…and that is something that people have to figure that out,” he said.

Those were the exact words from the second part of a WhatsApp conversation I had with my friend Marlon. But it’s the first part of our WhatsApp conversation that really sparked this blog post, and to think that our conversation started off with him sending me pics of his apt, since he’s in the middle of rearranging his living room to make space for a new piece of artwork he just bought. It’s one of those really big life-sized art pieces that I’ve had way too much fun teasing him about, but I’ll let him reveal that to the public if he wants to. lol.

Anyway back to what this blog post is really about…fearlessness and entrepreneurship…saying yes to your path and going all in, knees shaking and all.

So, with the ohhhs, ahhh and hmms out of the way regarding Marlon’s apartment photos, I launched into what was on my mind this past weekend and especially after 20 mins of meditation this morning. After vacilating for a while between my media brand SiliconCaribe and my digital marketing consulting brand getConnectid, I’ve decide to 100% commit my time and focus to growing SiliconCaribe as a Media business. To really focus on doing more digital content and events that I believe can create even bigger impact on people and businesses in the Caribbean and our Diaspora, to do our part in tracking and promoting #DigitalCaribbean and the limitless possibilities of it all.

It was also time to consolidate the lead that SiliconCaribe has had in being the source for information on the people, businesses and trends that’s driving Caribbean and Diaspora tech and innovation. I’m expecting more competition, so it’s time to pull a Usain Bolt and Elaine Campbell and put some distance between me and them and keep going, growing.

The writing has been on the wall for years and I was trying to serve two Masters for 10 years, because I was kinda too chicken shit to choose and I was cheating myself and my business, as both were not growing big and fast as they could.  Why? My leadership, ideas, energy was split.

Added to that, SiliconCaribe was growing, the work was being discovered by lots more people, taking on a life of its own especially these past two years, with the continuing rise of #DigitalCaribbean. Then there has been the increased sexiness of tech entrepreneurship, coupled with rising acknowledgement of the necessity of  innovation by Caribbean governments and businesses.  The Caribbean is waking up to the opportunities of this Digital Age and how best to position itself for success in the Global Digital Economy. And in knowing all of that, you know what I was worried about the most –  whether or not SiliconCaribe Media would be able to do the level of work I want it to do and also be profitable.

But was the reason I had been kinda procrastinating on things?

You see, in the past, it was always the consulting gigs that seed funded the blog, the initial Caribbean Tech events (including the ones that flopped), other experiments, plus the trips to Silicon Valley, Silicon Alley and Silicon Roundabout and just my life.

It wasn’t until these last couple of years where I stepped things up a bit with SiliconCaribe. I had become more consistent with blogging; the events we produced and co-produced with partners were really beginning to show more impact. I had also paused to assess, really look at all that had been done and what more could be done. How big could I think about SiliconCaribe in terms of it’s usefulness to the region and the impact in could have on people lives and businesses.

So what was this  recent dance with doubt about then?

I was was already tired of hearing myself telling Marlon and other friends in my inner circle, one thing,  then months later another. I mean, I had to tell myself, pick a path bitch and go make things happen like you’re used to…it’s time for another round of leveling up.

Further, I had also fallen out of love with Digital Marketing consulting from back in 2014/2015. Now while I loved all things social, and I was leveraging my extensive knowledge of it for SiliconCaribe, I was only hanging on to it for the money- I have a good rep, so it came easy. But I never saw myself growing it into a full fledged agency, I cringed every time I thought about it. Plus I craved more. I wanted spend more time doing work that matters to me and I figure that the money will manifest as it always does.

You see, I have found in SiliconCaribe…meaning, purpose, significance and I was never just doing it for the money, all these past 10 years I was doing this because it was fun, it came easy to me, flowed freely from me and there was no greater feeling seeing the growing impact and influence of our work in Jamaica and the Caribbean.  I could see, feel, hear the kind of impact it was having on people – the feedback, the comments, emails, DMs, calls, the requests for interviews, collaborations, advise were growing even more.

Being 100% focused on SiliconCaribe Media also merges my passions, skills, expertise with what I believe about the limitless possibilities for the people and businesses in the Caribbean to innovate and build economic wealth in this Digital Age.  And yes, the decision to do this and only this, just feels right. Period. In short, life had been speaking to me for a while, it was no longer whispering, it was shouting and I could not hide from it this time…I didn’t want to hide from it this time. I had to make a choice to go all in.

So now that I have gone all in. Maybe I had been overthinking this thing about…will it make money to execute the mission and be profitable thing? Yep. Because the signs are clear, there is already hard evidence regarding this, plus I kinda know in my gut that I/we will figure it out along the way – like every other successful entrepreneur and business does.

So what was going on with me this past few days?

I was in a loop of thoughts laced with fear and doubt, which usually calms down and evolve again into focus, fun and making things happen. And for entrepreneurs this happens daily, as Marlon said we just remain foolish enough and do what we want to do anyway. The trick is to now wallow, but to allow it to come and serve the purpose of reconnecting you with your why. Why did you start down this path in the first place? What is it that you see, feel and must do?

Thankfully, I’ve gotten better over the years in calming myself down and refocusing quickly. I meditate more; I go for long drives or to the beach just to sit and stare at the sea; I look at my vision board again to remember both my why and the path; I go to my usual inspiring Instagram channels; I call one of my inner circle friends like Marlon who know exactly what to say to me ( a bitchslap talk or an encouraging or soothing mantra), as our friendship creates a space of non-judgement, love and support.

This cycle of fear, doubt then clarity and massive action is a staple for us entrepreneurs, authors, creatives – in fact anyone who has decided to commit to doing work that matters most to them. We feel the fear and do it anyway, because better at trusting ourselves, trusting the process- knowing that regardless of what’s going on in our minds or around us at times – everything really does always workout of you.

Here is what Marlon said, in a manner that only Marlon could, would. LOL. LOL.


And I will leave you with this quote I grabbed from the Instagram Channel of Idillionaire.