309. Financial Planning Tools for Pilots, By a Former Airline Pilot

In this episode of A Wiser Retirement® Podcast, Casey Smith, President of Wiser Wealth Management and former airline pilot is with Grace Kennedy, Financial Planning Associate to discuss the unique financial needs of pilots and the smartest financial planning path for them. 

Airline pilots face a unique mix of high-but-variable income, mandatory retirement at 65, stringent medical requirements, and shifting industry dynamics. That’s why “pilot math” matters, your plan has to reflect guarantee hours, upgrade paths, commuting realities, union benefits, and specialized employer plans.

Related Podcast Episodes: 

• Ep 234: Pilots, Maximize Your 401(k) Contributions!
• Ep 309: What Pilots and Others Should Consider 5 Years Before Mandatory Retirement

Related Financial Education Videos:

• Pilots: Roth or No Roth... That's the Question 
• Why Financial Planning is Different for Pilots 
• Delta Pilots: Market Based Cash Balance Plan Explained 

Other Links:

Free 401K Allocation Guide for Pilots

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This podcast was produced by Wiser Wealth Management. Thanks for listening!

Chapters

• 0:00 Cold Open: Predatory Pitch Rant
• 0:21 Welcome, Hosts, and Setup
• 1:26 Casey’s Path: Cockpit to CFP
• 4:10 Today’s Pilot Career Reality
• 6:58 Volatility, Mergers, and Career Moves
• 9:52 Pay, Quality of Life, and Family Tradeoffs
• 13:19 Health, Medicals, and Career Risk
• 15:39 What Makes Planning “Pilot-Specific”
• 18:35 Why Specialized Knowledge Matters
• 21:20 Irregular Income, Guarantees, and Extra Trips
• 25:34 Building Wiser: Nights, Stand-ups, and Hustle
• 27:42 Retirement Accounts: Basics Before Tricks
• 30:28 Avoiding Mousetraps: Whole Life, Annuities, Options
• 34:20 Mega Backdoor Roth vs Brokerage Flexibility
• 37:06 Direct Indexing and Tax Efficiency
• 39:24 Free 401(k) Guides & Beating the Fee Machine
• 43:04 Dollar-Cost Averaging Mindset for Pilots
• 45:08 True Comprehensive Planning, Not AUM Drains