AsMother, welcome to the world of parenting a Jazz musician. I know how you feel. My son is just about to graduate from conservatory and it still can feel overwhelming at times. Looking at my son and his peers (he knows students at a wide range of conservatories) the key is to quote Don Braden, who runs the Litchfield Jazz Camp, “To play with as many different musicians” as possible. Find your scene and embrace it. My own son is the type to say, “Yes” when asked. That saying “yes” often put him in situations over his head but by doing that he gained a lot of experience and knowledge.
The big festivals that my son has applied to (and not been excepted to) are Banff and Stanford. They are quite hard to get into. What did our son do in the summer? He has taught (Litchfield and NEC and privately), gigged (lots of wedding gigs) and attempted to work at Starbucks…he quit after he realized that he could earn with one gig or teaching job with what he was earning working 4-8 hours. The first summer he attended the Keep and Eye on Jazz Foundation on full scholarship but he had to pay for his travel expenses. He turned that into a European trip to visit another friend he had met at school.
One other bit of advice I would give your son. Make sure that he spends time and effort when in school on his liberal arts classes and LEARNS TO WRITE!!! The reality of the art world is that these guys will graduate and they will have to write grants, applications for residencies, proposals, etc… If you can write well that can give you a big leg up in the real world. I have seen how one my son’s close friends, who is ridiculously talented as a musician but probably also has some untreated learning disabilities, has been held back by his lack of academic prowess. It is a shame because this young man is so talented and I suspect with the right tutoring he could indeed overcome some of his challenges. But I suspect his family’s culture doesn’t embrace the notion of learning disabilities and getting specific remediation.