i think my view is this >>85507723
the show makes it clear that getting hired was a huge deal to him. he worked in secret to get his degree and was so fucking happy when he got it, and was very excited to tell chuck abou tit. he had huge hopes of getting hired and you see what a huge disappointment it was for him when he was told no. it broke him. that was his hopes and dreams and chuck squashed those and this really affected him.
this is also shown when he does get a second chance when he brings the case to chuck and they take it to HHM and he is happy as hell ot work with chuck and so excited to get a second chance of being hired only to have his dreams squashed a second time.
ive always seen it as the show was clear that not being hired at HHM set jimmy back.