Wow, this is quite an experience. As a self-denying person myself, this is extremely relatable. The dread during the middle session hits me especially strong and it's just that relastic. It's nice to see someone make this feeling and experience into a game so this alone deserves a lot of praise. Well done!
For a little bit of criticism for the gameplay, I'd say it's a bit on the simple side, and I think having more variations of the sentences will make the game much challenging and enjoyable. Also, I am not sure if I am getting this wrongly, but "the work is terrible" and "you'll never amount to anything" maps to "school" and "work" respectively seems kind of wrong. Isn't it the other way around?
Anyway, this is a surprisingly nice entry in my opinion. Keep up the good work!