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Gain automation before compression - how much is too much?

Ive been experimenting with gain automation for my mix, its sort of a necessity for the music Im mixing - not because of major recording problems, but simply to get as much dynamic range out of the music and have it as natural as possible. Ive read a couple times andy wallace does this, along with a few other engineers, but think he does it after compression..

Automation

This is the problem I am having..I record my vocals, then use automation to even the volumes of the soundbites relative to each other... then I realize that the volume of the entire track needs to be changed... so then I am stuck with doing the the automation over again... I know this is a very rookie problem I am having and there is a easy fix to it.