In this week’s episode of Guiding Generations, Rabbi Shifman opens Sefer Vayikra with a powerful parenting message hidden in the Torah’s laws of sin offerings. Why does the Torah say “when the leader sins” instead of “if”? What does it mean for a generation when its leaders admit mistakes?

Drawing from classic commentaries—Rabbeinu Bachya, Rav Zalman Sorotzkin, and Rav David Feinstein—Rabbi Shifman explores three approaches to leadership, accountability, and risk-taking. With stories from school, insights from a global education conference, and a heartfelt take on modern parenting, he unpacks why embracing failure and modeling responsibility are essential to raising strong, thoughtful children in the 21st century.

Whether you’re a parent, educator, or community leader, this episode offers timeless wisdom to help you raise the next generation with courage, integrity, and humility.