In the first video of Southwest Airlines’ Fall 2025 Open Enrollment series, Jonathan Schultz, BS (Aeronautics) and Charlie Mattingly, CFP®, MBA from Leading Edge Financial Planning unpack what Southwest pilots need to know about sick time and short-term disability (STD).
They explain why one sick trip per month may be important for continuing to accrue both profit sharing and vacation time during a disability. For example, a 40 year old pilot would need 300 sick trips to cover one trip per month from age 40 to 65. The discussion also covers how sick time may help serve as your personal disability bank, the role of emergency funds, and when canceling STD coverage might make sense.
Key Topics Covered
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- Southwest Airlines Open Enrollment Introduction
- Importance of Sick Trips for Accruing Vacation Time and Profit Sharing
- Details of Short-Term Disability
- Ideas to Utilize Sick Time and Emergency Funds for Disability Emergencies
Actionable Takeaways:
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- Exercise caution when using sick time.
- Determine how much sick time you may need based on your age and years until retirement to continue to accrue vacation time and profit sharing during a disability.
- Consider canceling STD coverage if you can cover a disability emergency between your sick time and emergency fund, particularly between ages 60–64.
This conversation may help pilots gain clarity and confidence around open enrollment decisions. Watch, reflect, and share your feedback. We’d love to hear your questions and insights.
Connect with Charlie Mattingly
charlie@leadingedgeplanning.com 
865-240-2292
Connect with Jonathan Schultz
jonathan@leadingedgeplanning.com 865-684-4622
#SWAdisability #PilotFinance #SickTrips #DisabilityCoverage #LeadingEdgePlanning #SouthwestAirlines #AviationMoneyMatters #PilotLife #OpenEnrollment2025 #PilotMoneyGuys
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