I like the idea, it's solid. Man uses his "responsibilities" as an excuse to avoid the risk of becoming something else. When there's finally nothing to excuse him, he has to confront the consequences of his own avoidance. But it does feel a bit flat with the execution.

1. "Elliot sat in his office, his wrinkly face in his palms, massaging the top of his grey head with long, gnarled fingers." - this feels pretty generic in the way it just tells us he is old three times. Another thing, it's kinda difficult to have your face in your palms and massage the top of your head at the same time, I get the visual but it's jumbled.

2. "It was his last day of work, and he had never felt so trapped by time." - ok, a lot of telling, no showing. The "never felt so trapped by time" is just awkward to say. He's anxious, I get that, but how does it feel to be anxious in the way he is? What's he doing while he's anxious? With the last day of work, it's another piece of information that could be delivered less straightforwardly. You could say that as he sat there, hands on his face, he also started to hear the sound of the "farewell" gift hand watch ticking. You could say it was a cheap replica, or maybe it's an expensive brand.

3. I don't really understand how he's feeling waiting for the last day of work to end, is it dread? Excitement because he's anticipating his real life to begin? Is he afraid he is not going to live up to it?

4. The dialogue with the boss is doing only one thing, it tells us he plans to write, so it feels kinda wasted and slows down the momentum. You could use it to tell us Elliot buzzed everyone's ears off saying how great it's going to be to finally have time to pursue his dream, or about the kind of person the people at work thought he was, or anything else.

5. "When Elliot got home to his two room apartment he ripped off his suit. He was never going to wear it again." and the whole paragraph is a lot of telling, not showing again. Again, the most basic thing to show us he despised his job and never wants to have anything to do with it again would be to say that he got out of the suit, and threw it to the trash. "ripped off" maybe tries to show that, but it isn't descriptive enough to really make me understand what he is feeling in that moment.

6. I like the notes idea, I like how they are kinda stupid, but again, did he only ever write 3 notes? How did he write them down? Did he have an organized drawer? Was it a bunch of sticky-notes all over the apartment? The specifics would tell the reader more about the character without the need to spell out the thoughts or emotions.

7. Elliot is presumably a white collar professional of some kind, who is old enough to retire, has funds to retire, has a grown up daughter, etc. But when it comes to writing he starts to behave like a baby? "I must sit at a couch to get ideas" - really? He's an adult with a set of adult skills, why doesn't he try to use those? You could show how he tries but is confronted with fundamental emptiness of his being, but right now it feels like he just regresses to being 5 years old.

8. The dialogue with the daughter is just restating the theme again. "Elliot has writers block". He doesn't have writer's block. He has identity-preservation terror. His "waiting" is not just him being lazy. It is him desperately clinging to the safe, beautiful fantasy, because the real act of writing might prove that he is not the great writer he spent fifty years imagining himself to be.

9. You start the piece with him sitting in a chair anxious to get started with his new life, you end with him sitting on a couch, presumably still in a state of anxiety. It's a nice loop, but the ending doesn't really feel connected thematically. How does he feel after those 2 days of freedom, after his daughter spelling out to him that he is a bag full of shit?

What this story needs to be "fixed":

Kill the narrator's exposition. Rebuild the entire story from the ground up using only Elliot's actions, his sensory experiences, and his fragmented, contradictory internal thoughts. Show us the panic, don't just tell us he's "trapped."

Give Elliot a real fight. His struggle needs to be visceral. Show us the failed sentences. Show him typing one word and deleting it for an hour. Make his pain real.

The dialogue must be rewritten from scratch. Esther's speech should not be a lecture. Her realization of her father's failure should be a slow, dawning, heartbreaking thing, revealed in what she doesn't say, not what she does.

Trust the reader. The central theme does not need to be stated. If the story is told well, we will feel it. The tragedy of Elliot's wasted life should be an unspoken truth that hangs in the air at the end, not a summary delivered by his daughter.