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 on your stage of life, income level, and risk profile.

What You'll Learn from This Episode

• WIN Framework: How "What's Important Now" can help pilots reduce overwhelm and focus on the right goal at the right time.
• Debt vs. Retirement Contributions: When high-interest debt should take priority over 401(k) deferrals, and when to grab the match.
• Buy or Rent?: Financial and lifestyle factors to consider when deciding whether to buy a home at a new base or hold off.
• Avoiding the House Poor Trap: How overextending on a mortgage can block other savings goals and limit financial flexibility.
• College vs. Retirement: Why kids can take out loans but you can't borrow for retirement - and when it's okay to help with tuition.
• Time Horizon Planning: How your age, NEC contributions, and market exposure should influence your decision-making.
• Cash Balance Plans: A quick overview of what's changing at American Airlines and how it compares to other carriers.
• Real Talk on Tradeoffs: How to stack and sequence goals using your plan—and when the numbers make the decision clear for you.

Resources:

Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

In this two-part episode, Tim Pope tackles two critical topics for pilots heading into 2026: real estate strategy and savings goals. First, Jade Barnett of Beacon Relocation (sponsor) joins the show to break down current market conditions, what buyers and sellers can expect across various metro areas, and how to navigate PCS or base-related moves. Plus: a new listener-exclusive promo for Pilot's Portfolio listeners - 25% of your agent's commission back when working with Beacon.

In the second half, Tim addresses a listener-submitted question: “How much should I be saving right now?” He walks through how to think about savings rates based on where you are in your career, the impact of the NEC, and how time horizon and compounding influence the outcome. Whether you’re early in your career or 10 years from retirement, Tim outlines considerations to help you better understand your target savings rate.

What You'll Learn from This Episode

• Real Estate Market Snapshot: Why prices are softening and how buyer leverage is increasing, even with high rates.
• Pilot Relocation Planning: Tips for base transfers, PCS timing, and narrowing down options.
• Buy or Rent?: How to assess your current home and what a CMA (Comparative Market Analysis) can reveal.
• VA Loan Flexibility: How veterans and spouses can reuse or combine benefits strategically.
• Q4 Closing Trends: Why more buyers are closing in December and January.
• Buying with a Strategy: Spreadsheet mindset: compare square footage, districts, and yield.
• Boots on the Ground: Why talking to local agents early gives you an edge.
• Beacon's Year-End Promo: Pilot's Portfolio listeners who contact Beacon in Q4 2025 get 25% of agent commission credited toward closing costs - on both the buy and sell sides - Promo Code: BeaconPilot2025 (valid through all 2026 closings)
• Savings by Career Stage: How targets shift with your time horizon and how NEC contributions help.
• Compounding in Action: How even modest contributions grow with time.
  Early Saver Advantage: Why frontloading builds margin for the future.

Resources:

Visit https://www.beaconrelocation.com/ to learn more.
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

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:

Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

You've probably heard the saying, "The best day of your life is when you sell it": and no, we're not talking about boats. We're talking about self managed rental properties. In this episode, Tim is joined by Trevor Flor, Navy veteran, former Delta pilot, and now a real estate investment advisor specializing in DSTs (Delaware Statutory Trusts) and 1031 exchanges at Aimpoint Investments. Trevor breaks down how 1031 exchanges really work, why DSTs were created, and how this is one potential approach to consider.

What You'll Learn from This Episode

• 1031 Exchanges Demystified: How selling investment property can be one potential approach to consider, depending on individual circumstances.
• DSTs as a Solution: Why Delaware Statutory Trusts were created, how they enable fractional ownership, and when they work best.
• Three DST Strategies: Using DSTs as a primary, backup, or complementary approach depending on your goals and exchange value.
• Timeline Rules That Matter: The 45-day identification window and 180-day close deadline - and what happens if you miss them.
• Partial Exchanges and Cash Boot: Can you peel off cash from a sale and still do a 1031? Yes, but at what cost?
• Accredited Investor Requirements: What qualifies you for DST access and what documentation you'll need.
• Types of DST Properties: From multifamily and industrial to storage, hotels, and more - what's available and how it's selected.

Resources:

Trevor Flor’s firm, Aimpoint Investments: www.aimpointinvest.com
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

In this episode, Tim asks the question many pilots hear in the cockpit: Is your 401(k) a scam? He walks through why 401(k)s exist, how they replaced pensions, and what today’s airline plans actually offer: contribution mechanics, investment menus, legal protections, and employer contributions specific to the majors. Tim also shares a listener email requesting a cargo-carrier disability deep-dive and invites other cargo pilots to weigh in.

