The following is an email a friend of mine received after unwilling one of the head writers of a television show I managed to get contact information for. My friend emailed and received a very insightful response. With their permission (and sans any identifiable information) I am posting it here:
How's it going? Yeah, it's a tough gig, breaking in. It took me quite some time to get to a good place. And I had the same thing as you, where I was working production jobs, trying to get a break. And it's rough, because you rarely get free time to open your mind up to being creative.
I wish there was some magical advice I could give on what to do, how to do it and when to carry it all out. But really, it's just this, as far as I am concerned: if you are hyped up to write and want to dedicate your life to it, just stick with it.
I did, and even though there were times where I was really down and wondered if I would ever get a "real" writing job after doing all my specs and getting rewrites on loser indie films, I just kept going.
Even though that meant writing at home for awhile, and then taking a job to replenish the bank account, and then writing more, and then working more, I did it. So if you can do that, more power to you.
If you can get a job working with writers, that can really turn out to be a plus in a lot of ways. A lot of writers got their chances to move up by working as an assistant in the writer's office. Myself, included. The trick here is to know when to push yourself as a writer. Because you still have to do a good job, and they don't want to be bothered hearing about your aspirations all the time. But when it works, and they already know you and trust you, then you're in.
In television, a lot of it is getting in with a show runner/exec producer who likes being around you. There are tons of mediocre writers floating around in TV, and I've seen these people rise up. And it's obviously not from their scary talent. People hire writers in TV knowing that they have to spend tons of time in a small room with them, breaking story.
From my experience, you can get into TV writing one of two ways. Working up from an assistant is one of them. The other is, you come in cold. You have an agent pitching you as a new talent, and hope you can get someone to bite.
Agents always want what you haven't written, it seems. So be ready with everything. [Specs such as Six Feet Under, Smallville, Alias, The Sopranos and West Wing] might be considered old by now, in the agent world, because that was the hot spec show a few years ago. Now it's The Shield or Nip/Tuck, Lost or Desperate Housewives. And the agent would also probably suggest that you have a ... script [in the same style as the show you want to write for]. And also an original pilot. Sometimes a one-act play would be good to have, or a short story that shows your "voice."
Once you have what the agent needs to sell you, then it's very helpful. Staff writer positions are hard to come by..... So if you know anyone at all in the business, and can hit them up, you should. Agents won't deal with you unless you have a referral.
Well, I don't know if I've helped you at all. Feel free to e-mail me any specific questions you have, and if I can guide you, I will...
Best of luck,