184. How Do You Stay Resilient After Career Setbacks? w/ Capt Benny

21.FIVE - Professional Pilots Podcast

Benjamin Bailey (@flybenfly) joins Max and Dylan for an honest, hilarious deep dive into aviation’s influencer world, airline interview faceplants, and the realism gap on pilot social media. For professional pilots, this episode cuts through the curated BS to talk timing, authenticity, and bouncing back after setbacks. From CRM failures to career detours, Ben brings the real talk with a dose of humor. Hit play and subscribe for the stories you're not getting on your For You page.

Follow Ben on Instagram @flybenfly

Ben's WWII Aircraft Engine Youtube Channel @flightdojo

Show Notes

0:00 Intro

2:29 Upgrading to Captain

9:45 It’s All Timing

13:56 The Interview Gauntlet

31:24 Pilot Career Stories

48:38 YouTube Deep Dive

56:38 Spirit Story

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Have feedback, suggestions, or a great aviation story to share? Email us at [email protected]. Check out our Instagram feed @21FivePodcast for more great content (and our collection of aviation license plates).

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.