“Don’t wait until you have everything figured out. Just jump off the cliff and build the plane on the way down.” These powerful words from Jonathan Dickerson, CEO, founder, and head coach of New Image Fitness, perfectly embody his approach to entrepreneurship and the journey behind his thriving gym.
At just 26 years old, Dickerson is already living the entrepreneurial dream that many only talk about. What started as a gym born from a simple desire for a personal space to work out has become one of the fastest-growing fitness establishments in Trinidad and Tobago. This journey, driven by passion and perseverance, has been transformative for both Dickerson and his clients.
Growing up, sports were Dickerson’s first love. Whether it was track and field, basketball, tennis, or cricket, he was always the athletic one in class—though he also had a reputation as the class clown. As an only child, he admits he was naturally more introverted, but one person who helped him break out of his shell was his father, the first role model he had.
“My father shaped my mindset. He was always listening to motivational content, always pushing me to be mentally strong and overcome adversity. He built himself up from nothing, and that always stuck with me,” Dickerson recalls.
As Dickerson’s passion for fitness grew, he found inspiration in bodybuilding legends like Simeon Panda and Arnold Schwarzenegger, drawn to their discipline, strength, and commitment to personal growth.
Many of Dickerson’s clients today are entrepreneurs who share their life stories, offering him fresh sources of inspiration.
However, Dickerson didn’t always feel confident in his body. He reflects on a turning point during his adolescence.
“Honestly, what got me into exercising–I think it was getting roasted a lot as a young man, being skinny and everyone telling me, ‘You looking like you on your last day alive.’ So just consistently getting roasted on a daily basis, it kind of woke me up to smell the coffee. I sat down, and I locked in from 13 years old and never looked back since,” he shares.
The concept for New Image Fitness wasn’t born from a detailed business plan, but rather a personal need for a space to train. He recalls how the gym started in his father’s old network marketing space. After receiving permission to place his equipment there, he didn’t realize he would eventually need to pay rent. As he scrambled to make ends meet, the idea hit him: why not charge others for training sessions?
Soon, people began seeing results, word spread, and the gym grew. But it wasn’t until a 2019 cruise trip that Dickerson had his real moment of clarity.
“I was on this cruise, and I saw how life is supposed to be lived, compared to how I was living. That experience flipped a switch. From that moment, I took the business seriously,” he says.
The name New Image Fitness came naturally when Dickerson posted on Instagram asking for name suggestions. A follower’s suggestion, “New Image Fitness,” immediately resonated with him.
But then came the COVID-19 pandemic. Just as he was preparing to expand his gym, he watched as the government announced gym closures. Dickerson had just invested his savings into the space, expecting new clients to arrive the next day. This unexpected setback pushed him to innovate.
“During COVID, I turned into a hustler, so I was motivated, but I did not have the hustler spirit,” he admits.
He created an outdoor training system that complied with the government’s restrictions, allowing him to train four clients per hour in shifts. This innovative approach saved his business, teaching him the power of adaptability under pressure.
Today, Dickerson’s drive is fueled not just by successes, but by the fear of starting over.
“It’s the fear of failure, of not knowing what to do next. I feel like at this age we have to figure things out fast. I want to be the ultimate provider, to set up a future for my family even before they exist,” he shares.
His future plans? To strengthen the internal systems of the gym, focusing on customer satisfaction and retention. His ultimate goal is to expand across Trinidad and Tobago and establish New Image Fitness as a national brand.
For those aspiring to follow in his footsteps, Dickerson’s advice is simple, yet impactful.
“Don’t wait until you have everything figured out. Just jump off the cliff and build the plane on the way down.” It’s this mindset that turned his dream into a thriving movement—and he’s only just getting started.
It’s a lesson he continues to live by—through every rep, every client, and every leap forward.
