Making the Most of Your Second Lifetime

Are you making the most of your second lifetime?

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. 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 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?

“The real voyage of discovery consists not in seeking new landscapes, but in having new eyes.”




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