The words stand out in proud red felt on the collar of Richard Tyson’s high-school shirt – ‘Class of 2008’.

Messages of love and support and professions of lifelong friendship sprawl out in multi-coloured ink across the cloth.

It is 12 years since Tyson, known by friends and family as Richie, self-professed class clown and prom king, collected those exuberant farewell notes on an emotional final day at John Gray High School.

The ink has long gone dry, but his eyes shine bright as he reads the names and remembers.

Prom queen Patricia Simpson finds her own message in the montage.

She reads aloud, “Patty and Richie friends forever. I’ll always be here for you.”

School was a good time for Richie and Patty. Smart, confident and popular with pretty much everyone, they were the glue of their social group.

They went away to college on scholarships and are now back working in Cayman, trying to get their careers off the ground.

But what became of the rest of the group?

Some are running their own businesses, some are no longer with us, some left Cayman to look for opportunity elsewhere.

The post-high school pathways have been as diverse and varied as the handwriting on Tyson’s shirt.

There is the straight-A student who continued her education in Swaziland before going on to become an associate with a big-five accountancy firm in Cayman.

There is the boy with the tattoo, who skipped a lot of his final year. Now he is covered in ink from head to toe, running a successful trucking business.

There is the teen-mom, whose boyfriend was murdered just after high school, now encouraging her son through his own journey at John Gray.

Others have had more typical experiences, navigating the challenges of college, finding jobs and trying to get by at a time when the cost of living in Cayman is higher than ever.

Richard Tyson (right) and some of his classmates at John Gray in 2008.

In some ways, the experiences of this group, all now approaching 30, illuminate the challenges, the failures and successes of ‘the system’ and how, as a country, Cayman educates, develops and finds opportunities for young people.

Exam results – so often the barometer of success and failure for a school system – can only tell us so much.

What they can’t tell us is how many graduates went on to get good jobs, how many own their own home, how many became good parents, good friends, good citizens. How many are struggling to make it. How many are thriving in modern Cayman.

We reached out to Richie and Patty to help us track down some of their fellow John Gray graduates in order to tell a fuller story about education and opportunity in Cayman through the eyes of one class.

Click on the picture below to read their stories in full..

High-school royalty

Even for high-school royalty, making your way in the adult world is daunting and filled with challenges.

Both Tyson and Simpson were good students. They had strong parental support, got decent grades and were involved in the social and extracurricular life of the school.

Simpson remembers being surprised and honoured to be voted prom queen by her peers. It was not about being the top student, she recalls, it was more about getting along with everyone, being helpful and kind, and mixing comfortably with the different groups in the sometimes cliquey atmosphere of school.

Tyson, too, says he moved in many different circles and was focussed as much on making jokes and making friends as he was on academics.

Richard and Patricia in school

Both went on to the University College of the Cayman Islands and then received government scholarships to pursue higher education overseas.

Tyson got a degree in earth science and geology from the University of North Carolina and then won the prestigious Chevening scholarship, through the then Foreign and Commonwealth Office, and completed his master’s degree in environmental engineering and project management at the University of Leeds.

Simpson completed her associate degree in business administration in Cayman and a bachelor’s degree in management at Webber International University in Florida.

Life after college

Returning to Cayman after school was more difficult.

A recurring theme among the students who spoke to the Compass for this feature is the challenge of finding work in their chosen fields that matches their qualifications.

Tyson is grateful for the financial support he received to pursue his education. But he believes students on scholarships need more support when their studies are over.

“When I came back home, there was no job in my field,” he recalls.

“Everywhere said you need X years experience, but there is no opportunity to get that while you are away studying.”

There is a disconnect, as he sees it, between the scholarship investment made by Cayman in his education – which carried a condition that he return to the island to work for at least two years – and the comparatively little attention that was paid to where he might work and what he would do.

Prom queen and king, Patricia Simpson and Richard Tyson, 12-years-on. Photo: Alvaro Serey

He persisted with both his studies and his career ambitions and is now working in a somewhat-related field as an engineering technical officer at the Department of Environmental Health. He also runs his own events company, RoadLife Entertainment.

Career frustrations

Tyson believes these difficulties are common for young people coming back to Cayman, often with advanced degrees.

He said many were left wondering if it had been a waste of time and effort to study so hard, for so long, only to face knock-back after knock-back. He recalls the frustration of interviewing for positions, only to discover the job had been advertised for the purposes of renewing a work permit.

He believes government could do more to help returning graduates on their career paths.

“If government pays for someone to train as let’s say, a zoologist and they come back and work at a bank, I believe that is a disservice, not only to the government and the person returning, but also to the island as well.

“You have to protect that investment and make sure graduates have every chance to utilise that training.”

Even as he and his former classmates enter their 30s, he believes many of them are struggling to move up in their careers, despite having advanced qualifications.

“Unfortunately, there is no real succession planning or paths to promotion within jobs in Cayman in general,” Tyson says.

“You go away to school, you get good grades and advanced degrees and you see people getting further because they know the right person or they have been working there longer. Sometimes you wonder if it was worth it.”

He has seen friends in similar situations become disillusioned and leave the island to seek opportunities overseas.

Simpson can relate to that.

“When I returned home, my experience was hard,” she admits, “It was really difficult to find the job that you studied for.”

She eventually pursued an opportunity in a different area and now after a decade of work, including an six-month stint in England, has found her niche as a human resources manager.

“I am finally in a good place,” she says.

Her career has put her on the other side of the fence – looking at resumes and considering who to hire. and she enjoys the chance to advise and counsel others going through the same challenges that she experienced.

If she could advise her younger self, it would to be patient, to take what chances present themselves and build from there.

“This is the beginning of your career. You have to start somewhere,” she says.

Moving out of home

Finding a job was one challenge, financial independence and personal freedom was another.

Many of the former students we spoke to still lived with their parents.

Some told us they believed the idea of owning a home was not a realistic goal for their generation.

Simpson just moved out of her family’s home last year. She considers herself lucky to have parents that could house and support her as she struggled with the expense of living in Cayman on the relatively low wages of a young graduate.

Tyson faced a similar situation.

“You want freedom but you can’t afford it, right out of college,” he says. “It’s not happening.”

Friends reunited

A lot has changed since high school, but the pair, who remain friends, are still the social glue of their group.

When it came to organising the 10-year reunion, it was Tyson who took on the challenge of bringing everyone together.

The Class of 2008 at their ten-year reunion.

He enlisted the help of Simpson and a few others and they booked out Ristorante Pappagallo.

Around 150 people showed up, and some Skyped in from England or Spain.

The event was poignant because of the friends that had been lost along the way. A handful of classmates, including Tyson’s best friend Jordan Anthony Ebanks, have died in the decade since graduation, most of them in car accidents.

The reunion was a chance to pay tribute to them as well as to reconnect with old friends.

“We were just all happy to see each other again,… to kind of party together, eat together, catch up,” says Simpson.

It was surprising, says Tyson, to see where everyone had ended up and what paths their lives had taken.

There were plenty of success stories and a few hard-luck tales as well.

Despite the hardships they have overcome, Tyson and Simpson know they are among the lucky ones.

They have had friends who have struggled with employment, education and housing, who haven’t had strong families to fall back on.

“I’m fortunate enough to be where I am. But that’s not everybody’s situation,” said Simpson.

“I just hope that those that are struggling can get that support they need.”

Support local journalism. Subscribe to the all-access pass for the Cayman Compass.

Subscribe now