For a tale of how a software project that should have been wildly successful can go awry, read Dreaming in Code by Salon magazine co-founder Scott Rosenberg. This book details the development of Chandler, a next-generation personal information manager (PIM). Chandler was the brainchild of Mitch Kapor, creator of Lotus 1-2-3. Chandler was also creator of a highly innovative PIM, Lotus Agenda, nearly 20 years ago. Agenda was a free-form text-based information manager, with the capability to group related pieces of text and parse dates expressed in natural language (like “a week from Wednesday”).

From the start, the Chandler development team had difficulty making architecture, design, and feature decisions. When it did make decisions, it chose badly. For example, the development team eschewed Web technologies for its distributed, scalable, multi-platform application. Instead they chose to use the relatively obscure Python programming language with a multi-platform, and quite buggy, user interface toolkit. The team seemed stymied by minor feature additions, like the capability to support scheduling of bi-weekly events.

During the years spent in shepherding Chandler towards a 1.0 release (it’s currently at version 0.7), technologies like Google Calendar, which may not meet Chandler’s grandiose vision, are nonetheless becoming ubiquitous. If and when it is completed, Chandler will likely have an uphill battle to gain acceptance.