One of my friends is caught in a similar trap. He has been at the same company for 20 years, and his skills have degraded completely. He is a middle manager and he's been interviewing for the past year with zero success. The technology he has been working with is so out of date, no one is willing to give him a chance, and frankly, if I came across his resume, neither would I.

He is the product of getting far too comfortable early on, and being afraid of change. Once you let that sink in, then you get stuck and it becomes a self-fulfilling prophecy. I don't see him getting another job soon, and if he gets laid off, I think he's seriously fucked.

Meanwhile in 27 years, I've had over 10 jobs. I have no problems learning new technology, or jumping into a codebase and making code fixes the first day. I have a long trail of friends from all of my previous companies that I could call up and go for lunch with that day, and I still feel energetic about coding and learning the newest and latest. But I haven't been there long enough to effect change the way other long-timers have, and hence why I'm still a programmer as opposed to a tech lead or architect, etc.