Esther Dyson has a video series up at Release 1.0 on time. The first is on new calendaring and scheduling tools. This is a topic that's been on my mind a lot lately.
For example, this afternoon I had a meeting with a few of my grad students on a virtualization project we've got going. I needed the projector in the conference room, so yesterday I went on the department Web site, logged in, and selected the scheduling tool that allows faculty to reserve the room. It's a typical Web-based calendaring app--clunky, single purpose, and completely siloed from my other calendars. I remembered fondly what life was like before the tool when I could simply send a note to the department admin saying "Pls schedule the conf room for me tomorrow at 1:30."
I ran into a calendaring service a few days ago that has part of the feeling of sending off a note to your admin. The service, called SpongeCell, let's you schedule appointment with simple English commands. Type "schedule the conf room for me tomorrow at 1:30" into the box in the upper righthand corner and the appointment shows up in the calendar. This is still an early release, so things like recurring events are not yet supported, but it does have pretty good support for importing calendars and publishing RSS and iCalendar formats. SpongeCell even supports retrieving events via email for use from mobile phones.
Still, SpongeCell still suffers from one HUGE problem: i don't want or need another calendar in my life. I've already got too many. OS X's iCal does a good job of integrating calendars, as long as their in iCalendar format. Over all, as the video points out, calendars are still too hard to share, too difficult to integrate, and too complex to use. I have yet to find a planner, calendar program, or PDA that is even close to as helpful and efficient as an assistant. Not everyone can afford an assistant, but we'll know we've arrived when people who can don't--because the tools are that good.