Rethinking Free Will: Rabbi Simon Jacobson’s Guide to Transcending Circumstance
In moments when life feels dictated by external forces — whether by family upbringing, societal pressures, or the swirl of everyday challenges — the idea of free will can seem elusive. But what if your true freedom lies not in escaping your circumstances, but in redefining how you respond within them? Rabbi Simon Jacobson offers a powerful and practical framework for understanding and exercising genuine free will, transforming this abstract concept into a daily guiding light.
The Dignity of Choice: What Free Will Means
Rabbi Jacobson teaches that free will isn’t just about random options or sporadic decision-making. Instead, it is the very dignity of being human: the ability to choose your path even in the face of inherited patterns or difficult realities. One story he shares involves a person who grew up in a chaotic environment yet chose, day by day, to build stability for their own children. This isn’t about denying the influences of the past; it’s about harnessing your awareness to transform what comes next.
Rising Above Circumstance: A New Perspective
Rather than seeing yourself as a victim of circumstance, Jacobson encourages cultivating an attitude of inner ownership. Imagine a person passed over for promotion due to workplace politics. While the external factor is real, the internal choice is always available: to grow resentful, to give up, or to respond with renewed initiative and integrity. In this way, free will becomes a tool for rising above, not being defined by, circumstances.
Practical Steps for Exercising Free Will
- Recognize Your Triggers: Identify situations where you feel ‘boxed in,’ whether it’s family dynamics, financial pressure, or expectations from others. Use mindfulness techniques (like brief pauses or journaling) to interrupt automatic reactions and create space for reflection.
- Ask Empowering Questions: Instead of ‘Why is this happening to me?’, try ‘What is my next best step given these realities?’ Shifting from blame to agency opens doors to new responses.
- Make One Conscious Choice Each Day: Choose something small — like your tone in a tough conversation or the way you spend ten minutes in the morning. Consistent small choices build the muscle of freedom.
- Reframe Setbacks: View disappointments or failures as catalysts for growth. Try listing three ways you can learn from a challenging day, or reaching out to a mentor for perspective.
- Return to Your Why: Regularly revisit your core values and purpose. Write them down and reflect on how your current choices align. This ongoing review keeps your sense of agency sharp, especially under pressure.
When Free Will Feels Hard
There will be times when it feels easier to surrender to outside forces — whether it is the inertia of habit, societal trends, or even fear. Jacobson suggests turning these moments into opportunities for conscious redirection. For example, when feeling stuck in a cycle of negative thinking, pause and ask yourself: what would it look like to make a new choice, even if it is a small one? Sometimes, victory begins with a single different step.
The Universal Gift of Choice
Jewish wisdom teaches that the greatest gift bestowed upon each person is the ability to choose — and with that, the capacity to transcend. No one is immune to circumstance, but everyone holds the spark of dignity to chart a meaningful path. Whether in relationships, work, or spiritual journey, the power to decide is always present. By embracing this, you bring radical creativity and courage to every aspect of your life, reframing your story not as a product of circumstance, but as a statement of purposeful living.
For more illuminating wisdom on free will and personal transformation, stay tuned for upcoming masterclasses and resources at the Meaningful Life Center.


