Sheilagh Robertson was stumped when she was asked to envision her retirement.

She had been running The Harbourmaster, a speciality luggage and leather goods store in the Washington Mall, for 43 years. It was hard to imagine what she would do if she left the business.

“I joined Ignite’s business accelerator programme last year because I wanted to develop an exit strategy,” the 73-year-old said. “It is not crucial that it be done immediately, but it is definitely something that I have to do. I have been talking about retiring for the last ten years, but never really done anything about it.”

She came up with three things she wanted to spend more time on: her four grandchildren, travel and her passion for theatre.

“I don’t want to say the name of it just yet but rehearsals have started for a play that will be opening at the Bermuda Musical & Dramatic Society shortly. It will be serious after the fun of the pantomime.”

Growing up in Canada she was always interested in acting but never really got into it until she turned 40.

“Forty is a big year,” she said. “You are no longer a youngster any more. You have to think about the next phase of your life. I have always been involved with music. I played the flute with the Bermuda Philharmonic Society but I had never done any theatre. In 1989, I took a workshop in theatre put on by the Department of Community and Cultural Affairs.”

She got her first role in 1996, in BMDS’s production of Joseph Kesselring’s Arsenic and Old Lace as Martha, a barmy, elderly woman, partly responsible for murdering an old man. Her next role was Queen Hecuba in the Greek tragedy, Trojan Women.

“With that one I missed my cue to go on stage,” she said. “I don’t know what happened, but someone elbowed me to remind me. Fortunately, my line as I came on was, ‘Oh, I’m sorry I have been so long!’”

She also tried her hand at writing. In 2014, her play Too Many Elephants was accepted into Famous for 15 Minutes, BMDS’ annual competition. That gave her her first taste of directing.

“My actors were looking at me and I was looking at them,” she said. “I realised I had no idea how to direct a play.”

But she muddled through.

Her early years were spent in a field far removed from theatre. She studied bacteriology and immunology at the University of Western Ontario in Canada. It was there she met an economics student who became her husband, Gerald Simons. The couple celebrated their 50th anniversary last year.

After graduation she found a job as a lab technician but visited Mr Simons in Bermuda, several times.

In September 1971 the couple were in Bermuda waiting for her to board a flight back to Canada, when they bumped into Frederick Furbert who was then the principal of the Berkeley Institute.

She mentioned her science background and Mr Furbert, short a teacher one week into the school term, offered her a job on the spot.

“I had never taught in my life,” she said. “But my mother and sister were teachers. Maybe it was in the blood.”

She had one more week of vacation due to her so she agreed to try teaching for that amount of time.

“By that time my luggage was already on the plane,” she said. “I couldn’t get it back. I only had a carry-on with me with two outfits. It made for some interesting outfits, my first days teaching. I did get my luggage back after three days.”

She was inspired to start her own business after attending a brief workshop on entrepreneurship and gave up teaching after three years.

“I thought that would be a good idea,” she said.

She called her shop The Harbourmaster, because that was her husband’s nickname for her because she loved watching boats in Hamilton Harbour.

She opened the store in March 1975 on the upper level of the Washington Mall but moved downstairs to her current location after a short time. Her ambition was to fill a gap she saw in the local market for moderately priced leather handbags and luggage.

“There were really inexpensive handbags and designer handbags, but not a lot to offer in the middle,” she said.

As much as she loves the business, she does not have a large collection of leather handbags at home.

“I have one bag that I use,” she said. “I just can’t be bothered to be changing my purse all the time to match my outfit.”

Not being able to go to trade shows during the global health crisis has been hard.

“We are coming out of the pandemic and things are looking good going forward,” she said. “The pandemic meant I had to adapt and learn to do more things online. I’m not very good at that.

“I have had to deal with catalogues being online. They are good up to a point but it is not as good as feeling a product or trying the handbag on your shoulder to see if the straps are the right length.”

She was born in England. Her father, William Robertson, was Scottish and her mother, Marion, was from British Columbia, Canada. When Ms Robertson was seven her family moved to Arvida, Quebec, a small town 100 miles north of Quebec City.

“My father was a chemical engineer,” she said. “After that we moved around a lot. I went to many different schools in Canada.”

She and her husband have two sons, Duncan and Andrew Simons.

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