You’d think after 40 years of trading I’d know all the tricks. You’d think I’d tested every angle, squeezed every edge, and settled into a routine that couldn’t be improved.
Turns out, I was wrong.
The shift didn’t come from a new strategy or some secret tool. It came from data — and a willingness to rethink what I’d been doing for decades.
Here’s what changed everything: I discovered that weekly options produce better percentage yields than monthly options, even though you’re selling less time value. That sounds backward, right? It did to me too.
But once I made the switch from monthly trades to weekly expirations, the logic became impossible to ignore.
The funny thing is the general belief that the further out you sell, the more you collect. In raw dollar terms that can be true, but it isn’t true in percentage yield.
The numbers simply don’t support the notion that more time automatically means more profit, and once the data showed me that, the old assumption fell apart.
The Old Assumption vs. The New Reality
The big surprise for me wasn’t just the math. It was realizing how long I’d gone without questioning it.
I’ve been doing this for 40 years and I didn’t think of this. It took someone else showing me the deeper data to make me change course, and that willingness to learn — even after all this time — paid off more than I expected.
Volatility out to a year ends up being the least profitable trade, even though you’re selling the most time. It feels like it should pay more, and for decades I treated it that way.
But when you look at what actually produces yield instead of what feels like it should, the conclusion is clear.
When you step back and put all the data and criteria together, it all points in the same direction — weekly is the smarter play.
Why This Matters to You
This isn’t about abandoning convenience for the sake of activity.
Monthly trading is easier. It’s slower. It gives you room to breathe.
For a long time I didn’t care which method produced more because I wasn’t trying to trade efficiently — I was just trying to trade comfortably.
But if you want to maximize yield, the numbers are crystal clear.
Weekly expirations keep you nimble, let you collect premium more frequently, and avoid the dead time baked into longer-dated contracts.
The market rewards efficiency. It rewards precision. It rewards traders who follow the data instead of old assumptions.
And after four decades, I’m trading the way I should’ve been trading all along.
Trade well,
Jack Carter
Jack Carter Trading
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*This is for informational and educational purposes only. There is inherent risk in trading, so trade at your own risk.
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Disclaimer: We develop tools and strategies to the best of our ability, but no one can guarantee the future. There is always a risk of loss when trading. Past Performance is not indicative of future results. All gains cited are from a related service that uses the Cash Flow Agent. From 1/1/21 through 2/20/25, the average return per options trade alert published in real time (winners and losers) is 3.18% in 3 days, with a 96.1% win rate.
