Winer and his team don't email one another any more, and they claim radical productivity gains as a result of the switch to instant outlining:
We've been using this tool since November, internally at UserLand. We shipped Radio 8 with it. When we switched over our workgroup productivity soared. All of a sudden people could narrate their work. Watch Jake as he reports his progress on the next project he does. We've gotten very formal about how we use it. I can't imagine an engineering project without this tool.
If you read their outlines, which you can do because this experiment is being done in full daylight (if you're not a Radio user, you might try these renderings rather than the raw OPML files), you'll get a sense of the conventions that are evolving in this new space. Here are some of them:
Blog-like journaling is the basic style.
The top level of each item is date-stamped, and preferably includes a short description.
Older entries are archived (an easy manual operation in the outliner).
Wednesday, April 3
O'Reilly Network: Jon Udell: Instant Outlining, Instant Gratification
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