares her story of this adventure below!

Want to do the challenge yourself? Sign up for our Collective Interest list and you get the Wander Challenge Workbook for free! Click here to hop on and grab your free workbook.

For my wander challenge, I booked an impromptu trip down to Havana, Cuba for 5 days. I went down there numbly going through life and came back completely transformed.

I’m from South Florida and Cuba has always been an enigma to me. It reminded me of that scene from the Lion King where Simba and Mufasa stand atop pride rock:

Me: “But what about that shadowy place?”

The Embargo: “That’s beyond our borders. You must never go there.”

Naturally —  always the rebel — that alone spurred me from a young age to cross the 90 miles of ocean and check out this place for myself. I even tried to book a trip five years ago before the embargo was lifted, but realized it would be too expensive. So when Obama and Cuba began to mend relations, it was finally solidified in my mind that I would soon be getting down to Cuba.


Leading up to my trip, I was in a weird spot. I wasn’t necessarily unhappy in regards to work and personal relationships, but I wasn’t necessarily inspired either. I was content. Without realizing it, I had sunk into the typical routine, finding myself drifting from my entrepreneurial endeavors and once again treading the nine to five, working six days a week — a place I vowed to never be again. When the Yellow Collective released the theme, Wander, I brushed it aside. I consider myself travel savvy, I’ve ventured on a number of solo  trips across seas and lived for a stint in Honduras. I didn’t think this theme applied to me and shoved the periodical in my work bag.

One day at work, I realized something was very wrong. A feeling of frustration welled up inside me and I felt I couldn’t breathe. Jeans had just been banned, I was reprimanded for being a minute late to work, my job had shifted toward tasks I’ve been performing since high school, and I felt severely under appreciated (not to mention underpaid) for my skills.

How did I let myself get into this again!?! I rummaged through my bag in frustration, cleaning it out for some respiteful feel of control and found my Yellow Collective periodical.

I opened it and began to read the stories of women who refused to be undervalued. Who jumped headfirst into the unknown in pursuit of ideals.

I started working through the workbook and got less than halfway through before marking off five days around Memorial Day weekend to go to the one place I’ve always wanted to and never could. I went to my boss, told them the days I would be gone, and if they wanted to mark that against my PTO, I didn’t care. This was happening.

Long story short, Cuba was beyond everything I could have imagined. I’m glad I went alone because it opened me up to experiences that would never have occurred had I been there with someone else. I spent hours talking to strangers as we walked miles down the cracked sidewalks of Centro Habana.


I entered the homes of Cuban locals to share in their lives and attended impromptu dance parties in the middle of sun-drenched streets, where walls crumbled to the right and clothes hung on a line to the left.

I dined with complete strangers and for a brief moment in time shared in their stories.

I even met a sweet boy from Argentina who called on me as I stood above on a balcony in the middle of the night, just to walk the streets and continue a conversation we had at dinner.

And for the first time in almost two years, I got back to my first love: writing. Maybe it was the spirit of Hemingway still haunting the place, but I wrote and wrote and could not stop! On my last day, I went to the Cathedral and sat there in complete gratitude to God for this experience. For humbling me and empowering me at the same time.

For unlocking a part of my soul that I’ve been trying to dig at for years now, but couldn’t quite get to.

I went to Cuba as one person and came back, still me, but a more vibrant version of me. I came back in love with life and a refusal to simply float through it. No, I’m diving in.

Note: After her return from Cuba, Ashley was reprimanded for “abusing the vacation policy” and she promptly gave her two weeks notice. For more about Ashley’s wander experience, see the Journal tab at

Photos by: Liz Calka

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