Always Thinking. Always Learning.
While all of my school friends were on Hi5 creating virtual corners for themselves, I was still too preoccupied with TV and wouldn't even bat an eyelash at the whirring white box on the dining table. To me, the internet was only ever good for bingeing bands of movie trailers on Apple’s QuickTime video player. So, years later, when I landed an internship at a magazine as a wannabe writer, I found it ironic that I would be the one to manage the company’s digital newsletter. And, since taking up that internship almost 11 years ago, I am still stunned that the digital industry is the space where I earn my keep.
When I joined the workforce at 22 years old, digital for business was a lazy tide gently washing against our Caribbean shoreline. And though Facebook already crashed onto the scene to forever transform the ways in which we connect, not many Caribbean businesses, then, saw the dollars and sense behind things like engagement and affinity audience profiles. The publishing company I started working for was unlike most businesses in the region. The team had already spent two years experimenting with digital business plans by the time I traipsed through their office. And while I densely pursued a space for my name under the masthead, I was taken aback when charged with the obscure work of building a database and constructing a digital newsletter. As a wannabe writer I only aspired towards a by-line, and for the most part was a very reluctant “digital native”. Despite feeling indifferent towards things like my own Twitter profile - fuck I wasn’t even sure how to carbon copy (cc:) the right person on an email! - I was seriously committed to jump starting my career at this sophisticated lifestyle and architecture mag. It was the only motivation I needed to put aside my long-standing negligence of digital and get invested.
Little did I know that I just happened to be at the right place at the right time.
So, the work commenced on this supposedly dreadful task. It started with a lot of googling and continued with the shocking realisation that I was managing my very own mini publication. Colour me surprised. From concept to distribution I was creating magazine-style content for a small set of eyeballs. With this refreshed awareness I ascertained that Monday and Wednesday mornings were ideal for issuing content to subscriber inboxes. From that miniscule cache of data (the subscriber list totaled a modest 200), I was able to glean that the number of people opening the newsletters versus those who did not, was of significant value. This “shit-hound work” was getting interesting. I was a writer who was being read and on that sweet fact alone I became more invested in the project. The more I read and the more I researched, the more I could see with greater clarity the paths of strategy that would have a positive impact for the business and its newsletter subscribers - like I had a knack for it almost. With each subsequent issue, I applied more of what I learned, quickly making the newsletter a branded digital platform with exclusive deals and offers from Caribbean-based Hospitality and Tourism businesses. With each proceeding issue of the newsletter, I actively sought to outdo myself. Within twelve email blasts (shared over 4 months) I had managed to push the modest effort to its limit. I had exhausted my creativity with the content and was unable to push the issues further. It was at that moment I realised that I had way more to learn where digital was concerned. Google was simply not enough. My writer's brain could no longer carry me because let’s not forget, my strengths as a writer weren't even that good then. I had to level up. But where to begin? I was at a complete loss and was losing a lot of steam. Soon the task of publishing issues quickly became repetitive, and the crest of enthusiasm that excited me troughed into a crash of foam.
Starting off at that high a peak so early on in my career, revealed a desire within me to wrangle with the surf of the digital world. I surprised myself. That high had no comparison and my thoughts were consumed by a constant need to improve and learn more. Though I didn’t hold command of the language needed to fold code and user behaviour analytics into business, I was learning its pattern and general shape. With an almost insatiable appetite for it, that abstraction motivated me in the following days as I scoured the internet for courses or entry-level jobs at local companies, blithely believing that my resume was as impressive as I padded it to be. I should also admit here that I was blissfully unaware of the existing cadre of better qualified professionals returning to the same subset of limited career opportunities in my island home. Me and my American French degree, supplemented with a few months of intense googling, didn’t stand a chance in comparison to national scholars or people with degrees in Computer Science and IT. I should have just waved that degree as the white flag it was and moved on. But the taste of that work was still on my lips and I was brazen enough to give it all or nothing. So, I clenched my teeth, squeezed the shit out of my narrow experience and white-knuckled it on the ride down.
Ironic as it is, it was that uncouth naïveté (or maybe spartan arrogance) that landed me my first digital strategy job. One day during my frantic search, I happened upon a post calling for resumes suited to a junior digital specialist role. On sight of that post caption, I immediately followed up with a private-message expressing my interest. And, as luck would have it, I interviewed and was offered the job. I accepted the position acknowledging that I was embarking on a voyage of learning and so endeavoured to participate at every stage of every single client project in the shop. I made myself the de facto assistant to everyone, and for two years absorbed everything there was to learn about website and app development, performance marketing, budget optimisation, client services, crisis management, content strategy, business plan writing, and pitch presentations or RFPs. I learned early on that managing tasks in digital meant owning a project’s life cycle, end to end. Accepting all that (still with a chest-full of pride), I netted my share of small wins along with incredibly expensive mistakes. Man cannot work with zeal alone in these here parts. Man had to apply himself in a different way. During the first three years of my career, I had stepped into a space that already had a rhythm about it, making the likelihood of my initial stumbling unavoidable. I had a lot of catching up to do in spite of digital being an exception to the rule in Caribbean business at that time. I came to see that period of my life as a much needed education.
