So, when?

At what age should I leave pay to sings, Young artist programs, graduate programs behind?
This is a complex question, because before it is answered, you have to have a pretty clear road map of how you got to the point of asking the question. For instance, if you are a soprano singing soubrette roles, and you started vocal study seriously right out of high school, and you are now 35 years old, and still trying to get established, most young artist programs will be not possible, and a pay to sing will not help your resume a bit. On the other hand, if your are a budding lyric tenor, who didn't discover you had a voice until you were 30, and just started study at 32, you may find yourself answering this question differently. Graduate programs are a different story. We should also dilineate here between Master of Music, Doctor of Musical Arts, and Artist Diploma programs. Age will not be a big factor in M.M. or D.M.A. programs. while with Artist Diploma programs you might have to do a bit more research to find the correct answer. However, it should be noted that entering a D.M.A. program at an older age may help you with securing higher education employment, but will probably have no impact on you getting hired for professional work (unless you have the good fortune to get associated with a graduate program, where one of the artist faculty also has hiring responsibility with a professional company).