We were lucky to catch up with Jerrell Riley recently and have shared our conversation below.
Jerrell, thanks for joining us, excited to have you contributing your stories and insights. We’d love to hear the story of how you went from this being just an idea to making it into something real.
My journey started during the Covid pandemic. During this time, as everybody in the world sat home, I sat behind my laptop with boredom- just like everybody else but coupled with inspiration and time on my hands.
I started illustrating digital portraits of prominent figures in my home country of Trinidad and Tobago every single day of the pandemic. I illustrated musicians, comedians, music producers and even politicians. This daily cycle of creating portraits allowed me to develop my skill to a point where people started noticing another level of creativity from me- I started standing out because of the consistency and quality of my work.
As my work gained recognition from my friends and followers via social media likes and reposts, the people who I illustrated started reaching out to me directly which was incredibly mind blowing. I thought to myself “Is this really happening”? I couldn’t believe that through boredom and possibly one of the most uncertain times in recent history, that I was making a name for myself. I soon started working with and for some of the top artists/ companies from the Caribbean such as Machel Montano’s Monk Music Group, Kes The Band, Aaron ‘Voice’ St. Louis, The Caribbean Community and Common Market (CARICOM) and many others.
Through these jobs I was able to showcase my creative versatility through art forms such as Portraiture, Graphic Design, Animation, Merchandise Design, Creative Direction and other creative fields. I am now in my 6th professional year of running a design studio- Riley Design Studio, which facilitates a lot of major projects locally, regionally and sometimes internationally.

Jerrell, love having you share your insights with us. Before we ask you more questions, maybe you can take a moment to introduce yourself to our readers who might have missed our earlier conversations?
I got into this industry, through my instinctively creative spirit. Ever since I was a kid I always remember wanting to draw, wear cool clothes and paid a lot of obsessive attention to pop culture. I think those early years really showed me what I’m good at and what gets me excited in life.
Of course, without proper guidance, some talents can sometimes go to waste. Had it not been for my Mother’s belief in my creativity I don’t think I’d have made it this far. She was the one who put me in classes when I was growing up and eventually advised me to sign up for a Visual Arts degree in college. This guidance really put me on the path to gain a formal introduction to creativity.
It is only through my final year at college, specialising in Design I found my true passion for bringing something intangible to life. Final Year Design students had to design and bring a brand to life through several months of critiques from our lecturers. It is safe to say that that process was not for the weak but it prepared us students for the real world. My project was a fashion brand named Wide Awake and the brand was geared towards connecting fashion and Trinidad and Tobago culture.
After graduating with my degree and my final year fashion brand idea in 2017, I actually started creating designs under that same brand and started getting a lot of support from friends, family and social media followers- this was my first introduction into business. This fashion business of mine started doing pretty well at a small scale, had great sales, participated in fashion shows and networked pretty well. This went on until the pandemic came and this is when I decided to pivot.
Through this pivot I started going back to my roots by drawing but this time digitally. I trained myself beyond college how to properly execute portraits, logos, flyers etc. digitally. This was my reintroduction to the creative industry as an up and coming designer. From 2020 to present, I’ve learned how to serve clients on a personal level through direct contact, no manager, no middle man- just me and the client. This distinguished me as a go to designer because of my keen attention to detail and my understanding of the client’s heart for a project. The results of my branding work resonate most times because I don’t do it mainly for money, but to really try to connect and translate my client’s brand to my their audience.
I’m most proud of my ability to see a project/ brand through. Sometimes it’s difficult to bring someone else’s idea to reality. It’s their vision vs your understanding of it which can sometimes clash. I’ll be honest sometimes some projects don’t see the light of day but I can stand firmly and say that I put blood, sweat and tears out for people to realise their brand’s vision.

What do you think is the goal or mission that drives your creative journey?
The mission driving my creativity is 100 percent legacy. I’m terrified of waking up old one day and realised I’ve not chased my dreams. I have so many more ideas that I think can revolutionise the space that I’m in (Trinidad and Tobago) that it keeps me up at night. I don’t think I have control over getting up and trying again after sometimes failing.
It may be God’s calling on my life to pursue my ideas so aggressively, which to me sometimes is crazy because I’m a very shy person and rather blend it with the crowd. One day I hope to create something that represents my country that lasts for generations to come.

What’s a lesson you had to unlearn and what’s the backstory?
The main lesson that I had to unlearn is that rejection might be the end to your path, in fact, it’s just a stop sign to merge into another lane. I’ve been rejected so many times in my creative career that I’ve sort of become numb to it. I’ve pitched many ideas to potential clients and I’ve been ignored which used to hurt in the early days. But in hindsight, rejection allows you to refine and realign yourself for better opportunities that you’re prepared for.
Contact Info:
- Website: https://www.behance.net/jerrellriley
- Instagram: https://www.instagram.com/riley_wa/
- Linkedin: https://www.linkedin.com/feed/


Image Credits
Portrait Image of myself must be credited to The JOY Company Limited

