We’re used to hearing about retirement as a finish line – a moment to step back, slow down, and fade quietly into leisure. But for a growing number of people, the prescribed retirement age isn’t a deadline, it’s a doorway. In this series, we’ll meet the people who are rewriting the script on aging – and ultimately proving that sometimes, the most meaningful work begins when everyone else thinks it’s time to stop.
Paul Doyle, 76
Owner of The Crane, a Historic Caribbean Luxury Resort
HOME BASE: Barbados
CLAIM TO FAME: Canadian entrepreneur turned Caribbean hotelier who set up shop on one of the world’s best beaches.
HUMBLE BEGINNINGS: My background was quite working class: my dad was a factory worker in Toronto and my mom raised two boys at home. We watched what we spent, and bought two-day-old bread because it was less money. But no complaints, it was wonderful.
THE PIVOT: I went to university for psychology and I was teaching – I thought that would be my career. Then a friend introduced me to a business that could be run during school holidays, and I enjoyed being a small-time entrepreneur. Later, I started a reinsurance business in Barbados and moved my family there in 1988. That same year, I heard that a historic hotel, built in 1887, was for sale on the southeast coast of the island. The Crane Hotel was only 18 rooms then – now there are 306 – and I didn’t pay much for it. The down payment came from the sale of my Toronto house.
SLOW GOING: One night we literally had zero people staying here; it was a struggle. But I knew I had an amazing site: 40 acres [16 hectares] on the sea and this gorgeous Crane Beach, with the sounds of the waves and the fresh air and breeze coming off the Atlantic. Back then there was a TV show, Lifestyles of the Rich and Famous, and they rated it one of their Top 10 beaches in the world. So we had that.
SALES PITCH: To raise money to grow, I brought in three experienced timeshare salesmen. But we’d spend half of the money we’d make on marketing, including gifts to people who agreed to listen to the presentation. And the sales were pretty slow. One weekend, a guest wanted to talk about the time-share program, but none of the salespeople were available. So it was left to me to explain how it all worked. That’s when it occurred to me to say, “Listen, I’m the owner. I’m not going to pay out a commission and haven’t given you a gift to listen to me. So if you buy anything today, it’s half price.” An
hour later, he bought the rights to four peak season weeks, our biggest sale ever – and later that day another couple staying at the hotel approached me about the same deal. A new business model was born and we haven’t changed it in almost 30 years.
MILESTONE MOMENTS: So many of the Barbadian old-timers who I’ve met had their honeymoon at The Crane or got married here. And I really believe we have a responsibility to celebrate the history – so we’ve stayed true to architectural features like coral walls and timber frame ceilings and decorating with mahogany furniture as was originally done.
FRESH PERSPECTIVE: With our newest property, East, about 20 minutes from The Crane, we don’t have that historical mandate. The architecture is very modern: huge floor-to-ceiling windows, panoramic ocean views, private pools for every residence, flat roofs ready for solar panels, an apiary. It’s in a former fishing village and we buy fish from the community. One woman who still takes her boat out lives in the house just before you enter the resort. The guests know her, everybody waves at each other, it’s just part of the culture.
DREAM WEAVER: Someone once said, if you love what you do, you don’t work a day in your life. I live and work in my bathing suit and T-shirt, no shoes. I’m in paradise. –As told to Shanda Deziel
A version of this article appeared in the Feb/March 2025 issue with the headline ‘The Non-Retirement Plan,’ p. 30.
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