I did covered calls once upon a time. It is far from free money, given the capital risk. Am not posting to dissuade anyone but here is what can happen. Obviously the downside risk is much greater than the upside. If a bear market occurs or simply some of your inventory of covered call stocks start to crash, you can only roll out the call options so much, and collect so much on premiums. You may find that the inventory of stocks for which you have covered calls are becoming the worst stocks to own, and that you are having to select lower and lower strike prices for longer and longer expiration periods, even LEAPS. Maybe a partial solution is to pick stocks that seem unlikely to go substantially down, though they will have less appealing premiums. Not sure. But it is not free money, though for a while it may seem so. I use to relay it was the best thing since sliced bread...until it wasn't.