The 7 Deadly Sins of Investing (Pt. 1) – Market Timing, Diversification Mistakes & More Artwork

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/

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The Wealthy Pilot's Podcast: Financial Flight Controls for Today's Commercial Airline Pilots

The 7 Deadly Sins of Investing (Pt. 1) – Market Timing, Diversification Mistakes & More

July 31, 2025 • Scott Osborn

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 news. If you're over 50 and starting to think seriously about protecting your nest egg, this is one episode you won’t want to miss.

Here’s some of what we discuss in this episode:

🌪️ Why market timing usually backfires

🧺 The trap of owning “too much” of everything

🚫 How overconfidence could lead to under-diversification

🚀 Why past performance isn’t a future guarantee

💰 Discipline beats chasing returns

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