Heston Kessell is used to learning outside the lines.
Today, he is a senior at the University of Guelph in Canada, completing an honours degree in economics.
Next year, he plans to take another step abroad with a master’s programme at the University of Bristol.
It is a confident plan, but his route to this point was never predictable.
Mr Kessell, 23, grew up in Bermuda and spent his high school years in a small homeschool community. Depending on the year, the group had about 15 to 20 students. Their days were structured but compact, typically running from morning until about 1pm. Lessons were built around workbooks or online programmes, followed by independent learning and whatever else the afternoon had in store.
For young Heston, that rhythm mattered. It created space for him to flourish.
Homeschooling was not framed as an experiment in being different. It was a practical decision rooted in care and realism.
“My mom just wanted me to have the best education possible,” he said. “Private school wasn’t an option for us, so she tried to explore all the alternatives.”
A couple of his friends were already in the homeschool group and spoke highly of it
“We decided to try it and just recognised that if it didn’t seem like a good fit, then we could always make a change,” he said
It worked. Even so, Mr Kessell does not romanticise it.
“There were probably some social aspects of a traditional school experience that I missed,” he said.
“The homeschool group was much smaller than any other school, so naturally I was around a smaller pool of people every day.”
But he does not describe those years as isolating.
Exploring interests
“Despite that, I made great friends both at the homeschool group and at other schools.”
The biggest gain was having agency over his own learning path. “I was always naturally curious and motivated to learn on my own,” he said.
“The extra time outside of school let me explore my own interests in topics like computer programming, which ultimately became very useful later on.”
When he switched to Bermuda College, the adjustment was not the shock people might expect.
“I think homeschool somewhat prepared me for Bermuda College, as they both require a lot of independent learning,” he said.
While he was there, he found a pathway into Bermuda’s international business world.
“I stumbled into the ILS Bermuda College Initiative and got my first exposure to Bermuda’s international business sector,” Mr Kessell said.
“It was through that programme that I learned about all the opportunities to work in re/insurance or professional services and set my sights on trying to enter that world.”
He also realised that finishing my degree overseas was a real option.
From there, he started making choices with transfer in mind. “Academically, I tried to choose courses at Bermuda College that I knew would transfer into an overseas program,” he said.
“Since I didn’t go to a normal high school and didn’t have standardised exams like GCSEs, I was also relying solely on my Bermuda College transcript to apply to universities.”
He also credits the college’s practical guidance in walking him through their articulation agreements with other schools.
Scholarships made the move possible, and he did not leave that to chance.
“Initially, I worried that my non-traditional educational background might put me at a disadvantage in scholarship applications,” he said.
“So, I focused on distinguishing myself in other ways, mainly by showing consistent initiative and engagement with the insurance industry, which was offering the scholarships.
“Once I knew the path I wanted, I fully committed to becoming an ideal scholarship candidate. Any free time I had outside of college or work, I used to attend networking events or study to complete insurance designations, like the associate of reinsurance.”
He also built relationships deliberately.
“Whenever I met someone, I made a point of following up with a short thank-you note and a LinkedIn connection request,” he said.
“A mentor’s advice also led me to start working towards professional designations, which really helped mark my dedication to the industry.
“By the time I applied for scholarships, I had managed to finish two professional courses that I could add to my resume.”
He does not tell the story as a solo effort.
“I’ve been helped by a lot of people along the way, and I wouldn’t have made it half as far without their advice and guidance,” he said. “I try to show that gratitude and to stay intentional about building and maintaining relationships.”
Economics – which became a passion at Bermuda College – has remained the centre of the story at university.
“I had an incredible economics lecturer, Craig Simmons, whose lectures helped transform my interest into something deeper,” he said.
“My conversations with Craig showed me that economics is a field uniquely good at developing paradigms and mental models for evaluating scenarios and making optimal decisions.”
Paying thanks
Mr Kessell reflected on the support of his family and community, particularly Bermuda College, the ILS Bermuda College Initiative, and Bermuda Foundation for Insurance Studies.
He added: “I’d also like to thank Ernst and Young, the Association of Bermuda International Companies, and L&F Indemnity Limited for their generosity and support through scholarships. Without their support, I wouldn’t be in university today.”
Mr Kessell’s education journey may seem unique in our little island of Bermuda. But perhaps it should not be. Perhaps other students who struggled in the traditional classroom, or those labelled “problem students,” might have had a better chance of succeeding if they had been offered the same kind of option.
There is a moment in a child’s life when they first pick up a crayon with chubby fingers, gripping it in a balled-up fist. Whatever they create, their parents love it. That same child, years later, is scolded for “colouring outside the lines”.
Maybe that is the wrong lesson.
Maybe not all of us were meant to produce strait-laced work that fits neatly into a familiar picture, the yellow sun in the corner, the red cottage in the middle, the green grass underneath. Maybe, like Mr Kessell, the freedom to draw outside the lines is exactly what supports one’s journey on the path to success, not just through school, but into a life that finally fits.
