What does it mean to be a GRANDparent? In this episode of Connecting Jewish Grandparents, Rabbanit Sharona Hassan explores the Torah portion of Lech Lecha, Avram’s transformation into Avraham, Sarai’s transformation into Sarah, and what name changes teach us about identity, growth, and becoming the grandparent we want to be.

Discover more at grandplan.pro and explore Becoming the Grandparent You Want to Be, Sharona’s course for intentional Jewish grandparenting. If you enjoy this episode, please share it with a grandparent, and rate and review the podcast to help more grandparents discover the joy of meaningful family connections.

How can grandparents build stronger relationships with their children and grandchildren? Communication doesn't always lead to connection. Sometimes we talk without listening; other times, fear of saying the wrong thing keeps us silent.

Inspired by the Tower of Babel in Parashat Noach, in this episode of Connecting Jewish Grandparents, Rabbanit Sharona Hassan explores how listening, openness, and a willingness to understand one another can bridge generational differences and strengthen family relationships.

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We may imagine grandparenting as a kind of Gan Eden, perfect existance, filled with closeness, family, Jewish traditions, and meaningful connection.

But what happens when reality looks very different?

Rabbanit Sharona Hassan's class shares how the Torah begins with this very question and provides guidelines for managing the struggle.

This episode of Connecting Jewish Grandparents explores disappointment, family relationships, Jewish grandparenting, and the challenge of finding meaningful connection when grandparenting does not unfold as we imagined.

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And join Becoming the Grandparent You Want to Be, a six-week journey through Torah wisdom and the real questions of modern Jewish grandparenting. https://grandplan.pro/profile/workshop

What does it mean to carry on when one chapter ends? For Jewish grandparents, Simchat Torah offers a powerful lens on legacy, Jewish continuity, and what we pass from one generation to the next.

V’zot HaBeracha brings us to the final moments of Moshe’s life. Like Yaakov before him, Moshe blesses the next generation. Then the Torah ends, and we immediately begin again with Bereishit. At the same time, the story moves forward with Yehoshua.

We move backward and forward at once, carrying the past while stepping into a future we cannot see.

For grandparents, that raises an important question: What are we carrying forward, and what are we placing in the hands of our grandchildren?

And Simchat Torah carries the weight of October 7. How do we carry on without leaving memory and loss behind?

In this episode of Connecting Jewish Grandparents, Rabbanit Sharona Hassan explores Moshe’s final blessing, Jewish legacy, Simchat Torah, and what it means to carry our traditions forward while allowing the next generation to make them their own.

Becoming the Grandparent You Want to Be: Join my six-week workshop exploring Torah wisdom and the real-life questions of modern Jewish grandparenting.

Early Bird: Save $110 when you register by September 30.

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Sukkot is called 'Zman Simchateinu', the season of our joy.

But what does it mean to be commanded to be happy?

And what does Sukkot’s agricultural harvest have to teach us about grandparenting, grandchildren, and finding joy in the relationships we have?

For Jewish grandparents, the “harvest” of our lives can be complicated. We may have hopes for our grandchildren, our relationships, and the Jewish traditions we want to pass on. But our grandchildren are not a project we can control. They are unique people with their own personalities, interests, choices, and paths. Sukkot invites us to stop and look at the harvest we actually have. What has grown that you may not have noticed?

In this episode of Connecting Jewish Grandparents, Rabbanit Sharona Hassan explores Sukkot, happiness, and the harvest, and what they can teach us about intentional grandparenting and building meaningful relationships with grandchildren.

Want to go deeper? Learn about Becoming the Grandparent You Want to Be, a six-week journey through Torah wisdom and the real-life questions of modern grandparenting. https://grandplan.pro/profile/workshop

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Is it too late for grandparents?

What if the relationship with a child or grandchild isn't what you hoped it would be? What if you've made mistakes, missed opportunities, or simply don't know how to bridge the distance?

Yom Kippur asks us to look honestly at what isn't working, but it doesn't leave us stuck there. Teshuvah means turning. And sometimes, even when we can't control what happens next, there is still a way to turn toward the relationship we wish we had.

This Yom Kippur, let's ask: What is still possible?

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Rosh Hashanah invites us to recognize God as King through the powerful themes of Malchuyot, Zichronot, and Shofarot.

But these ideas can also help us think about our own families: What do we honor? What do we remember? And what are we calling the next generation toward?

As we prepare for Rosh Hashanah, this episode of Grand Plan explores how the values we celebrate, the stories we tell, and the hopes we express shape our families and influence what our children and grandchildren carry forward.

Try bringing this question to your Rosh Hashanah table:

What does our family treat as most important, and how do we know?

And if you are a grandparent who wants to be more joyful and intentional in your relationships with your grandchildren, my six-week workshop, Becoming the Grandparent You Want to Be, begins in mid-October. We explore grandparenting through Torah, reflection, conversation, and practical ideas for strengthening family connection. Learn more about Becoming the Grandparent You Want to Be: https://grandplan.pro/profile/workshop

What kind of legacy do we leave our grandchildren?

As Moshe approaches the end of his life and leadership, much of his message has been about remembering: remember what you have learned, keep the mitzvot, serve Hashem, and don't forget where you came from.

But in Parashat Nitzavim-Vayeilech, Moshe gives Yehoshua a different kind of message: חזק ואמץ, be strong and courageous.

Moshe knows he won't be going into the Land with Yehoshua. He can't tell him exactly what will happen or make sure everything goes well. Instead, he gives him something he can carry with him: confidence, courage, and the belief that he can move forward.

As we approach Rosh Hashanah, this offers a powerful way to think about grandparenting and legacy. Our legacy isn't only the stories we tell, the traditions we pass down, or the memories we create.

Sometimes, our greatest legacy is the voice we leave inside our grandchildren that says:

You are strong. You are capable. You can do this.

What do you want your grandchildren to carry with them into the year ahead?

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