As I've said elsewhere, your choice of language must be driven by what libraries you want to use. I read Land of Lisp earlier this year and went through the Rac

As I've said elsewhere, your choice of language must be driven by what libraries you want to use. I read Land of Lisp earlier this year and went through the Racket guide a few months ago. Currently I'm rewriting my blog using Seaside on Pharo Smalltalk. The one thing that keeps coming back to bite me in the ass is that there are few libraries available for any of these languages. When libraries are available, they're poorly documented. Of course, this is becoming less of an issue in Common Lisp thanks to QuickLisp. There's a Racket book coming out next year, which might help with adoption and result in better libraries. Still, it will take years before any of these languages catch up to Python/Ruby/Java. Edit: I thoroughly enjoyed learning and playing with all three languages. Smalltalk, in particular, felt very natural. It has the eerie property of seeming like an extension of your brain.