TLDR: Knowing how time decay works, the rule of thumb that I used for choosing an option's expiration date is: 1. If I'm selling an option, I choose an expiration date that is around 30 days. 2. If I'm a buyer of an option, I choose an expiration date that is more than 1 year.
Story time
If you do not know what an option is, do read the Explained Simply: Options series here
In the market, there aren't many things that are guaranteed....