What's Your Career Worth? 2026 Updates - Airline Compensation & Trends with Kit Darby

Spirit Airlines Shutdown: What Pilots Should Do Next

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 retirement age. He also explains why your 401k remains protected, why rushed rollover decisions can create long-term tax consequences, and how thoughtful planning can create flexibility during uncertain times. What You'll Learn from This Episode * Why aviation career disruptions require stabilization before optimization * How emergency funds and brokerage liquidity create flexibility during uncertainty * Why understanding your household burn rate lowers financial anxiety * What Spirit pilots ages 55-59 need to know about the 10% IRA penalty * How bridge strategies can help pilots reach age 59.5 more efficiently * Why your 401k remains protected during airline bankruptcy proceedings * Why rolling retirement assets too quickly can create backdoor Roth complications * How lower-income years may create Roth conversion and tax-planning opportunities * Why reviewing your tax withholding now could improve near-term cash flow * How pilots near retirement should think about flexibility, income, and lifestyle changes Resources: Listen to How to Prepare for Retirement During Turbulent Times [https://podcasts.apple.com/us/podcast/pilots-portfolio/id1718915375] Schedule An Appointment [https://calendly.com/d/ck72-3sp-r58]Our Practice’s Website [https://360aviationadvisors.com/]Send Us Your Questions: info@pilotsportfolio.com [info@pilotsportfolio.com] This episode is sponsored by: Beacon Relocation [https://www.beaconrelocation.com/] 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/ [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.

What's Your Career Worth? 2026 Updates - Airline Compensation & Trends with Kit Darby

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 fast, contracts were being reset, and hiring pressure was reshaping the industry. In 2026, the story is more nuanced: compensation remains strong, but fuel costs, slower hiring, cargo volatility, and uncertainty show why income alone is not financial security. Kit Darby breaks down airline compensation, career value, retirement benefits, and expert witness services. What You'll Learn from This Episode * What pilot compensation says about the value of an aviation career. * Why regional pay, mainline contracts, and retirement contributions should be compared carefully. * How strong income creates planning opportunities, plus tax, retirement, and cash-flow complexity. * Why the pilot shortage story has shifted from shortage to supply and demand imbalance. * How fuel costs, capacity decisions, aircraft delays, and cargo volatility can affect airline economics. * Why pilots should prepare for downturns before they arrive. * How expert witness services can calculate career value after injury, loss of medical, or death. Resources: Schedule An Appointment [https://calendly.com/d/ck72-3sp-r58]Our Practice’s Website [https://360aviationadvisors.com/]Send Us Your Questions: info@pilotsportfolio.com [info@pilotsportfolio.com] Kitdarby.com [https://kitdarby.com/wp/] 2023 Major Airline Salary Survey [https://drive.google.com/file/d/17LkTFIGSadFhnEp9V3dFvq8RyoIMbi15/view?usp=drive_link] This episode is sponsored by: Beacon Relocation [https://www.beaconrelocation.com/] 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/ [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.

How to Prepare for Retirement During Turbulent Times

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 episode focuses on structuring your portfolio appropriately, avoiding emotional decisions, using strong current income strategically, and gaining clarity around spending and withdrawals before retirement begins. What You'll Learn from This Episode * Why market turbulence has a greater impact as you approach retirement * How to assess whether your stock, bond, and cash allocation fits your timeline * Why large emotional investment decisions can be costly late in your career * How to use strong current income to reduce future retirement pressure * Why separating required and discretionary spending creates flexibility * How to begin planning your withdrawal strategy across different accounts * Why rebalancing and stress testing are key before retirement * How to recognize if your plan is ready for coordination, not just accumulation Resources: Schedule An Appointment [https://calendly.com/d/ck72-3sp-r58]Our Practice’s Website [https://360aviationadvisors.com/]Send Us Your Questions: info@pilotsportfolio.com [info@pilotsportfolio.com] This episode is sponsored by: Beacon Relocation [https://www.beaconrelocation.com/] 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/ [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.

Discipline First, Freedom Later: A Pilot-to-Pilot Money Conversation

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 chapter. The conversation covers budgeting through uneven airline pay, building safety nets before they are needed, tracking net worth over time, paying off debt, and using discipline to create options. André also talks about how his family background shaped his relationship with money, how marriage changed the financial picture, and why he now thinks more about multiple income streams, not just one airline paycheck. This is a practical, honest episode for pilots who want to hear how a peer thinks through real financial tradeoffs. What You'll Learn from This Episode * Why André describes his financial life with one word: discipline.  *  How his upbringing shaped his early money habits.  *  What being furloughed in 2020 taught him about preparation.  *  How he budgets around uneven pilot income.  *  Why tracking net worth helped reinforce consistency.  *  How paying off debt increased his sense of freedom.  *  Why multiple income streams matter more to him now.  *  How he thinks about risk, investing, and portfolio choices.  *  The financial habit he values most, and one he is still improving. Resources: Schedule An Appointment [https://calendly.com/d/ck72-3sp-r58]Our Practice’s Website [https://360aviationadvisors.com/]Send Us Your Questions: info@pilotsportfolio.com [info@pilotsportfolio.com] This episode is sponsored by: Beacon Relocation [https://www.beaconrelocation.com/] 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/ [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.

When Do Pilots Need More Than Automation? What to Do When Your Financial Life Gets More Complex

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 through where automation still shines, where it can quietly create blind spots, and how to recognize when your financial life needs more strategy, judgment, and oversight than financial autopilot can provide. What You'll Learn from This Episode * Why automation works so well early on, especially for emergency savings, 401(k) contributions, and habit building. * How your financial life changes as income, assets, taxes, and goals become more complex. * The difference between accumulation and coordination, and why they require different thinking. * Why automation executes instructions well, but does not evaluate multi-year tradeoffs like Roth conversions, retirement timing, or where and when to raise cash. * How backdoor Roths, tax withholding reviews, and large purchase decisions often require more than a set-it-and-forget-it system. * Why target date funds can be useful, but may also involve tradeoffs in control, customization, and tax efficiency. * How to tell if you have outgrown automation-only, including the kinds of questions that signal you are in the coordination phase. * Why taking back control does not mean doing everything yourself, it means making sure the right strategy is in place. Resources: Schedule An Appointment [https://calendly.com/d/ck72-3sp-r58]Our Practice’s Website [https://360aviationadvisors.com/]Send Us Your Questions: info@pilotsportfolio.com [info@pilotsportfolio.com] This episode is sponsored by: Beacon Relocation [https://www.beaconrelocation.com/] 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/ [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.