What You'll Learn from This Episode

• Pensions vs. 401(k)s: Why pensions faded (PBGC oversight, funding issues)
  and how 401(k)s became the primary retirement tool.
• How Airline 401(k)s Work: Salary deferrals: pre-tax and Roth, after-tax
  contributions, investment menus, brokerage window.
• Contribution Limits & Employer Money: What “up to $70,000 per year”
  includes: deferral, after-tax non-Roth, NEC; why big plans mean lower-cost
  funds.
• Ownership & Vesting: Immediate vesting when dollars hit your account: what it means if you stay or leave.
• Legal Protections & Risks: 401(k)s protected from creditors, suits, bankruptcy; IRA and Roth IRA bankruptcy protection to ~$1.7M through 2028; civil-suit rules vary by state; QDROs in divorce are the exception.
• Beneficiaries that Bypass Probate: Keep beneficiaries current to speed
  distributions and reduce taxes.
• What Might Be Coming Next: In August order asks DOL to review alternatives
  in 401(k)s: private equity, private credit, crypto, real estate, digital assets

Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

In this episode, Timothy P. Pope, CFP®, discusses the newly signed "One Big Beautiful Bill Act" (OBBBA), breaking down the key tax changes and how they'll directly affect your bottom line. Tim explains the impact of maintaining current tax brackets, the increased standard deduction, and significant enhancements to State and Local Tax (SALT) deductions. He covers new provisions for charitable deductions, expanded child tax credits, and special interest deductions on U.S.-assembled vehicles. Additionally, Tim details the substantial improvements to 529 education savings plans and their greater flexibility moving forward.

What You'll Learn from This Episode

• Unchanged Tax Brackets: Why maintaining current brackets impacts your tax planning and financial strategies.
• Higher Standard Deductions: Understand the new deduction levels and how they apply based on your filing status.
• SALT Deduction Increase: Details on the jump to a $40,000 limit and phase-out thresholds starting at certain AGI levels.
• Charitable Contributions: How even non-itemizers can benefit from deductions of up to $2,000.
• Child Tax Credit Boost: Explanation of the credit increase to $2,200 per child and the associated AGI phase-out.
• Vehicle Interest Deduction: Insight into the tax incentives for financing U.S.-assembled vehicles.
• 529 Education Savings Expansion: Review major improvements, including higher withdrawal limits and new Roth IRA rollover opportunities.

Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

In this final episode of the Loss of Medical series, Timothy P. Pope, CFP® turns the spotlight on United Airlines. Tim offers a full breakdown of United’s disability coverage—from how benefits are calculated to the contractual caps and offsets that impact long-term payouts. He also reviews the ALPA supplement options, including monthly add-ons and a lump sum feature.

What You'll Learn from This Episode

• United’s Disability Formula: Learn how the 1026-hour rule works and what it means for your monthly income if you lose your medical.
• Understanding the Cap: Why pilots earning over ~$358k in 2025 could be limited by a hard monthly maximum.
  Tax Treatment: United’s benefit is after-tax by default - Tim explains why that can work in your favor.
• NEC Contributions While Disabled: Where it goes and why it still matters for your long-term savings.
• ALPA Supplement Options: Review of United's three ALPA disability add-ons-Base, Plus, and Lump Sum - and how to assess what’s right for you.
• Life Insurance Observations: A brief comparison of United’s life insurance benefit versus other major carriers - and why pilots should negotiate for more.

Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.

In this episode of Pilot’s Portfolio, Timothy P. Pope, CFP® continues the Loss of Medical series with a deep dive into what happens if a Southwest Airlines pilot loses their medical. Tim outlines why Southwest’s program may be the most pilot-friendly of all the majors, including generous long-term disability benefits, a built-in COLA, a flexible tax election, and the unique “new hire bridge” benefit for newer pilots. If you fly for Southwest—or are considering it—this episode is packed with practical details and planning tips to help you protect your income and plan ahead.

What You'll Learn from This Episode

• How Southwest Calculates Disability Pay: From average earnings to TFP-based formulas for newer hires.
• Understanding Elimination Periods and Coverage Timelines: What happens after 60 days and how long benefits last.
• COLA Adjustments and Sick Bank Top-Ups: How Southwest increases benefits over time and allows you to supplement with accrued sick leave.
• Tax Election Options: When and why to choose taxable vs. non-taxable disability benefits—and why timing matters.
  Union Supplement Plans (SWAPA): Option A vs. B explained, plus how to backfill income gaps with short-term and long-term strategies.

Resources:
Schedule An Appointment
Our Practice’s Website
Send Us Your Questions: info@pilotsportfolio.com

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.

We try to provide content that is true and accurate as of the date of publishing; however, we give no assurance or warranty regarding the accuracy, timeliness, or applicability of any of the contents. We assume no responsibility for information contained on this website and disclaim all liability in respect of such information, including but not limited to any liability for errors, inaccuracies, omissions, or misleading or defamatory statements.

Links to external websites are provided solely for your convenience. We accept no liability for any linked sites or their content and remind you that we have no control over their content. When visiting external web sites, users should review those websites’ privacy policies and other terms of use to learn more about, what, why and how they collect and use any personally identifiable information.

Usage of this content constitutes an explicit understanding and acceptance of the terms of this disclaimer.