The tough part for me is, how to find leads? I have a lot of contacts from previous jobs but nobody I know who could give me any kind of freelance work. How do you bootstrap this?
I don't know your specialty, but in design or programming, you only really need a good example of your work to get started. Try the monthly freelancer posts on HN. Worst case, here's a list of RSS feeds I used to follow (some can filter by freelance/anywhere): http://news.ycombinator.com/item?id=2465077