Missed the Hedge, Gained the Insight: Reflecting on a Market Opportunity I Let Pass

in LeoFinance10 days ago


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Every investor has moments they look back on thinking, “I was right… but I didn’t act.” That was me recently as I watched the U.S. markets dip sharply, driven by renewed economic uncertainty and tariff-driven headlines. I had been preparing for something like this. I had just closed out a batch of put options that hadn’t played out as planned—fortunately exiting before they expired worthless—but I was already eyeing the next opportunity. The volatility index (VIX) was signaling an almost eerie calm, especially considering the macro noise. It felt off.

My plan was to roll forward some put positions, hedging against what looked like an increasingly fragile market narrative. But I didn’t pull the trigger.

The market’s behavior lately has felt incredibly binary—sharp swings up and down with little warning. That type of action makes it tough to build conviction unless you’re staring at the market 24/7, which I’m not. I’ve also been trying to stay disciplined, avoiding the trap of attempting to time every move. So, I waited.

Unfortunately, the timing of my decision didn’t work out. The drop came. Volatility spiked. And the hedge I had been contemplating would’ve played out exactly as I envisioned. It was a miss, plain and simple.

But not a loss.

Because what this experience really gave me was confidence—not in my ability to perfectly time the market, but in my ability to read it. The signals were there. My thesis was sound. I journaled my reasoning before the move even happened, which now serves as a confirmation that my framework is sharpening. That’s an invaluable win for the long game.

More importantly, this reinforced the importance of thoughtful preparation. Even though I didn’t act this time, I was in the right headspace. And when the next opportunity arises—because there’s always another—I’ll be better positioned to act with clarity and conviction.

Going forward, I’m leaning into more activity in the options space—not with reckless frequency, but with targeted, purposeful moves. There’s a lot of uncertainty still brewing under the surface, and where there’s uncertainty, there’s potential. Whether it's hedging downside or taking advantage of mispriced risk, I’ll be ready.

Sometimes, missing the shot is what makes you realize your aim isn’t that far off.

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