...is thinking about resigning from his job.

He doesn't really want to as such, it's just that the job he loved so much 2 years ago has degenerated into months of ceaseless, thankless, pointless toil with no sign of relent.

Obsolete programming tools, long-term unremedied design failures, catastrophic project hand-overs, meaningless and impenetrable task/implementation specs, nightmarish test/fix/document cycles...

He's worried that if he stays there much longer then his skills are going to atrophy away to nothing, leaving him unable to easily obtain alternative gainful employment. But seeking new employment in these troubled economic times also holds anonymous terrors.

What should he do?

Man, I'm glad I'm not that jerk.