Dwayne Holness
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31 March 2026, 9:00 AM·0 of 8 min read·
EntrepreneurshipThought Leadership

The Doors That Changed My Life
Were Windows of Opportunity

The doors that changed my life never looked like doors. They looked like last-minute phone calls, unpaid favours, and flights I didn't book for myself.

The doors that changed my life never looked like doors. They looked like last-minute phone calls, unpaid favours, and flights I didn't book for myself. Every major turn in my career came from something I almost didn't recognize in the moment.

I call them windows of opportunity. Moments where things align, a door cracks open, and it's on you to see it and step through. Most people miss these moments because they show up looking ordinary. A favour. A phone call. A last-minute ask. But behind that ordinary moment is a view so vivid it changes how you think about what's possible.

The camera was the key

One of the first people to believe in me was a rapper named G-Swag. Early days. I was still figuring things out with the camera in Jane and Finch. G-Swag kept coming to me for music videos. His views climbed. Other artists noticed. And suddenly everybody wanted a "Dukeydukez" video.

That recognition was fuel. But G-Swag gave me something bigger than reputation. He flew me to Cuba. Based on nothing but my skills and my camera.

Coming from Jane and Finch and jumping on a plane to Cuba had never happened in my life. It wasn't a vacation. It was proof that the thing in my hands could take me places I'd never been. That a skill, combined with showing up, could open doors that money alone couldn't buy.

And here's what I want you to sit with: I didn't have the biggest equipment. I didn't have everything figured out. I had a little camera and a vision. That's it. You don't need the biggest tools. You don't need all the answers before you start. Use what you have. Get creative with it. Make magic. That little camera, the same one people would later look at and say "that's it?", that camera changed my life. That camera made Dukez.

Beenie Man came to Jane and Finch

Around 2009, Beenie Man came to Toronto for a music video. I got invited to the set as a spectator. I watched how the top directors worked and told myself, man, I hope to get there one day.

But I wasn't just watching. I was connecting. I ended up talking to Beenie Man himself. He had an artist named Versatile who needed a video. I had the resource to give him one. Versatile only had a couple days in Canada.

The next morning, I drove to their hotel. We crammed into a Benz SUV, not enough seats for everybody. It reminded me of Jamaica, the essence of family and community. We drove to Jane and Finch and the whole community was outside. Waiting. Welcoming them. We shot in Driftwood. Everybody wore High Class t-shirts. Beenie Man wore one. Versatile wore one. International artists supporting what we were building locally.

After so many times the news would paint us as a bad community, this was a moment that showed what Jane and Finch is made of.

That shoot led to a phone call. Versatile wanted me to fly to Jamaica to shoot a video. That one trip unlocked four to five visits a year. I met Junior Reid, Popcaan, Busy Signal, Sizzla. My videos ended up on TVJ, Jamaica's top channel. My work was playing on national television in the country I was born in.

My camera wasn't just a tool anymore. It was a bridge. Back to my family. Back to my roots. And forward into a career I hadn't imagined.

The overnight edit that changed everything

Fast forward to 2019. My cousin Chronixx, who'd become one of the biggest names in reggae music, had brought me on tour with him. His tour manager also managed Lauryn Hill.

One day I got the call. Lauryn Hill's team needed a tour promo video re-edited. The previous version was rejected. When did they need it? Tomorrow.

Tomorrow. I almost fell out of my chair.

I took the files. Hours of footage. I put my headphones on, turned the lights down, sat up straight, and went to work. Editing like that is a puzzle. You stare at all the pieces with no idea how they fit. You lean back. You stand up. You listen. And eventually, the pieces start to flow. I sat at that desk for eight hours straight.

The next morning, I delivered the file. A few hours later: ping. Lauryn Hill loves the video.

She posted it. Tagged me. Everything changed. People from everywhere were reaching out.

A week later, another message. Lauryn Hill would like to take you on tour.

I showed up to edit one video. Now she wanted me on the road.

You never know what doors will open if you keep showing up.

Sight versus vision

There are two types of people. The one who has sight and the one who has vision. The one with sight sees things for what they are, looks at what's already done. The one with vision sees the window, opens the door, and creates a whole world in their mind of what's possible. That world guides their direction and every decision they make.

I think about my friend Jordan Oram. We co-directed a Joe Budden music video together back around 2011. Years later, he got a call from director Karena Evans, who'd landed the opportunity to direct Drake's "God's Plan." Jordan was brought on as cinematographer. He called me in tears. Watching someone I'd been close with reach that level showed me what raw talent becomes when it's positioned right.

These windows of opportunity don't just open for you. They open for the people around you too. And if you're paying attention, every one of them teaches you something about where your own steps are leading.

The window that bought my mother a house

Not every window of opportunity looks like a stage or a tour bus. Some look like a client relationship that grows past the invoice.

I had a client who was a real estate developer. Our relationship started the way most of mine do, through a project. I was building out his strategy and marketing. But while I worked on his brand, I was paying attention. Learning how he thought about money, property, and building wealth that lasts beyond a paycheque.

One day I told him I wanted to buy my mother a house. He didn't brush it off. He sat me down and told me exactly what to do. Save up sixty thousand dollars. Then come back to him.

So I did. I went quiet, put my head down, and saved. When I came back with the money, he started the process immediately. With his knowledge and connections, he cut what could have been years into a fraction of the time. We closed on my mother's dream home within one month.

That's what happens when you provide value to people who are ahead of you and pay attention while you do it. Our relationship grew past projects. I'd go to his house every Sunday for a haircut and hang out with his friends. I was the small fish. But I showed up consistently. I was reliable. I was hungry to learn. And they saw that.

If that window hadn't opened, I wouldn't have become a property owner as quickly as I did. Today I own multiple single-family and multifamily properties. That first house for my mom was the door. Everything since then came from walking through it.

The calculation

I calculate every window. If I take this opportunity, where does it lead? What doors open from this one decision? What do the next ten steps look like?

A flight to Cuba off my camera work led to Jamaica, which led to TVJ, which led to touring, which led to Lauryn Hill. None of it was a straight line. All of it was calculated. Not in a spreadsheet. In my mind. In my willingness to see the window and walk through.

Within five years of incorporating Corex Creative in 2019, we generated $2.5 million in sales. Every one of those dollars traces back to a window of opportunity I could have missed. A phone call I could have ignored. A last-minute edit I could have said no to. A little camera I could have been embarrassed by.

The windows are there. They're always there. The question is whether you're looking up long enough to see them. And whether you're willing to step through before you feel ready.

Because readiness is a myth. Action is the calculation. And the door won't stay open forever.

Written by

Dwayne Holness

Filmmaker, brand strategist, and creative director. Founder of Corex Creative, a Toronto-based creative media agency building cinematic brand stories for founders and thought leaders.

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