The Best Narrative Books about Making Software
I used to regularly read books about the making of great things. I wanted to learn everything I could from historic leaders and how they succeeded and failed. My favorite genre was the project narrative, books that followed the making of something.
At first I read books strictly about software, but I soon found I learned more from bigger subjects. McCullogh’s The Great Bridge, about the Brooklyn Bridge, earned one of the first rereads in my entire life as I was spellbound by the leadership, engineering and personal struggles in what had seemed so ordinary a thing (a bridge). Reading about NASA’s space race, the London underground, and The Hoover Damn all factored deeply in my own thinking about how to lead projects.
My fifth book, The Year Without Pants: WordPress.com & The Future of Work is my attempt at the genre. And unlike most books on the subject I deliberately wanted to write it from the first person. I wanted to tell an insider story in the way I’d tell it to a smart friend over some beers, and not dodge the tough, honest and uncomfortable parts integral to learning how to lead teams and projects.
Having read dozens of project narrative books I found the limitations of journalists, people who rarely had insider expertise or who traded honesty for access, frustrating. I recall how deeply disappointed I was by Steven Levy’s coverage of the making of the iPod in the Perfect Thing, portraying a false (to me) world where everything goes perfectly well and everyone is happy about everything. I know real projects are messy and the larger the stakes the more complex and emotional the challenges, and the more careful a writer needs to be about offering lessons.
While writing the new book I returned to my library to see which software project narrative books still had power for me. Here are some of them, with a short review:
Soul of A New Machine, Tracy Kidder. Everyone refers to this book as the classic since it popularized both software and general audience books about it. But many people mistakenly recall the book as a heroic, inspiring tale. It isn’t. If you read it now, which I did, the story is harsh and said. It’s a poorly managed death march led by a jerk who practices mushroom management. It’s fascinating how times have changed and if you read this book decades ago I recommend a reread. It will seem like a different book.
Show stopper!, G. Pascal Zachary. I read this in 1994 while working at Microsoft and found it wild. Punching holes in walls over bugs! Dave Cutler, the protagonist of Windows NT, seemed like a mad-man, and like Soul of A New Machine, at the time it released there was something I admired about his intensity and the drama. Now he just seems like an asshole, someone who would fail Sutton’s No Asshole Rule instantly. It also captures one slice of Microsoft in it’s prime, just a couple of years before the company’s pinnacle of public admiration at the Windows 95 launch.
Dreaming in Code, Scott Rosenberg. The most thoughtful book written by a journalist about a software project, Dreaming in Code wraps the tale of a project gone very wrong with big questions about why most software projects fail. The project in the book is code named Chandler, Mitch Kapor’s failed attempt to redesign personal information software. The tragedy of the book is how abysmal the management of Chandler was, with basic leadership mistakes made at every key point along the way. Kudos to Kapor for allowing Rosenberg truly honest access. My deepest criticism of the book is I just wish Rosenberg had been on a more competently managed project as it would have granted him better answers to the questions he asked. I think of The Year Without Pants as my response to Dreaming In Code, taking a first person approach to some of the same questions.
Mythical Man Month, by Fred Brooks. Published in 1975, a few years before Soul Of A New Machine, Brook’s offers insights on leading software projects wrapped around his own experiences at IBM. I was heavily inspired by his style in writing Making Things Happen, about my lessons learned at Microsoft from 1994 to 2003 (inspired even by the fact such a hybrid book were possible). MMM is thin on specific advice, and more of a collection of ways to think about making software. Many of his ideas didn’t catch on, and there are exceptions to Brook’s Law, the most well known advice from the book. But the honesty and humanity in his writing is a hallmark of my favorite kinds of writing about the making of things.
What narrative books about software are your favorites? I’m sure I’m forgetting some good ones.
