Back-to-school season is full of instructions.
New teachers explain the rules. Parents remind children what they need to bring, when they need to wake up, how to get to class, and what is expected of them. There is a lot of information being passed from one generation to another.
But I wonder whether the most important message a child needs at the beginning of a new school year is one that doesn't appear on the syllabus:
I see you. I believe in you. You are capable of more than you know.
That makes me think about grandparents.
We aren't our grandchildren's teachers. We aren't their parents. We don't have to manage the homework, enforce the bedtime, or make sure every rule is followed.
We have an opportunity to offer something different.
Perspective. Confidence. Belief.
We can be the person who says, "I've watched you grow. I know what you're capable of. I believe in you."
This week's double Torah portion, Nitzavim-Vayeilech, brings us to the end of Moshe's leadership. He knows he will not be entering the Land with the people. He knows he will not be there to guide them through everything that comes next.
Throughout Sefer Devarim, Moshe has been teaching and reminding. Remember what you experienced. Keep the mitzvot. Serve Hashem. Don't forget where you came from.
But now, as he prepares to leave, his message shifts.
He turns to Yehoshua and tells him:
חזק ואמץ Be strong and courageous
It is a remarkably different kind of message.
Moshe cannot give Yehoshua instructions for every situation he will encounter. He cannot guarantee that things will go well. He cannot even accompany him into the Land.
What he can give him is confidence.
You can do this.
And perhaps that is another way to think about legacy.
We often think about what we want our grandchildren to remember from us. The stories. The recipes. The traditions. The Jewish values. The family history.
Those things matter enormously.
But what if we also ask:
What do I want to strengthen in the people I love?
What do I want my grandchild to believe about themselves because I was their grandparent?
Perhaps they need to know that they are brave.
That they can recover from mistakes.
That they can try something difficult.
That their voice matters.
That they are loved, not because of what they accomplish, but simply because they are themselves.
As we approach Rosh Hashanah, we spend a great deal of time thinking about ourselves. What did I do well this year? Where did I fall short? What do I want to change?
Perhaps this year we can add another question:
Who do I want to strengthen?
Not control.
Not shape into the person I think they should become.
Strengthen.
That feels like a very different kind of grandparenting.
And perhaps it begins with three simple things:
Joyful. Notice what brings your grandchild alive.
What makes them laugh? What are they excited about? What makes them light up?
Make room for that joy. Sometimes telling a child, "I love seeing you so happy," is itself a powerful form of encouragement.
Intentional. Think about what your grandchild might need to hear from you right now.
Not what you think they should hear.
What might actually strengthen them?
"I know starting at a new school can be scary."
"I've seen you handle hard things before."
"You don't have to be perfect."
"I believe in you."
Choose one message, and say it.
Connection. Ask your grandchild:
What's something you hope you can do this year that you haven't done before?
Then resist the temptation to tell them how to accomplish it.
Listen.
Ask another question.
Let them imagine themselves becoming that person.
Because sometimes the most powerful thing a grandparent can give is not an answer.
It is the experience of having someone who knows you well enough to say:
חזק ואמץ.
I see you. I believe in you. Go forward.
As we enter a new year, may we think not only about the legacy we will leave behind, but about the strength we can place inside the people we love while we are still here to give it.
Want to Explore Your Own Grandparenting?
After the chagim, I’m opening the next round of my six-week workshop, Becoming the Grandparent You Want to Be.
Together, we’ll explore what it means to be a joyful, intentional grandparent through Torah, reflection, conversation, and practical ideas for strengthening our relationships with our grandchildren.
The workshop begins in mid-October, and I’d love to have you join me.
Learn more about Becoming the Grandparent You Want to Be
Wishing you a Shabbat of joyful, intentional connection, and a Shana Tova.
Rabbanit Sharona Hassan
Founder of Grand Plan
Did you listen to the Connecting Jewish Grandparents: The Grand Plan Podcast this week? Please listen, rate, review and share.
Spotify: bit.ly/JewishPodcast
Apple: bit.ly/JewishGrandApple
You can sponsor a weekly connection email or Connecting Jewish Grandparents podcast episode.
Use this learning in honor or memory of someone you love.
A parent.
A grandparent.
A child.
Whether celebrating a joyous life-cycle event or honoring the memory of those no longer with us, it is a meaningful way to connect the generations and mark a legacy.
If that speaks to you, I would be honored to include your dedication. https://grandplan.pro/profile/sponsorship
Grand Question
