Everyone says "buy the dip." Nobody tells you what it feels like when your retirement account drops six figures in three weeks.

The Setup

I retired at 66 with a portfolio heavily weighted toward tech — about 35% of my total retirement assets. Oracle was my largest single position at roughly $180,000. I had held it since 2019 and watched it climb steadily.

Then came the correction. In the span of three weeks, Oracle dropped nearly 40%. My position went from $180,000 to around $108,000. That is $72,000 gone. Not on paper — it felt real. Every morning I checked. Every morning it was worse.

What the Textbooks Don't Tell You

The financial literature says: "Stay the course. Time in the market beats timing the market." All true. But nobody prepares you for the emotional reality of watching decades of saving evaporate in days.

The first week, I couldn't sleep. I calculated what that $72,000 could have bought — two years of living expenses, a kitchen renovation, a year of travel.

The second week, I started rationalizing. Maybe I should sell and cut losses. Maybe tech was over. I opened my brokerage app probably thirty times a day.

The third week, something shifted. I went back to my original thesis: Oracle's cloud business was growing, enterprise spending wasn't going away, and the dividend kept coming. I had bought for reasons, not for a price target.

The Recovery

It took eleven months. Eleven months of holding through doubt. Oracle eventually recovered and went on to new highs. My position ended 2025 up 15% from the original cost basis.

What I Actually Learned

First: Your risk tolerance in a bull market is a fantasy. You do not know your real risk tolerance until you are down six figures. I thought I could handle a 40% drawdown. Turns out I can — but barely.

Second: Having a written investment thesis matters more than any chart. When everything in my brain screamed "sell," I went back to my notes. The thesis hadn't changed. The price had.

Third: The 65-to-70 window is uniquely difficult for drawdowns. You are freshly retired, your income has stopped, and every dollar feels irreplaceable. This is not the same as a 45-year-old riding out a correction with thirty years of earnings ahead.

If you are entering retirement with concentrated positions, know this: the drawdown will come. The question isn't whether you can handle it intellectually. It is whether you can handle it at 3am when your stomach is in knots.

That is what nobody puts in the brochure.