The OptimalWork Podcast

#320: What turns “I have to do this” into “I want to do this”—especially when the task is difficult? Kevin and Sharif explore how deeper judgment transforms an apparent loss into a worthwhile cost, and then into an opportunity to grow and serve others. From the pull of doomscrolling to the awkwardness of a difficult conversation, they show how urgency can bypass thoughtful decisions—and how reframing helps us see something worth choosing. Drawing on Aquinas’s account of prudence, they explain how to bring our highest ideals into everyday work, making the best path more attractive.Find more at https://OptimalWork.com

#319: Fear can make a difficulty seem insurmountable; desire can make getting what we want seem like all that matters. Kevin and Sharif explore how both can distort understanding and turn careful reasoning into rationalization. Drawing on Aquinas’s account of prudence, they connect everyday choices—from buying a car to putting off important work—to three questions that help restore perspective: Whose good is being served? What’s the hardest part? And what would real excellence look like here?Find more at https://OptimalWork.com

#318: How do people make good decisions without getting trapped by their first impression? Sharif and Kevin explore the first act of prudence—counsel—and why clear thinking begins with making genuine contact with reality. They unpack the role of intuition, experience, memory, and advice, while showing how anxiety and desire can turn an initial hunch into premature certainty. Kevin explains why strong intuition should be a starting point rather than a conclusion, and offers a practical question from Daniel Kahneman that can expose hidden assumptions, reopen curiosity, and help people see options they may have missed.Find more at https://OptimalWork.com

#317: In this episode, Sharif and Kevin explore prudence as the virtue behind good decision-making — not simply knowing what to do, but discerning what truly serves the people entrusted to us and then putting that decision into action. Drawing on Augustine’s definition of prudence as “love rightly discerning what helps or hinders the beloved,” Kevin breaks prudence into three practical movements: counsel, judgment, and command. Along the way, they examine why premature certainty, rushed solutions, and good intentions without concrete action can derail even thoughtful decisions, and offer a simple practice for identifying where one’s own decision-making tends to break down.Find more at https://OptimalWork.com

#316: Dr. John Gottman identifies four stages in the breakdown of a relationship: defensiveness, criticism, stonewalling, and ultimately contempt. Each of these reflects a deeper issue— a lack of humility. In this episode, we delve into the third stage: stonewalling. Stonewalling means putting up obstacles to forming bonds with others. While defensiveness and criticism most concern one’s attitude, stonewalling goes deeper and touches upon one’s attention. Stonewalling at its most extreme implies an inward collapse of attention, an unwillingness to attend to others.Find more at https://OptimalWork.com