Justin Masterson on Emotional Maturity, Leadership, and Living with Intention

In this episode of The One Big Thing, I had the privilege of sitting down with former MLB pitcher and current high school coach Justin Masterson. You might know him from his days on the mound with the Red Sox, but what really struck me in our conversation was his heart for people and his deep insights on emotional maturity.

We talked about what it means to grow—not just as a leader or athlete, but as a human being. Justin shared how his definition of maturity has evolved into the ability to handle emotions well, especially in the face of hardship. Whether he's coaching teenagers, navigating marriage, or serving in his community, he’s learned that staying relational and grounded is key.

In this episode, we dive into:

• The emotional weight athletes carry behind the scenes
• How to lead with empathy and humility in high-pressure environments
• Practical tools like the “CAKE” acronym and quieting techniques to regulate emotions
• Why identity and belonging are essential for real transformation
• Honest stories of failure, forgiveness, and fatherhood

I even share a personal story about a moment I blew it as a dad—and what it taught me about grace, humility, and the power of saying “I’m sorry.”

If you’re someone who wants to grow in emotional intelligence, lead with more compassion, or just be a better version of yourself, this episode is for you. We’re not aiming for perfection—just progress.

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About Justin Masterson

Justin Masterson is a former Major League Baseball pitcher who spent eight seasons in the big leagues with the Boston Red Sox, Cleveland Guardians (formerly Indians), and St. Louis Cardinals. Known for his resilience and leadership on the mound, he made history as the youngest Red Sox pitcher since Babe Ruth to win a playoff game and was selected as an All-Star in 2013. His career highlights include pitching an immaculate inning and recording four strikeouts in a single inning.

After retiring from professional baseball in 2017 to prioritize family, Justin transitioned into a life of service and mentorship. He now coaches varsity baseball at Fishers High School in Indiana, where he also helps develop athletes’ mental skills through programs like “Awaken the Tiger” and “Eye of the Tiger.” He’s a substitute teacher, motivational speaker, and host of The Justin Masterson Show podcast.

Justin and his wife founded the Fortress Foundation in 2013 to support individuals in need, and they continue to work with organizations like PHARE Warrior and Wayfinders. Above all, Justin is passionate about helping others grow in emotional maturity—defined as the ability to stay relational and grounded in the face of life’s biggest challenges.

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