I've favorited more comments in this thread than anything else on HN ever. Thanks for the great thoughts. I can add tangentially that these questions, these considerations, were pursued almost maniacally by David Foster Wallace, especially later in his life. You may find satisfaction especially in his last, unfinished novel, The Pale King, which purports especially to treat the immense spiritual gravity that he thought pertained to boredom itself, the awful tedium that so many of us have to suffer in the modern marketplace. Not, like, the boredom of having nothing to do on a rainy Sunday afternoon, which I don't think exists anymore; more the ugly struggle to, as you say, find a meaningful life amid meaningless work and interactions.