Jake to Jacques
The best day of my life was when I dropped chemistry for art.
To 2007 · Jamaica
I grew up in Jamaica, where I was born. My mother is an artist, and my father is a doctor who invents things, so they were always making things, working with their hands. Before I knew what design was, I was doing still life drawing, logos for fun, and découpage.
The first thing I did in terms of graphic design was a logo for a fake company called Jake’s Tronics. Tronics, not electronics, Tronics without the elect. It was the first time I designed for a brief, and ever since then I’ve been leaning into my love of art and design.
In my professional life I rebranded back to Jake, because of not speaking French, imposter syndrome, and it confused the hell out of the people I’d worked with for years. I grew up Jake. Jacques is my birth name, but it’s kind of an evolution of childhood to adult life. But I have lots of what my colleagues call “brand equity” in Jacques.
I didn’t know what I wanted to be. Growing up in Jamaica in the 90s and 2000s, anything creative was sort of bucketed, at least in certain pockets. I remember taking a career test, and floral designer was the recommendation. That did not fit. I had a dream, though, of sitting on a patio in Italy and working on my computer, just working remotely in Italy. Funnily enough, I ended up on a porch in Little Italy, in Toronto, working remotely. Destiny, am I right?
2007 · The Bahamas
Then we moved to the Bahamas. When I applied to OCAD, in Toronto, I didn’t spend much time on my portfolio, because I thought those aspects of my personality would carry me. I did not get into OCAD the first time around.
That devastated me. What did that do for me, though? It gave me the time to stop and invest in myself.
2008 · The year in between
I worked for a couple of companies in the Bahamas and learned about professional design. At Media Enterprises, with Joanne Smith, I learned what it took, and I learned the tools: CorelDRAW, poster design. At a printer I learned print production. Then I worked in advertising at the Bahamian airports, for the one company that had all the advertising in the airport, and I got my first taste of reach.
I also learned customer service. I was calling people, looking for payments. I learned how to be the bad guy, and I learned how to interact with people.
2009 · The second try
The second time around, I spent more time on my portfolio. I learned about presentation, not just putting work together but binding it, presenting it and providing a pitch. I got into OCAD, and in 2009 I moved to Toronto.
2009 · OCAD
In first year I was finding my groove and my design skills, and learning that it’s not just about being the best. It’s about understanding why you like something. (That’s the professor’s cow, from Taste is triage.)
I failed a course at OCAD, and part of the reason was that I didn’t show enough process. I didn’t push myself. It’s important to document process, to say why.
We had a print shop, so, thinking back to my print days, I used to print everything off and look at it. I wasn’t thinking about saving the trees at that point (shame on me). I would print everything off and compare, and that’s when I learned that minor changes matter, and found the joy in the small changes.
I fell in love with Russian constructivism, Josef Müller-Brockmann, and those early graphic designers, and I still, to this day, find that aesthetic coming through.
2012 · The website instead of the thesis
I vibe coded my way into tech. In the last year of university I essentially abandoned my thesis to develop my website. I was way more interested.
I remember taking a course on computer development, or something to that effect, and being amazed by this one guy who could code a nav bar. Looking back on it, maybe he reused something he’d built before, but it was just so fast, and there was no AI. So I learned what the first line in an HTML file is, the doctype, and those foundations.
It led me to coding websites to show my work instead of focusing on the work itself. I don’t know if that was me being lazy or me finding my niche, but it was the beginning of me learning how to code.
2012–13 · The fellowship
That’s when Myplanet came. They were accepting fellows to their fellowship program, and getting in showed me how to work in a team. We worked in teams in school, and I enjoyed it, but I really learned how when Myplanet showed me and we developed projects together. That led to me being hired, in September 2013, as a Creative Rep.
I remember coming in with hubris the first week and saying we should never be centring typography. At that time web design was all about centred type and skeuomorphism, and I was coming from graphic design: heavy grids, expressive type, left-align everything, very prudish type-snob kind of stuff. So that was a transition for me, opening up to the world of type and recognising my own ego. The designers around me taught me that it’s not just about the type at the end. It’s the process that they put into it. Again, it’s the process, the thought, understanding the user.
2017 · The comparing years
I became a Visual Interface Designer in 2017. Throughout that time I never felt like the best designer in the room. Never felt like a strong researcher. I never felt like the strongest visually. I love the details, and all of this led me to find my own shortcomings, and for years I focused on those, comparing myself to others.
A lot of the work I did as an enterprise designer isn’t stuff I want to put in a portfolio. It’s not everything you can or want to show. What did I gain from it? An understanding of my own work, and where I needed to put more time.
2017–20 · VQC
For years I had been teasing at this idea of design QA. At the time it was called VQC, visual quality checking. I wasn’t seeing the thing I designed get built the way I wanted, or at least I was skipping steps. I was skipping the why, the argument. I was giving devs the final thing and not the why or the process, and for whatever reason things didn’t look good. I had some projects that didn’t go great.
The thing I noticed was that when I got in there and got my hands on it, I could express it. I may not have been able to say why, but I had the ability to express my desires through code. At that point it was all manual. I was bugging a lot of developers, asking them questions, and people who had been very patient with me taught me the way to work with code. They showed not only the ability to work in the browser with a design background, but the desire to teach, and the openness to let designers influence the front end.
For years after that I pursued the idea that the front-end layer is ours, and we should own it. Obviously there was much more to it.
2020 · COVID
Then COVID, and I had an opportunity. Guess why? Because I was on part time. I thought I was invincible. I’d been at the company for years, always asking myself whether I was still learning something new, and I found myself with 50% time off. What was I going to do with that time? I put it into learning the front end.
We were seeing user researchers and interaction designers losing their jobs because of the commodification of design, templates coming out, the Shopifies. No one was designing buttons anymore. It was one of many shifts the industry has had, and probably the one I remember the most, and I lost a lot of good friends to it. It made me ask what the value of what I do is. What do I bring?
Every headline was, should designers code? At that time, the answer was yeah, probably. Half of the world was saying no. I ignored most of that and leaned into it, because guess what? I wanted to do it anyway. (I wrote about that year in Designing your own relevance.)
So I was working on our website, working on customer websites, learning from developers, teaching other designers how to code. That was when I found my niche, and since then I’ve let go of the ego of comparison. It was never an ego thing. It was about releasing that ego.
2025 · Now
With AI and the tooling around us, a lot of the documentation I wrote about how to do this, literally how to check out a repo, how to create a new branch, how to squash and merge, is a non-issue now, because Claude can do it. What I still have is the judgement layer, from having done the thing. That’s what I’m building: all the complexity I had to learn manually, which was only a portion of what developers know, captured from the designer’s side into an agentic harness, so others can benefit from that experience.
A lot of my career has been vibe coding. I just didn’t have the name for it.
I think back to Jake’s Tronics, the first time I put pen to paper and said, this is the goal, and here’s the design. Compared to the work I’m doing now, it’s incredibly different. The imposter’s always there, but I’m enjoying what I’m doing, and when I find myself comparing, I take a step back and look at my own journey. The process takes the end result and gives it an argument.