Retail investor: I sell calls against my shares to lower my cost basis. Smart, right?

Me: On companies you actually want to keep?
Retail investor: Yeah, my long term holds.
Me: So you're collecting pennies to "lower your basis"... while risking your best long term company getting called away the second it runs higher?
Retail investor: ...I do get nervous on big green days.
Me: That's the key thing... You're sabotaging the exact companies you wanted to keep, for a tiny discount on your basis to feel smart.
Retail investor: So lowering cost basis isn't worth losing the shares?
Me: Never on companies that you bought at a great price. The move is to let them run and you'll make much more money in the long run most likely.
Don't sell calls on great companies at good prices to shave a few bucks off basis...
You're capping your upside... for pennies.
Sell portfolio secured puts. Take the cashflow to buy more shares/calls.