His feelings are soaked in sadness, lack of hope.

Just what comes to mind after reading everyone's take on it, and then your excerpt again:

It isn't easy to know what's right when your entire world seems at cross-purposes.

This evokes the "bummed out" feelings expressed here and sounds (to me at any rate) classical/literary enough for the job.

Juan and Judith have detected the echo of the previous question, on the expression "un vacío de inoportunidades", presumably from the same source:
http://www.proz.com/kudoz/spanish_to_english/general_convers...

I still think that the idea expressed by "inoportunidades" can be summed up as awkwardness: "inoportunidad" meaning lack of "oportunidad", a state in which everything is "inoportuno", badly timed, inopportune: in a word, awkward. It doesn't really mean hopelessness or despair, though it probably induces those feelings.

For "abismo", I like "pit", a deep hole you can't climb out of. You often talk about being in a pit of despair, for example. Surprisingly (perhaps), the expression "pit of awkwardness" is not all that uncommon:
https://www.google.es/search?num=100&q="pit of awkwardness"&...


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Note added at 3 days21 hrs (2014-09-27 16:21:32 GMT)
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I just want to comment briefly on the points arising out of Gallagy's comment. I'm not claiming that this proposal of mine is necessarily the best translation; I like it, but people must decide for themselves, and I respect others' subjective judgement. What I do object to, though, is the idea that we should decide whether expressions are natural or idiomatic on the basis of Google hits. We should use our own judgement as native speakers, regardless of how often other people have used the expression. I freely admit that I regularly Google phrases I'm thinking of using when translating, mostly out of curiosity, to see what comes up; but in literary translation I wouldn't decide between alternatives on the basis of numbers of hits.

If people only ever wrote combinations of words that pass the Google hit test, no new expressions would ever be used and the language would be impoverished. Great works of art (and I'm not of course suggesting that my translation is in that category) constantly use expressions that occur nowhere else. Actually, if you Google many perfectly natural combinations of four or five words you find only a handful of hits.

I entirely disagree that "a pit of awkwardness" is something a non-native would write (meaning that a native wouldn't). As a matter of fact, natives have written this. Here's a brief review of Freaks and Geeks (1999) by Strawberry Sarayan, an NYT journalist and daughter of the poet and novelist Aram Sarayan:

"The clothes, the haircuts, the bottomless pit of awkwardness… nothing before or since has captured the true pain of adolescence in the 1980s - or, indeed, any decade - so perfectly."
http://www.telegraph.co.uk/culture/film/3670461/Judd-Apatow-...

This is mildly gratifying to me, and useful for the purposes of argument, since it supports my claim that this is not a non-native expression, but it's hardly decisive, and just because a respected professional writer wrote it we don't have to like it. We really must have the confidence to decide for ourselves what sounds OK and expresses what we want to say.