After overcoming that initial unwillingness to wade in digital water, I then had to confront the encroaching and unavoidable current of the larger digital world: my job as a creative professional depended on my ability to navigate through slip streams. I was hired by companies that knew it before I did, and they pushed me into the crow’s nest of their ships. From there I could make out the ripples moving through the small effort of the work I managed and how it would eventually build enough momentum to push a business forward. I was also forced to look my future dead in the eye, quickly realising that my options were not as wide as I believed them to be. So instead of falling back on my ineptitude with technology, instead of mooring myself to old ideals, instead of latching myself to hubris, I focused on what was surely coming. I was diligent enough to do the job well regardless of the very little I knew. I plundered every sense of initiative I had to make projects efficacious for client business and have since used those lessons learned to guide every turn on my career.
In retrospect, I was discovering my niche and I am still proud of every single newsletter issue with a high bounce rate, every campaign where I overspent, and every email I clumsily shared with an unsuspecting executive. Without those failures, I would not know how incredible it is to have a newsletter with a 95% open-rate, to have a campaign deliver click-through-rates above the industry standard, or what it’s like to do more than just carbon copy (cc:) but also blind carbon copy (bcc:) an email. Not many people get to experience that kind of failure - I was working in an environment that saw my mistakes as teachable moments. The early reluctance I felt when I first encountered the computer has ebbed long time ago and since that time I have discovered even more about the world of business. Wins aside, what I think about these days is how much further ahead would I be if I had just closed off QuickTime one trailer short and used the computer instead to surf the world wide web glistening before me then. Finding my sea legs was just the beginning, there was still more to learn regarding the rhythms of the world and how digital can help used to ride the wave of transformation. Thankfully I managed to strengthen those leg muscles just in time because the voyage between then and now was brimming with larger more important lessons.
Now, as the Chief Digital Officer of a multinational agency (with plenty-plenty humbling experiences behind me), that familiar something in the air pulls me back to 2009 when I first wobbled with inexperience. I recently found myself climbing back into the crow’s nest to try and make sense of this niggling. From the vantage point, I noticed a faint shift signaling things worthy of attention - problems, opportunities, and ideas that I know island people can leverage for the collective good. Allow me to explain. Because the Caribbean - as a whole - is finally rousing to best-practices in digital, it is important to take stock of the puzzle strewn before us and ascertain which are the straight-edged pieces of this picture. We are still in the middle of a mad scramble to assemble that puzzle from the center out, and I’ve noticed the institutional onslaught of the pandemic, breaches on national trust on the part of government, failing financial institutions that leave the elderly standing in long lines trailing through the hot sun and rain to collect their monthly pension, falsehoods proliferating and spreading rampantly through social media as news, and the disconnect between the unethical misuse of personal data and marketing plans (to list a few) are concealing crucial corner pieces from our frames of reference. These are blind spots, as it were, and the reason someone needs to climb into the crow’s nest ever so often in the first place. We need that bird’s eye view. We are too far down the ship’s hull to make sense of where we are headed.
As the ship tilts with undesirable lean, here are the specific questions and thoughts on my mind:
Why does it feel like we’ve been left behind in digital? How has digital shaped us, culturally? Do we drift within virtual borders (like China) or are we castaways lost on the map? There are loads of resources, tools, and platforms available and we only ever use the unsuitable or ineffective few to manage our archaic systems. Why have we been so slow to move? Is the regional population aware of their respective digital rights? And, how can we apply digital success to strategy for Caribbean businesses proactively?
The more I think about these things the more steadfastly I commit to re-enforcing our connection with the global current. A true connection strengthened by best-practices that work for us. And therein lies a manifesto of sorts -an exploration in digital of the paradigms swinging on an axis of thinking and learning about certain Caribbean histories, island cultures, and modern moods. But, we’re being pulled to somewhere and I’m not sure that it’s in the direction of our north star, yet.
I intend to share more essays about the things I’ve learned with whomever is willing to lend an ear. There is so much more that we can do together than apart. This project, these essays and videos are my attempt at collating things that I see from this crow’s nest that I mentioned. It isn’t an exclusive space though. I’m hoping to connect and have conversations with people who have also managed to climb up there in hopes to better understand our digital industry.
Feel free to hoist your flag and share a dm with me on linkedin.
