Directing / Screenwriter

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Well basically I was just curious on ways to get to be part of these careers. I always would love to either be a screenwriter or actually get to direct what I write. Of course, I am just a college student with no money and though I do have some hollywood connections, I just feel like it's still a far fetched dream. What are ways other directors made it big, or how does one start off small and work their way up?