Out-of-the-Money (OTM)

DTE (Days to Expiration)

Enter at 30–45 DTE for optimal theta/gamma balance. Close or roll at 21 DTE or 50% profit — whichever comes first.

Assignment

Not a disaster — it's the plan in the wheel strategy. If you only sell puts on stocks you'd own, assignment is just the next step.

Roll (Rolling)

Roll for a net credit or don't roll at all. Rolling for a debit just delays a loss. Best done before the position goes deep ITM.

Annualized Return

Looks impressive but is misleading if you ignore losses. Track actual account returns, not annualized returns on winners only.