I'm glad you enjoyed it! Regarding the last thing you mentioned, the the third category isn't "work" but more broadly "The Future". That's why "You'll never amount to anything" goes there - it echoes the protagonist Nothing's fear about his future prospects (the future tense is also a hint). "This work is terrible" refers to schoolwork, not a job.
(I think my own choice to use "find perfect job" instead of "find perfect career" earlier in the game might have caused some confusion. I believe the latter would have made it more clear to players how old Nothing actually is.)
Thanks for playing!