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Expected to die, today he’s inspiring others to truly live.

World-renowned inspirational speaker + national bestselling author John O’Leary wants to help you wake up from accidental living so you can do, be, achieve and impact more through your life.

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  • Every Thursday, John interviews an amazing guest on their story, successes, failures, lessons, and life to help you uncover tips to apply in yours.

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Oct 13, 2021

Lt. Col. (ret.) Waldo Waldman is a Hall of Fame leadership speaker and New York Times bestselling author of Never Fly Solo. After overcoming his massive claustrophobia and fear of heights, Waldo became a highly experienced and decorated combat veteran, with over 2,650 flight hours and 65 real-world combat missions.

Today, Waldo shares tools and techniques to overcome obstacles, break performance barriers, and take charge during times of change.

This episode will leave you ready to recommit yourself to excellence, to diligently prepare for every mission and collaborate with others through trust, mutual support, and courage.


  • Courage-monger: champion for those who want to take action in their lives when feeling debilitated by fear, doubt and uncertainty.
  • Even terrified of heights and small spaces, Waldo knew he wanted to fly planes after visiting his dad at work as an airplane mechanic.
  • Passion has to be greater than fear.
  • Make your friends your mentors and your mentors your friends. Instead of being fearful of those that are better than him, Waldo chooses to befriend them and model after them.
  • In spite of his fear of heights and claustrophobia, Waldo became Instructor Pilot of the Year out of 308 others.
  • Responsibility trumps passion.
  • When faced with adversity, distract yourself from yourself by focusing on the win and those who are depending on you.
  • Ask with honor. Take with honor.
  • "You can't coach the uncommitted."
  • "Your comfort zone is your danger zone."


  1. Q. What is the best book you’ve ever read?
    A. How to Win Friends and Influence People by Dale Carnegie.
  2. Q. What is a characteristic or trait that you possessed as a child that you wish you still exhibited today?
    A. Sense of silliness.
  3. Q. Your house is on fire, all living things and people are out. You have the opportunity to run in and grab one item. What would it be?
    A. My harddrive .
  4. Q. You are sitting on a bench overlooking a gorgeous beach. You have the opportunity to have a long conversation with anyone living or dead. Who would it be?
    A. My twin brother
  5. Q. What is the best advice you’ve ever received?
    A. Be careful with who you spend time with.
  6. Q. What advice would you give your 20-year-old self?
    A. You're on the right path. It's okay to take the road less traveled and face your fears.
  7. Q. It’s been said that all great people can have their lives summed up in one sentence. How do you want yours to read?
    A. He gave people wings to fly.