The Questioning Mind: Rabbi Simon Jacobson’s Guide to Curiosity, Freedom, and Spiritual Growth
Imagine a world where questions are not just tolerated, but deeply celebrated. Where curiosity is recognized as the heartbeat of both spiritual and personal growth. This is the landscape Rabbi Simon Jacobson paints—a place where asking “why” is an expression of true freedom, not rebellion.
Why the Freedom to Question Matters
Throughout Jewish tradition, the art of inquiry defines the path to wisdom. Rabbi Jacobson often points to the Talmud, where even the greatest scholars are challenged by students and colleagues. It is not the answers alone that drive understanding, but the ongoing conversation—the willingness to challenge assumptions, wrestle with concepts, and voice doubts. In his words, “There’s nothing as free as questions.” The true dignity of being human begins with having the right to ask—not just the right answer. It is by encouraging questions from a young age, such as at the Passover Seder table, that families transmit not only knowledge, but the courage to seek and grow.
Healthy Skepticism vs. Defensive Silence
Rabbi Jacobson shares candid stories from his own life, recalling moments when his honest questions were discouraged or misunderstood as defiance. Rather than being shut down, he found the drive to dig deeper—a journey that rewarded his skepticism with meaning and faith. Jewish wisdom cautions about the difference between healthy skepticism (born of real curiosity and a desire to grow) and unhealthy questioning (used simply to avoid growth or responsibility). When curiosity is nurtured, it blossoms into wisdom and authentic discovery, while silencing questions creates spiritual stagnation and fear. The Jewish tradition insists: teach your children never to fear a question, and never accept blind conformity.
Practical Steps to Cultivate Inquiry
- Create Safe Spaces for Dialogue: At home, school, or work, encourage open conversation. Make it clear that no question is foolish and that courageous inquiry is a virtue.
- Practice Active Listening: When someone asks a question, listen fully. Resist the urge to rush to answers—sometimes exploring the question together is even more valuable.
- Examine Your Own Assumptions: Consider a belief or habit you hold—why do you do it this way? Challenge yourself to revisit the foundation.
- Reframe “I Don’t Know”: Rather than a sign of weakness, treat not knowing as an exciting doorway to discovery.
- Teach Children to Ask: Make question-asking part of daily routine. Celebrate curiosity at the dinner table, during story time, or any learning moment.
From Four Questions to a Lifelong Journey
The Four Questions of Passover symbolize much more than a ritual; they invite us to approach every moment with openness and wonder. True dialogue, as Rabbi Jacobson teaches, is a dance of seeking together, not a scripted exchange of answers. A healthy questioning mind fuels innovation, resilience, and spiritual vitality—qualities desperately needed in today’s ever-changing world.
Next time you are confronted by a mystery or a contradiction, resist the urge to hide the question. Let it lead you, shape you, and become the spark for your next level of insight.
If you are hungry for a deeper dive into the value of questioning and freedom within spiritual growth, watch the full class: 3 Vital Lessons For Today: Pre-Passover Workshop.
