Barbara Stewart, CFA: The Smartest Things People Ever Did—Global Stories of Risk, Change, and Reward

Barbara Stewart, CFA, returns to The Enterprising Investor to share findings from her latest Rich Thinking study, based on candid conversations with 54 people across the globe. This year’s central question—“What’s the smartest thing you ever did?”—unlocks an inspiring range of stories about personal and professional transformation.
From a Singaporean ballet dancer who defied expectations, to an Argentine executive who discovered the Japanese concept of ikigai, to an Australian entrepreneur who rebuilt his life after addiction, Barbara explores how risk-taking, mindset shifts, career pivots, and geographic leaps often lead to unimagined success. With trademark warmth and insight, she illustrates how the boldest moves can become the smartest decisions.
Listen to the full episode for powerful, real-life stories—and explore the Rich Thinking summary on the Enterprising Investor blog for even more global insights.