Believe it or not, I used to be shy. Now, that didn’t stop me from being a chatterbox in school, but if I’m honest, I hid from the spotlight for a long time. Until I discovered spelling bees, that is.
Around the fourth grade, I became what I fondly refer to as a “word nerd.” Back then, I was an avid reader, with my weekly Highlights subscription (if you’re a Gen Xer you may remember these) and my Nancy Drew mysteries, but the school spelling bee is where I began to find my voice. In junior high, I was introduced to sales by selling Girl Scout cookies — and I hated it! The very thought of asking for the sale made me panic, but my younger sister’s bold confidence taught me how to approach strangers so I, too, could obtain my top-seller badge.

Fast forward to my early 20s – fresh out of college and back in St. Thomas with my journalism and advertising degree in hand and my first job as a newspaper advertising sales rep at the Virgin Islands Daily News — go figure! I still had not mastered the art of selling (and it IS an art), but I was giving it my best shot. In 1993, the opportunity to fulfill my childhood dream of becoming a beauty queen presented itself and I jumped at the chance to compete for Miss U.S. Virgin Islands. If I won, I’d represent my home at the Miss Universe Pageant in Mexico. If I didn’t, at the very least, I would conquer my shyness and fear of public speaking — both key skills if you wanted a career in sales. At first, I didn’t care if I won, but after putting in the work, I could almost taste my victory in those final days. For those who don’t know, a major part of the Miss Universe criteria is writing and delivering a speech, and this was my first time speaking solo before a live audience.

Ultimately, I placed as first runner up after a hard-fought competition and began the journey to believing in myself. After that, my sales career got a little easier. Why? Because I started to build my confidence. My philosophy at the time was, “if I can strut across a stage in my swimsuit in front of this tough crowd, then I can certainly sell ads.” Trust me, that was no exaggeration, because Virgin Islanders – and Caribbean people in general – will tell you like it is whether you want to hear it or not!
That moment made me believe in myself and showed me for the first time that I had a voice, and a place – out front and on stage – and it was time to stop hiding. I’d go on to win the Miss Caribbean Maryland Pageant in Baltimore, Maryland a few years later, but this was how I begun the process of facing my fears and pressing on.
What mountain have you overcome that changed the trajectory of your life? Leave a comment and share with someone who may need to read/see this.
For me it was definitely leaving a great computer sales job (at least I thought so) for a tech specialist and IT support position at a private school! All sorts of opportunities presented themselves after that. The coolest part was that this school, although in Texas wore the exact same plaid pattern as my tiny little elementary school in the USVI. Maybe that was a sign.