Becoming an Entrepreneur Later in Life

By Joyce Wayne

When I was much younger, Freedom 55 advertisements encouraging retirement were everywhere. Early retirement was all the rage, but even back then, while imagining an early retirement, I was concerned that I wasn’t suited to “doing nothing.” Today Freedom 55 is almost forgotten as increasing numbers of older Canadians are launching their own businesses instead of retiring. Entrepreneurship is a growing trend as baby boomers discover how rewarding a second career can be. A study by CIBC illustrates that the propensity to be self-employed increases with age. Between 15 and 54 years of age, wanting to start a business climbs slowly until it hits 64 years of age, and then the desire to be your own boss increases dramatically.

During the month of October, thousands of small business owners come together for the annual celebration of entrepreneurship. Business people take advantage of events, seminars, resources, and other opportunities as they celebrate, learn, and network with other entrepreneurs and small businesses. It’s become the time of year to recognize and laud the significant contributions of entrepreneurs and small businesses to local communities, provinces, and the entire Canadian economy.

This week I spoke to Allan Dale, who is firing on all cylinders as he grows his consulting business. For Dale, Freedom 55 translates into new careers, inspirational experiences and an active and successful life while ageing.

From his rural home in Prince Edward Island, Dale runs two companies; the first is Bespoke Consultancy Services, which launched in January 2020. He describes it as the place to “take your ideas and creations and connect them with other like-minded people.” Dale says he “likes to make connections,” and I can understand why. He’s energetic, affable and inventive. His second business, Gale Force Wins, launched a year later in 2021. It’s a popular media and podcast content creation company that Dale operates with his long-time buddy Gerry Carew.

Before starting his business, Dale was in the Royal Canadian Navy for 30 years. He exited nine years ago to join the University of Prince Edward Island, where the university’s President was setting up an innovative engineering partnership that connected directly with the engineering industry. Dale spent four years at PEI’s School of Engineering. He found all 75 clients for the placement program across the globe, everywhere from Pakistan and Nepal to the E.U., where students travel to gain hands-on experience in their profession.

While at the university, Dale attended a leadership seminar. The keynote speaker was Lisa Taylor, the head of the Challenge Factory. This consultancy firm helps organizations and communities shape the workplace of the future. Taylor spoke eloquently about the future of work, and Dale remarks he “felt as if Lisa was speaking directly to me.” Consequently, he enrolled in Taylor’s program, after which Dale knew he could become an entrepreneur and that he would launch his own communications consulting business. He exited the Challenge Factory program with three clients of his own.

“My sweet spot is making the connection,” says Dale. With his consulting company, Dale often introduces companies to where technological advances in their field have developed and helps them to make that leap. Primarily he helps “organizations who want their products accepted by a broad audience, but do not have the resources to tell their story compellingly,” adds Dale.

With his media company, Gale Force Wins, he and Gerry Carew, in one and a half short years, have recorded 135 podcasts, each focused on inspiration. If you tune into the podcasts, you’ll hear inspirational stories from everyday people who accomplish remarkable feats. They do good things. The podcasts are emotionally-driven stories about real people who touch your heart and can provide the courage and drive you might need to take risks and accomplish new goals. There’s a folksy quality to these podcasts that’s hard to beat.

Dale believes that growing dependent on a weekly paycheque can “beat the risk out of people. It starts as early as grade school,” he says. “I believe in people who believe in themselves.” Dale’s recommendations to those thinking about launching their own business are:

  1. Figure out what you are good at and what gives you a good feeling.
  2. Articulate that and share it with the person you trust the most.
  3. Make a list of 50 people you could talk to about your idea.
  4. Get going and let your vision take you on a journey.

When our interview concluded, I was already pitching my ideas to Allan Dale. He exudes the entrepreneurial spirit and makes it sound easy, even if it takes, as Dale himself exemplifies: brains, fortitude, and an adventurous spirit.

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