Something That Expires is Usually “Bad”

Almost every Friday I see some of my options contracts expire. The expiration date was reached, so the contract is now “worthless.” When you sell options, that is a good thing. Many things that expire must be discarded. “Expired” is usually bad (like food, medicines, or safety items), but it can be good when you mean it in a context where aging past a date is intentional and harmless. If an option contract expires it opens a door of opportunity to earn even more cash.

My Monday Morning Review

There are two simple steps in this process. The first is to review the options (if any) that expired on Friday. Here is a screen image of my Fidelity Investments activity download for July expired contracts. The July 17 contracts included two PUTS for 200 shares of RPD in my traditional IRA account.  That means I did not have to purchase the RPD shares. As you can see, most of the expired contracts were CALLS. I get to keep my shares, and I can sell new contracts on my shares of AVXL, GAIN, VYM, and F.

YTD I have had 318 contracts expire worthless. That is wonderful, as that means I could enter into 318 new opportunities for selling contracts and making even more money on the new contracts. To put that in perspective, during 2026 (YTD) I traded 407 contracts, and the average income from those trades is $268.49. Each trade takes less than five minutes to complete. If 318 contracts expired, that increases the potential income from doing a new contract each time a contract expires.

So let’s ask a question. What can you do that takes five minutes to add $268.49 to your checking account? I’m not certain many could come up with any good and legal ideas.

Monday Step Number 2

The second step is to open Fidelity’s Trader+ software and look at my positions. The review takes less than a minute. I only want to see the “SHORT” (options contracts) positions and I sort them by expiration date. As you can see in this image, I have four contracts that expire on Friday. One is a PUT and the other three are CALLS. If I don’t roll those contracts to a higher price, and if the price doesn’t reach the contract strike price, then I can sell new contracts a week from today.

Back to Basics

Fidelity offers some good basic training on the YouTube platform. Here is a good place to start.
What is Options Trading And How Does it Work? | Fidelity Investments

Two Reminders For Trading Options on Trader+

If you want to trade options on Fidelity’s platform, I highly recommend that you start using the Fidelity Trader+ software. It is free to download, install and use. It is possible to trade options on the website, but I haven’t found that to be as user friendly as Trader+.

You cannot just start trading options without requesting that functionality. You have to apply for options trading. You can do that online at the Fidelity website. Each account you manage can be set up for options trading. I think the ROTH IRA is the best account for options trading. It helps you minimize income taxes and gain real income. The traditional IRA is also a good account type, bearing in mind that you will ultimately pay income taxes on any withdrawals from that account as regular income.

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