I think the answer has to be "yes". As an old hand, I can tell you it gets harder to find each next job. Now, I don't think (most) managers look at a candidate and say, "Forget that guy, he's too old." It's more subtle than that. I'm not sure hiring managers are even aware that they're doing it. But man, it's out there.
To start out, let me say that I don't believe the world owes every old hand a living even if they haven't kept up to date with our fast-changing industry. If there is no longer much demand for Pascal programmers, well that's just the way the world is. But lets look at some facts.
- The great majority of practicing developers entered the field since 1995, when the software world began to really take off. That means that in 2012, the average developer has less than ten years' experience. These devs learned Java in school, and took their first jobs during the dot.com boom building web sites. Nothing wrong with that, except that the resumes of this cohort of devs all look pretty much the same. And they look different than the resumes of older devs who learned C in school and developed standalone windows apps. It is a truism that "we like to hire ourselves." The resumes of old hands just don't look like the resumes of younger devs doing the hiring.
- The current trend in interview techniques is a coding interview. Coding tests have to be short, artificial problems. They are in this way exactly like Computer Science homework problems. Coding tests emphasize book learning and mathematical aptitude over experience and intuition. Such interview techniques reward the recent graduate, and gratify the egos of new hires with insufficient experience to program intuitively. Old hands bring many skills to the job; design experience needed to distinguish true requirements from marketing obsessions, coding experience needed to estimate schedules, process experience needed to improve practice, interpersonal experience that brings awareness of destructive team and management behaviors, and a degree of maturity about the work environment. These skills are hard to recognize if you don't possess them. I find interviewers rarely ask questions about these skills.
- An experienced developer costs about twice what a new hire costs on an hourly basis. Good senior developers totally earn that pay through higher productivity and avoiding rookie mistakes. If the manager is not an experienced coder, they may not recognize that a senior person can really be that much more productive.
- Fast-growing employers with positions to fill typically have young teams, obsessed with the desires of the young. Indeed, the first time I began to think of myself as old was when I signed onto a startup during the dot-com boom. I was surrounded by twenty-somethings that all seemed to desire the same three things; to get rich, not by working hard over a lifetime, but by lucking into the right dot-com; to buy a big, fancy Lexus or Infinity car; which they believed they could employ to get sex with no commitment. I found these goals incomprehensibly naive. I just wasn't the same as they were. I interviewed with one company where everybody played in the same rock band. I might have done better at that interview had I played rhythm guitar. Silly me, I talked about programming. I had another interview with a hip young new-media company terminated after 45 minutes (and before any technical questions), presumably because I wasn't hip and young enough.