Suggested reading

This article outlines Bogleheads.org site owner Alex Frakt's suggested reading books.

"Most of this information is freely available somewhere on the web, but it can be very helpful to have everything laid out in a logical, consistent format. I think everyone should read at least one book from the general investing section. I also strongly encourage everyone to read about investor behavior, since that's the source of the most costly investing mistakes. It's covered in the better general investing books, but I list a couple of dedicated titles for those who want to delve further into the topic. The books in the financial history section are for those who wish to go beyond the basics. A more comprehensive list is available on the Book recommendations and reviews page of the Bogleheads Wiki. Each one of these titles is worthy of inclusion on its own."

General investing
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The Bogleheads' Guide to Investing
An easy to read, comprehensive guide to investing. It is suitable for investors of any experience level, and would be a good choice for a first investment book. It's written in a number of short chapters in light-hearted, plain language. It does not go into a high level of detail on most subjects, but the information presented is well-chosen, supplemented with lots of charts and references to other books and information if you want to delve deeper into a subject.
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The Bogleheads' Guide to the Three-Fund Portfolio
The most popular portfolio on the Bogleheads forum. This all-indexed portfolio contains over 15,000 worldwide securities, in just three easily-managed funds, that has outperformed the vast majority of both professional and amateur investors. If you are a new investor, or an experienced investor who wants to simplify and improve your portfolio, this short, easy-to-read guide will show you how.
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All About Asset Allocation

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Common Sense on Mutual Funds
A very readable classic updated to cover the events of the '00s.
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The Investor's Manifesto
You cannot go wrong with Bill Bernstein's books, this is my #1 choice for anyone interested in going beyond the most basic investment primer. My previous favorite all-in-one investing book, The Four Pillars of Investing, is an earlier work by Dr. Bernstein that covers much the same ground, but is a bit longer and more technically oriented. Note the link is to the latest version, with a 2010 postscript that brings the book up to date. For reviews and content, see the original version.
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Wise Investing Made Simple
Larry's books on bonds and alternative investments are also excellent for investors thinking about moving beyond the basic asset classes.
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The New Coffeehouse Investor
Too light on content for my tastes, but a short and fun read and perhaps the best choice for introducing investing concepts to those who need to know them, but are unwilling to take on something more comprehensive. Our members give out a lot of these as gifts.
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Retirement planning
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Bogleheads Guide to Retirement Planning
This book was a collaborative effort by the members of the Bogleheads forum and covers the entire spectrum of retirement planning, including: investing, taxes, retirement plans, personal finance, insurance and estate planning issues. The book is an invaluable aid in helping understand and plan out the confusing array of financial options that we all face from the very start of our working lives all the way through retirement. As the investing section is necessarily brief, I would pair this book with one from the previous section.
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Investor behavior
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Why Smart People Make Big Money Mistakes and How to Correct Them
An updated version of this classic.
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Rational Investing in Irrational Times

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Your Money and Your Brain

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Financial history
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Devil Take the Hindmost

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Boxed set: Capital Ideas, Against the Gods, The Power of Gold

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A Random Walk Down Wall Street

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