Who are you when the role that helped define you no longer fits?

For years, Oscar Chacon's identity was shaped by structure, service, teamwork, and the uniform he wore as an officer in the United States Air Force and Space Force. But when he transitioned into civilian life, he found himself confronting a much more personal question:

Who am I beneath the role?

In this episode of Permission Slip-Ups, Oscar joins Kate and David for an honest conversation about identity, masculinity, leadership, vulnerability, and the uncertainty that often accompanies major life transitions.

Together, they explore:

• Why our careers, responsibilities, and accomplishments can quietly become our identity
• What happens when the "why" that once guided us begins to change
• Why so many men feel pressure to become the lone wolf and figure everything out alone
• How vulnerability creates trust, connection, and more authentic leadership
• What it means to become whole rather than perform an image of perfection
• How community, curiosity, and personal agency can help us move through uncertainty
• Why fear asks, "What if?" while faith responds, "Even if"

Oscar reminds us that we do not need to have a grand philosophical answer for where our lives are going. Sometimes the next honest answer is enough:

"I just want to wake up happier."

This conversation is for anyone moving through change, questioning who they have become, or searching for a life that feels more authentic, meaningful, and aligned.