As summer winds down and grandchildren head back to school, they are preparing more than new backpacks and sharpened pencils. Your grandchildren are stepping into systems of rules, expectations, and authority. They will be asked to trust teachers, coaches, administrators, and new routines, sometimes without fully understanding why things work the way they do.
Parashat Shoftim is surprisingly concerned with this very question. It lays out judges, witnesses, leaders, priests, and systems for making decisions and resolving disagreements. The Torah recognizes that a community cannot function if every person simply decides for themselves what is right.
But Judaism doesn't ask us to trust blindly, either.
So what do we teach our grandchildren about trust?
We don't need to tell our grandchildren, "Trust every authority."
We can teach something more valuable: how trust is built.
Trustworthy people keep their word. They listen. They admit mistakes. They apply rules fairly. They can explain their decisions. And when something goes wrong, they have a way to make it right.
Our grandchildren are watching us learn these lessons, too.
Three questions to explore with a grandchild:
1. Who is someone you trust, and what makes you trust them?
This gets them thinking about the qualities of trustworthy people.
2. What do you do when you think a rule isn't fair?
This opens a conversation about authority, disagreement, and respectful questioning.
3. What makes someone trustworthy? How can you be that person for someone else?
This turns trust from something we expect from others into something we practice ourselves.
As our grandchildren return to school, may we help them enter new systems with both confidence and discernment: knowing when to trust, knowing when to ask questions, and always striving to become people worthy of trust.
As we enter Elul, the month of preparation for Rosh Hashanah, it is also a time to look honestly at our relationships. Perhaps trust is one place to begin: Who trusts me, and what have I done to earn that trust?
Wishing you a Shabbat of joyful, intentional connection,
Rabbanit Sharona Hassan
Founder of Grand Plan
PS. If I had the pleasure of seeing you in Seattle, it was wonderful and I hope to see you soon.
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