MAB,
That is a good story about your artist friend asking about the music business now. Also good advise from you and I seriously doubt if the concept of "being yourself" is anything new around Nashville.
I couldn't begin to imagine the number of artist's showing up in Nashville, over the past 50 years, that tried to sound like Patsy Cline, Johnny Cash, Merle, Waylin, or more recently Martina, Faith, Garth, Taylor or you name them. Personally, I take great pride that my music sounded nothing like any of those former artists......... wait a minute........ maybe that was my problem. Ha!!!
Seriously, I like your suggestion of knowing when you've made it in the music business is when someone pays you for being you. Much like the phrase you often quote your father Grady telling you "do what you love and find a way to get paid for it, and it's not a job" (or something like that).
However; I'd like to point out something and remind you (and others) not everyone that works with you; will not be able to make a living in music just because they don't hit the big time. Oh Sure!!! Talent is a huge factor but we all know many with performing skills can make a decent living but they are going to have to work for it and travel to where the work is. Still, if that is what they love to do and they are getting paid for it; maybe it's not so much of a job for them.
For example; I made a decent living in the construction trade and didn't have to travel beyond an hour from my home most of the time. However; it wan't what I wanted to do and after many years of doing that, I became to hate it.
Now I realize also; those artists that travel on the road for years, trying to make a living, may get discouraged and later hate it also; so it's almost like to two edges sword. Also like the saying goes "Damned if you do, and damned if you don't".
It's certainly a tuff decision and I'm almost happy I had limited talent and didn't have to deal with the question really talented artist's may face. Because I had not real talent for performing, I was forced into a work profession that allowed me a decent retirement plan; although I didn't realize it, I was only chasing a pay check to pay my bills. I truly feel sorry for the artist's and songwriters that poured their hearts and souls into their musical dreams only to be faced with being in their 40's, 50's and having to realize that dream was just not going to happen.
S.O.B. It truly is a difficult business and requires a lot of thought and perhaps even more luck.
Anyway, that is my opinion on the subject. Hope you respond.
OD