Professional Life Coaching

Do you ever get tied up in knots?

  If you do, you’re not alone—life can be very complicated. So how can you free yourself to make meaningful change? One way is to work with a professional life coach whose training and experience equip her with the skills to help clients move forward in their lives. A 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.

My name is Jean Sheppard, and I’d like to be that coach for you. 

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 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?

One’s destination is never a place but,
rather, a new way of looking at things.

Henry Miller


What can you envision?

Creative thinking inspires ideas.
Ideas inspire change.

Barbara Januskiewicz


Want to be more creative?

 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. I am a member of the Retirement Coaches Association, which is based in the United States. 

Whether we meet in person, 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