This one was different.
I didn't stop to to read the entire thing, but the man was in his mid-50's and the first line of the writing on the sandwich board was "Almost Homeless." The next few lines were about how he was some sort of manager who lost his job recently and he was handing out his resume to anyone who would stop and take it.
9 hours later when I was headed home, I could see him from across the street. Still wearing the sandwich board and still handing out resumes. At least I saw someone stopping and talking to him and hope that maybe he got a lead or an interview and hopefully won't be "Almost Homeless." for much longer.