HARVEY INCONSISTENCIES

So im watching suits again and when they have a flashback harvey asks jessica to step up for him. He says he's an associate thats kicked more ass then anyone else. Then that reminded me of mike asking harvey to help with his dinner and he said he "came into the league a sophomore" which meant in that context that he didn't come as an associate therefore didnt have to do the dinner. Then I remembered jessica always saying she picked him out the mailroom which solidifies my point.

am i going crazy or can i not see something so obvious or am i right? LMK because this actually confused the hell out of me, thanks!