48 Hours to Expiry: My Game Plan for This Week’s Options Madness

 We’ve all been there. You open your brokerage app, and the screen is a sea of green and orange. It’s Wednesday, January 14th, and I have a handful of positions expiring this Friday. Some are "set it and forget it," but others? They’re requiring some serious math and a bit of soul-searching.

If you’ve been following my journey, you know I love selling premium. It’s that sweet "Theta decay" that lets me sleep (mostly) soundly while time eats away at the value of the contracts I’ve sold. But this week, things are getting spicy.

The Elephant in the Room: My Confluent (CFLT) Dilemma

Let’s talk about the big one: CFLT. I sold a $23 Call that expires this Friday. Right now, that contract is trading at $7.65.

Here is where the personal math comes in: My average cost for CFLT is $18. Because the stock is trading so high (implied price around $30.65), my "sold" call is deep in the money. If I do nothing and let it expire:

• The "Loss": I’ll feel like I'm losing out on that extra $7.65 per share of upside.

• The Reality: I’ll be forced to sell my shares at $23. Since my cost basis is $18, I’m still walking away with a $5/share profit (plus the original premium I collected).

It’s a "task failed successfully" moment. I’m being "forced" to take a profit, even if I’m leaving money on the table. Do I buy it back to keep the shares, or just take the win and move on? I’m leaning toward letting the shares go and high-fiving myself for a successful trade.

The Rest of the Roster

While CFLT is the headliner, the rest of the portfolio is a mix of "easy wins" and "sweaty palms":

• The "Free Money" Crew: My short calls on SMCI ($53), SOUN ($22), and HOOD ($135) are all trading for $0.01 to $0.04. These are essentially dead in the water. I’m happy to let these expire worthless and keep every cent of that premium.

• The ROBN & SOFI Puts: These are a bit closer to the pin. My ROBN $56 Put is at $1.05. If Robinhood dips below $56 by Friday, I’m buying 100 shares. Honestly? I don't mind owning the stock at that price, so I’m letting this one ride.

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The $950 Lesson: Transparency, Puts, and the Reality of the "Moonshot"

• The Reddit Moonshot: I have one RDDT $300 Call I bought for pennies. It’s worth $0.03 now. Is Reddit going to $300 in 48 hours? Highly unlikely. But hey, every portfolio needs a little "what if" energy.

There’s a specific kind of silence that happens when you open your portfolio and see a trade you once had high hopes for sitting at a -99.7% loss.

For me, that’s the RDDT $300 Call.

I bought this back in October 2025. At the time, Reddit was the darling of the market, the $300 price targets were flying around from analysts, and I felt like I was catching a rocket ship. I put $950 on the line. Today? It’s worth $3.

It’s a "good loss." Why? Because it’s a reminder that even when you’re right about a company (Reddit has actually performed well), you can still be wrong about the timing and the theta.

My Strategy for Friday

When you're selling options, you have to be okay with the outcomes. For me, Friday is about simplification.

1. CFLT: I’m likely going to let the shares get called away. A profit is a profit, and I can always sell puts to get back into the position at a lower price later.

2. Lotto Tickets: I'll let the RDDT call expire. It was a cheap thrill.

3. The Sells: I'll let the OTM calls expire to clear up my "Positions Held" screen for next week's trades.

Trading isn't just about the charts; it's about managing your own psychology when the clock is ticking.