Over the past 5 years, I’ve read many blog posts with similar titles. I always knew that eventually I would be writing mine (didn’t know that when the time came the choice would be so quick).

I joined my previous company 3 years ago, and was asked during my interview “Rory, what do you want to do in 5 years?” and I blurted out “Start the next Facebook”, which basically meant “Start a successful online company”. Three years later, I wasn’t much closer to achieving that. I was getting dragged out of I.T. and development(my passion) and was getting pushed into marketing. (I appreciate it’s good to cross-train and I did learn from the last few months reporting to the Director of Marketing), but I felt stagnant and I wasn’t progressing in the direction that I wanted to go. 

I came across Slash Roots - Code For The Caribbean Fellowship, it looked interesting. I’ll be the first one to tell you, I’m not very civic minded so that aspect of it didn’t really appeal to me. What did though, was that I would be able to develop and craft my skills and the kicker: I would be based in the new JGX Labs incubator during the program. They had me there. I’ve applied to a few incubators before, didn’t quite work out but that’s life we continue and we strive ahead. I sent in my application and was fairly confident.

So I had the nice comfortable job, living on my own in Montego Bay, doing what I didn’t like while on the other hand I had a much more “risky” option to join this Fellowship that’s only 6 months and come December; I just figure something out.

I received an email for an interview and took a day from work, drove into Kingston and attended. The vibe was good, the interview was very conversational and I had fun with it. After that I met up with a fellow Rubyist to discuss a project and then visited the JGX Labs to check out the space. Those two meetings really helped me to make my decision, I went home that night so “motivated and inspired” to create product (and that they are other Jamaicans who are actually doing it) just being in Kingston I rarely felt like that in Montego Bay.

It was recommended that I do a PROs/CONs table, not sure if I actually got around to it, but it came down to:

Do you want to “appear to be enjoying” life ie.) Working at a big company (the largest of it’s niche in the Caribbean) feel good when telling people where I work, OR do you want to follow your dreams and then actually enjoy it. As I said three years ago, my dream is to build great online companies, sure I won’t achieve that by strictly being a CftC fellow but it’s pushing me in that direction. On my first day, we were doing Stanford : Designing Thinking Workshops - which has helped my thought process in identifying, defining problems and coming up with solutions. Currently we are identifying pressing issues affecting Jamaica and implementing solutions. The first being JUTC bus schedules. Now being based at the Lab I’m surrounded by persons focused on nothing else but building their companies, that alone is so much motivation.


Did I make the right decision?


Will I regret it?


Even if you flop and broke in 6 months?


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  1. rorycw posted this