152. 2025 Pilot Hiring: What's Happening And What Should I be Doing About It?
21.FIVE - Professional Pilots Podcast
Release Date: 01/07/2025
202. Would You Start Over at a Fractional in Your 40s?
21.FIVE - Professional Pilots Podcast
This week Dylan and Max dig into the recent Challenger 650 accident in Bangor and the very real pressure corporate crews can feel when winter ops get sporty. In the Mailbag, they hit union negotiations, whether helicopter flying is actually a smart career pivot, a truly elite ripped-pants-in-cruise story, and a listener correction on landing the Osprey. For Flight Advice, they tackle a big mid-career question: if you had to start over in your late 40s, is a fractional the better move than going back to the bottom of an airline seniority list? It’s safety soapbox, career therapy, and just...
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201. Why Are Wrong-Airport Landings Still Happening?
21.FIVE - Professional Pilots Podcast
Dan Boedigheimer from Advanced Aircrew Academy joins Dylan and Max to break down why wrong-airport and wrong-surface landings still happen, and what professional pilots can do to stay ahead of them. For Part 91 and bizav crews especially, it’s a practical discussion on building better habits when nobody is spoon-feeding you the safety data. They get into visual approach traps, pilot monitoring duties, stabilized approach discipline, workload, fatigue, and what actually makes recurrent safety training stick. Listen in, then subscribe so you don’t end up chasing the bright shiny airport like...
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200. Live show: James Onieal answers listener questions
21.FIVE - Professional Pilots Podcast
Dylan and Max are joined by James Onieal (Raven Careers) for Episode 200, covering everything from conferences and networking to cadet programs, cargo hiring, and fractional life. They also dig into the latest conflict in the Middle East and what rising oil prices could mean for airline pilots—from hiring pressure and route economics to the broader ripple effects across the industry. The conversation gets into why pathway programs can be helpful, but also how debt-heavy options can limit your flexibility when the market turns. Add in pipeline patrol as real CRM-building time, a healthy dose...
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199.5 How Do You Build Fortune 100-Level Flight Ops at your Small Flight Department?
21.FIVE - Professional Pilots Podcast
Dylan and Max sit down with Aaron, Software Architect at Airplane Manager, to talk business aviation ops tech and where AI is headed. If you’re running lean (two pilots, one tail, no dispatcher), this is the roadmap for reducing busywork without losing operational control. They dig into integrations, offline trip tools, and why “apps” might just become background APIs. Listen in and subscribe for more pilot-to-pilot ops talk. Check out the software Dylan and Max both use to run their departments: Show Notes 0:00 Intro 2:01 Airplane Manager Overview 11:07 App, AI, and Security 21:08...
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199. At What Point Should You Just Eat the Hotel Food?
21.FIVE - Professional Pilots Podcast
Dylan and Max recap a jet-lagged Japan ski mission, widebody travel wins and fails, and the realities of surviving brutal time zone changes. In the Mailbag, they dig into Saab war stories, Autoland edge cases, NBAA training standards, airline-branded watches, and career wins from listeners making the jump into jets. The Flight Advice segment centers on a sobering accident discussion and the risks of slipping from airline discipline into lightly regulated operations. As always, it’s equal parts technical insight, hard-earned perspective, and questionable footwear choices. Show Notes 0:00...
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198. What Does “Stay Flexible” Actually Mean for Pilot Spouses?
21.FIVE - Professional Pilots Podcast
Late-night musings from Dylan and Max: corrections on “newest airports,” a touchdown-point math fix, and Max’s Cub antics after an oil change—including a surprise landing on BLM dirt near Lake Pleasant. Then: the inaugural JSX ATR into Scottsdale, a Japan trip preview, a wild “Gleaming the Cube” airport intro, Jepp AMM taxi chart nerd-out, ForeFlight layoff chatter, and Airplane Manager’s new AI. The mailbag brings career moves, SOP love, a real-world bird strike at rotation, and finally: Flight Advice from a pilot spouse (Marie) asking what “stay flexible” really means when...
