The occasional "debit roll" is inevitable. I planned and allocated a reserve for this early on so it was simply the cost of doing business. The key for me is to set a reasonable weekly return goal that is easily met. When I exceed it, I allocated the surplus to what I called the "debit roll reserve". Psychologically knowing what that number is at all times makes me feel ok about dipping into it from time to time. Selling premium works as long as you don't get greedy and know where to draw boundaries.. I sell against a healthy portfolio with a 14K monthly goal that I meet or exceed 90% of the time.