Rhesa Lessey

Rhesa Lessey

In the podcast episode we speak with Rhesa Lessey founder of Things TT. She shares how she started and grown a marketplace for small to medium sized businesses. Her love for all things Trinidad and Tobago, technology and sleep.


How do you define creativity and what does it mean to you?

Creativity is the ability to express your imagination and emotions through one or many art-forms.

How much of your creative ability do you think is innate? Or is your creativity a skill that you have developed?

Most of my creative ability is innate, but growing up I did do a short course in graphic design which has helped me a lot today.

When did you realise that you wanted to express your creativity? Was it encouraged by others (e.g., parents)?

Maybe at the age of 4 years old? I would always paint and draw growing up. I would tell my parents I wanted to be an artist.

What is your standard for evaluating your creative work and the works of other people? Do you think that monetary rewards can be compatible with creativity in general? Are financial rewards relevant to your projects?

I believe art is subjective, but I do believe that art should make you feel something, whether that feeling is happiness, sadness, enlightenment, etc.

I do believe that monetary reward is compatible with creativity. The world is full of Warhol's, Picasso's and Kanye's!

If people didn’t care about my service I would feel less motivated to pursue

Do you think the views of other people influence your perception and evaluation of your creative endeavours? What role do you believe the culture that you live in plays in your creative efforts?

People, environment, culture, they all influence perception and evaluation. If people didn't care about my service I would feel less motivated to pursue it. That doesn't mean I would stop but validation is important.

The current culture of Trinidad and Tobago has influenced me, but my desired impact on our culture plays an even bigger role in my creative efforts. I want people to know how amazing Trinbagonian entrepreneurs are, which is why I continue to host Things TT year on year.

Does your creative work come easily or do you struggle with your ideas? What obstacles (if any) do you experience when you are creating? If you do face obstacles, how do you get past them?

I do struggle, there is no telling when, where or how inspiration will come to you. When working with a timeline it's a big struggle if those ideas aren't flowing the way I need them to. During those times I try to be kind to myself. I watch TV. I read a book. I take a drive. I colour. Last year I actually spent a lot of time in my adult colouring book and it helped a lot.

My first draft is never the final product

Is there something that you do to put yourself into a creative state of mind? If so, what? How do you make the leap from a "Spark" in your head to the action you produce?

Like Nike, I just DO IT! I think you just have to start. My first draft is never the final product so there is no harm in simply starting whatever project is on the table at the time.

Was the way you express your creativity now always your ambition? If so, when did you know for sure?

The way I express my creativity changes ALL THE TIME. I've tried drawing, painting, graphic design, fashion design, blogging, entrepreneurship, adult colouring- the list goes on.

Which creative people do you admire? Why?

Sue Tsai, is a young talented New York artist with a strong business sense. A lot of her talent was innate but her ability to scale her art and make it a huge business empire is inspiring.

Who or what has helped you to persevere and not quit?

The Things TT vendors, every call, email or WhatsApp message I get asking "When is the next market?" motivates me.

Do you believe that it is essential to be accepted by others as being creative or is just doing what you love to do enough to justify your work? Explain.

It depends on your goal if your profession revolves around your creative outputs you have to decide to either serve your niche or tailor your product without sacrificing too much of yourself to meet the needs of a bigger market.

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Has rejection ever affected your creative process? Explain.

Of course. Rejection is a negative feeling. At first, it slowed me down, but ultimately it caused me to reflect and revise my plans for the better.

Have you ever doubted your talent? If so, how did you work through your doubt?

Of course, rejection and disapproval have caused doubt, but that doubtfulness has been important to help me revise my plan or become more confident in it.

What piece of work are you most proud? Why?

My markets and the ability to hold them consistently since 2013 despite any challenges that may have come my way.

What is your ultimate creative goal and how attainable do you think it is?

To continuously learn new ways of expressing my creativity. I think this is attainable once I keep an open mind and invest in myself.

What is the best advice you've received that helped you move forward on your creative journey?

Input = Output

To a young Creative emerging in your field, what advice would you give them?

You have to spend time investing in yourself to be the best and this needs to happen on a continuous basis.

For what would you like to be most remembered?

For being completely invested in anything I do. I never want to be partly invested in anything I do.

If you were a crayon, what would be the name of your colour?

Rose gold!


We thank Rhesa for stopping by it was great chatting with her. Go follow her and do visit one of her market events. Find more info via Facebook, Instagram and Twitter or her website.


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A Creative Professional with over twenty years experience. Which he gained during his time spent at a few of Trinidad’s top advertising agencies. Then functioning as the Regional Creative head of the Caribbean’s largest retailer. Contributing to the development of the group’s regional marketing strategy. Forming the regional Design Strategy. Conceptualisation and execution of all creative, marketing and advertising communication for the group’s brands. With oversight of regional and local creative teams and creative processes. He continues to sharpen his creative edge. A passionate, twenty-four hour creative junky. Admirer of sexy typefaces, lover of words and aspiring life long learner. He is also the founder of A BigBox Of Crayons. An online and offline community for creative thinkers + makers in Trinidad & Tobago.