Episode #718 The Courage to Try: Why Your Most Audacious Decision Can Change Everything
"The coward's way out is to talk yourself out of being audacious."
— Ray Dillman
Founder, Discipled Warriors • Retired U.S. Army Major
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What if courage isn't feeling ready, but refusing to let fear make the decision for you? Ray Dillman's journey from an uncertain young soldier to Green Beret, educator and ministry founder reveals what can happen when we choose to step toward the difficult thing.
Episode Summary
Sometimes one decision changes far more than the immediate circumstances around it. For Ray Dillman, one of those decisions was saying yes when a Special Forces recruiter unexpectedly asked if he wanted to try out.
Ray joins Audley for a wide-ranging conversation about courage, purpose, resilience, faith, teamwork and what it means to move toward difficult things instead of allowing fear to decide for you. Drawing from 23 years in the U.S. Army, including service as a Green Beret and Ranger, Ray explains why even highly capable people need a team, why being good at something doesn't make you more important than the person beside you and why mission success depends on everyone understanding their role. His military background and subsequent career in higher education are independently documented by his publisher and former university.
The conversation also moves into purpose, childhood experiences, faith and the choices that quietly shape our lives. Audley connects Ray's experiences to his own journey through podcasting and basketball, exploring how decisions that seem disconnected in the moment can make remarkable sense when viewed backward.
At its heart, this is a conversation about choosing to try. Listen in and consider what might become possible if fear no longer gets the final vote.
Key Takeaways
KEY TAKEAWAY 1
Confidence can be built after the decision. Sometimes you discover what you're capable of only because you attempted something before knowing whether you could succeed.
KEY TAKEAWAY 2,
Individual excellence never eliminates the need for a team. The strongest mission succeeds when people understand their different roles and trust one another to perform them.9
KEY TAKEAWAY 3
Your past can quietly shape your present. Recognizing old patterns gives you an opportunity to decide whether they still deserve authority over the life you're living today.
KEY TAKEAWAY 4
Fear does not automatically mean stop. When something matters, courage may simply mean refusing to let fear talk you out of taking the next step.
Meet Our Guest
Ray Dillman is the founder and steward of Discipled Warriors, a Christian ministry focused on equipping men to become spiritual leaders through biblical teaching, accountability and community. He holds a Ph.D. in Educational Leadership and is a retired U.S. Army Major.
His 23-year military career included service as a Green Beret and Ranger, command of the U.S. Army Sniper School and teaching at the United States Military Academy at West Point. After retiring from the Army, Ray spent a decade as a professor and director at Mid-America Christian University, where his roles included Director of Institutional Effectiveness.
Ray launched Discipled Warriors in 2024 and later wrote the Discipled Warriors Handbook, a 228-page resource designed to anchor the ministry's approach to biblical discipleship, purpose, stewardship and spiritual leadership.
Audacious Insight
The Hardest Thing You Try May Change What You Believe You're Capable Of
AUDACIOUS INSIGHT SUMMARY
A difficult decision can give you something success alone cannot: evidence that you're capable of stepping into uncertainty and finding your way through it. That evidence can quietly reshape how you approach every challenge that follows.
Audley's Personal Insights
One thing Ray said stayed with me: his decision to try Special Forces became evidence he carried into everything that followed. Once he'd climbed that mountain, other difficult things no longer looked quite as impossible.
That resonates with me because I can look backward at my own life and see the same pattern. Starting a podcast in 2008 eventually led to this conversation. Becoming a basketball commissioner, trying different roles and stepping into unfamiliar spaces rarely made complete sense beforehand. Looking backward, the dots connect.
Maybe that's part of what living audaciously really means. You don't always know where a courageous decision will lead. Sometimes you make it because something within you says, try it anyway, and years later you realize that decision changed what you believed was possible.
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