Dr. JayR McIntyre sits down with Charles Flanagain, founder of Rise Resiliency and a retired U.S. Air Force Chief Master Sergeant who spent thirty years in uniform across nine countries and ten major global operations. Charles traces his path from Detroit, where he left home at seventeen to join the Air Force, through a career that reached the top one percent of the enlisted force, and into the harder fight of building a business and finding his footing as a civilian. He opens up about losing teammates to suicide, his own anxiety crisis late in his career, and the decision to seek mental health help through the front door so the airmen under his command could see him lead by example. The conversation breaks down the mindset required to lead at a high level, the discipline and accountability behind lasting resilience, and what it means to build a legacy that outlives you. Charles closes with the mission behind Rise Resiliency today: coaching, keynote speaking, and mentoring the next generation through partnerships with organisations like 100 Black Men and the Boys and Girls Clubs of America.
The mindset required to lead at a high level
Discipline, consistency, and personal accountability
Building a legacy that outlives you
Navigating challenges while staying focused on purpose
Charles Flanagain’s path from Detroit to the Air Force at seventeen, and thirty years of service across nine countries and ten major global operations
The hard transition from thirty years as a top one percent enlisted Chief Master Sergeant into founding Rise Resiliency during COVID
Charles’s own mental health journey, including going public with getting help so his airmen could see him lead from the front
Rise Resiliency's work today, including facilitation, keynote speaking, and mentoring through partnerships with 100 Black Men and Boys and Girls Clubs of America
“Leadership isn’t a title, it’s a decision you make every single morning you show up.” (Charles Flanagain)
“I want to go in the front door, and I want to type on the computer, I want to fill out my sheet, because my airmen are sitting in that room and I need them to see me, probably the most powerful enlisted person on the base, getting help.” (Charles Flanagain)
“We got to check in on each other, man, a lot.” (Charles Flanagain)
“I’m living proof that where you start does not determine where you finish.” (Charles Flanagain)
“I told you motivators, we don’t bring anybody on the platform that we’re not inspired by.” (Dr. JayR McIntyre)
[00:00:36] - Dr. JayR opens Season 6 and thanks Los Angeles Tribune and Riverside before introducing Charles Flanagain
[00:01:33] - Charles traces his roots to Detroit, Michigan and joining the Air Force at seventeen with his mother signing for him
[00:03:05] - Charles explains the origin of Rise Resiliency, founded in 2021 during COVID after contracts fell through and a shaky start as a small business owner
[00:08:28] - Charles reflects on retiring as a Chief Master Sergeant, in the top one percent of the Air Force enlisted force, and how much harder the transition to entrepreneurship was than expected
[00:11:16] - Charles speaks on losing teammates to suicide and the importance of checking in on each other
[00:19:00] - Charles describes insisting on going through the front door for mental health help so his airmen could see him lead by example
[00:28:57] - Charles outlines Rise Resiliency's facilitation and keynote work, including partnerships with 100 Black Men and Boys and Girls Clubs of America
[00:37:38] - Charles closes with his message that leadership is not a title but a decision made every single morning
Notable Guests/Resources:
Charles Flanagain is the founder of Rise Resiliency, a leadership and empowerment coaching company based near Chattanooga, Tennessee, offering facilitation, keynote speaking, and executive coaching. He is a retired U.S. Air Force Chief Master Sergeant who served thirty years, including nine countries and ten major global operations, reaching the top one percent of the Air Force’s enlisted force. He is a certified leadership and empowerment coach through the International Coaching Federation, a board member with the Boys and Girls Club in Cleveland, Tennessee, and works nationally with 100 Black Men and Boys and Girls Clubs of America. Learn more at riseresiliency.com and connect with him on LinkedIn and Rise Resiliency’s social channels.
Sponsors mentioned: Los Angeles Tribune, Riverside, Seven Eagle Academy.
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