I understand the feeling, what worked for me was "you know what, fuck it, I will just plan it more loosely, let's see what goes wrong or who is unhappy".

Most of the times, everybody is happy even if things are not perfectly planned, and then they thank me for the "effort" (which was minimal, and sometimes can introduce confusions, as I need to adjust the date or the style as more constraints become evident).

I sometimes think it's a problem of my education of engineering as well, because I want everything planned well, think of all exceptional cases, etc.