Scott Rosenberg. Dreaming in Code: Two Dozen Programmers, Three Years, 4,732 Bugs, and One Quest for Transcendent Software

A few years ago, I saw an announcement about a revolutionary new program that promised to change the way we manage our digital lives. We often keep to do lists in one program, manage our email with another, handle our schedules with a third, and so on. But what if—oh, what if indeed!—all these functions and more were gathered into a single program that made swapping information between these different spheres seamless and easy? What if an incoming email could be turned into a to do item as it arrived and then attached to a date in your calendar? (What? You can do that now in Gmail? Remember that this was a few years ago, and Gmail still lay in the future.) Cool! And this project was open source! It was being developed under the leadership of a software veteran, Mitch Kapor, who made a fortune on Lotus 1-2-3, and was now helping to bankroll the project out of the goodness of his very good heart. It sounded to me like all kinds of awesome.

But when I checked out the actual program, called “Chandler,” it quickly became clear that the project was still in its infancy. Indeed, it carried a warning that you should not under any circumstances trust it with important information. When I downloaded and installed it out of curiosity anyway, I quickly realized that the warning wasn’t just a modest cover-your-ass disclaimer. Chandler was buggy and incredibly slow.

After that, every once in a while—especially when trying to organize my digital life—I would wonder what happened to the project that promised to change everything. But whenever I did check it out, Chandler seemed to have made little progress since I last looked. I would wonder idly what was going on, and then move on.

And now I know what was going on, because the project had a chronicler, Scott Rosenberg, who followed it for three years and then wrote a book about it. Dreaming in Code is about the many setbacks, delays, dead-ends, and minor triumphs that took the project from a glimmer in Kapor’s eye to . . . well, not to the release of a polished product, unfortunately. By the time Rosenberg gave up waiting and published his book in 2007 the project still wasn’t complete. (The 1.0 release didn’t actually happen until the end of 2008.)

Dreaming in Code uses the story of Chandler to explore larger questions about software development. It asks why software is so hard to write, often so buggy, and why software projects are so plagued by cost overruns and scheduling disasters. Of course most human projects of even modest complexity are radically imperfect. But each branch of human endeavor has its own special difficulties, and software design is not an exception.

Software developers may find the book interesting, but they should be prepared to wade through a lot of background material that Rosenberg needs to assemble in order to make this story accessible to non-programmers. This is not the most elegant book ever written, but the story moves along at a decent clip, especially considering that the story is often about the lack of progress with Chandler, and it does a reasonable job of conveying its central message: that software setbacks and disasters happen to even the smartest and most hardworking of us.

As for Chandler, you can see for yourself how it turned out. It seems a bit slow on start up, and it still lacks many of the features originally imagined for it all those years ago, but it looks nice and runs on Mac, Windows and Linux.

As for me, I’ve since migrated most of my stuff (email, calendar, etc.) to web services like gmail. I’m not completely happy with that solution: gmail has legendarily bad customer support if something goes wrong, and it’s not open source, so I can’t look at the code and learn from it the way I could with Chandler, or customize it in ways not imagined by its creators, the way I can with emacs. So for now, I’m still dreaming of the perfect solution to my digital disorganization.

Nada (0)

Timothy Garton Ash. The File: A Personal History

The East German state subjected its citizens to a virtually unprecedented degree of scrutiny. The system of surveillance was run by the Stasi, the East German secret police, but it relied on an extensive network of informal collaborators, or IMs (Inoffizielle Mitarbeiter). At the time of its collapse in 1989, at a conservative estimate roughly one in 50 adults had a direct connection to the Stasi.

When the East German state collapsed, it collapsed so quickly that the Stasi found themselves unable to shred most of the hundreds of thousands of documents about its citizens that it had assembled so dilligently over the years. Most countries at a similar point simply pause for a moment and then continue to destroy the evidence, or file it away forever, hidden. Germany, by contrast, embarked on the unprecedented experiment of allowing everyone with a file to see it for him or herself. Care was taken to protect innocent parties named in the files, but everyone had a right to learn the identity of anyone who informed, betrayed, or reported on them.

Some couldn’t bring themselves to look; some discovered that they had no file; some were able to cast away long-harboured suspicions of acquaintances who turned out not to have informed on them. Others were not so lucky, and some of their stories are horrifying. One woman

had been imprisoned for five years under the communist regime, for attempting to escape to the West. Now she found out, by reading her file, that it was the man she was living with who had denounced her to the Stasi. They still lived together. Only that morning he had wished her a good day in the archive.

Timothy Garton Ash lived in East Germany during the late 1970s and early 1980s. He subsequently wrote a book critical of East Germany, and was banned from the country. Not surprisingly, he had a file. The File is about Ash’s attempt to track down and speak with everyone named in his file, from the casual acquaintances acting as IMs who filed reports about him to the officers who supervised the case. The book follows him as he criss-crosses the country speaking with people and working through the file comparing its reports with his own recollections and diaries.

There’s nothing earth-shattering in Ash’s file, but that doesn’t stop him from writing an absorbing account of this moral, personal, political and historical detective work. The File is so much more than simply a superb book about life under the East German regime and Ash’s mostly harmless brush with the Stasi. It’s a finely written meditation on memory, betrayal, the psychology of rationalization and evil, and chance. Recommended.

Nada (0)

Explananda turns five today. Happy birthday, Explananda!

We’re currently at 2,340 posts (for a total of 643,511 words) and 5,049 comments (for a total of 307,511 words) (—that is, before publication of this post).

According to our site tracker, we’ve had 208,000 visitors in the past five years. Almost all of them came in from Google and left immediately, presumably disappointed. Thanks to those of you who stayed, and were presumably disappointed.

Update: Whoops. As Upyernoz points out in the comments, we started by importing most of the posts from my old blog. So the posts tally above is wrong. The comments tally, however, is accurate, since my old blog didn’t have comments, and the site tracker is accurate, since it’s only been tracking this site.

Howls of outrage (10)