My H1 2026 stock options report card: every stock, every win, every loss

Disclaimer: I'm not a licensed financial advisor and this isn't advice to buy or sell anything. These are my real numbers, shared so you can see what this strategy honestly looks like — losses, repairs and all. Past performance is also not an indication of future performance.

At the start of July, I sat down to go through my H1'26 trade report from my stock option activities in H1'26.

For context, I left corporate in June, so for the majority of H1'26, I was trading part-time and took a month off in June to travel.

The headline numbers

Quick plain-English refresher on how I make this income: I sell promises.

Mostly, I promise to buy a quality stock at a price lower than where it trades today, and I get paid cash upfront for making that promise. If the stock never falls that far, I keep the cash and the promise expires. If it does fall, I buy the shares — at the discounted price I already said I was happy with.

That cash upfront is the $40,495. The -$5,973 is the net of every gain and loss along the way.

Overall: the income engine collected more than what it cost me.

Looking through the trade logs, two key learnings from H1:

Lesson #1: it is hard to trade out-of-the-money (OOTM) calls profitably on a consistent basis

In June, I started testing a new strategy which is to buy OOTM long calls on stocks that are on a bullish price action momentum, i.e I paid a small capital in return for unlimited upsides. These are typically quite speculative and opportunistic, and they didn't really turn out well. So they dragged down the P&L by ~$8k. If I hadn't made these trades, the total income would have been ~$48k in H1.

Buying OOTM calls are like buying lotteries and hoping to hit a big jackpot. To be consistently profitable, one has to get BOTH the long term direction run AND the expiry date right. And nobody is able to do this consistently well.

Lesson #2: assignment is not the end of the world. It's just buying a stock you already wanted, at a discount you already chose.

"But what if you're forced to buy the shares?"

This is the #1 fear people have about selling these promises. It even has a scary-sounding name: assignment.

In six months and 53 trades, it happened to me exactly 4 times. Here's what actually happened in each case:

Netflix — assigned, then sold higher. I promised to buy at $80. The stock fell, so I bought 300 shares at $80. A few months later I sold them at $88.81. That's +$2,642 on shares I was "forced" to buy — on top of income collected along the way.

Bank OZK — assigned, still holding a winner. Promised to buy at $45, got the shares. The stock now trades around $52 at the end of Jun'26. That's +$2,836 of gains sitting on those shares, plus the income that came before.

ServiceNow — assigned once, my best stock of the half. One of my nine trades ended in assignment. The purchase price was $100 per share. Current price of NOW is at $95 (as of 2026-07-24). I am perfectly happy to continue holding the shares. Overall result on this one stock: +$10,099.

Adobe — the one that's underwater. Bought 200 shares at $215; they now trade around $205, so I'm down about $2,000 on paper. But the income I've collected on Adobe (+$6,063) means the position overall is still slightly positive. I am holding the shares at relatively cheap valuation of $215, so I am happy to keep holding on to them. Meanwhile, I keep collecting premiums by selling covered calls at higher strikes.

In summary: three of the four assignments made money, and the fourth is roughly break-even.

The one rule that makes all of this work: Only ever make these promises on companies you'd genuinely be happy to own at that price.

Do that, and the "worst case" stops being scary — it becomes shopping with a discount coupon while getting paid to hold the coupon. Skip that rule and chase the highest payouts on junk stocks, and assignment really can hurt you.

That's the entire difference between income investing and gambling.

Disclaimer: I'm not a licensed financial advisor and this isn't advice to buy or sell anything. These are my real numbers, shared so you can see what this strategy honestly looks like — losses, repairs and all. Past performance is also not an indication of future performance.