I Made a Marine Cry: Leadership, Authority, and Learning from Mistakes | Olaolu Ogunyemi

What happens when a leader realizes their approach caused real harm?

In this episode of My Favorite Mistake, U.S. Marine Corps officer and leadership mentor Olaolu Ogunyemi shares a defining moment early in his career—recognizing that his leadership style, while well-intended, crossed a line and made a Marine cry.

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Rather than defending his authority, Olaolu reflects on the gap between intent and impact, and how that moment forced him to rethink what effective leadership really looks like. We talk about learning from mistakes, the difference between fear-based compliance and true accountability, and why psychological safety is essential—even (and especially) in high-pressure environments like the military.

This conversation explores how leaders grow when they confront mistakes honestly, respond with humility, and commit to changing their behavior—not just their words.