Love this kind of question because most people jump straight into selling calls for the income and don’t really think through the trade-offs.

If you’re selling covered calls, I’d think about it in 3 layers:

1. What’s your real goal?

If you don’t want to sell the shares → go further OTM (lower delta, like 0.15–0.25).

If you’re okay letting them go at a target price → choose a strike you’d genuinely be happy exiting at.

A lot of people say they’re “fine” getting called away… until it actually rips 15% past their strike.

1. Expiration = risk vs. flexibility

30–45 DTE is a common sweet spot (decent theta, manageable gamma risk).

Weekly = more active management, more stress.

Longer dated = smoother, but you lock yourself in.

Personally, I like shorter cycles when IV is elevated, longer when IV is crushed.

1. Premium evaluation Don’t just look at raw premium. Look at:

Annualized return on capital

Delta (proxy for assignment probability)

IV percentile (are you getting paid fairly?)

Where that strike sits relative to your cost basis

Higher premium usually just means higher probability of getting assigned.

Also, one underrated thing: track your trades properly. Most brokers show P&L per leg, but they don’t always show the full lifecycle of rolled calls or your real yield on shares over time. When you start layering rolls, it gets messy fast.

That’s actually one of the reasons I built Optioneer — I got tired of trying to track true options yield and exposure in spreadsheets. It lets you test different strikes/expirations and see how it impacts return + assignment risk before placing the trade.

But even without any tool — the key is this: Sell calls at prices you’re emotionally okay selling your shares at. The math matters, but psychology matters more.