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
63 episodes
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, it’s easy to wonder if now’s 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 “scary good” 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 ‘boring’ 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 Didn’t Age Well: Investment Predictions Gone Wrong
Some financial gurus love to predict doom and gloom, but what happens when their “I told you so” doesn’t 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 it’s 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 you’re 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 it’s 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 don’t 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 it’s not a bad time for adults to hit the books too, especially when it comes to retirement. So, let’s 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
We’re back for Part 2 of the “7 Deadly Sins of Investing,” and these final three may be the hardest to overcome, because they’re not technical; they’re emotional. Scott explores how fear, greed, and impatience can quietly creep into our financi...
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12:38
The 7 Deadly Sins of Investing (Pt. 1) – Market Timing, Diversification Mistakes & More
We’re kicking off a special two-part series on the “7 Deadly Sins of Investing.” In this first installment, Scott unpacks four of the biggest behavioral missteps investors make, especially when emotions run high or market headlines dominate the...
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14:28
Investing During All-Time Highs: Strategies For Success
The market’s hitting record highs, but does that mean it’s too risky to invest right now? In this episode, Scott breaks down what all-time highs actually mean for long-term investors. You’ll hear how short-term fear often leads to poor decision...
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12:19
Financial Advisor Reacts To Dave Ramsey’s 9-Step Retirement Plan
Dave Ramsey is one of the most recognized voices in personal finance. His 9-step retirement plan is simple, direct, and built for mass appeal. But is it really the best path for your retirement? You'll hear where Scott agrees, where...
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28:42
The Big Beautiful Bill Breakdown: What It Means For You
The Big Beautiful Bill (BBB) is here, and with it comes tax updates that could shape your financial strategy for years to come. In this episode, Scott and Marc break it all down in clear, practical terms: what stays, what changes, and what it m...
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16:30
5 Types of Independence Every Retiree Needs
As we celebrate the Fourth of July, this episode explores what independence truly looks like in retirement, beyond fireworks and freedom. Scott dives into five core areas of independence that every retiree (or future retiree) should be aiming f...
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21:30
Smarter Estate Planning: Why You Need a Plan Now
Estate planning is something we all know we should do, but it’s often pushed to the bottom of the list. In this episode, Scott shares a heartbreaking real-life story: a close friend’s brother died suddenly at 42. Recently divorced, wit...
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20:55
Retirement Breaking News: The 4% Rule Gets a Makeover?
The 4% rule gets talked about like gospel in retirement planning. But let’s be honest, it’s always been more of a rough guess than a golden rule. Now, its original creator is revising it to 4.7%. So, does that mean your retirement paycheck just...
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19:39
The Lazy Way to Retire? Let’s Talk Target-Date Funds
Target-date funds just passed $4 trillion in assets. They’re now the default investment in many 401(k)s, and millions of Americans are using them without really understanding how they work. So, are they a smart choice… or just the easiest one?&...
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17:24
5 Ways Wishful Thinking Can Damage Your Retirement
A little hope is good for the soul, but when it comes to retirement planning, wishful thinking can lead to serious financial mistakes. Today, Scott’s walking through five common examples of wishful thinking that can quietly damage your retireme...
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20:48
Why Type A Investors Should Probably Do Less
Today, we’re talking about Type A personalities. If you’re driven, competitive, and goal-oriented, then you’re part of the club that often struggles during difficult markets. When things get tough, your instinct is to work harder, push more, an...
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15:01