What's the point anymore

When I tell people that I don't know what I want to be when I grow up, and that I'd be happy to take their suggestions, they usually think I'm kidding. I'm not. Since I graduated from college seven years ago this May, I have done the following:

• Applied to PhD programs in sociology at University of Notre Dame, University of Minnesota, and Loyola University Chicago. Got into Loyola. Maybe if I'd gone, I wouldn't feel like such a failure now.
• Spent a year substitute teaching, mostly lonely and alone.
• Applied to PhD programs in sociology at New York University, Boston College, University of Wisconsin, Portland State University, University of Chicago, University of Texas (Austin), Georgia State University, Arizona State University, and University of California-San Francisco. Got into Chicago's MA program; actually went.
• Got my MA, then worked in a small law office, mostly catching up on reading and boring myself to death.
• Applied to law school at Indiana University, University of Kentucky, University of Washington, Ohio State, Tulane, Georgetown, American, Northwestern, and Hamline. Got into Hamline, then discovered that it's a Tier 4 law school. Didn't want to go that badly.
• Went to work at a job I hated, with people I didn't like. But it paid well.
• Applied to the only PhD programs that accept mid-year applicants at Emory, University of Maryland, and University of Louisville. Got into U of L, am about to finish my second MA, this one in Women's and Gender Studies.
• Applied to only one PhD program for the 2009-10 school year, University of British Columbia. Got rejected.
• Applied for the Masters of Science in Social Work program at U of L. Will start Marriage and Family Therapy program in the summer.

I still feel like I've failed, because I've wanted a PhD for so long. (The law school thing was an ill-advised offroad adventure from that, I'll admit. Though I did like the law classes I took, and I liked the kinds of things I encountered at the law office where I worked, in hindsight it's a very good thing that I didn't get accepted to law school.) Doing the MSSW/MFT thing almost feels like settling, especially since what I really want to do is teach. (However, I don't know if that's actually what I want to do. It seems like something I'd want to do from the outside, but past experience has shown that what a job looks like from outside is usually pretty different from what it's actually like. I need a professor who will turn their class over to me for a semester. Then we'll see how I feel about it.)

So at what point do you give up on the dream? It's been seven years, and I'd estimate that I've spent close to $3000 applying for schools, not counting the sheer amount of work-hours I spent working on applications and the like. That's half a year's rent for a nice one bedroom in Louisville. Maybe I just don't have it in me. 

Maybe I'm not cut out to get a PhD. It's getting harder and harder for me to find professors who were willing to write letters of recommendation for me. I'm not positive, but I'm pretty sure that's a bad sign. It doesn't mean that I can't go back later and get a PhD, but for now, all signs point to 'stop.'