JEAN SHEPPARD

Are you contemplating retirement?

The prospect of retirement can be exhilarating. With fewer responsibilities and more control of our time, we may envision long days of leisure and pleasure. 

For many of us, however, that novelty all too soon wears thin. We may feel unmoored without a deep sense of purpose or lonely without compelling social engagement. We may crave opportunities to share our talents and skills, to offer what we know and believe to those who follow. Financial resources and good health are very important to a rewarding retirement, but perhaps even more important is a ‘growth mindset’ that ensures we flourish in this stage of life—in ways we might not even anticipate. 

An effective coach starts from the assumption that the client is creative, resourceful and whole and asks powerful questions that open up fresh ways of thinking and bright new possibilities. For example, what stories you have told yourself about who you are? Do these stories enhance or restrict the life you want to live? How can you free yourself to make meaningful change? What kind of planning will serve your goals? As the writer Antoine de Saint Exupéry observed, “A goal without a plan is just a wish.”

My name is Jean Sheppard, and I’d like to be that coach for you. My training and experience have equipped me with the skills to help my clients embrace the opportunities offered by this unique period of their lives. 

We’ll start from where you are and figure out, through stimulating and conversations, 

where you want to go and how to get there.

Here are some other questions we might be asking ... 

What I bring to the coaching process …

When I was sure I would be young forever, the times themselves encouraged me to act on any and all calls to adventure. I worked in public relations in London, England, studied acting at the Neighborhood Playhouse School of the Theater in New York, and earned a diploma from the Swedish Institute for Massage Therapy, also in New York. I held a variety of jobs in Canada: I was a correctional officer in a minimum security prison for young men, a waitress, and a legal secretary, and, briefcase in hand, I briefly sold telephone security systems to small businesses (well, one—no plaques for me). I kept hoping I would find a vocation. I am grateful that, ultimately, I did.

In 1986 I began a long and very rewarding career at Havergal College, an independent school for girls in Toronto where I taught academic English, media studies and dramatic arts while earning a Master of Education from the University of Toronto. When I left teaching, I created Saying It Forward to help people give the future a present. I also received a Master of Fine Arts in Creative Writing from the University of British Columbia and completed professional coach training with Adler Learning and the Certified Retirement Coach organization.

Whether we meet in person, by phone or online, I believe that all my experiences have prepared me to help you create the life you want.