It's certainly an example of a recurring theme which I have recently demanded, so I certainly should praise that. I could see this being a fairly good running joke - provided he thinks of some funnier uncomfortable truths than "you'll never find a programming language that lets you express yourself right." And today's comic is better than the first one - this has an ok joke, where the last one was just trying to make you feel sad. Honestly what this feels most like is an edited version of the last Well comic.
(And as long as I'm linking to the new xkcd: could be better! message board, let me encourage you to head on over there and see how things are going. It's the continuation of the xkcd: could be better! blog, because a message board is a smarter way to organize that sort of thing. it's fun, people!)
Lastly, Randy, you have got to change it to the "Well of Uncomfortable Truths". It just sounds so much more natural, plus you can avoid all the ugliness of the design you currently have on the sign, as pointed out by commentor the_cuddlefish on the last post (go to the comments and search for "seattle").