It is surprising how many middle aged obsolete technology professionals you will find if you care to visit your local job career transition networking meetings. It not always that the people don't want to learn a new skill set, but more times than not, its a matter of cost of training. Its hard to fork down money for a training program if you are not working. Moreover, there is another problem in that people are reluctant to lay down cash on a skill set if they are unsure that it will be used in two years. I remember learning COM & OLE. I thought that it was hot shit. Well, it was more worthless than Elvis paraphernalia in another two years. Moreover, most head hunters or corporations will not want you if you only have a training program or a homemade portfolio (or open-source project). Its hard enough selling yourself to upper management if you have the skill set, but are an outsider without business contacts. There is an strong and established good old boys network for most upper end jobs. About the only way to circumvent it is if you know something that some business owner cannot find something thought his connections. I worked in finance, and it is ironic how many people knew each other from early childhood.
On the other end of the age spectrum, I have met many a Ph. D. s in fields that had a glut of people, e.g. medical sciences or in fields that do not have a high demand, Philosophy, Mathematics, Literature, or Oceanography. Most of these former students had unrealistic expectations of job prospects or believed that somehow they would be the one to overcome the odds and land a professorship. After about a two year job search, most come to the realization that they should have became a "short order chef: which has better career prospects. Being broke and destitute, they are looking to retool to become a programmer or bank administrator or "tech writer" and have the mental aptitude to learn what is necessary.