After their conversation with philanthropists Kim Duchossois and Jessica Swoyer Green, Amber and Tom return to explore one of the thorniest questions in generosity: If you have more, should you give more? What unfolds is a candid, thoughtful look at the tension between purpose and self-preservation — between the call to give and the instinct to save.
Drawing on wisdom from Jewish teaching, Christian Scripture and behavioral science, Amber and Tom dig into why giving is hard to do — yet why it feels so good — and how to know how much giving is “enough.” They wrestle with questions about timing, limits, legacy and control: Is it better to give now or later? How much should we direct our gifts? And what do we owe our children — security or the opportunity to struggle and grow?
It’s a warm and honest conversation about generosity, trust and the values that guide us when the stakes are high.
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