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I Exited a Winner Today — So Why Do I Feel Kinda Crappy About It?

June 26, 2025

Today I closed a winning trade. Booked a gain. The kind of thing I tell others (and myself) to celebrate.

So why do I feel bad about it?

Maybe “bad” isn’t the right word. More like unsettled.

Here’s the situation:

The stock had started to break down a bit on the daily chart, so I followed my process and exited. Textbook move, right?

But here’s what’s bothering me…

The stock is still above its 50-day moving average.

It’s still in a hot sector.

And I had January 2027 calls. That’s over 18 months until expiration!

With that much time, why did I feel the need to micromanage?

This is one of those moments where the trade was technically breaking support, yes — but the bigger question I’m sitting with is: Did I kneecap this trade too early? Did I cut off a potential monster winner because I was too zoomed in?

My risk was defined. I could’ve ridden it longer.

Maybe smaller sizing would’ve helped me let it breathe?

Maybe I’m just overthinking? (I do that.)

But one reminder that helps bring me back to center:

I can always get back in.

Just because I closed it doesn’t mean the door’s locked. The market is fluid. So am I.

I don’t have all the answers. But I’m showing up, asking better questions each time.

That’s the job.

I review this trade, along with a few other profitable exits and stop adjustments in this week’s All Star Options Jam Session.

Watch it below. 👇

Remote video URL

Sean McLaughlin | Chief Options Strategist, All Star Charts