Loss could be more than everything that you have made. The problem with option selling is not just the information asymmetry or the tail risk, it's the inability of cutting losses when you are wrong, aka caught in a "rogue wave" due to not just an increasing gamma but an acceleratingly increasing gamma (gamma doesn't just increase it increases faster) but when you are right, you are only getting compensated by the previous gamma and totally cut off by the potential increase in profit by the accelerating gamma. When you are selling options, the premium is only compensating for the CURRENT gamma at the time when you sell the option but when a "rogue wave hits, if you are on the right side of the market, the market just takes off from you and you are totally cut off from the additional profit that is available from the market because all of the option prices are higher now adjusted by the accelerating gamma and you run the risk of buying at the top because if the underlying goes the other way, the gamma accelerates in the opposite direction then you will lose money on the long option now potentially turning your originally winning shorts into a potential loss but when you are on the wrong side of the market, then you either have to pay double or triple to buy back the short leg to cut your losses because the short leg option price has now been quickly adjusted for the new gamma which is 2X or 3X higher than the gamma that the premiums compensated you for or face assignment which may or may not be offset by the hedging long leg if the underlying price just happens to be ATM with the hedging long leg. Either way, you lose more than what you've earned.
Selling options may look to be a way to earn income but you ALWAYS earn less than what you can potentially lose, ALWAYS because of this increasing and forever adjusting gamma and the more that you sell, the more chance that you will lose. If you sell OTM, then you earn peanuts and when the "rogue wave" hits, if you are hedged, you get creamed by the assignment and when you are not hedged, you become bankrupt like James Cordier because the peanuts you earn is never enough to compensate the losses. When you sell ATM, you earn more peanuts so you can offset the losses from assignment better but you lose more often if you are hedged and if you are not hedged, you become bankrupt like James Cordier again and you become James Cordier faster and more often. If you sell ITM, your loss would be much smaller because now you are actually on the tail risk now riding on the "rogue wave" itself but you will now ALWAYS lose with only a small chance of you making a profit because as strong as the "rogue wave" hits, it actually doesn't happen often, that's why it's called a tail risk. It's like life. When you are doing the right thing, you are rewarded with peanuts, earning a measly income but when you do something wrong, you get sent to the electric chair. And the longer that you live, the more chances that you will do something wrong. You don't do wrong things all the time but this ONE time that you did something wrong inadvertently or being at the wrong place at the wrong time, or whatever you get sent to the electric chair. But if you always do wrong things aka selling ITM, then you are always in jail not really dying but always locked up and you only get this one small chance that you might be able to escape and live forever on a paradise island that has no extradition treaty with any country.