Pilot’s Portfolio

Professional pilots can accumulate more than just 401(k)s, IRAs, Roth accounts, and brokerage accounts over the course of a career.

Airline benefits can also include Health Reimbursement Arrangements, Retiree Health Reimbursement Arrangements, deferred compensation plans, market-based cash balance plans, Employee Stock Purchase Plans, and other employer-linked accounts that work differently from the accounts pilots manage directly.

I...

As pilots move through their careers, financial accounts can start to build up across different stages of life.

A current 401(k) or TSP. Old employer plans. Rollover IRAs. Roth accounts. Backdoor Roth opportunities. An HSA. A taxable brokerage account. Spouse accounts. Each one may have been opened for a good reason, but over time the full picture can start to feel scattered.

In this episode of Pilot’s Portfolio, Timothy P. Pop...

In Part 1 of this conversation, Timothy P. Pope, CFP, started with the first step in tax planning: understanding what the tax number actually means. If you missed that episode, stream it here:

In this following part, Tim continues the tax conversation by moving from deductions to longer-term planning, exploring taxable brokerage accounts, investment tax efficiency, tax-loss harvesting, embedded capital gains, and why pilots may bene...

After a short summer break, Pilot’s Portfolio is back with a refreshed format and a new Season (4)!

This next run of episodes is built around real questions Timothy P. Pope, CFP® receives from professional pilots and their families in planning conversations.

This is a two-part deep-dive on one of the biggest questions professional pilots bring to the planning table: “How can we pay less in taxes?”

Whether the number ...

Is now a good time for pilots to buy a home, or does it make more sense to wait?

In this episode of The Pilot’s Portfolio, Timothy P. Pope, CFP® welcomes back Kevin Walker, and Jade Barnett, respectively CEO and COO of Beacon Relocation, for a mid-year housing market check-in.

Tim, Kevin, and Jade revisit earlier real estate forecasts and discuss how today’s market is actually playing out, from higher mortgage rates and s...

In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy Pope, speaks directly to Spirit Airlines pilots and families navigating an unexpected and deeply challenging career disruption.

Tim focuses on the practical financial side of the situation, including emergency funds, household burn rate, retirement-account decisions, lower-income-year tax opportunities, and the unique considerations facing pilots nearing r...

In this updated re-issue of one of Pilot’s Portfolio’s early conversations, Timothy P. Pope, CFP®, revisits a timely question with compensation expert Kit Darby: what is a pilot career really worth?

Tim adds 2026 reflections throughout, connecting Kit’s insights to today’s planning reality: income should become flexibility, resilience, and long-term options.

When this episode first aired, pilot pay was rising ...

In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy Pope, breaks down how airline pilots should prepare for retirement during periods of market turbulence, particularly within the final five years before leaving the workforce.

He explains the shift from accumulation to retirement readiness, and why volatile markets don’t require a new philosophy, but a more disciplined and coordinated approach. The ep...

In this Peer-to-Peer episode of Pilot’s Portfolio, our host, Certified Financial Planner™ and GA pilot, Timothy Pope sits down with First Officer André for a grounded conversation about discipline, freedom, and how financial habits shape long-term confidence. André shares his path from flight instructing and corporate flying to Envoy, furlough, and eventually American, along with the financial lessons that came with each chap...

In this episode, our host Timothy Pope looks at automation in financial planning and investing. For many pilots, automation helped build the emergency fund, grow the 401(k), and create strong saving habits early in the career. But as income rises, taxes increase, and decisions become more complex, automation by itself usually is not sufficient.

Tim explains the shift from simple accumulation to financial coordination. He walks throu...

In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP®, Firm Principal and Client Advisor at 360 Aviation Advisors™, is joined by Kevin Walker, Co-Founder/CEO, and Jade Barnett, Co-Founder/COO of Beacon Relocation, to discuss how listeners have received nearly $39,000 back through Beacon’s real estate program.

They break down how the model works on both the buy and sell side, how credits can come back as a check or ...

In this Q&A episode of Pilot’s Portfolio, Timothy P. Pope, CFP®, Founder and Principal of 360 Aviation Advisors™, answers three listener questions that surface real-world friction inside airline retirement planning.

First, a Southwest pilot asks whether taking NEC as Roth impacts their ability to contribute or convert to a private Roth IRA.

Next, a Delta pilot seeks clarity on the difference between 401k, 401a, Roth, and af...

In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy P. Pope explains a new option for Southwest pilots, taking their NEC as Roth starting in 2026. He covers what NEC is, how Secure 2.0 made Roth employer contributions possible, and how Southwest is rolling this out.

Tim walks through what changes when you elect Roth NEC, including how it shows up on your W-2, what happens with federal income tax and FICA, a...

In this episode, our host, Certified Financial Planner™ and GA pilot, Timothy P. Pope looks at how money can support or strain relationships, especially for professional pilots who spend long stretches away from home. He talks about income differences, schedule pressure, and clashing money styles, and how those can quietly build resentment if they are not discussed. Tim shares examples from his planning work and his own marriage, a...

In the first episode of Season 3, our host, Certified Financial Planner™ and GA pilot, Tim Pope recaps 2025’s market and policy shifts, and he explains why diversification and tax-centered planning made the difference this year, especially for high-income pilots.

Tim also highlights key tax law changes, reflects on aviation incidents that underscore the importance of estate planning, and previews what is ahead for the podcast ...

This episode was requested by listener feedback! Our host, Certified Financial Planner™ and GA pilot, Tim Pope compares long-term disability (LTD) coverage for FedEx and UPS pilots, examining how each plan works and how they stack up across the industry. He breaks down union and core benefits, highlighting key differences in benefit duration, tax treatment, monthly caps, waiting periods, and income offsets.

The episode also explores...

In this time-sensitive episode,  Certified Financial Planner™ and GA pilot Tim Pope unpacks the new Market-Based Cash Balance Plan (MBCBP) for American Airlines pilots ahead of the December 15 opt-in deadline. He explains how the plan captures NEC spillover beyond 401(k) limits, who qualifies, and how it differs from other carriers.

What You'll Learn from This Episode

• Plan Basics: How the MBCBP captures NEC spillover when 40...

In this episode of Pilot’s Portfolio, Certified Financial Planner and GA pilot Tim Pope helps pilots close out the year with clarity and confidence. As 2026 approaches, new tax and retirement contribution rules are set to take effect—and Tim explains what they mean for your paycheque, your savings, and your strategy. From 401(k) and IRA limit increases to the controversial new Roth “catch-up” rule, this epis...

In this episode, we tackle a question many pilots ask themselves: what should I be working on right now? Whether it's debt repayment, buying a home, saving for retirement, or funding your kids' college, it can be hard to figure out which goal takes priority. Our host, Timothy P. Pope, CFP introduces the "WIN" framework: What's Important Now, and walks through how to use your financial plan to identify the highest-impact move based ...