This book was excellent at first, then it frustrated, then it wavered between those two emotions for the remaining pages. About halfway through he acknowledges how someone could view his ideas as contradictory. For example, he juxtaposes Chapter 17 "In Praise of Melancholy" with Chapter 18 "Stop Moaning; Be Merry." That's fine, but the changes come quickly, and they don't compliment one another as well as they could. Sometimes the chapters feel like they are unfinished or could have gone deeper rather wider in reference across different texts. (The added section at the end titled "Further Reading" gives you a clue about his desire to let you know he's read many books in preparing this book. And yet, he seems to include books he found bland, but spent time looking through. Why do you want someone to do a lot of reading to tell you what's worth a shoulder shrug?)
I thought he was at his best when he was praising the will of the individual to find and create his own happiness, to break free of controls like government or the debilitating pangs of guilt. But then he talks about how people should live in communes and many other pieces of advice that seem to directly restrain the individual. Moreover, it's strange that he rails against external control and advocates freedom, while putting commands at the end of each chapter, like "Start a Guild" or "Cut Up Your Credit Card." When he's telling me things I should do to be free, one of which is "Say yes," the word that kept coming to me was "no."
A lot of his chapters could have been contained inside other chapters. For example, "Chapter 8: Stop Competing" was weak, and the negative sentiments could have gone in "Chapter 4: Reject Career and All Its Promise" and the positive sentiments could have gone in "Stop Working, Start Living," the last chapter on play. Or, they could have all been combined in one extended chapter on the complexities of work. So it comes off as being somewhat sloppy and pandering, even though the book is strongest when it sheds all consideration for what people think. Ironically, if he'd refined his philosophy and made it shorter (or "simpler"), I think it would have been stronger. As it is, the 29 chapters have large doses of filler.
Still, this was a fun book to read and think about and there are good ideas here. You have to find what you like and not get worked up over the abrupt changes in philosophical direction. Take what you like, leave what you don't. But if you needed me to tell you that, I wonder how much help this book could please you.