Southwest Airlines
Resources and Advice Focused for Pilots of Southwest Airlines and their Families
Southwest pilot families have access to a variety of retirement savings options, including your company 401(k), Profit Sharing, 401(a), Excess Benefit, and Top Hat plans. These plans come with unique features—such as company contributions, contribution limits, and tax strategies—that can be complex to navigate. In addition, understanding Southwest’s health benefits and selecting the right insurance options adds another layer of decision-making.
At Leading Edge, we help you navigate the nuances of your benefits and build a strategy that fits your financial goals—so you can make confident decisions for your future.
We also offer investment management for your Southwest 401k through Schwab, helping you stay on course with your retirement strategy.
Navigate Health Emergencies with Confidence
Aviation professionals face unique stressors – especially when it comes to maintaining their medical certification. Even minor health issues can lead to major financial consequences if you’re not properly prepared. As aviation families ourselves, we understand the stakes and the stress. Pilots have several ways to protect their income and their families from the financial impact of health emergencies. These include:
Short-term disability insurance
Long-term disability insurance
Loss of license coverage
Accrued sick time
Emergency savings
We work with pilot families to evaluate their options and create a tailored plan that fits their unique needs. And when a health emergency does occur, we’re here to help you navigate the financial side—so you can focus on recovery.
Resources for Southwest Airlines Pilots
I Just Got Hired at SWA… Now What?
- April 17, 2026
- LEFP
In this episode, Charlie Mattingly, CFP® and Jon Schultz, BS (Aeronautics) break down the critical benefits decisions new Southwest Airlines pilots face during Indoc and
Race to 72
- February 27, 2026
- LEFP
https://www.youtube.com/watch?v=fNI920TeInc In this episode, Kevin Gormley, CFP®, CPA, PFS, breaks down the “Race to 72” and why mastering the sequence of your 401(k) contributions is
Roth Catchup Rule Change
- February 13, 2026
- LEFP
In this episode, Charlie Mattingly, CFP®, MBA, and Andrew Christopher, CFA®, MSF, break down the new Roth Catch-Up Rule Change and why it may have
SWA Market Based Cash Balance Plan (MBCBP)
- January 23, 2026
- LEFP
In this video, Andrew Christopher, CFA®, MSF and Charlie Mattingly, CFP®, MBA break down the Southwest Airlines Market-Based Cash Balance Plan (MBCBP) and why it
SWA Pilots: Understanding New IRS 401(k) Rules for 2026
- December 30, 2025
- LEFP
In this episode, financial advisors Andrew Christopher, CFA®, MSF and Charlie Mattingly, CFP®, MBA from Leading Edge Financial Planning break down the upcoming IRS rules
SWA Health Insurance Open Enrollment
- October 30, 2025
- LEFP
In this session of Southwest Airlines Open Enrollment 2026, Jonathan Schultz, BS (Aeronautics) and Charlie Mattingly, CFP®, MBA from Leading Edge Financial Planning break down
SWA Open Enrollment Term Life Insurance and GVUL
- October 23, 2025
- LEFP
SWA Open Enrollment Loss of License and Long Term Disability
- October 20, 2025
- LEFP
SWA 2026 Open Enrollment Sick Time and Short Term Disability
- October 7, 2025
- LEFP
Beware If Moving to Low Tax State
- August 22, 2025
- LEFP
Thinking of Relocating? Beware If Moving to a Low-Tax State In this video, Kevin Gormley, CFP®, CPA, PFS and Jason Reagan, CFP®, RICP from Leading
