I think it would. I'm sure many people would relate to it. /r/me_irl has a success of its own.
There are many many people who feel guilty because their life could be more successful. It's a very hard thing to unroot out of your mind, but laughing about it is a huge relief.
It wouldn't be popular. People crave escapism.
The very fact that you're satirising exactly that is what defeats the purpose.