Here are some lesser-known books I’ve loved, that you won’t find in typical recommendation lists – the deep-cuts.

Replacing Guilt: Minding Our Way

This book is all about the role of guilt. When is it useful, when is it not, what can be done about it.

This could have easily been packaged like a best-selling pop-psychology book – padded to 200 pages with a sampling of the same anecdotes we’ve all read 100 times, fitting a narrative to the life of a celebrity or two to lend credibility, and repeating the same core message a hundred times. Instead it felt like reading a well-organized journal entry. I both respect the author for taking the path less traveled, and love the format for its own sake. I wish more books like this existed. It’s sort of in a class of its own.

It has the same sort of epistemological flavor as LessWrong posts, which is beyond rare to find outside that one niche community.

Harry Potter and the Methods of Rationality

Speaking of the LessWrong community – imagine Harry Potter, but he’s a hardcore rationalist and actually cares about both figuring out the world he’s thrust into, and winning. This feels a bit similar to Ayn Rand’s books – the point is to express a philosophy, and the plot and characters are only tools to accomplish that. If the characters need to be caricatures, or if you need a 50-page monologue on objectivism/probability theory, then so be it.

I love this as a format, and I think this is a better way to communicate how one sees the world and how one should act in it, than any philosophy book. We naturally relate way more to characters and stories, than direct instruction – I became more of a stoic after reading Hitchhiker’s Guide to the Galaxy, than after reading Meditations.

It does drag on a bit, in the middle. Eliezer got a bit too carried away with his wizarding-world version of Ender’s Game, and the 300-page homage can get a bit tiresome.

How to Live: 27 conflicting answers and one weird conclusion

Derek Sivers is a guy I respect a lot, after reading his much more popular book “Anything You Want”, about his business CD Baby. He creates his own path, and does it with careful thought about what he really wants. I think everyone could do with a bit more of both of those qualities. I really try to live by a couple of his maxims, like “The standard pace is for chumps” and “Useful, not true”.

Anyway, this book is a series of very short essays, on how to live a good life. But they’re totally in conflict with one another. It’s like you asked 27 people from entirely different philosophies and ways of life, how to live. This could have come across as hokey or gimmicky, but it’s executed really well. Some really felt like they fit, but then the next chapter I’d have almost a visceral negative reaction to another. Introspecting on my own reactions was a fascinating little exercise in self-discovery. How to live a good life is perhaps the biggest question there is, and I think this book does a great job of helping you clarify that answer for yourself.

Thankfully this one has become a bit less of a deep-cut in recent years – originally you could only get this on his online store, and that made it a lot less popular than it deserves.

Mother of Learning

For a long time, the only way you could read this was as a web-serial, on RoyalRoad. It’s since been published, but still won’t show up on any fantasy book recommendation lists, and I’m not sure why – it’s one of the best I’ve ever read.

If you enjoy time loops, smart protagonists, well-thought-out magic systems, or just feel like you need to burn some time by reading nearly 3,000 pages – check it out.

Metamorphosis of Prime Intellect

I’m not usually one for content warnings, but there are parts of this book that are truly disturbing. I think if it weren’t for the gratuitous violence and other explicit content, this book would be way more popular than it is.

This is one of the most interesting books I’ve ever read for its exploration of post-scarcity societies, the role of a benevolent ASI, and what’s left to find meaning in when there’s no struggle, death, or conflict. The backstory in the book – of the creation of the AI – is one of the most fascinating little stories I’ve read, and sometimes I re-read just those sections of the book.

I don’t want to give away too much, but if you’re at all interested in any of the things above, and don’t get bothered by disturbing content, give it a whirl.

Rationality: From AI to Zombies

I don’t even know how to bundle this book up into a nice description. Instead, I’ll describe the person: Eliezer Yudkowsky is an AI researcher with an eclectic mix of interests – AI alignment, probability, game theory, psychological biases, quantum theory, cryopreservation, the list goes on. Above all, he’s interested in thinking clearly. Well, that guy wrote a bunch of incredibly interesting posts, and put them in a book.

If I could make everyone in the world read one book, it would be this one.

Give me your deep-cut book recommendations!

I would love to hear them. My reading obsession is bottle-necked by a lack of good books with novel content. Please email me if you have any suggestions. You can find my email in the footer of this post.