With his eyes open, he no longer can cope with the lame blubiness of his career, but he finds him self pigeonholed by his old job description. He doesn't have the credentials to strike off into a job that would allow for more professional growth. But he had no idea that the many small development choices he'd been making over time would lead to this crisis. Now what?
I'm not normally found arguing in favor of the grad school option, but every tool has its use. If you're in a place where you can't imagine getting a job outside of the narrow boundaries of your resume, you need a different environment with different friends and colleagues. It's time to escape the resume-ruled world for a while and get a master's degree.
When you emerge from school it will be like being born again: Society will understand it when you declare that you no longer want to be known as a Blub guy -- you'll have moved to a higher plane, or at least a different one. Plus you'll have a lot of smart friends who might want to help start a company.
Other options include: start a company [1], downshift your career (find the job that you think you want, find the entry-level job that leads toward that, and get that job -- swallow your pride), build some independent projects (websites or open-source projects) and launch them... or all of the above.
[1] Here on news.yc I'm contractually obligated to include this advice somewhere in every post.
If that's what you're asking about, I can talk about that, although my first advice will be to forget all about it. ;) But that's not what I'm recommending in the post above. I'm not even recommending going to grad school for the credential, exactly. I'm recommending going to grad school because it's a great, society-approved excuse to quit your job, get the hell out of your cubicle, take some interesting classes, do some small and interesting projects (either for school or on the side) with a bunch of other smart people who have similar interests, and change the direction of your resume.
(There are obviously other ways to accomplish the goal of changing your career's direction, and one of those might be better. But this particular scenario -- a person who feels trapped by their own job history -- just smelled to me like someone who might prefer the grad school route. It's a fairly safe, classic, and well-respected way to mix your life up a bit for a year or two.)
I've never looked for open source lisp projects myself, but I'd give a site like github a try (just search for Lisp).