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This type of post only surfaces during a bull market, when greed tug at us the hardest, making satisfaction elusive. Ever since making my first public equity investment in 1996, I’ve been hooked, wrestling with the constant mental tug-of-war over how to be at peace with my investment decisions. Maybe you fight the same battles.

During the spring 2025 stock market meltdown, I deployed most of my rental home sale proceeds into the stock market. I started buying too early—in early March—only to watch stocks keep falling. Still, I kept dollar-cost averaging through mid-April. Eventually, the market rebounded.

Of the proceeds I invested during March and April, about $500,000 went into individual stocks, mostly in tech. Of that, $40,000 went into Meta, a long-time holding in my rollover IRA.

My first new Meta buy was on March 10 at $591.76 a share. When it dropped to $488.50, I felt like

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