I know a lot of super artsy talented people from their mid 20s to about 40 who went to top schools. Some have made it. A surprising number had early successes which they couldn’t sustain. One notable case was a big success, floundered a bit and became a high school teacher, but kept plugging at her dream, and seems poised to have her career really take off. There are some grad programs in these fields which help, but you usually have to have at least some demonstrated success to get into them. Here’s a link to one of the best. http://tisch.nyu.edu/grad-musical-theatre-writing
Sometimes I think half the English and arts faculties at NY private schools fall into these categories. My offspring’s public school alma mater has a “rep” for giving its own grads struggling to make it jobs.My neighborhood has a local community theatre and it employs some very talented “wannabes” and “never quite made its” as instructors. The current overall “boss”–not sure of his title–was in Rent on Broadway for a lot of years. Not one of the "big roles’’ but not just ensemble either.
A very common “paying the bills” job for these “kids” is working for Kaplan or some other test-prep company.
One of my D’s childhood friends is a singer-songwriter. Her “day job” is as a recording “engineer.” She used to run a recording studio in Brooklyn. A lot of fairly famous people recorded there and that helped make contacts. Nowadays, most of her success involves writing songs for movies. Her only degree is from SUNY. She’s not famous, but I’m sure almost everyone on this board has heard one or more songs she wrote.
We had a really talented singer in our neighborhood who has been in several Broadway shows. She got her only degree in accounting. For a lot of years, she worked for Account Temps. She took short term assignments which allowed her to pay the bills while still auditioning.
Two of the more talented “kids” I know who gave up after trying for a number of years are now working at consulting firms. One was a double major in math and physics but spent all his undergrad years directing plays.
I don’t know if this helps…but I don’t think the young man should be rushing into a grad program. He should be getting involved in Hasty Pudding, Harvard Lampoon to network, getting internships etc.