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Jerry Witkovsky


Lifelong Chicagoan Jerry Witkovsky (MSW, University of Illinois) has been a beloved mentor to thousands of individuals and generations of families. This is thanks to 47 years of professional leadership – 18 of them, as general director – of Chicago’s Jewish Community Centers.

In 1995, Crain’s Chicago Business Magazine named Jerry named one of the city’s “Most Effective Nonprofit CEOs”.

Since retiring in 1997, Jerry focused his considerable energies on grandparenting. He loves to help multigenerational families work (and play) together to create a rich family life.
He spearheads annual orientation programs for grandparents in a growing roster of Chicago public and private high schools. Programs are designed to keep grandparents engaged with their grandkids during the crucial teen years. ​

His joyful commitment to his six grandchildren and one great grandchild, and to their parents (aka his adult children) and his passionate belief in the transformative power of becoming a “Teaching-and-Learning” family, is at the heart of his book, The Grandest Love: Inspiring the Grandparent-Grandchild Connection. He takes those ideas a step further and adds a prescription for action in the Grandparent Connection School Kit.


When grandchildren are young, a sweet treat or new toy is enough to inspire their unconditional adoration. And then they become teenagers. Suddenly it’s not so easy anymore, for you or them. Where Two Worlds Meet: A Guide to Connecting with Your Teenage Grandchildren is a new book that gives grandparents a roadmap to stay connected and even deepen your relationship with your grandchildren as you both age. It is an action-focused guide by Social Worker and community leader Jerry Witkovsky and marketer and interculturalist Deanna Shoss. The book provides insight and guidance on how grandparents can better understand life through their teenage grandchild’s eyes.

With the ongoing mental health crisis amongst teenagers, the role of grandparents, a supportive role, helps teens realize they aren’t alone and have additional advocates for their health and wellbeing. “The more we understand teens and stress, the better grandparents will be equipped to support them,” Witovsky says.

Where Two Worlds Meet looks at grandparenting through an intergenerational lens. The book recognizes that the world grandparents grew up in differs from the one we live in today. “Open yourself to your grandchildren,” Witkovsky and Shoss say. “Experience the world as they see it, and don’t be afraid to let them into your world too.”

Each chapter of Where Two Worlds Meet focuses on an action item that grandparents can take, from how to engage in storytelling about life’s milestone events, to leaving a legacy of values. Forgiveness and reconciliation with the generation in between, your grandchild’s parents, is also a critical component that’s covered in the book.

When grandparents and grandchildren become closer, all three generations benefit. “A thriving, powerful family is about multidirectional relationships between grandchildren, parents, and grandparents, and how all of us can connect more deeply,” Witkovsky says. “It’s not just the elders of the group who have something to share, but every member of the family.”

Episode 75. Connect with Your Teenage Grandchildren
June 16, 2022

Episode 75. Connect with Your Teenage Grandchildren

When grandchildren are young, a sweet treat or new toy is enough to inspire their unconditional love. And then they become teenagers. Suddenly it’s not so easy anymore, for you or for them.

Episode page