To difficult to run wire?

[SactoJim]

Wanna run a wire from right above rear view mirror (inside roof cavity) to pass side piller and exit just below the dash.

Can this be done or am I opening up a can of frustration in attempting this?

Tried running it under the window rubber, but it holds the rubber out just enough to bug me.

This is for a amplified antenna cuz I shaved the factory one. They just don't work very well when mounted under the dash or surround by metal and it works best on the window.