Vogue, yes, it’s definitely somewhat messed up, especially considering the the fact that one is supposed to teach one’s son a trade, the ketubah obligation of the man to support the wife (not vice versa), and Chazal’s strong views in favor of combining Torah study and work (Avos 2:2). In truth, there are a variety of ways of being a good Jew, and the man learning/woman working model is only one of these ways. But there are a few things to keep in mind.
First, it is extremely common, perhaps the norm, for secular Jews and non-Jews (of all social classes and groups) nowadays to spend their 20s being economically dependent on their parents or the government. This can mean living with one’s parents, being a grad student for 5-10 years and living on poverty wages (often with food stamps), moving from one random low-paid job to another, getting a college degree in an impractical subject and then aimlessly traveling around, etc. There was even a long NY Times magazine article recently called “What is it about 20 somethings?” So being economically not on solid ground in one’s 20s is kind of normal. As long as you eventually figure out a way to get a reasonable income sooner or later, it’s not really that crazy.
Second, in every generation Judaism changes, and sometimes these changes are positive, or negative, or both positive and negative. Even if there are certain practical or hashkafic distortions (such as the emphasis on fulltime learning as a lifetime occupation for the masses) in a certain generation, we should see things in the big picture, and try to steer Judaism in the right direction as best as we can, while doing the things we know we’re supposed to do — Torah, mitzvos, maasim tovim, etc. Eventually people and ideas will arise to correct whatever distortions are going on in a particular generation — and we can encourage that process through our own individual contributions.