I know what you mean. I am still trying to learn all this, but I have been sucking lately at the weeklies. My timing is off on my entry. I just got really lucky with NFLX this week. That chart was way oversold. I only bought yesterday for next week's, so I would have had a little more time. I don't like holding on Friday or even Thursday for that matter. I usually end up getting burned. This one just worked out.
I bought RCL yesterday at .10, could have sold at about .25 and watched it go below were I bought it. I thought f it, I might as well hold until today, they are worthless anyway. I got really lucky and ended up selling them for .48 today.
This is what I have to keep in remembering "there is always another trade". You have profit take it and move onto the next one. Easier said than done, I know. I still get that FOMO that I have to get over.