Cherries and Clover
Between 17 and 23 my life goal was to be a filmmaker. I worked on about 40 small productions usually as the director, writer or editor - the largest of which was an independent film I played almost every role in creating (except acting): from writing to financing to directing and even some heavy post-production special effects to hide the mistakes of an incredibly hectic production carried out by an all-teenage cast and crew.
Personally, I now find the film to be too sweet for my taste but considering I was 17 when I wrote it, it's fine.
You can watch it on Amazon Instant Video and DVD (once I renew the rights agreement).