Humility and Confidence: Rabbi Simon Jacobson’s Guide to True Greatness
Few qualities are as widely praised and yet as deeply misunderstood as humility. Is humility about playing small, hiding your strengths, or denying your own worth? Or can it be a path to powerful self-confidence and genuine connection?
Rabbi Simon Jacobson offers a refreshingly counterintuitive view: True humility is not self-effacing weakness, but a dynamic blend of mindful openness and flexible strength. His teachings reveal why humility is not only compatible with confidence—it is its deepest foundation.
The Paradox of Humility: When Nothing Is Greater Than Something
Imagine two people in a group setting. One constantly insists on their opinion, pushing others aside for recognition. The other listens, adapts, and even allows room for better ideas—even if they are not their own. Which person leaves a bigger, more lasting impression?
The paradox at the heart of humility, as Rabbi Jacobson explains, is summed up in the Chassidic phrase: “When nothing is greater than something.” The one who is not self-consumed, the one who makes space for others, becomes a true leader—respected, flexible, and deeply impactful. This stands in sharp contrast to arrogance, which fosters selfishness, conflict, and even abuse.
Why Humility Is Rare—and So Valuable
Modern culture often equates self-worth with self-promotion. As a result, humility can be dismissed as impractical or naïve—a relic better left in books than in boardrooms. But Rabbi Jacobson urges us to see humility as a mark of true greatness, not weakness. Being humble doesn’t mean lacking healthy self-esteem. Instead, it’s the ability to yield, to listen deeply, to stay flexible, and to allow others’ strengths to shine alongside your own.
How to Marry Humility with Confidence
- Practice Daily Reflection: Spend a few minutes each day reflecting on your talents and positive qualities and how you can use them to benefit others. Humility is not pretending you have nothing to offer; it’s freely using what you have for a greater good.
- Yield During Conversation: The next time you’re in a discussion, consciously pause and invite another person to share their view. Notice how it feels to make space for someone else, and how it can actually elevate the whole conversation.
- Turn Mistakes into Growth: Humble people readily admit their faults and treat mistakes as stepping stones, not shameful secrets. Journal about a recent error and list one lesson learned. This transforms humility into a growth superpower.
- Balance Self-Respect and Self-Transcendence: While it’s vital to respect yourself, leave room for perspectives and strengths beyond your own. Humility is a foundation, not a ceiling.
From Humility Comes Real Power—and Real Relationships
Humility lays the groundwork for trust, empathy, and deep connection. At home, in friendships, or at work, the humble person builds bridges by seeing the dignity in everyone—including themselves. Rabbi Jacobson’s approach invites each of us to see humility as the force that frees us from narrow ego and ushers in a richer, more meaningful impact on the world.
When humility is paired with healthy confidence, it sparks a unique greatness: the power to lead, to grow from every encounter, and to transform both yourself and your relationships.
If you want to explore these insights in more depth, watch the full class here.
