The essential dilemma: Is taking a regular job growing up or selling out?
A committed slacker with an occasional background in marketing, Dan Kennedy gets a chance to join the rat race while keeping his cool when he is offered a job at Atlantic Records in 2002. On the inside, he finds the mixture of chaos, capitulation and fear that you’d expect of a major record label in the early 21st century. But despite the bewilderment and flashes of contempt inspired by his new surroundings, Kennedy can’t suppress the desire to fit in. He splurges on pricey picture frames and pricey Barney’s windbreakers, thinking that these, maybe, are the kinds of things successful people do.

Sharp-eyed and sharp-tongued, Kennedy sticks his pins were they hurt; the names are changed not to protect the guilty, but to give him free rein. Not withstanding its fits of wicked point-settling, the book has a poignant core, since Kennedy is struggling with himself as much as anyone around him. Is taking a regular job growing up or selling out? Is his quasi-bohemian telecommuting lifestyle a matter of principle, or is it just that no one’s offered him enough money to sit behind a desk? Kennedy’s ill-advised, ambivalent, and occasionally successful attempts to fit in to a culture he doesn’t understand and often doesn’t respect give the book an undercurrent of self-examination that contrasts with Kennedy’s sometimes glib attacks on his bosses.

A spoken-word performer as well as a contributor to McSweeney’s and GQ, Kennedy knows how to punch up his writing with well-timed interpretation, although it’s odd to hear him talk about music for so long without actually hearing any.