A new technology may in fact be much more productive to work with than an old one. Does someone with COBOL experience have an advantage or a disadvantage in learning Python vs someone who is just starting? Which is larger, the amount of useful knowledge they bring along, or the amount they have to discard?
There are sage old programmers that I look up to. But there are also a lot who just burned out and quit, tired of the new technology treadmill. I'm not sure which I'll become.