The OptimalWork Podcast

Latest Episodes:

319. Why Bad Decisions Can Feel Reasonable Sep 28, 2026

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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: Prudence, Fast and Slow Sep 21, 2026

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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.

Find more at https://OptimalWork.com

317. How a Good Decision Becomes an Action Sep 14, 2026

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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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[Rebroadcast] Professional Humility IV: Stonewalling Sep 07, 2026

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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.

Find more at https://OptimalWork.com

[Rebroadcast] Professional Humility III: Critical Spirit Aug 31, 2026

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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.

Find more at https://OptimalWork.com

[Rebroadcast] Professional Humility II: Defensiveness Aug 24, 2026

Show notes

#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.

Find more at https://OptimalWork.com

[Rebroadcast] Professional Humility I: The Core Elements Aug 17, 2026

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#313: In this episode of the OptimalWork Podcast, Sharif and Dr. Kevin Majeres delve into the significance of humility in leadership and team dynamics. They explore the concept of humble leadership, the detrimental effects of pride, and the four horsemen of team dysfunction: defensiveness, criticism, stonewalling, and contempt. The conversation emphasizes the importance of cultivating humility as a means to foster better relationships, enhance team cohesion, and promote personal growth. The episode concludes with actionable steps for developing humility and the transformative power it holds in achieving mastery in various aspects of life.

Find more at https://OptimalWork.com

[Rebroadcast] Navigating Challenges with Extreme Ownership Aug 10, 2026

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#312: In this episode, Sharif and Dr. Kevin Majeres discuss the concept of Extreme Ownership, as introduced and developed by Jocko Willink and Leif Babin. Willink and Babin learned this concept from their time serving as Navy Seals and have gained popularity adapting it to other contexts, like business and relationships. In this conversation, Sharif and Dr. Majeres discuss the nuances of this approach, and share applications to challenges faced in various contexts, from the classroom to the boardroom.

Find more at https://OptimalWork.com

[Rebroadcast] Developing Mastery IV: The Optimizing Stage Aug 03, 2026

Show notes

#311: In this installment of our series on mastery, Sharif and Dr. Kevin Majeres explore the third and final stage: the optimizing stage. The optimizing stage of mastery has deep connections to other core concepts of OptimalWork like deliberate practice, continual growth, and above all service. In the optimizing stage, we can go beyond the automaticity characteristic of the implicit stage (stage two) and develop our mastery to such a degree that we can pour our entire selves into a task. In this way, the optimizing stage of mastery is also connected to flow, the state of peak focus, when we become, as it were, fused with the present task.

Find more at https://OptimalWork.com

[Rebroadcast] Developing Mastery III: The Implicit Stage Jul 27, 2026

Show notes

#310: In this episode, Sharif and Dr. Kevin Majeres explore the second of the three phases of mastery: the implicit phase of mastery. This phase is the most dangerous, because it is where bad actions can become automatic habits, and where good habits can become plateaus. Fortunately, there are ways to avoid these pitfalls. The implicit phase of mastery is also closely connected with flow. The next episode will cover the final stage of mastery: optimizing strategies.

Find more at https://OptimalWork.com

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