This is exactly the path I ended up taking.
I blew my first opportunity at college. I simply wasn't ready for the freedom. I slacked off, and didn't take it seriously. I did "OK" grade-wise, but lost much of my financial aid, and couldn't make it for a second year.
Spent the next few years maturing. Moved out of my folks house after finding that I simply couldn't live with them anymore. Moved in with my then-girlfriend (now wife) in her college dorm for a while. Eventually got our first apartment. Was in shit retail jobs for a few years.
Networking is everything. One of the guys I knew from a retail gig ended up manager of a dial-up tech-support department, and got me a job there. Busted my ass in that tech-support hellhole, sponged every bit of knowledge I could, and eventually moved into Web Design, then Web Development. I kept picking up server admin experience along the way.
Got a job offer on the east coast for more than twice what I was making, doing a webmaster/admin gig. Moved. The bubble burst, the company went under, and I was unemployed for a little more than a year and a half. What sucked was that the jobs I was applying for either rejected me out of hand (no degree), or were just far enough outside my experience that they didn't want to take a chance. I hadn't built up a significant enough volume of experience to open those doors without the degree.
Finally, after more applications and resumes than I can count, I got a sysadmin position at a small company. Intolerable conditions and expectations were the order of the day. After about 3 years of that, I needed to get out.
And that's how I landed my current job, as the second sysadmin at a slightly larger company. I'd finally accumulated a large enough body of experience in my field that my lack of a degree wasn't a concern. I had exceptional references, which I'm sure helped quite a bit. Great people here, and a much better environment. We're understaffed - but then again, who isn't? In this economy, I'd much rather have too much work (and reasonable expectations) than not enough!