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 enough chaos to keep things on brand.

Juan Brown Bangor Crash Video

Air India Phuket Hard Landing Show Notes

0:00 Intro

3:56 Challenger 650 Crash & Deicing

26:26 Getting Too Comfortable

31:08 Pilot News & Musings

40:23 Reviews & Comments

43:52 Mailbag

1:04:01 Flight Advice

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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.

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 an amateur.

Check out Advanced Aircrew Academy

Show Notes

0:00 Intro

1:29 Landing at the Wrong Airport

7:18 Mitigation Strategy

14:07 When Do They Realize?

23:24 Continuing Education

36:35 Upcoming Events

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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.

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 of uncertainty, and the usual Episode 200 live-show chaos. Connect with James Onieal Show Notes

0:00 Intro

2:08 Hiring, Furloughs, and CFI

24:15 James Question Extravaganza

1:01:16 Listener Questions

1:10:26 Special Guests

1:17:02 Max Almost Crashed

1:24:31 Final Questions & Thoughts

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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.

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: Airplane Manager Show Notes

0:00 Intro

2:01 Airplane Manager Overview

11:07 App, AI, and Security

21:08 Flight Operations Efficiency

36:18 Evolving Best Practices with Tech

49:39 Final Thoughts

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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.

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.

Southwest Airlines Breitling Interest Form

Dave's Cosmic Subs

TimeShifter Jet Lag App

Show Notes

0:00 Intro & Travel Updates

9:23 Restaurant Dilemma

17:46 Gulfstream SVS Flier & Clawdbot

27:59 NTSB Report Update

37:52 Reviews & Comments

41:45 Mailbag

1:00:19 Flight Advice

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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.

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 you've got kids, a career, and possible commuting in the future. Episode 71 What's it like to be Married to a Pilot and Raise a Family Gleaming the Cube movie Show Notes

0:00 Intro

6:46 Max's Cub & Musings

18:29 AMM Charts & ForeFlight Layoff

21:47 Reviews & Comments

24:14 Mailbag

35:15 Flight Advice

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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.

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 Pilots

44:35 Practice Updates: Tax Prep

48:01 Pilots Portfolio Podcast & Final Thoughts

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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.

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 zoom. Flight Advice closes with a CFI weighing a pay-your-own 737 type rating in Dubai (plus a non-pro-rated five-year contract) vs staying stateside and waiting out hiring—spoiler: lots of red flags and lots of "talk to expats first." Show Notes

0:00 Intro

2:56 Max's Musings: Airport Design

15:11 Allegiant to Acquire Sun Country

24:28 Dylan's Recurrent Training

33:14 Small Flight Department Counseling Session

44:25 NBAA Opps Manual Integration

56:16 Rolex GMTs vs 21Five Watch

1:07:08 Reviews & Comments

1:16:34 Mailbag

1:36:24 Flight Advice

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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.

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 whether a regional/fractional move makes more sense). Luggage Review Series Show Notes

0:00 Intro

4:02 Musings: Training & Self-Landing Planes

28:03 Other Incidents

50:55 Caribbean Airspace Shutdown

56:07 Reviews

1:01:15 Mailbag

1:24:21 Flight Advice

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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.

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 here to learn more. Show Notes

0:00 Intro

4:15 Big 3 in 2026

11:52 Rejection Rates

15:23 Cadet Program Pipeline

26:08 Corporate Pilot Q&A

32:32 Regional FO Q&A

40:46 CJO or More Interviews

48:50 No Legacy Offers After Furlough?

59:29 Retirement Gameplan

59:29 GED & Education

1:20:20 Final Thoughts

Our Sponsors

Tim Pope, CFP® — Tim is both a CERTIFIED FINANCIAL PLANNER™ and a pilot. His practice specializes in aviation professionals and aviation 401k plans, helping clients pursue their financial goals by defining them, optimizing resources, and monitoring progress. Click here to learn more. Also check out The Pilot's Portfolio Podcast.

Advanced Aircrew Academy — Enables flight operations to fulfill their training needs in the most efficient and affordable way—anywhere, at any time. They provide high-quality training for professional pilots, flight attendants, flight coordinators, maintenance, and line service teams, all delivered via a world-class online system. Click here to learn more.

Raven Careers — Helping your career take flight. Raven Careers supports professional pilots with resume prep, interview strategy, and long-term career planning. Whether you're a CFI eyeing your first regional, a captain debating your upgrade path, or a legacy hopeful refining your application, their one-on-one coaching and insider knowledge give you a real advantage. Click here to learn more.

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. Click here to learn more.

Vaerus Jet Sales — Vaerus means right, true, and real. Buy or sell an aircraft the right way, with a true partner to make your dream of flight real. Connect with Brooks at Vaerus Jet Sales or learn more about their DC-3 Referral Program.

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. Click here to learn more.

VSL ACE Guide — Your all-in-one pilot training resource. Includes the most up-to-date Airman Certification Standards (ACS) and Practical Test Standards (PTS) for Private, Instrument, Commercial, ATP, CFI, and CFII. 21.Five listeners get a discount on the guide—click here to learn more.

ProPilotWorld.com — The premier information and networking resource for professional pilots. Click here to learn more.

Feedback & Contact

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