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197. What’s Changing with Airline Pilot Retirement in 2026?
21.FIVE - Professional Pilots Podcast
Financial planner Timothy P. Pope of 360 Aviation Advisors returns to break down 2026 retirement updates that matter to pro pilots. From new Roth catch-up rules to Southwest's bold move on NEC contributions, he digs into the real tax impacts for airline crews. Bonus: comparisons across the majors, advice for CFI's just starting out, and a hangar office update. Listen in and get smarter about your money. Show Notes 0:00 Intro 3:23 What’s New: Retirement Considerations 13:26 Southwest Airlines & Carrier Benefits 32:28 Retirement For Younger Pilots 35:29 Financial Planning for Younger...
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196. How Much Chaos Can You Fit Into One Runway?
21.FIVE - Professional Pilots Podcast
San Diego continues its reign as the busiest single-runway “how is this legal?” airport, plus we nerd out on new terminals, recurrent training wins, and a Challenger sim surprise when Dylan’s seat decided to yeet itself at ~90 knots. In the Mailbag, we hit ferry flying as a niche career path, a home-buying reality check from Diamond Dog Tim Pope (mortgage recasts, baby), and a training-center SOP rant that’s painfully relatable. We also kick off the 2026 ops-manual push with the “latest touchdown point” concept and how to actually mark it on ForeFlight without fat-fingering your...
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195. Would You Let the King Air Land Itself?
21.FIVE - Professional Pilots Podcast
First show of 2026: we talk Garmin Autoland in a King Air and why internet speculation is the fastest way to sound like a jabroni. We also hit the chaos of international ops (Mexico permits/APIS pain) and tease the Chicago Layover Guide dropping soon. In the Mailbag: Coeur d’Alene layover intel, a legendary lav story, Pilot Pete confusion gets cleaned up, airline-switching “sunk cost” drama, and surviving an unhinged sim instructor. Flight Advice is a big one: a 2,000-hr pilot with a baby inbound weighs staying in a single-pilot piston twin 135 gig vs taking a King Air 200 EMS job (and...
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194. What Will Pilot Hiring Really Look Like in 2026?
21.FIVE - Professional Pilots Podcast
James Onieal from Raven Career Development returns to break down what pilot hiring is shaping up to look like in 2026. We dig into majors, regionals, corporate paths, and why movement can feel slow right up until it suddenly isn’t. From CFI logjams to corporate and furlough realities, this episode is all about timing, strategy, and expectations. Subscribe and listen to stay ahead of the hiring curve. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Click to learn more. Show Notes 0:00 Intro 4:15 Big 3 in 2026 11:52...
info_outlineJames Onieal joins Dylan and Max to unpack the turbulent landscape of pilot hiring in 2025. From overhiring at the majors to regional pilots struggling to stand out, James offers no-nonsense advice on how to stay competitive. Whether you’re a CFI with big dreams or a seasoned military pilot planning your exit, this episode is packed with actionable insights for navigating the year ahead. Tune in for a mix of hard truths, strategies, and a few good laughs!
Get in touch with James Onieal
Show Notes
0:00 Intro
2:22 2025 Hiring Forecast
17:46 Too Much Flight Time and No Offer?
30:21 Diversity, Equity, and Inclusion
36:53 Rapid Fire Scenario Advice
46:48 Flight Advice
1:03:56 Ramifications of Commuting
1:23:38 General Rapid Fire Advice
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Tim Pope is a CERTIFIED FINANCIAL PLANNER™ and a pilot. His financial planning practice provides services to aviation professionals and aviation 401k plans. Tim helps clients pursue their financial goals by defining them, organizing & optimizing resources, planning, implementing, and monitoring their financial plan. Visit https://link.21fivepodcast.com/timothy-pope to learn more. Check out Tim's new podcast: The Pilot Money Podcast
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