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Fly the Transition

The Origins of Fly the Transition

Fly the Transition is the newest podcast from Flying Midwest Media.

As Podcaster and Pilot  Jim Schilling expanded his exposure to aviation through the Flying Midwest Podcast, he continued to encounter people with something in common. More and more people he encountered had found their way into aviation as a second career. He found these stories to be fascinating, entertaining, and inspiring. 

So where did they come from? What were they doing before? What made them realize and chase their dreams?

In exploring those questions, Jim created the Fly the Transition Podcast as a way to share those stories and inspire others to realize and chase their own dreams. 

 Join Jim as he tells the stories of those who have taken the leap into a new career in aviation. Hear the answers to all those questions and the journeys his guests have taken to accomplish their dreams. 

 This, is Fly the Transition. 


Jim Schilling


Jim Schilling is a co-host and producer for the Flying Midwest Podcast.
Jim is a four-year veteran of the United States Air Force. His service in active duty was in the Security Forces field and he was stationed at Nellis Air Force Base in Las Vegas, Nevada. Post-military, Jim has spent the last 16 years in law enforcement.
Jim began private flying in 2012. He holds a Private Pilot certificate and is Instrument-rated. He is currently holds a Commercial Single-Engine rating. When he isn’t podcasting, he is working towards his CFI.  Jim is a part-owner of a 1974 Beechcraft Sundowner and recently purchased a hangar that has been affectionately named “The Beechhouse.”
Jim is former member of the Civil Air Patrol. He has served in positions from squadron Emergency Services Officer to Assistant Inspector General for the Minnesota Wing. He has been an aircrew member and served on numerous search and rescue missions.
Outside of aviation, Jim enjoys finding creative outlets. He enjoys landscape, nature, and aviation photography. Some of his favorite photographs have been taken on hikes with his family at state parks around Minnesota.
Jim is married with two children and lives in the north metro of Minneapolis.