Episode 37

Diane Hessan: On Creating More Serendipity and Improvising Your Way Through Life (#37)

Diane Hessan is a nationally recognized entrepreneur and expert on the American voter. Her new book, Our Common Ground: Insights from Four Years of Listening to American Voters, will be published in June and is available for pre-order now. Her work has been featured on CNN, NPR, The Wall Street Journal, The New York Times, Forbes, Fortune, and includes more than fifty columns for the Boston Globe.

Diane is the founder and Chairman of C Space (formerly Communispace) and is a well-known disruptor in the market research industry. She serves on multiple boards and has been appointed to the Boston Globe’s editorial board. Her many honors include the Most Admired CEO award and Boston Power 50 awards from the Boston Business Journal, and Ernst & Young’s Entrepreneur of the Year.

In this episode, we talk about how serendipity has played a leading role in her success journey, and how to create more opportunities for serendipity to occur in our own lives. We discuss the power of saying Yes more often, the nature of taking risks, and how she learned early on to improvise her way through life.

We also discuss her upcoming book, and how there is more common ground among American voters than they get credit for.

About the Podcast

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Cool Change
Embrace Life Transitions with Purpose and Joy

About your host

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Chuck Allen

Chuck Allen is the host of Cool Change, a podcast for thoughtful humans navigating life’s transitions with intention and heart.

Drawing on decades of coaching, leadership, and lived experience, Chuck helps listeners design lives that feel more aligned, adventurous, and meaningful. Whether exploring personal growth, career shifts, or new chapters in relationships, Chuck brings a warm, reflective voice to conversations about change — and the possibilities it unlocks.