Pilot Career Advice, Checkride Failures, & Going Independent (ft. Theo - Corporate Pilot)

In this pilot episode, we dive deep into the realities of building a career in aviation—especially when the journey doesn’t go as planned. Jason is joined by Theo, a corporate pilot flying the Challenger 650, to talk shop, share stories, and give real, honest advice for pilots navigating setbacks.

▶️ Topics Covered:

• Life flying the Challenger 650
• Challenges of old tech aircraft & flying into island airports
• Advice for pilots who failed their LOE or checkrides
• The mental toll of aviation setbacks
• Real recovery stories from pilots who bounced back
• Why becoming an independent CFI might be your smartest move in today’s market
• Is your flight school ripping you off?
• What to do when your flight training drags on unnecessarily

💬 This episode features real talk, zero sugarcoating, and actionable advice for anyone dealing with checkride failures, airline rejections, or just wondering what the next move should be.

🔥 Whether you're just starting out or at a career crossroads, this one’s for you.

👇 Drop a comment with your thoughts or questions—we may feature your topic in a future episode.

📲 Join the Pilot Discord:
Connect with airline pilots, corporate pilots, DPEs, and other students building their careers inside our FREE community.

🎧 Subscribe for more pilot career content.