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After all this disappointment and frustration, he wants to be a writer ?
I can't imagine a worse transition. He's just setting himself up for years of struggle. I've published 17 books in many genres, seen my essays and fiction become homework at colleges across the country, spoken in half a dozen countries outside the U.S. on tour, and won some prizes, but the writing life is worse than acting and filled with constant ego blows.
At least acting offers you a community in a show of whatever kind, but writing is very solitary, which makes the downs harder to take. And for everyone thinking "If only I can sell a book, everything will change," here's the epigram of my mystery The Edith Wharton Murders, quoted from novelist Daniel Magida:
The only thing worse than not being published is being published.
It's true, it's true, it's true.
He doesn't sound like someone who feels compelled, so I'd warn him to try something safer.