Director & Cinematographer of Editorial, Documentary, Branded Content, & Music Videos.
I think one thing that might be missing from this discussion is how to make the leap into freelance or shooting weddings, or doing whatever. Very few are so gifted that they simply "decide" to be a freelancer and suddenly - boom, they have work. Even as I write this, I don't work full time in film. I actually have three jobs, and support a family. I shoot freelance when I can get it, I work as a Film-maker In Residence for a film-making organization (make video content & teach), and still work a retail job. All the while, I still self-fund my own projects and shoot lots of my own content.
What's the moral? Find ways to do lots of work that you care about - in any way you can. Do lots of it, and put yourself on deadlines like you were paid to do it. Meet lots of people to work with. Network network network (Something I suck at, but organizations like Raindance (www.raindance.org) are great for). Eventually you will do good work, and have worked with lots of cool and talented people along the way. I'm still on that journey, and I think my work still has a LONG way to go - but that same plan got me the job at Raindance, films in majors festivals, freelance directing work, etc).
...And the most important thing to remember is this: https://www.youtube.com/watch?v=BI23U7U2aUY&feature=youtube_gdata_player