Parrot's roadmaps haven't historically been a great source of encouragement or accurate information. Our goals have often been overly optimistic with the result has been that most of the time spent dealing with our roadmap has been spent pushing back uncompleted tasks. The current system has been based on tickets attached to a specific version of Parrot which it was hoped would be completed by the time that version of Parrot rolled around. Sometimes the tasks had champions, sometimes not.
Unfortunately these tickets are often placeholders for ideas that are fully-formed only in the mind of one person. This prevents otherwise willing developers from jumping in and makes tasks hard to re-start after a break. There are also tasks that have received a good deal of attention but that simply haven't been completed. These tasks make the roadmap into a reminder of what we haven't accomplished rather than a list of our accomplishments and a source of encouragement.
Parrot's hackers have been hard at work making valuable contributions, but work has been largely independent of the current roadmap. It's always a challenge to keep an accurate roadmap in a project based on volunteer tuits, but whiteknight and I are sure that we can do better.
He and I chatted briefly on #parrot earlier this evening about how we want to structure Parrot's roadmap in the future. What we'd propose follows:
The roadmap will be based on major versions (essentially calendar years). Each year at the post-x.0 Parrot Developer's Summit, we will finalize the roadmap for that year. This roadmap will be wiki-based, since the wiki integrates nicely with Trac's ticket system but also allows a more flexible structuring of information. We will have a solid plan for the next year centered around the supported (.0, .3, .6 and .9) releases. The roadmap will list only major features which have a champion* and which we are confident we will be able to deliver. If we aren't confident of being able to deliver a feature in time for a supported release, it's better to have a release with no planned roadmap items than to have a pleasant fiction. We will also have a fuzzy plan for the following year, though it shouldn't be considered binding. Anything beyond two years will be planned only in a very general sense. We will maintain a wishlist for tasks which we want to undertake but don't have any dedicated volunteers, so that such features won't be lost or clog up the roadmap.
Parrot has an unfortunate history of over-promising and under-delivering. This has not helped our reputation among other OSS hackers and I want us to correct the trend. I want our new roadmaps to center around promising only what we're highly confident of being able to deliver. Establishing a track record will take time and effort, but two or three years from now I want to be able to look back with pride and say that we proved we could deliver what we promised.
*In this case, a champion means that this person is dedicated to seeing a feature to completion. "Owner" is another way of communicating the idea.