Why is it that I have 3 college degrees, an extensive work history and subject myself to taking a leak in the wind looking for work?

Job searches are always difficult and challenging. Many factors could be contributing to your sense of defeat. One possibility is that your job search is too restricted, and if that's the case, you will improve your chances by being willing to move where the jobs are, being open to positions in fields other than your specific study background, and being flexible in your expectations about the position. Another possibility is your approach to the search. Are you getting lots of interviews? If so, then you are filling out applications well, and you have a strong resume. If not, those factors need to be improved. If you're getting to the interview, but no further, then your interviewing skills need some attention. Investigate programs which train "job hunters" in interview strategies. Evaluating the source of the problem is your first step in getting it solved.