There's an important conversation or set of conversations I need to have that I've been worried about for a long time, and it has seemed like Mercury Retrograde is in the way. I've talked about these things with the same person in the past, so I would normally classify it as banging one's head on a brick wall and to be avoided, but unfortunately it's essential and unavoidable unless some miracle happens.

But I think based on what you have said and also this page which has a similar outlook:
https://www.sagegoddess.com/what-is-mercury-retrograde/
"Mercury Retrograde is a cosmic do-over. If you want to try again – at a relationship, a project, an idea, a conversation – you get a second chance with Mercury who (from our view) stops, backs up, and gives you another shot."
that maybe Mercury Retrograde might even be a better time for it?