Dreaming In Code, by Scott Rosenberg

This is the story of a typical software project: one that failed. Okay, failed is strong considering the Chandler project still exists, but with millions of dollars spent to build an email and calendaring tool that doesn’t appear to be as full-featured as Outlook or even Gmail it certainly doesn’t qualify as a success. Rosenberg doesn’t try and draw any conclusions, but simply presents a fascinating tale of how so many smart people can spend years working hard yet accomplishing little.

I’ve worked on many different software applications in my career, some successful and some not. There is a great quote from one of the Chandler developers Andy Hertzfeld (yes, that Andy Hertzfeld) about successful teams: “To make a great program, there’s got to be at least one person at the center who is breathing life into it. In a ferocious way.” Looking back at the groups with which I’ve been involved this statement really resonated. My favorite two employers (ObjectSpace and Evity) had this in spades. Less favorite places, didn’t. Does this mean the key to good software is passion? No, but a lack of it seems to be an indicator in at least my personal job happiness.

While I won’t say that this book gives a great insight into why projects fail, what it does do is show how many seemingly small decisions add up to a large miss. Chandler originally wanted to be a peer-to-peer application, but this turned out to be too hard so it was dropped. “No silos” was another credo, meaning that instead of having your email in one mode (silo), your calendar in another, and notes in a third, there would just be a single place for everything. Also very difficult, this morphed into something else that ended up not looking much like silos at all. These are just two examples of the many divergence points covered in this book showing how good ideas go bad. For anyone that doesn’t understand why software development is so difficult this is a must-read. For those that do “get” software, this is a familiar story but still worth reading. Highly recommended.

First Sentence:

Michael Toy places his palms on his cheeks, digs his chin into his wrists, squints into his PowerBook, and begins the litany.