Building a good life in Bermuda

  • Headley Stephenson sometimes gets emotional thinking about how far he has come (Photograph by Jessie Moniz Hardy)

    Headley Stephenson sometimes gets emotional thinking about how far he has come (Photograph by Jessie Moniz Hardy)

  • Doting grandad: Headley with granddaughter, Moao

    Doting grandad: Headley with granddaughter, Moao

  • Retired mason contractor Headley Stephenson (Photograph by Jessie Moniz Hardy)

    Retired mason contractor Headley Stephenson (Photograph by Jessie Moniz Hardy)

  • On the job: Headley Stephenson was a mason contractor for more than 40 years

    On the job: Headley Stephenson was a mason contractor for more than 40 years

  • Headley Stephenson was a mason contractor for over 40 years (Photograph supplied)

    Headley Stephenson was a mason contractor for over 40 years (Photograph supplied)


Colleagues teased mason contractor Headley Stephenson when he first formed his own company.

“They said we remember you were wearing sneakers when you stepped off the plane,” said Mr Stephenson, who came to Bermuda from Jamaica in 1969. “In those days, wearing sneakers meant you were poor. They thought they were belittling me, but all of that was a springboard for me.”

Today, it is Mr Stephenson who is having the last laugh. He formed Stephenson Construction in 1981, during a building boom on the island.

He got so many calls from people looking to hire him he felt like a doctor on a ward, going from patient to patient.

“Everyone was calling for Stephenson Construction,” he said. “I was supported by many of the architects. They made sure I had work.”

He said the early days of Stephenson Construction were exciting times for him.

“My business provided jobs for foreigners and locals,” he said. “Today, some people who learnt their trade with Stephenson Construction now have their own businesses.”

But he said he always made sure he was home with his Bermudian wife, Helene, and daughters, Twalisha and Headilene, by 5.45pm. He has always been a family man. On July 16, he and his wife, a retired teacher, will celebrate their 46th wedding anniversary.

If Mr Stephenson got into construction at the right time, he also got out of it at a good moment, retiring four years ago.

“I had a great time in the industry,” he said. “You have little ups and downs, but I think the recession, when it came, has thrown a lot of people off. People weren’t using up the garage to make apartments, any more. They weren’t adding on two little bedrooms.

“All those things dried up. It is a tough time now in the industry.”

He might be retired, but he does not spend much time lounging about. He loves gardening, growing bananas, fruit trees and vegetables — something he did not have much time for when he was in business.

Sometimes he gets a little emotional thinking about how far he has come in life.

He grew up the fourth of eight children in rural Jamaica.

His father, Joseph, was a farmer who planted crops such as coffee and plantains, and his mother, Mary, was a homemaker.

“It was struggling times with eight children,” he said. “It wasn’t easy. Sometimes I look back at where I am coming from, and it makes me cry.”

He can remember his mother walking a long way into town to sell things in the market.

“Sometimes she’d come back with a shirt or a pair of pants for us,” he said.

But despite his family’s economic challenges, he had a happy childhood. He and his siblings all got along, and still do. “There was no fussing,” he said.

He returns to Jamaica often to see his family. His daughter, Twalisha, now lives there, and he owns the Pink Rock Inn in Ocho Rios, Jamaica.

Mr Stephenson fell in love with construction as a teenager, watching a building go up at school. He was fascinated to see the foundations being dug, and the floor poured.

“When I saw the building finished, it was great,” he said. “I said ‘when I grow up, I would like to be like this contractor man’.”

At 15, he left school, and worked as an apprentice for a mason contractor in the area. In those days apprentices usually did not get paid, but this contractor was kind enough to pay him three shillings a day.

“I saved from the little I got,” Mr Stephenson said.

And he also got a lot of encouragement, not only from his boss, but also clients.

“The boss would take me on a job, and the owner would say, you’re going to go a far way,” he said. “You are so neat. This job looks very, very good. So I got that uplift.”

When he was 25, a friend from Kingston suggested they move to Freeport, Grand Bahama to try to make a go of it in construction. But a few days before they set off, Mr Stephenson talked to someone who had been to Bermuda.

“He said to me that they do a lot of fishing in Bermuda, but not much construction,” Mr Stephenson remembered. “I said, I will try Bermuda. I had never even heard of Bermuda before I talked to that man, but I cancelled my reservation and booked for Bermuda. The friend I was going with to Freeport was very disappointed with me.”

But when Mr Stephenson arrived in Bermuda, he found his new boss did not have much work for him.

“I felt like I was wasting my time,” he said.

After less than a year, he left his first boss and went to work for Gil DeSouza as a foreman for 11 years.

“He saw what was in me, and so started to give me my own jobs,” Mr Stephenson said. “I gained a lot of experience working with him.”

His advice to young people coming into things today is to test the waters.

“Try,” he said. “If you are a good worker, and produce good jobs, then that speaks for itself and people will call you.

“People still call me today. A lady called me today and said ‘you’re Stephenson. Oh, you did some work for me years ago. Part of my ceiling has come down, could you come around and look at it?’.”

He plans to have a look at it for her, soon.

In addition to contracting, Mr Stephenson and his wife ran an ice-cream shop across from TCD in Pembroke for five years. They closed it when it got to be too much.

These days, Mr Stephenson is thankful he is still strong and healthy.

He celebrated his birthday on Friday, with his family.

“I really want to thank my late parents for their support,” he said. “Without them, I wouldn’t be here today.”

He and his wife have one little granddaughter Moao, whom they say is the love of their life.

* Lifestyle profiles the island’s senior citizens every Tuesday. Contact Jessie Moniz Hardy on 278-0150 or jmhardy@royalgazette.com with their full name, contact details and the reason you are suggesting them

You must be registered or signed-in to post comment or to vote.

Published Apr 9, 2019 at 8:00 am (Updated Apr 9, 2019 at 7:37 am)

Building a good life in Bermuda

What you
Need to
Know
1. For a smooth experience with our commenting system we recommend that you use Internet Explorer 10 or higher, Firefox or Chrome Browsers. Additionally please clear both your browser's cache and cookies - How do I clear my cache and cookies?
2. Please respect the use of this community forum and its users.
3. Any poster that insults, threatens or verbally abuses another member, uses defamatory language, or deliberately disrupts discussions will be banned.
4. Users who violate the Terms of Service or any commenting rules will be banned.
5. Please stay on topic. "Trolling" to incite emotional responses and disrupt conversations will be deleted.
6. To understand further what is and isn't allowed and the actions we may take, please read our Terms of Service
7. To report breaches of the Terms of Service use the flag icon

  • Take Our Poll

    • "What is the most significant reason for Bermuda residents choosing to leave the island?"
    • Too small
    • 3%
    • Different way of life
    • 4%
    • Cost of living
    • 77%
    • Gang activity and general crime
    • 3%
    • Jobs/professional advancement
    • 8%
    • Education
    • 2%
    • Attitudes towards gays
    • 3%
    • Total Votes: 5235
    • Poll Archive

    Today's Obituaries

    eMoo Posts