My 2024 Birthday Week



It’s my Birthday Week on the MILMO Show. Every year for my birthday, I like to interview someone special in my life. In past years, I’ve interviewed my Mom, Dad, and my 97-year-old grandmother. This year is no different. I have a very special guest to help me celebrate my birthday on the show.

In this episode, my brother, Brian Flanigan, is in the hot seat answering all of my questions. He shares the biggest challenges he has faced retiring from the Air Force, the best thing he got out of the military and advice for people getting ready to separate or retire. He even shares his experience of being diagnosed and fighting cancer on active duty.

My brother, Lt Col Brian Flanigan (retired), is a pilot for Southwest Airlines. Prior to his military retirement he was the Director of Operations, 2d Special Operations Squadron, Air Force Reserve Command, Hurlburt Field, Fla. He led operations for Air Force Reserve Command’s only Special Operations Command Remotely Piloted Aircraft MQ-9 Squadron. He also oversaw persistent combat operations as a geographically separated unit in support of special operations forces in multiple areas of responsibility.

Brian graduated from the University of North Carolina at Wilmington in 2001 and received his commission through USAF Officer Training School in 2003. He earned aeronautical ratings as both a senior pilot and navigator, and spent the majority of his career in special operations assignments within the AC-130U and MQ-9 communities. During his 20 years of service, Brian served as Wing Inspector General and Wing Executive Officer. Additionally, he has flown over 400 combat missions supporting special operations in Operation IRAQI FREEDOM, Operation ENDURING FREEDOM, Operation FREEDOM’S SENTINEL, and Operation INHERENT RESOLVE.

Episode Highlights

Childhood memories:
  • Christmas morning traditions
  • Fixing a car’s turn signal with a manual toggle switch
  • Mowing the lawn with a makeshift lawnmower
Brian’s wrestling experience and life lessons learned from it:
  • Mental toughness
  • Persistence and hard work
  • Applying wrestling lessons to life challenges
Brian’s motivational sayings and their meanings:
  • “Dollar bets” – spreading resources and seeking opportunities
  • “How bad does it have to get?” – prompting action on issues
  • “If it was easy, everyone would do it” – valuing hard work
  • “Aim small, miss small” – importance of attention to detail
Brian’s military career:
  • Experience as a special operations pilot
  • Challenges in leadership
  • Fighting cancer while on active duty
Advice for military personnel:
  • For new recruits: Serve with purpose, excel at your job, and own up to mistakes
  • For those transitioning out: Prepare early, utilize available resources, and expect cultural differences
Personal insights:
  • Best thing from serving: Serving the country and building relationships

Episode Resources

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