I’m 62: Should I File For Social Security Or Wait?
Filing now could put money in your pocket sooner, or it could quietly cost you tens of thousands over a lifetime.
Southwest’s New NEC Roth Option: What Pilots Must Know
With little advance notice, Southwest rolled out a new NEC Roth option that allows company contributions to flow into a Roth 401(k), creating a powerful opportunity for long-term tax-free growth. Here's what you need to know.
Cash Balance Plan or HRA? A Tough Call for United Pilots
The election window for 2027 Pilot Contributions is open until December 31 for the proposed United Airlines Pilot Cash Balance Plan (the ‘CBP’).
The 5 Retirement Questions Smart People Ask
In this episode, Ryan continues last week’s discussion on elevating the retirement planning conversation for pilots
Why Better Questions Build Better Retirements
Most people think the key to better retirement planning is getting better answers, but Ryan argues it really starts with ask-ing better questions.
Planning for Retirement When You Marry Later in Life
Getting married in your 50s often means you’re combining lives, but not necessarily combining finances. How do you build a retirement plan together when you’ve both already built your own?
The Airline Pilot’s Hidden Tax Problem: Avoid a Massive RMD Shock
This Veterans Day episode of The Pilot’s Advisor features Zach Smith from Pilot Tax for a deep dive into one of the biggest challenges facing airline professionals: retirement tax planning
What To Know About The “First Year Rule” Of Retirement
Today, Ryan explores how to navigate this critical phase, offering practical insights to help you create a strong foundation for a retirement that’s rewarding, balanced, and full of purpose.
Does Dave Ramsey’s 9-Step Retirement Plan Work for Pilots?
On today’s show, Ryan digs into where he agrees, where he disagrees, and what he thinks is missing from Dave Ramsey’s approach entirely.
No Empty Nest in Sight? How Pilots Can Still Land a Smooth Retirement
Raising kids used to follow a predictable pattern: they grow up, move out, and you finally get the house to yourself. But for many pilots today, that “empty nest” moment keeps getting delayed.
