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The Bogleheads' Guide to Retirement Planning

4/5. Excellent and comprehensive. This book won't tell you everything you need to know about taxes or health insurance or estate planning, but by God it will make sure you can have an intelligent enough conversation to be asking the right questions. The chapters on investment focus – unsurprisingly, if you know who Bogle is – on passive index investing. I wouldn't necessarily recommend this as the first investing book to read in your entire life, but if you have been plugging dutifully away at your 401K and want to think about the bigger picture of long-term planning, you really can't do better than this. Docking a star just because it lacked that "putting it all together" chapter that could have elevated this from very helpful to truly remarkable. But this book holds up well for being more than five years old (most finance books have a very short shelf life) with the glaring exception that it doesn't get into the Affordable Care Act, for obvious reasons.

Why am I reading this now? Well, because when you aren't already a millionaire, time is your greatest asset, and I've got that. Plus, I'm in the extremely weird position of being thirty and making more money in the next couple years than I likely will for the rest of my life (weird career trajectories can do that) so this is the time I need to get my shit together. More finance books to follow.

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