182. When the Flight Department’s Broken, Do You Stay or Go?

21.FIVE - Professional Pilots Podcast

A listener asks the question every pro pilot eventually faces: should you stay put and try to fix what’s broken in your flight department, or cut bait and move on? Dylan and Max bring in Jenny Showalter and Jim Lara to explore the real-world tradeoffs. From career coaching to leadership insights, they share what to weigh before pulling the ripcord—or digging in to make change happen. It’s candid talk about loyalty, burnout, and how to navigate tough calls in business aviation.

To contact Jenny Showalter, visit showalter.com

To contact Jim Lara, visit graystoneadvisors.com

Show Notes

0:00 Intro

2: 23 Unprofessional Operations

14:59 Structure, Culture, Excellence

28:01 Plan B

33:38 Investigation Red Flags

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The statements made in this show are our own opinions and do not reflect, nor were they under any direction of any of our employers.