After years of bar gigs, singing in keys that were a bit outside of my comfort zone, I figured out that this probably didn't help my range any.
I've since shifted a lot in what I sing, and particularly the key. I experimented a bunch by singing what I wanted to be able to sing comfortably, and THEN picking up my guitar to see what my "natural" key was. That's helped a bunch.
The often ignored advice to go get some vocal lessons from a good coach would have probably helped me extend my range when younger, but we do tend to lose some of that ability as we get older.
Luckily, the folks I play with have no problem with doing stuff in odd keys, as they understand that my voice has a very limited range now.
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