When do I say "I'm done trying" or should I even think like that?
This is perhaps the most personal question there is. And I guess to begin, I think it depends on what you are trying to accomplish. If your inwardly stated goal is making a living as professional classical singer, and you are not getting at least some movement in that direction, and you are in your forties (this will of course vary greatly depending on your voice type, etc.) then you may want to take a look at whether to continue. On the other hand, if you have made peace with keeping a "hand in the game" singing an occasional gig, teaching, and generally feeling a part of the singing world, there is no reason to not continue. What will be important to know is what auditions to pursue or not pursue, depending on what decision you have come to. In my next posts, I will break this down further, but suffice it to say, that I come down squarely on the side of "chasing your dream". I just hate to see it when people put themselves in audition situations that are not appropriate for where they have landed - in other words - "know thyself".