I understand I am selling low, but it’s priced low by the market for a reason. So I guess the question is - is it better to be selling constantly/mechanically regardless of volatility, or wait for volatility to spike? While you are waiting for that moment, I may be taking in crumbs every week/month that add up.
Personally, I am trying to figure out a compromise where I must sell at least some regardless of volatility but keep enough dry powder to triple the size on vol spike. Recently, it just feels like I am leaving free money on the table
There's a number of factors, but here are a couple of big ones:
To put it simply, IV is directly correlated to both the price of the option and the range of movement of the underlying (expected move.) Obviously, you want to sell
high and buy
low - and since you're normally selling at some distance from the ATM strike, you want the range of movement in the underlying to decrease or stay the same (no, or little movement means the your option has little chance to go ITM before expiration.)
But at low IV, you're upside down on everything. You're selling
low and getting paid for a narrow expected move... but the only place IV has to go from the bottom is
up - which means that 1) the price of the option will increase and 2) so will its expected move. I.e., you have now taken money out of your own pocket, and put yourself into a scenario of
increasing risk.
In super-low vol, the reasonable approach is to
buy - because then, you're buying
low and expecting the price to increase (so you can sell high.) You're also buying when the range of movement is small... and the guy who sells it to you had better price it right, because now he's the one taking the chance of it increasing against him.