The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots
Welcome to The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots, where we navigate the skies of financial success with your host, Scott Osborn, The Pilot's Planner. Each episode, we soar through the challenges and opportunities unique to pilots, from debunking myths to mastering best practices in financial planning and investing. As demand for pilots reaches new heights, so too does the complexity of their financial landscapes. With Scott's expertise we tackle common pitfalls and strategic wins that can significantly boost a pilot's financial trajectory. Whether you're an aviation professional or just fascinated by the financial skies pilots navigate, this podcast promises insights that can help anyone plot a course toward financial independence. https://thepilotsplanner.com/
Episodes
73 episodes
What to Expect When You Become A Financial Planning Client
đą Get your customized planning started by booking a call: http://callosborn.com/ âď¸ Order your no-cost âWealthy Pilot Toolkitâ today:
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18:20
Should Geopolitics Drive Your Investing?
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16:08
Should Pilots Listen To Economists In 2026?
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20:50
Trump Accounts: Free Money or Future Headache?
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16:11
401(k) Contribution Limits for 2026: What Pilots Need to Know
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16:50
Year-End Financial Reflection & Planning For 2026
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14:48
United Airlines Cash Balance Plan: Allocating Your Contributions
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11:47
2026 Key Planning Numbers Every Pilot Should Know
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13:21
MBCB Plan for American Airlines: Should You Opt In or Not?
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16:12
Thanksgiving, Gratitude & Growing Wealth: Essential Pilot Financial Strategies
đą Get your customized planning started by booking a call: http://callosborn.com/ âď¸ Order your no-cost âFinancial Flight Control Toolkitâ today: https://keap.page/lde199/the-pilot-s-planner-toolk...
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12:58
Automating Savings Outside of 401k For a Smarter Retirement
Most pilots automate their 401(k) savings without thinking about it, but what about everything outside that one account? Scott breaks down how to automate savings into the other tax buckets that will actually give you flexibility, control, and ...
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16:10
Delta Pilots: Unlocking the Power of Your NQDC Plan
In this episode, Scott breaks down the Delta Non-Qualified Deferred Compensation (NQDC) plan, showing how it differs from a traditional 401(k) and how you can strategically use it to manage your taxes and retirement income. He explains the elig...
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12:56
The Market Is Scary Good. What Does That Mean For You?
When the market feels unstoppable, itâs easy to wonder if nowâs the time to invest or sit tight and wait for the next drop. In this episode, Scott explains what it really means when the market is âscary goodâ and how to stay grounded when emoti...
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15:07
Are Bonds Back? What Pilots Need To Know in 2025
Bonds used to be the âboringâ part of a portfolio. They were considered safe, steady, and not very exciting. But with yields at multi-decade highs, a lot of people are asking: Is now the time to give bonds a bigger role in your investment strat...
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14:31
401(k) Misconceptions: What Pilots Need to Know About Taxes, Contributions & Strategy
Most people know their 401(k) is key to retirement, but few understand how each account type affects their taxes and long-term flexibility. This episode breaks down the differences between pre-tax, Roth, and after-tax contributions, helping you...
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20:33
Should You Have More Than One Financial Advisor?
If having two financial advisors sounds like double the wisdom, think again. In this episode, Scott explains why splitting your money between multiple advisors can actually create confusion, gaps, and unnecessary risk in your financial plan. Us...
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14:20
That Didnât Age Well: Investment Predictions Gone Wrong
Some financial gurus love to predict doom and gloom, but what happens when their âI told you soâ doesnât actually hold up? In this episode, Scott takes a hard look at the loudest voices in the industry and why chasing their bold claims often le...
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18:24
The Truth About Downsizing in Retirement
Downsizing in retirement often sounds like an easy decision, but itâs rarely that simple. In this episode, Scott breaks down some of the most common downsizing myths - like whether a smaller home really lowers monthly expenses - and explains wh...
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17:35
Are September & October Really Bad Months to Invest?
September and October often get a bad rap in the investing world, but are they truly risky months? In this episode, Scott breaks down the truth behind these "turbulent" months. While data shows September's historical slight negative returns, it...
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15:21
How To Catch Up If You're Late To The Retirement Party?
Falling behind on retirement savings can feel overwhelming, especially if youâre only just hitting your financial stride in your 30s, 40s, or even 50s. In this episode, Scott tackles the big question: How do you catch up if you feel late to the...
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19:33
College or Retirement? Why Many Parents Are Sacrificing Too Much
According to a recent survey, the emotional and financial burden of paying for college often exceeds expectations. And itâs affecting everything from retirement plans to mental health. In this episode, Scott unpacks what families are really fac...
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19:36
Are You Wealthier Than You Think? 5 Wealth-Building Habits for Pilots
Most people donât feel wealthy. But what if your day-to-day habits are quietly building serious financial strength? A recent article from Kiplinger outlined five surprising signs that you might be richer than you think. And none of them involve...
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16:12
Pilots: Can You Pass This Retirement Planning Quiz?
The kids may be heading back to class, but itâs not a bad time for adults to hit the books too, especially when it comes to retirement. So, letâs test your knowledge with a quick financial pop quiz and see how ready you really are.Her...
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18:46
Top 3 Rental Property Mistakes Pilots Should Avoid
This week, Scott sits down with Jason Watson from WCG CPAs and Advisors to talk about the top 3 mistakes high-income pilots should avoid when investing in rental properti...
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29:48
The 7 Deadly Investment Sins (Pt. 2) Fear, Greed & Impatience
Weâre back for Part 2 of the â7 Deadly Sins of Investing,â and these final three may be the hardest to overcome, because theyâre not technical; theyâre emotional. Scott explores how fear, greed, and impatience can quietly creep into our financi...
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12:38