The OptimalWork Podcast

#323: Two people can do equally excellent work—and be changed by it in completely different ways. What makes the difference? Kevin and Sharif explore how bringing love into a task transforms more than its outcome: it shapes the person doing it. Drawing on Aquinas’s account of prudence, they reveal why order means far more than organizing your desk or checking off tasks. A simple question—“Who is this for?”—can turn ordinary work into a daily practice of love, strengthening your capacity to serve others both at work and at home.

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#322: A great plan can end with nothing changing. Kevin and Sharif explore the missing link between knowing what to do and actually doing it: command, the culminating act of prudence. Drawing on Aquinas, they distinguish three ways good intentions break down—never truly deciding, failing to start, and retreating when difficulties arise. They show how three questions can strengthen follow-through: Who will this benefit? What would excellence look like? What’s the hardest part? Along the way, they explain why love produces readiness to act—and how coaches can encourage growth without taking over.

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#321: AI can produce better work in seconds—but what happens to the person doing the work? Kevin and Sharif explore the hidden cost of outsourcing challenges that build skill, judgment, and character. Drawing on Aquinas’s distinction between making and doing, they examine what separates AI assistance that supports growth from shortcuts that bypass it. From student essays to professional work, they show how AI can help people reflect, weigh options, and engage difficult tasks while preserving the thinking, choices, and effort through which they grow.

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#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.

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#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?

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#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.

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#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.

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#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.

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#315: 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 second stage: criticism, or what we call a critical spirit. A critical spirit often arises from hyperfocusing on someone else’s flaws, conflating those flaws with their identity, and viewing them as fixed and unchangeable. It can also serve as a kind of projection—an unconscious act of attributing our own shortcomings to others. Recognizing a critical spirit within ourselves, however uncomfortable, can open the door to profound personal growth. By addressing the root of this behavior, we not only improve our relationships but also cultivate greater humility and self-awareness.

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#314: Dr. John Gottman describes four stages in the breakdown of a relationship: first defensiveness, then criticism, then stonewalling, and finally contempt. Each of these is a manifestation of a lack of humility. Having laid out the big picture in our previous episode, here we do a deep dive into the first, defensiveness. We explain how it arises and how it relates to key concepts in our approach, like Reframing, Growth Mindset, and Threat Mode.

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