Is this supposed to be a metaphor for startup life? It kinda fits for me...
From what I can tell, he's trying to dig himself out of a relationship he isn't happy in instead of just leaving. If he works hard enough digging deeper, maybe he can drive her away instead of having to own disappointing and hurting her, or it will collapse on him and he can be liberated in death and still remembered as perfect and a martyr. If only he had a father who could tell him, son, stop digging. This woman isn't your mother, accept yourself. Strike this set, grieve, and move on.
Or he's just a nerd with a shovel, but it's never just a nerd with a shovel.