197. What’s Changing with Airline Pilot Retirement in 2026?
21.FIVE - Professional Pilots Podcast
Release Date: 01/27/2026
207. Would You Sign a Five-Year Non-Prorated Training Contract?
21.FIVE - Professional Pilots Podcast
Max recaps a wild GA camping trip involving gale-force winds and a midnight arboreal emergency, while Dylan discusses the "superpower" of vibe-coding your own aviation tools with AI . The Mailbag tackles the dilemma of choosing between a quick class date with a restrictive five-year contract or waiting for a better "wholly owned" offer . Finally, Flight Advice addresses a contract pilot who is being ghosted on $10,000 worth of invoices and expenses . Show Notes 0:00 Intro 2:24 Max’s Musings: Flights & Camping 23:13 Pilot Numbers, FAA, & AI Coding 30:10 Reviews 31:39 Mailbag 42:06...
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206. Is your leadership style actually just manipulation?
21.FIVE - Professional Pilots Podcast
Dylan and Max sit down with Kyle Freiberger and Mike Sferrazza from First Class Leaders to bridge the gap between technical proficiency and effective aviation leadership . This episode explores why traditional CRM often fails to address the human element and how pilots at any rank can cultivate influence through self-awareness and emotional intelligence . The guys dive into the "Take the Lead" framework, the DISC behavioral tool, and the critical shift from defending your intentions to owning your impact on the crew . Learn more about Show Notes 0:00 Intro 2:11 Starting First Class Leaders...
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205. Is Airport Parking the Worst Part of Being an Airline Pilot?
21.FIVE - Professional Pilots Podcast
This week Dylan and Max kick things off with Atlantic Bucks, the new IRS reporting threshold, and a spirited rant about airport parking, employee lots, and the endless misery of hotel vans. In the mailbag, they dig into helicopter careers, the real risk-versus-reward tradeoffs, and what that path looks like compared with airplanes. Flight Advice gets into career strategy for a maintenance pro trying to break into flying and a young regional FO deciding between staying put, jumping to 135, or chasing a bigger airplane. It’s part career counseling, part curbside therapy, and very much a...
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204. What Can We Learn Before the Final Report Arrives?
21.FIVE - Professional Pilots Podcast
Juan Browne of the blancolirio YouTube channel joins Dylan and Max to talk about how he breaks down aviation accidents and incidents in near real time. For professional pilots, it’s a sharp discussion on separating facts from opinion, finding teachable moments, and managing the gap before the NTSB final report arrives. They get into ADS-B, ATC audio, comment-section corrections, GA repeat offenders like VFR into IMC and loss of control, plus a few backcountry Husky war stories. Check out the Juan Browne's on YouTube Show Notes 0:00 Intro 3:00 How It Started 9:10 The Process of Making a...
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203. Is Commuting Worth Three Years of Seniority?
21.FIVE - Professional Pilots Podcast
Why is Max recording at night, and why does every aviation headline lately feel like another runway-incursion autopsy? This episode covers TSA chaos at Sky Harbor, a rough New York accident discussion, eVTOL optimism, and Max’s descent into experimental-airplane condition inspection misery. In the Mailbag, the guys debate NBAA landing-distance math, hear a loud call to bring back listener stories, and defend Max’s musings like true professionals. In Flight Advice, they tackle a brutal career question: keep three years of United seniority and commute, or risk starting over at Delta for a...
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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...
info_outlineFinancial 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 Pilots
44:35 Practice Updates: Tax Prep
48:01 Pilots Portfolio Podcast & Final Thoughts
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