This podcast episode redefines the concept of risk in financial planning, shifting the focus from volatility to shortfall, and emphasizes the practical implications of this change for individuals and families. Tarlie discusses how traditional finance theories fall short in addressing real-world complexities, advocating for asymmetric preferences and multi-period optimization. Through examples like Fred Smith's volatility-seeking strategy, the conversation reveals the nuanced nature of investments while underscoring the importance of aligning financial goals with effective planning tools like Nebo. The episode culminates in a call to recognize path dependence and the power of belief in embracing innovative financial solutions.