If you want to become a pilot, you first have to learn to fly

Who do you want to be when you grow up?

As far as I knew, I wanted to be a pilot!

My actions, however, said otherwise by the time I got to high school. I was as nosey as Pinocchio.Tuned in to all the chatter in the classroom, I constantly searched for lurking opportunities to gain share of wallet/lunch money.Here’s how my day looked: 

  • Sold printed lyrics to songs to the croakiest of voices 
  • Sold music cassettes to unassuming customers. Ran an audio line into my birthday gifted boombox from my computer and recorded it to the tape as I played the music from Winamp (dates me, I know!).  
  • Leveraged music download platforms and sold CDs. Customized with their name on the label and all! Had a monopoly for a while until CD burners were no longer novel. 
  • I loved animals….but! Loved selling them more. Bred them and sold them right back to the pet store I bought them from (God bless Hobby Hut in Jamaica!) 

The list goes on and on. By the time I was in 9th grade, I had a pager on my waist, flyers on bulletin boards around the school, slinging a multitude of commodities, and getting ready for “expansion” to other high schools where I coincidentally did extra classes (obviously if I’m focused on everything else except class).

My behavior didn’t match my pilot ambition. My ambitions were more like finding and exploiting opportunities to make a buck. (Once I knew this, it changed how I approached everything. My purpose couldn’t have been more explicit.

A few questions I constantly ask when reflecting on the philosophy of  “who do I want to be when you I grow up ? “:

·         What provides the most joy when doing it?

·         What takes away my energy and makes me feel drained when doing it?

·         What articles do I read when scrolling through the internet or browsing editorials?

·         Who are my top 2 celebrity heroes, and what do they do? … What are they known for?

·         When out at an event, what conversations am I most in tune with?

·         If three topics are being discussed, what is the one I’m ready to jump in on?

·         What subjects were my favorite in high school? (Where could I get a “B” at a minimum without trying too hard?

Knowing who you want to be is one of the hardest exercises that exist. It involves introspection, vulnerability, and questioning. Once figured out, it sets the tone for purpose, fulfillment and everything that follows.

Hungry, Curious,

By about 10th grade, my parents became worried. They realized I had no interest in the subjects I enrolled in (predominantly sciences). My dad, seeing what motivated me…gave me a challenge. He would gift me USD20 for each subject I got decent enough grades for when graduating high school. I saw that as seed money for something. I won the challenge and got prize money of a whopping $160.

One day, my best friend’s dad, whom I call uncle Don, was a bank exec doing the usual routine of carrying us home from school. I told him about my “windfall” and asked him for his experienced advice on what I could do with it. He asked me the amount again and then laughed hysterically until tears rolled down his cheeks.” $160? A few beef patties, perhaps”. Upon gaining exposure and knowing my passions, he advised me to learn how to invest in stocks and recommended studying Investopedia.com.

That I did! For about two years, I became obsessed. I created trading simulator accounts and invested my hard-earned prize and lunch money. So much so that I could jump in on a school project conversation with JMMB and convince them to give me a summer internship based on my zest for the field. That led to my career at JMMB with progressive roles, starting from teller to fixed-income trader within four years.

This example of being hungry and obsessed has played out multiple times. In my venture for eCommerce that started about six years ago, I enrolled in courses, raised my hands at work to moonlight on related projects, and created an eCommerce website of my own. When the time came, and I interviewed at Walmart eCommerce, the GM for the division, Eric, said, ” I like you, but you have no eCommerce experience. I worry you will go in a room leading others and they don’t follow your lead because you don’t know the ins and outs of the eCommerce world”.

My response was, “if you’re worried about me understanding eCommerce, worry not. I helped Diageo launch its eCommerce division (moonlighting), and I’m certified in digital marketing and eCommerce operations (courses I paid for and did myself). My passion for the field led to my creating an eCommerce operation, which you can check out at Momandbub.com, where I sell baby apparel (a site I launched that sold one shoe by that time!). If you fear me not understanding the customer journey, how to improve conversion by optimizing traffic across the funnel, creating amazing customer experiences built around occasions, and improving logistics and return processes to optimize the P&L…worry not…I got that covered in real life but not on paper.”. I was eCommerce before I was eCommerce, which landed me the opportunity.

I've understood that to become a pilot, learn to fly and be a pilot on your own accord before formally being called so by others.

Everyone needs to know....

Knowing what you want and preparing to become it is one thing..but there’s a reality that …no one is self-made! (Yup, I said it!). Someone has to take a bet on you, and
they can’t do so if they don’t know your M/O.

Once I started my journey of being obsessed, I also ensured everyone knew how obsessed I was… bringing it up in every conversation—seeking others who are as passionate and more experienced, asking questions, and remaining open and curious. Somewhere along the way, I got advice, tips, and nudges. I got support from the people who could help drive the journey.

I’ll never forget the day I heard the CEO of JMMB (Keith Duncan) talking about the plans to enter Dom Rep. I knew I wanted to be a part of the action and had the lofty goal of being a
Fixed-income trader. I was merely an investment advisor at the call center. When Keith finished his company address, I walked over and asked, “How do I get to be a part of the action? I’m obsessed with this space, and everything I’ve been doing is in pursuit of this”. He said, “Your story reminds me of Paul Gray’s, who now heads the treasury division. Reach out to him, share this story, tell him we spoke, and you won’t regret it.”

That I did, Paul guided me for a few months, sharing training material and mentorship. He also challenged me to open a simulation account on the currency trading platform called Oanda and call him e when it’s doubled. About three months later, I reached back out. “Here are my login credentials; I tripled it.” 

I honestly don’t think he checked the account to this day; my drive, obsession, and willingness to succeed are what I suspect he was on the lookout for. When the opportunity presented itself, I was given the opportunity to interview for the fixed-income trader role. In the final round, Paul asked, “Why you for this?”. My response was, “I may not be the most qualified on paper, but if anyone you interview for this role is more ready, hungry, or passionate than I …let me know, and I’ll shake their hand and say congrats”. At 21 years old, I became one of the youngest
fixed-income traders in Jamaica for the largest investment firm. A goal I would never have achieved if the world didn’t know my obsession.

I’ve witnessed this example many times in life. As we continue our journey, we must repeatedly ask the above questions as our “grown-up” ambitions change based on new information, exposure, and life stages.

Today, my world has nothing to do with investment banking, but the underlying passion for finding and exploiting opportunities using data remains. That said, I’ve met journalists who now lead businesses; my wife Shara is a dentist who remodels kitchens, and my close friend Corrie is an anesthesiologist who curates spices. My past sales director at Diageo, Brian, is a vet who sold spirits and now runs a large leasing operation. The list goes on. What’s important is staying in tune with whom we want to be and going after it boldly. Pursue the arduous work of figuring out your fighter jet ambition, sacrifice to learn how to fly it on your own time and dime, and scream it to the mountain tops to let the world know you’re here for it.

This is Steven.