162. Can You Really Plan for an Unplannable Career?
21.FIVE - Professional Pilots Podcast
Release Date: 03/25/2025
210. What Should Pilots Do When the Paycheck Stops?
21.FIVE - Professional Pilots Podcast
Timothy P. Pope joins Dylan and Max to talk through the financial side of Spirit’s shutdown and what professional pilots can learn from it. For airline and bizav pilots, the big takeaway is simple but not always fun: stabilize first, optimize later. The crew digs into emergency funds, burn rate, 401(k) rollovers, IRA traps, benefits, life insurance, and why raiding retirement money is usually the nuclear option you try very hard to avoid. Listen, subscribe, and maybe give your emergency fund a little love. Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His...
info_outline
209. Should You Trade Quality of Life for Airline Seniority?
21.FIVE - Professional Pilots Podcast
Dylan and Max kick things off with DoubleTree cookie restraint, San Diego seafood, 40-plus Vegas strategy, DJ juice, and the emerging menace of the commuter life vest. In the Mailbag, listeners bring dumpster-diving charter pilot stories, bankruptcy bassoon suggestions, skydiving-adjacent book recommendations, and a heavy airline-industry “what if” about another major demand shock. Dylan also recaps his first Atlantic crossing in years, complete with CPDLC confusion, Gander relief, and some unpaid product shoutouts. Flight Advice tackles whether a 36-year-old Caravan pilot with a young...
info_outline
208. How Should Pilots Compete After Spirit’s Shutdown?
21.FIVE - Professional Pilots Podcast
James Onieal from Raven Career Development joins Dylan and Max to unpack Spirit Airlines’ wind down and what it means for Spirit pilots, regional pilots, CFIs, and anyone trying to move up the aviation ladder. The conversation gets into why experience alone will not carry you through an interview, especially when 2,000-ish highly qualified pilots suddenly enter the market. James breaks down logbooks, PRD files, recommendation strategy, corporate aviation, oil-price uncertainty, and why “preferential interview” does not mean “automatic job.” Raven Careers — Helping your career take...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outline
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...
info_outlineMax shares a wild story involving VFR ops in a jet and a last-minute divert to Deer Valley when Scottsdale Tower ghosted them. We cover the final chapter of Hard Landing in the book club and reflect on takeaways from the book. In the mailbag, we talk about MU-2s doing angel work, the A&P to pilot career path, and the latest 737 LRD drama. Flight Advice: Should I keep my survey job or finish my CFI? Oh, and we may have created a secret pilot Freemason society while we were at it.
More info on the Cargo Cat Pilots Podcast here
Show Notes
1:21 Max’s Musings: Cutting the Line
12:48 Starlink Update
17:05 Southwest Changes
19:34 Hard Landing Book Club: Final Chapter
35:32 Carbon Cub Updates
39:36 Reviews & Comments
41:53 Mailbag
58:41 Flight Advice
Be sure to subscribe to 21Five's Youtube Channel to see our luggage review videos!
Our sponsors:
Move your airplane without breaking your back or the bank! Max said the Amigo AeroTow's affordable T1 tug has 'changed his hangar life'.
Learn more about AeroTow's family of aviation tugs and see why its earning rave reviews from top 40 aviation podcast hosts around the globe.
Use code "21five" at checkout for $100 off any AeroTow product!
--
Harvey Watt, offers the only true Loss of Medical License Insurance available to individuals and small groups. Because Harvey Watt manages most airlines' plans, they can assist you in identifying the right coverage to supplement your airline’s plan. Many buy coverage to supplement the loss of retirement benefits while grounded. Visit harveywatt.com to learn more!
--
Advanced Aircrew Academy enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. We do this by providing high-quality professional pilot, flight attendant, flight coordinator, maintenance, and line service training modules delivered via the web using a world-class online aviation training system. Visit aircrewacademy.com to learn more!
--
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 podcast: The Pilot's Portfolio podcast
--
Employee Compensation Software That Answers "What's the Going Rate?"
The AirComp Calculator™ is business aviation’s only online compensation analysis system. It can provide precise compensation ranges for 14 business aviation positions in six aircraft classes at over 50 locations throughout the United States in seconds.
--
VAERUS MEANS RIGHT, TRUE, AND REAL.
Buy or sell an aircraft the right way, using a true partner, to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales | Learn more about the DC-3 Referral Program
--
The 21.5 Podcast is supported by our friends at ProPilotWorld.com - The Premier Information & Networking Resource for Professional Pilots
--
Do you have feedback, suggestions, or a great aviation story to share? Email us info@21fivepodcast.com Check out our Instagram feed @21FivePodcast for more great content and to see 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.