This game was written for the Neo Twiny Jam in 500 words or less.
It's a Texture game, which I haven't seen a lot of recently. This system has you drag verbs onto nouns (or, here, resume sections), both causing changes when you actually drop it and tooltips when you hover.
The humor (or pathos, depending on how you view it) comes from the self-criticism or uncertainty or Sisyphean task of dealing with all of this.
I found only one ending, but I found it multiple times.