I like the fact that you were really trying to draw us in with the cliff scene- you tried. Ah, I know that sounds like a terrible insult...but really, it's not. You've got mad style skills and you've pulled it off well.
However! This story is a contradiction in all the little clues it gives- at first we get, 'ooh! Cynical hero! He's talking to himself!' but then it switches over the the 'awake' thing, and we get the 'so it was all a dream'...which doesn't really fit. Pick one.
CYNICAL HERO: This guy's life is crap and he acknowledges this with all he's got. Add in more sarcasm and more pitfalls so he's got more to complain about- but don't forget to make him likeable. Challenge of a lifetime, I know.
'TWAS ALL A DREAM: Make this more surreal- strange, twisted details and a lilting sense of description ('soft' words, roundabout phrases) will do the trick.
And of course, you might say, "I was going for something else entirely!" But...you certainly confused me, so you're going to want to pick one of the two, or something recognizable or similar. You can use elements- the 'doom is a'coming' character or the surreal setting- but make sure that it's clear what's going on.
You can do something that's not been done before...but make sure it's actually been, you know, not done before.
Other than that- I did enjoy the yelling at God. I found that amusing. If you want a more sarcastic setting, I'd definitely bring that one out.
