I liked this post on John August's site--it's the story of a young guy working to get started in Hollywood as a writer/director and details his constant scrambling for jobs. But you can see that he's leapt in both feet first, all the way. The comment discussion is worth looking at, too. Adam's story works great for the young kids fresh out of college, but obviously, that sort of thing is a lot trickier once you've got the wife, kids, and house.
On a similar note, I've been meaning to mention this great post by Malachy Walsh (now a proud papa!) about his new camera and starting to make some movies on his own. He's got me wondering if I should start doing something similar (in all my copious spare time?). Back in college, I had a blast making short films, and they were pretty popular on campus. But there was no outlet beyond that really. Now, with YouTube, there's this odd distribution channel already in place (though with tons of competition).
My screenwriting career is nearly dormant, but I've been tempted to get involved in making more movies and I know that part of the reason why it's been so hard to get a movie made is that movies are made (a lot like theatre) by people working together with their friends. Trying to just send out queries and scripts through the mail and e-mail, even if you get agent or manager, is banking on the longest of longshots. I've had a couple different agents and a manager, but sooner or later, they fade away, because I'm just a voice on the phone, or characters in an e-mail. I could be wrong, but it seems like if you really want your scripts to get made, you need to be friends with people who are actually making movies.
I don't think that mean that you necessarily have to live in LA, but it's clear why it helps. I'm not leaving Boston for a while, so if I want it to happen, I'm going to have to get to know filmmakers around here.
Making your own movies is the story behind I'm Through With White Girls, which I blogged about earlier. An actress wanted a role for herself, then read a script written by a friend, and saw something she wanted to play. Rather than wait around, she and her sister decided to produce the film themselves. They hired another friend, who was also a young actress and director, to direct. They raised the money and made it happen. Sometimes, maybe most of the time, that's just what it takes. The stories we read in the press about a script getting plucked of the blue are just fantasy fodder.