I agree and disagree to an extent. My near double masters, has helped and hurt. I have lost out on a good number of positions because they felt do to my schooling, that I would cost too much for that they wanted to pay, or that I did not have enough experience to match the level of degrees. So it was the catch 22 for almost 2 years. Not enough experience to match the education, but could not get the experience because they did not want to pay for the education.. I think that the differentiation is getting stronger though and not weaker as the workforce is even more divided. You and I are in an age group that is 10 years older than these young bucks and I see it as getting more and more difficult to compete with others who already have those degrees when neither have experience. I would also of course recommend that since you realize your issue that you address it up front in the interview. There is a strong possibility that you could have improved your chances by changing your interviewing strategy. It was always addressed, but something I could not magically change in their eyes. But either way, I am at a good company, the money is not good, and the commute blows. But steady pay of a lower rate is better then unsure pay at a higher rate at this point in my life.