The Principles of Successful Freelancing by Miles Burke
The Principles of Successful Freelancing is a comprehensive introduction (if that's not a contradiction of terms) to striking out on your own as a freelancer. This book is perfect for someone who is considering moving to freelancing or possibly for someone just starting out.
Mr. Burke covers all of the basic areas of starting and running a freelance business. He discusses how to set up your business and your office, how to sell your services, how to manage your money, and how to give good customer service, which is ultimately the most important aspect of a personal freelancing business. He also addresses how to balance work and life beyond work, which is hard in general and specifically hard in a one-man shop. He concludes with something I haven't seen in a "start you own business" book - where to go next. Do you want to remain as a one-man shop, do you want to grow into a "real" business, or do you just want to "retreat" to the old 9-to-5 job? I don't recall a book like this consider the option of going back to the grind.
Each chapter concludes with two "case studies" - Emily and Jacob. These two characters represent two very different people who might want to go into freelancing. The studies at the end of each chapter explain how these personality types might react to the issues and challenges discussed in the chapter. This device helps the reader envision how he or she might deal with the issues discussed.
Early on, I got the mistaken impression that this book was a bit fluffy. The typography has a fair amount of white space, and it looks kinda arty rather than serious and dense. (OK, I grew up with punched cards and line printers. When's Matlock on?) But, by the time I finished the book, as I looked back across it, I really couldn't think of anything that wasn't covered. Sure, there are whole MBAs built around marketing, and this book only has one chapter on it, but the Mr. Burke provides a perfectly reasonable introduction to the subject. I think I got this "fluffy" mis-impression because immediately prior to reading Successful Freelancing I read Eric Sink's The Business of Software, which is very detailed about a few aspects specifically related to running a small software business. Successful Freelancing covers a wider range of topics, and it is not aimed specifically at software freelancers. If anything, it's aimed more at web designers who probably like nicer typography.
To conclude, The Principles of Successful Freelancing is a great first introduction to the idea of freelancing. It covers all the bases to help someone evaluate whether or not to go into business for himself.