As a non-native speaker, I really try to avoid the subjunctive whenever possible.
Of course, just not using it when perhaps it should be used is certainly an option (and it's one that I employ quite/too often), but whenever I’m aware of a legitimate, nearly synonymous, indicative alternative to the “ … que + subjonctif” clause in question, I try to remember to use it.
In the case of “bien que,” my go-to subjunctive-avoiding alternative to try to capture “although/even though” is:
So I’d translate your sentence as:
“Il était malheureux, même s'il travaillait/même s'il avait un boulot."
Although this might be an incorrect/less precise/less fancy translation, I personally find it a bit less harsh on my inner ear than hearing myself using the indicative with a well-known “ … que + subjonctif" clause.