Investing Lessons & Mistakes to Avoid

Investing Lessons & Mistakes to Avoid

July 10, 2026 · 26 min

About this episode

This episode discusses key investing lessons, common mistakes to avoid, and the importance of continuous learning and emotional discipline in investing.

1. Annual Themes, Learning, and Risk Each investing year tends to coalesce around distinct themes that are difficult to identify upfront and only become clear through observation and adaptation. Reviewing prior years helps reveal recurring patterns and informs future strategy. "You either make money or you learn something." Even profitable years yield process insights and highlight missed opportunities, reinforcing resilience and long-term skill building. Investing is like golf: just when your "swing" feels right, conditions change. Continuous refinement is essential because evolving market environments expose new weaknesses. Appropriate risk-taking is crucial for young investors. Under-allocation to equities can be the bigger mistake given long-term upward market drift and compounding. Understanding what you own reduces perceived risk and helps investors ride out volatility and buy dips with conviction. 2. Long-Term Strategy vs. Short-Term Trading Passive, buy-and-hold investing generally outperforms frequent trading, which often triggers taxes on short-term gains and causes investors to sell winners too early. Asset allocation over market timing: set target allocations (e.g…

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Host: Crosby Advisory Group

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