buckworks - 8:09 pm on Feb 2, 2010 (gmt 0) [edited by: buckworks at 8:13 pm (utc) on Feb. 2, 2010]
You are to be congratulated on sound preparation for taking such a big step! I wish you much satisfaction!
Here are my thoughts on your questions:
1. Develop solid skills for driving traffic, and also a solid, sustainable plan for monetizing it effectively.
2. Being your own boss is a blessing and a burden both at once. You have to be a self-starter, there won't be anyone to tell you what to do or when to do it. You'll need to be good at organizing your own work AND following through to make sure things get completed. Half-finished projects are a huge waste of resources.
3. My biggest mistake was that I should have started attending PubCon's about three sooner earlier than I did. I've made lots of little mistakes along the way but they're all part of the learning curve.
4. It's very satisfying not to have a regular j*b. I mostly work on my own sites, and I do some selective SEO/PPC consulting. I often can't tell whether I'm working or playing.
5. Once I quit I never went back. It helped that I had a spouse with a steady job, though.
Tell us more about your business plan. In general terms, what will generate your income, and how will you market it?
[edited by: buckworks at 8:13 pm (utc) on Feb. 2, 2010]