About Me

My name is Jean Sheppard, and here’s 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. After I left teaching, I received a Master of Fine Arts in Creative Writing from the University of British Columbia. I also trained at Adler Coaching in Toronto and, not long after, was certified as a retirement coach by the Retirement Coaches Association, based in the United States. I offer individual and group coaching and workshops online.

Whether we meet by phone or online, I believe that all my experiences have prepared me to help you make the changes you want.


Jean Sheppard is that rare find:  a compassionate soul who pays careful attention to her clients’ needs, gently encouraging them to clarify their thinking and question their self-limiting assumptions.  Her outstanding listening skills and strong desire to assist have helped me to tease out a better way of handling some of my problems, and I am deeply grateful to her.

Jo Meingarten 
Writer and Editor

I am in awe of Jean Sheppard’s ability to pose questions that provide a diving board into a pool of fresh ideas. Right after our first session, I decided to start a journal while so much of our conversation was fresh in my mind and I was energized about it all.

Sindy Shetzen
Mathematics Teacher

Jean Sheppard is an exceptional coach who was extremely helpful to me when I was transitioning into retirement. She is thoughtful, insightful and respectful and has a knack for asking the right questions, which allowed me to explore my future options in a more expansive way. I highly recommend her as a very skilled coach and/or mentor.

Kalman Green
Management Consultant

“The real voyage of discovery consists not in seeking new landscapes,

but in having new eyes.”  

Marcel Proust