As the year wraps up, our host Tim Pope highlights key planning reminders for pilots: open enrollment choices, tax strategies, 401(k) adjustments, and life changes like marriage, divorce, child birth, or buying a new home. He also covers Roth conversions, gain harvesting, FSA timing, and estate document updates. 

What You'll Learn from This Episode

• Open Enrollment Considerations: What to review before re-electing benefits, especially if your airline changed providers or you’ve had a major life event.
• Life Transitions and Benefits: How marriage, divorce, childbirth, or military retirement can affect your insurance, estate, and legal plan decisions.
• 401(k) Strategy: How to check your contribution progress, set your 2026 target, and re-evaluate Roth vs. traditional deferrals.
• Roth Conversions and Tax Bracket Planning: Why timing and bracket awareness matter when converting pre-tax dollars.
• Tax Gain Harvesting: How a low-income year might open a window to reset capital gains with little to no tax cost.
• Backdoor Roth Contributions: What deadlines actually apply and how to execute this multi-step move.
• FSA and Dependent Care Planning: Ways to prepare for upcoming expenses and reduce taxable income.
• Withholding Checkups: How to avoid surprises (or big refunds) in April by making Q4 adjustments now.
• Balancing Values and Financial Planning: Why it’s okay to spend money when it aligns with what matters to you, and how Tim applied that to a recent family mountain biking expense.

Resources:

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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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