Connecting Jewish Grandparents

Are grandparents blessed with everything? In Parashat Chayei Sarah, the Torah describes Avraham as old and blessed with everything, just after he has nearly sacrificed his son and buried his beloved wife, Sarah. How can a man who has experienced such profound trauma and loss be described as having everything? Rabbanit Sharona Hassan explores the Torah commentators' interpretations of Bereishit 24:1 and unpacks the relationship between gratitude, grief, and what it means to feel truly blessed.

In this episode of Connecting Jewish Grandparents, discover how ancient Torah wisdom can transform the way we see our lives, our families, and our relationships with our grandchildren. Can gratitude help us recognize our blessings even when life doesn't unfold as we hoped? How can we model this perspective for the next generation?

Explore more Jewish grandparenting resources at grandplan.pro, including Grand Plan Weekly and Becoming the Grandparent You Want to Be. If this episode speaks to you, please like, share, and leave a review to help more grandparents discover Connecting Jewish Grandparents.

What does it mean to be Jewish? In Parashat Vayera, Rabbaneat Sharona Hassan explores four core Jewish values through Avraham in Beresheit 18: healing and preserving life, hospitality and generosity, standing up for justice, and fighting to save others. From Avraham welcoming guests with a lavish meal to his bold argument with God over the fate of Sedom, discover how Torah offers timeless lessons about Jewish identity, compassion, and moral responsibility.

How do we live our Jewish values, and how do we pass them on to the next generation?

Subscribe for more weekly Torah insights and Jewish grandparenting wisdom. Visit grandplan.pro to explore Grand Plan and Becoming the Grandparent You Want to Be. If this episode speaks to you, please like, share, and leave a review to help more people discover Connecting Jewish Grandparents.

As a Sephardic Jewish educator and founder of Grand Plan, Sharona connects ancient Torah wisdom to modern Jewish life, family relationships, and grandparenting.

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 https://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.

Want more? Sign up for the Grand Plan Weekly, with Torah insights and practical ways to make the weekly parasha actionable for grandparents. bit.ly/SignUpGPW

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.

Learn more and register: https://grandplan.pro/profile/workshop

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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?

Learn more about Grand Plan and Becoming the Grandparent You Want to Be http://grandplan.pro/profile/workshop

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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Do you ever look at another grandparent and wonder why their relationship with their grandchildren seems easier, closer, or more abundant?

This week, in connection to the Torah portion Ki Tavo, Rabbanit Sharona Hassan explores the first fruits, the gift of inheritance, and a powerful reminder: you can tend what has been entrusted to you, but you cannot control every part of the harvest.

Learn more about Grand Plan at grandplan.pro

Grandparenting doesn't always go as planned. Parashat Ki Tetzei offers a deeply Jewish perspective on the hurt, disappointment, distance, and complicated family relationships that can make grandparenting painful, and asks how we can continue to love and connect when reality falls far short of what we imagined. Rabbanit Sharona Hassan looks at how this Torah portion, the month of Elul, and the painful parts of grandparenting align in the need for acceptance and growth.
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How are we teaching our grandchildren to trust? Rabanit Sharona Hassan shows us how Parashat Shoftim offers powerful Torah wisdom about trust, authority, justice, and building systems worthy of confidence. Explore how Jewish grandparents can help grandchildren develop discernment without becoming cynical. Learn more about Grand Plan and the gift of Jewish grandparenting at grandplan.pro

What does Parashat Re'eh teach about perspective? This episode explores the Torah's opening word, "Re'eh" ("See"), and how choosing how we see life's challenges can transform our relationships, our faith, and our legacy.

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What kind of God are we passing on to our grandchildren? In Parashat Eikev, Moshe reminds us that faith is transmitted through lived experience. Discover how your relationship with Hashem may become one of your greatest legacies.

Learn more about Grand Plan and the power of Jewish Grandparents http://www.grandplan.pro

What can the Shema teach Jewish grandparents about passing on faith, values, and identity to the next generation?

In this episode of Connecting Jewish Grandparents, Rabbanit Sharona Hassan explores Parashat Va'etchanan and the layers of meaning within Judaism's most familiar prayer. The Shema offers a powerful blueprint for intergenerational connection: building relationship, cultivating love, teaching intentionally, and embodying our values in everyday life.

Discover how grandparents can move beyond simply sharing Jewish traditions to creating meaningful, lasting connections with their grandchildren.

This episode is available for sponsorship. Subscribe to Grand Plan Weekly at GrandPlan.pro for weekly Torah insights and practical ways to create joyful, intentional connections with your grandchildren.

How do Jewish grandparents build a meaningful legacy? In this episode of Connecting Jewish Grandparents, Rabbanit Sharona Hassan explores Parashat Devarim and Moses' final address to uncover three practical lessons on intentional legacy, Jewish grandparenting, and passing on faith, values, and family traditions to the next generation.

This episode is available for sponsorship. Subscribe to Grand Plan Weekly at GrandPlan.pro for weekly Torah insights and practical ways to create joyful, intentional connections with your grandchildren.

How do grandparents build a lasting legacy?

In this episode of Connecting Jewish Grandparents, Rabbanit Sharona Hassan explores Parashat Matot-Masei through the lens of inheritance, legacy, stewardship, and joyful, intentional connection. Discover how the Torah's teachings on vows, family inheritance, and the journeys through the wilderness offer timeless wisdom for Jewish grandparents seeking to pass on values, traditions, and faith to the next generation.

This week's episode is available for sponsorship in honor or memory of a loved one, to celebrate a simcha, or to support Grand Plan's mission of strengthening Jewish families through grandparents. To sponsor a future episode or sign up for Grand Plan Weekly, featuring practical Torah insights and one joyful, intentional connection each week, visit GrandPlan.pro

What will your grandchildren inherit from you?

In this episode of Connecting Jewish Grandparents, Rabbanit Sharona Hassan explores why Parashat Pinchas may be the Torah's most important portion for grandparents.

Discover the many forms of legacy found in the parsha, from family values and traditions to leadership, faith, and belonging, and learn how to intentionally decide what you want to pass on to the next generation.

If you're seeking Jewish grandparenting wisdom, meaningful family connections, and practical ideas for building a lasting legacy, this episode is for you.

Episodes are available for sponsorship in honor or memory of a loved one, to celebrate a simcha, or to support Jewish grandparents around the world in creating joyful, intentional connections across generations.

Enjoyed this episode? Sign up for Grand Plan Weekly, where each week's Torah portion is paired with three simple, actionable ideas to help you create more joyful, intentional connections with your grandchildren. grandplan.kit.com

How do you answer a grandchild's endless questions of "Why?" And what happens when there simply isn't an answer?

In this episode of Connecting Jewish Grandparents, Rabbanit Sharona Hassan explores Parashat Chukat, the Torah's ultimate example of a chok - a commandment beyond human understanding. From the mystery of the Red Heifer to life's biggest questions about loss, illness, disappointment, and uncertainty, this episode offers practical wisdom for grandparents navigating difficult conversations with grandchildren.

Discover how Jewish wisdom can help grandparents teach resilience, faith, and emotional strength, even when we don't have all the answers. Learn why one of the greatest gifts a grandparent can offer is not certainty, but the ability to live thoughtfully with unanswered questions.

If you're looking for meaningful Jewish grandparenting insights, ways to strengthen family relationships, and tools for building a lasting legacy across generations, this episode is for you.

To sponsor an episode of Connecting Jewish Grandparents in honor or memory of a loved one, visit Grand Plan or reach out to learn more about sponsorship opportunities. https://grandplan.kit.com/profile/sponsorship