Great thread, just read the whole thing. Glad I lurk OOT every long now and again still,
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I also have some questions for the OP as he's done an amazing job of staying involved and offering up useful opinions.
My sister graduated from college several years ago and wants to be a TV writer. She has had several jobs "in the industry" at more or less some level of administrative assistant at companies ranging from "we get really crappy movies distributed" to "we're involved (own the rights to) with creating TV shows" to "we make, including the writer of, high quality nonfiction TV shows for cable." Each position seems progressively better and more helpful on paper. But being an administrative assistant is not her ideal job (I'd imagine for most creative people it's essentially a logistical cluster F - she's ok but not great at it).
She is in writing groups, does find time to work on spec scripts/whatever, has some contacts but not sure they're super helpful.
I've looked at a couple of my sister's spec scripts and the original one seems very good to me (I'd be part of her target audience though), especially the dialogue and characterization (for the pilot at least). She's not a comedy writer, would likely work best on 1-hour shows that work in some humor (Firefly, Pushing Daisies - maybe this was 30 mins or technically a comedy, House, etc.)
My main questions are...
1) At what point should she throw in the towel? She just turned 28.
2) If she's actually good (she seems good at writing spec scripts, is smarter than me imo, and is doing one of the things she likely is "best" at), what is she *not doing* to get a position like writer's assistant or acquire game-changing friends (staff writers, agents, etc.)?
3) I have pretty much zero contacts to leverage for her (well I know one writer on the George Lopez show....somewhat). While I don't love networking, I have a strong background in selling creative ideas & work to clients so can certainly "sell" if I want to. Is there anything specific I can do to help her?
tl:dr: My sister is working on breaking into TV writing. I think she's good and would like to help - how best can I help?