I like my non-fiction with a clear authorial voice, and Sims' provides that. He's a little on the ra-ra side, and this feels very businessy-non-fiction, which are both negatives for me. He tells a few in-my-life anecdotes (like the ones about knowing Russert as a child), all of which grated. My sense is that he's someone who came from a mildly oppressive, or at least overly structured (competitive? with high expectations?) background and he wants to make sure kids don't have their Creativity Crushed by Educators.
The thesis of the book is perfectly aligned with one of my most basic beliefs. There's no point in putting together a Grand Plan for doing something you've never done before. You don't know how to do it yet, so you should pick a piece that is close to something you do know how to do, do it, and then see what happens before deciding whether to proceed and if so, how. The biggest hole in Sims' analysis is his failure to understand that innovators who "prototype" or write a "shitty first draft" or otherwise do a rough version of something which they then refine _already have a long history of doing what they are doing_. This is actually the biggest thing missed by people who attempt to understand "creativity" and/or innovators, so I don't really blame him personally. It's still annoying. You can't think if you don't have anything to think with -- while Sims' sort of gets at this with his diversity-of-real-world-experience, it's not in a very helpful way.
The next problem is his handling of the idea of "healthy perfectionism" vs. "unhealthy perfectionism". He seems to think that "healthy perfectionism" is compatible with creativity/innovation, but that "unhealthy perfectionism" is not. Without getting into the details of the difference, I will merely note that he didn't include _any_ Jeff Bezos examples in how creative people are "healthy perfectionists". There's a lot of fantastic (for suitable definitions of fantastic) innovation out there that's really kind of crummy, even when it gets out into the world. It's a sort of 80/20 crummy, usually in an arena where making it 90/10 or 100% Teh Awesome would actually make it worse, or at least accessible to fewer people. 80/20 approaches are more compatible with incremental or user-driven development anyway; ignoring them seems to miss the point.
The third problem is the interpretation of Wiseman's luck research. I'm not familiar with Wiseman's work, so I can't speak to the original analysis, however the story told in this book about the self-defined unlucky people being told to count photographs in a newspaper and not noticing the thing in the newspaper that said to stop counting is open to at least one other interpretation than the ones on offer. It's a serious issue with real world consequences and revolves around our ability to notice "unrelated" things when focused on a task. My experience with innovators and successful entrepreneurs is that this ability to notice "unrelated" things while maintaining task focus is Important. Wiseman's strategies to improve luck may help with this, but I suspect there are other approaches that would address this specific problem even more.
The hands-down _best_ part of the book _separate_ from the thesis of the book is the brief section where he describes taking his rough, 3 page book description and shopping it around. "I'm interested in right brain thinking" made me cackle -- and I don't think Sims' understood what she was getting at at all, which is just as well, really. This section did more to explain why there's so much dreck out there being published by the Big 6 than anything else I have ever seen. Ever.
The best part of the book relative to the thesis is the title: both the original ("Experimental Innovation") and the original subtitle, which became the title: "Little Bets".
It's sort of a mess, so I'm not prepared to recommend it, but I feel like Sims might be capable of highly readable and worthwhile non-fiction, so I'll keep an eye out for further work. You could skim it at the library, maybe.
I may supplement this if it turns out to be one of those odd books where the back matter is better than the narrative.