This guy’s problem is that he never really had a career plan, so to speak. He majored in the humanities, and then fell into what sounds was some kind of support or mid-level IT position that’s very dependent on system-specific knowledge and experience, not fundamental IT concepts.
What this means is that he basically never had a very firm foundation for his career. Rather than building on what he learned in college, and getting that base, he basically took a 90 degree turn and jumped into IT without any background.
So when he got laid off 3 years later, he basically had 3 years of experience at a relatively low level job, and was laid off basically as part of the big 2002 tech bust, when a lot of other people like him also took it in the neck.
What he didn’t realize was that when companies started hiring again, he wouldn’t look so attractive to employers with no tech degree and little experience to separate him from the thousands of other “warm bodies” who filled a lot of IT positions from the mid-90s through the early 2000s. From my experience in IT, there was a bloodbath among this sort of IT worker in the 2002 bust; most truly technical people eventually got rehired, but the inexperienced undereducated types really didn’t.
In other words, why hire this guy with 3 years of experience, when they could hire a kid out of college with a tech degree for less, or hire a guy with similar experience AND a tech degree for the same money? So this guy never realized this and never took stock of where his career was going- just believing that eventually he’d find a full-time gig and be happy.
And the older he gets, and the less relevant his experience is, the worse it’ll get. And he’s in a particularly terrible part of the country for that kind of thing- Silicon Valley is not a good place to try and work in IT if you don’t have the chops for it.
If I was in his position, I’d seriously consider moving and/or going back to get retrained in something else. Perhaps teaching? School districts are always looking for teachers, and with a degree in the humanities and IT experience, he’s got a few more options than others as far as what he could teach.