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.

In this week’s Guiding Generations, Rabbi Shifman explores two powerful parenting lessons from Parshat Behaalotecha. Why does the Torah stress Moshe’s unparalleled humility—and how does it connect to his prophetic clarity? And what does the story of Miriam’s punishment teach us about praising our children without inciting jealousy? Through deep Torah insights and relatable stories, Rabbi Shifman teaches us how to raise children with humility, recognize their potential without overexposing them, and cultivate a perspective that sees godliness in every soul. A must-listen for parents and educators alike.

In this week’s Guiding Generations, Rabbi Shifman explores Parshas Naso through the lens of parenting—unpacking the mysterious laws of the Nazir and their surprising relevance to raising children. Why is it the father, not the mother, who makes a child a Nazir? What does this teach us about setting aspirations versus affirming self-worth? Rabbi Shifman draws a powerful distinction between the nurturing role of a mother—making a child feel good about who they are—and the father’s mission: showing the child what they could be. Join us for a thought-provoking discussion on how to raise children not just to be “good,” but to pursue greatness—by helping them taste their true potential.

🎧 Listen now and discover why sometimes 30 days of holiness can shape a lifetime of purpose.

In this week’s episode of Guiding Generations, Rabbi Shifman draws a powerful parenting lesson from Parshat Bamidbar. Why are the Levites counted from just 30 days old, while others are counted from age 20? And what does this have to do with how we raise our children—with rewards, discipline, or love?

Through the lens of a famous story about Hillel and a would-be convert who wanted to become Kohen Gadol, Rabbi Shifman explores the difference between extrinsic rewards that manipulate behavior and sincere expressions of relationship that deepen connection. This episode unpacks how to guide children from incentive-driven action to internalized values, helping them move from doing for reward… to doing from love.

🎧 Listen now and learn how to build lasting relationships with your children—starting with how and why you offer praise, gifts, or goals.

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This week on Guiding Generations, Rabbi Shifman reflects on a traumatic incident in his school community and draws deep parenting insights from the double Parsha that concludes Sefer Vayikra. In a world where blame is quickly assigned and values are easily lost, Rabbi Shifman challenges us to confront the real message: Are we raising our children with shared Jewish values, or outsourcing their growth to culture, technology, and circumstance? Through the lens of the Tochacha (rebuke) and the lasting legacy of the Avot, we explore how true connection—rooted in Torah, tefillah, and chesed—can anchor our families, even when everything seems scattered. A powerful episode about responsibility, unity, and the kind of parenting that doesn’t wait for crisis to inspire growth.

👉 Listen now and discover how to turn hardship into heartfelt leadership.

In this episode of Guiding Generations, Rabbi Aaron explores a surprising insight from the Book of Numbers with the help of Rabbi Mordecai Shifman. Why does the Torah mention that Nadav and Avihu had no children—and what does that teach us about parenting, leadership, and legacy? Discover how the Torah’s census reveals a deeper message about individuality, and why raising the next generation isn’t just about rules and rituals—it’s about connection, direction, and purpose. Tune in to learn how the Torah elevates our natural drives and how real parenting means guiding—not perfecting—our children.

🎧 Listen, reflect, and share—because every child counts.

In this week’s Guiding Generations, Rabbi Shifman explores a powerful lesson from Parshas Emor. Why does the Torah detail the background of the blasphemer? What connection is there between striking another Jew and cursing Hashem Himself? Rabbi Shifman uncovers a profound truth: every Jew is a living ambassador of God. As parents, this insight reshapes how we view ourselves — and how we teach our children to view their role in the world. Through stories of ancient sibling rivalry and modern-day lessons, Rabbi Shifman highlights how a child’s actions toward others reflect a deeper relationship with Hashem, offering practical parenting wisdom on how to instill dignity, self-worth, and responsibility into the next generation.

In this powerful episode of Guiding Generations, Rabbi Shifman explores a surprising truth from this week’s double Parsha: even the greatest students of Rabbi Akiva—24,000 of them—were lost not due to a lack of love, but a lack of respect.

What happens when closeness erodes boundaries? Why does Torah emphasize “don’t do to others what you wouldn’t want done to you” rather than simply “do unto others”? And how can we apply these insights to parenting, ensuring our love for our children doesn’t overshadow the foundational need for mutual respect?

Drawing on deep Torah wisdom, practical psychology, and timeless stories, Rabbi Shifman unpacks how to raise children who not only feel loved—but respected, seen, and valued.

Perfect for parents, educators, and anyone seeking to deepen the relationships that matter most.