According to the intro, "How to be the Luckiest Person Alive" is supposed to "unleash the core that will drive you from desire to ambition to meaning." Readers can be forgiven if they are still a confused. This book isn't The Secret and it's not going to help you figure out what your life means. It also won't talk about luck.
So what does the book actually cover? A lot. An awful lot. Everything from whether to buy a house, what to do when you're suddenly wealthy, why to avoid college, and how to fire employees. It's nominally about some very high-level generalities about running startup businesses.
The biggest problem is that everything is in lists. Long lists. Long lists with little supporting detail or emphasis. Any real points quickly get lost as he races from one bullet to the next, with no hint which is essential, which is a joke and which is just filler. In one classic chapter, he rattles off over 80 "rules" for a business. Some some like crucial, vital pieces of information like "get a customer" and "be profitable". These rules sound like they can make or break a business and should always be followed. Other rules sound like handy tips, like "have killer parties" and "at Christmas, donate money to every customer's favorite charity." By the time you've droned through ten pages, everything blurs and the really key ideas (whichever they were) are lost. And since it is just a long list of rules, most readers will forget them before the chapter is done.
After he goes through several anecdotes including an uncomfortable chapter when he seems fixated on how much sex and drugs he did in college, the useful content more or less fizzes out. There's no real conclusion and nothing to wrap it up. Instead, as if to ensure that we forget everything, we get almost 100 pages of direct reprints of various blog articles which are, you guessed it, more lists. And since they were blog posts, each chapter is disconnected from everything which came before and after.
He writes very well as a blogger. The list format is a natural fit and writing short, self-contained essays is a virtue. As a book however, it is a failure. My advice is to subscribe to his blog and skip the book.
