Professional Retirement Coaching

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 ... 

Retirement may be an ending …

but it is also a new beginning.

Catherine Pulsifer


How will you re-invent yourself?

Daily structure lends itself to purpose,

and purpose means movement.


Mary Blissard

How will you bring meaning

to each and every day? 

Life doesn’t get easier or more forgiving.

We get stronger and more resilient.

Steve Maroboli

What support will you offer

those who follow?

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.


“As your life changes, it takes time to recalibrate … You might also find that

retirement is the time when you stretch out and find your potential.”

Sid Miramontes


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