Go Ahead, Take The Leap

Back in 2013, I took a life-changing vacation.

I had just had my heart broken by the first man I thought I could marry. We were supposed to go to South Africa together for Christmas to visit some of his extended family—cancelled. Not only did I feel a gaping hole in my heart, but the three weeks I had taken off from my finance job at the time felt like another one. I couldn’t sit around for all of it. So I booked a solo trip to Curacao, a tiny island in the Netherland-Antilles, right near Aruba.

Don’t ask me how I found this gem! I don’t remember, but it was supposedly safe, had a gorgeous beach, a Marriott resort (points!), and some activities if I felt up to it.

I had no agenda. I would do exactly what I wanted. Heal. Relax. Drink wine. Cry. Get a massage. Cry some more. This whole “go take care of you” thing was rare occurrence for me, a woman whose brain was ALWAYS ON and loved to take care of other people.

The vacation turned into what my friends would call my Eat Pray Love. I concurred.

I met a wonderful man, a bartender named Nadim, at the resort where I’d eat dinner each night (because that’s what you do on solo vacations—pretend to read a book until an interesting person steals your attention). He was a local whose family had left Venezuela years ago due to political unrest and was super pumped to show me his island. While I heard my mother’s voice freaking out that I would be the next Natalie Holloway and telling me not to go, I trusted him—he felt like a genuine, good person. And he was.

We packed up his car with the essentials (Amstel Bright, cheese, and sandwiches) and he took me on a road trip across the island to his favorite cliff to, you know, cliff jump. I’m a former competitive swimmer who’s used to swimming in a pool, and if there were “jumping” from any height, it was off the high dive diving board.

We arrived at this gorgeous cliff; I remember like it was yesterday.

He jumped (a head-first flip, actually).

I screamed.

He laughed, looking up at me from the water, and screamed, “Jump!”

I knew I’d regret it if I didn’t do it. Peer pressure? No—okay, maybe a little.

This was a step outside my comfort zone, the kind of moment that ignited my spirit. I needed it.

So I jumped! It felt incredibly exhilarating—I felt so alive. This moment woke something in me. It broke through my fear and made me feel like I could conquer anything I put my mind to. I was forever grateful.

I kept in touch with Nadim, who later took some of my Chicago friends cliff jumping too. A lot of “firsts” happened for me when I returned home from that trip, small steps I took over time to continue challenging myself to choose more joy, more adventure, more truly living. I embraced what a life with less fear could be. It most definitely hasn’t been easy, but that journey continues for me today, in my work and in my life.

It doesn’t take jumping off a physical cliff to ignite that feeling of possibility; it does take a commitment to trying something new. Choose the discomfort over certainty and a willingness to learn the lessons along the way, because they will most definitely challenge you to stay on your path.