In this week’s Guiding Generations, Rabbi Shifman unpacks a striking lesson from Parshas Chukas that flips our understanding of gratitude on its head. Why was Moshe Rabbeinu afraid to confront Og Melech HaBashan—even though Og’s original intent was malicious? The Torah teaches that gratitude isn’t about someone’s intentions, it’s about the benefit we received.

As parents, we often hear, “You only did that for yourself!” Rabbi Shifman explores how to raise children who internalize true hakaras hatov—appreciation—even when it feels undeserved. This episode will shift how you view relationships, entitlement, and the foundation of respect in your home.

In this week’s Guiding Generations, Rabbi Shifman unpacks the powerful lessons of Parshas Shlach and the story of the Meraglim (spies), showing how even righteous leaders can resist growth when it threatens comfort. Through the lens of parenting, he explores how relationships—whether with Hashem, a spouse, or our children—are tested not at their beginning, but when they’re called to evolve. What do we do when our kids resist the next stage of independence or responsibility? How do we teach them to embrace discomfort as the path to deeper connection and meaning? Tune in for a moving reflection on how challenge doesn’t break relationships—it reveals their true strength.

In this week’s episode of Guiding Generations, Rabbi Shifman explores the devastating story of the Meraglim (spies) from Parshat Shlach and uncovers a powerful parenting and relationship insight: why some relationships falter when faced with new challenges. Were the spies righteous or wicked? Why would leaders of such stature sabotage the mission into the Promised Land? Through deep analysis and a relatable parable, Rabbi Shifman teaches how our ability to grow through discomfort—whether in parenting, marriage, or faith—defines the strength and future of our most important relationships.

Tune in to learn how to help your children and your marriage evolve through life’s inevitable transitions—and why avoiding challenge may feel safe, but stunts real growth.