What Happens If I Lose My Medical At Southwest Airlines

In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP® continues the Loss of Medical series with a deep dive into what happens if a Southwest Airlines pilot loses their medical. Tim outlines why Southwest’s program may be the most pilot-friendly of all the majors, including generous long-term disability benefits, a built-in COLA, a flexible tax election, and the unique “new hire bridge” benefit for newer pilots. If you fly for Southwest—or are considering it—this episode is packed with practical details and planning tips to help you protect your income and plan ahead.

What You'll Learn from This Episode

• How Southwest Calculates Disability Pay: From average earnings to TFP-based formulas for newer hires.
• Understanding Elimination Periods and Coverage Timelines: What happens after 60 days and how long benefits last.
• COLA Adjustments and Sick Bank Top-Ups: How Southwest increases benefits over time and allows you to supplement with accrued sick leave.
• Tax Election Options: When and why to choose taxable vs. non-taxable disability benefits—and why timing matters.
  Union Supplement Plans (SWAPA): Option A vs. B explained, plus how to backfill income gaps with short-term and long-term strategies.

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This episode is sponsored by: Beacon Relocation

Beacon Relocation is a real estate firm helping pilots and air traffic controllers save money on their real estate transactions. By tapping into their network of over 1500 real estate agents across the country, pilots can save 20% of the real estate agent’s commission towards your closing cost on the sale or purchase of your home. Visit https://www.beaconrelocation.com/ to learn more. 

Timothy P. Pope is a Certified Financial Planner™and principal owner of 360 Aviation Advisors, LLC (“360 Aviation Advisors”), a registered investment advisory firm. Investment advisory services are provided through 360 Aviation Advisors, in its separate and individual capacity as a registered investment adviser. Podcast episodes are provided through Pilot’s Portfolio, in its separate and individual capacity.

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