Mark, It is part of human nature to ask, “What might have been?” I know that you have consistently said that you should enter a trade with a definite notion of what you expect to get out of it, but people being people, will always be tempted to think that the grass is greener on the other side of the fence. Until you have been burned by chasing those rainbows, and have the ability to stop and see what changing your focus leads to, you will have a hard time overcoming that urge.

For myself, I found that focusing on what the cumulative gain that I earn each year from selling puts, allows me to bypass the urge to double down and go for the “big one.”  Each individual trade is a small, but meaningful, gain.  (Yes, there is an amount that I consider too little to be worth the risk.)

There is a certain amount of capital that each one of these trades puts at risk; if I make three, four, or even five put sales before I get assigned, then the (net) cumulative dividends received can amount to 20-30% (sometimes a little more) of the amount at risk. To buy just about anything at such a discount (even Facebook) is usually a very good deal. So keeping the focus on this fact, helps to keep me from fretting that I let one get away by not buying the stock outright, or in the case of a CC, not buying back the covered call.