The Questioning Mind: Rabbi Simon Jacobson’s Guide to Curiosity, Freedom, and Spiritual Growth

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Introduction: The Power of a Question

Imagine a classroom where every child is encouraged to raise their hand, not just for the right answer, but to ask a question that no one else thought of. Now, picture a family dinner where children and adults alike are invited to voice what puzzles them, delighted in the unknowns rather than silenced by uncertainty. According to Rabbi Simon Jacobson, this spirit of inquiry is not merely an academic exercise—it is the heartbeat of spiritual growth, personal freedom, and meaningful living.

Why Questions Matter: Lessons from Jewish Wisdom

Throughout Jewish tradition, questions have played a central role. The Talmud is essentially a book of questions, arguments, and counter-arguments. The Seder night at Passover is built around “The Four Questions”, empowering even the youngest to ask “why.” Rabbi Jacobson shares that questioning is not an act of rebellion, but a sign of a living, dynamic soul.

He often reflects on his own childhood curiosity, admitting that his most impactful teachers were those who welcomed questions—even the challenging ones. When questions were brushed aside, he felt uninspired. But when met with honesty, even a simple “I don’t know yet,” those questions became stepping stones toward understanding. In his words, “The question of a wise person is half an answer. You’re already on your way just by asking.”

Healthy Skepticism vs. Locking the Mind

Rabbi Jacobson distinguishes between healthy skepticism—searching for truth—and unhealthy skepticism, the kind that uses questions to justify one’s own position without openness. The former leads to clarity and growth; the latter, to endless debate with no resolution. Jewish wisdom encourages every individual to ask, probe, and even challenge, but always with an honest desire for understanding rather than the need to score a point.

Cultivating a Questioning Mind: Practical Steps

  • Encourage Questions at Home and Work: Whether at the dinner table, in class, or during meetings, set aside time for “question sessions” where every voice, regardless of age or status, is respected. This builds not just knowledge, but mutual respect and creativity.
  • Practice Respectful Listening: When someone poses a question—especially one that sounds strange or difficult—honor it with real attention. Sometimes acknowledging a question is more important than answering it right away.
  • Frame Questions Constructively: If faced with a challenge, try asking “What can I learn from this?” or “Is there another angle I haven’t explored?” This reframing often leads to deeper solutions and personal breakthroughs.
  • Reflect on Your Own Questions: Keep a journal of questions that arise throughout your week—about faith, relationships, or your own purpose. Over time, you’ll see patterns, and often the process of questioning itself brings growth.
  • Validate Children’s and Students’ Curiosity: Help young people see their questions as a sign of their unique value. Teach them that their voice matters by giving real answers when you can, and a promise to search together when you don’t know.

Breaking the Fear of Asking

All too often, people fear that their questions are foolish, disrespectful, or a sign of weakness. Rabbi Jacobson’s message is the opposite: asking is an act of courage and dignity. Silencing questions, especially in children, invalidates their spirit and voice. Instead, he encourages nurturing a culture in families and communities where curiosity is seen as a path to both knowledge and self-worth.

Universal Wisdom: Why Questions Set Us Free

Questions are the language of freedom. When we ask, we refuse to be locked into mechanical thinking or rote living. A questioning mind remains open—to growth, to empathy, and to the possibility that every day holds new mysteries worth exploring. Jewish wisdom, as Rabbi Jacobson reminds us, teaches that for every answer, there’s another question—and that’s the true secret to an expansive, meaningful life.

If you’re inspired to explore these ideas further and deepen your spiritual journey, discover more profound insights by visiting the Meaningful Life Center’s library of teachings and classes.

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