1. Invite him to write a short story for an anthology, thus making him feel warm and fuzzy and part of the literary elite. Do, however, let him know of the need to submit the story by the given deadline, because the industry, as we all know, moves at a hurricane pace.
2. When the poor demented loser submits what he thinks is a good story by the deadline, inform him casually that the deadline has been indefinitely extended, though you think the book might come out sometime next year.
3. Later, tell him you liked the story and youre definitely including it, causing him to giggle gleefully and hum a merry tune as he eats his reheated food, watches Friends reruns and reminds himself that THIS is why he quit all his jobs and cut himself off from society in general.
4. tell him some time later exactly how little hes getting paid for this story, so that he remembers yet again how futile it all is, and that he might be getting a lot more money (and potential test-drive satisfaction) by selling condoms.
5. let all be for a while.
6. tell him the story has been dropped from the anthology because it didnt quite fit the tone of the entire thing. suggest other places that might accept a story that shabby.
7. if you feel like adding insult to injury, ask him kindly whether hed like to submit another piece, which might be accepted if its any good.
8. give him a good therapists number, ask his friends to keep sharp objects away from him for a few days, and wish him good luck for the MBA entrance tests later in the year.