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

SWA Open Enrollment Term Life Insurance and GVUL

Join Kevin Gormley, CFP® and Charlie Mattingly, CFP®, from Leading Edge Financial Planning for a discussion on life insurance options available to Southwest Airlines pilots

SWA Open Enrollment Loss of License and Long Term Disability

In this video, Jonathan Schultz, BS (Aeronautics) and Charlie Mattingly, CFP®, MBA from Leading Edge Financial Planning break down the key details of Southwest Airlines’

SWA 2026 Open Enrollment Sick Time and Short Term Disability

In this video, Jonathan Schultz and Charlie Mattingly, CFP® from Leading Edge Financial Planning unpack what Southwest pilots need to know about sick time and

Beware If Moving to Low Tax State

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

Pilots & the 2025 One Big Beautiful Bill: What You Need to Know

In this video, Kevin Gormley, CFP®, CPA, PFS from Leading Edge Financial Planning breaks down how the new tax bill may impact pilots at every

Effectively Utilizing Roth Funding to Prevent a Potential Retirement Income-Tax Bomb!

I was working with a client family recently and we took a moment to appreciate the fact that because they started saving in Roth IRAs

The Opportunity of a Lifetime: New Pilots are Making More Income than Ever Before!

The Opportunity of a Lifetime: New Pilots are Making More Income than Ever Before! What an amazing time to be a professional pilot! You have