Online Calendars – Are They Back?

I have been playing with a lot of the new calendar programs out there — CalendarHub, Trumba, and Planzo — and I find them all to be pretty cool. They all have subtle differences and I am slightly partial to Planzo over the other two. However, playing with all of these calendaring applications has made me think hard about my own data management strategy and what unmet needs I have. Then I read this article on CNet called “Tech executives: Time is of the essence” and it really struck a chord with me. I am always looking for new ways to keep my various calendars and devices in sync. To summarize, here are the devices/applications that I am trying to manage:

-Blackberry 7100t with Blackberry Service (personal)
-Treo 650 with GoodLink (work)
-Microsoft Outlook hooked up to Exchange (work)
-Microsoft Outlook standalone on a home PC (personal)

To some this might sound complex. To me, it’s just reality. I don’t think that it is necessarily that different from what a lot of my other friends in technology have to manage, save managing two smart phones.

I think there are really three different problems I (and I assume others) need to solve:

1. How do I keep all of my calendar information up to date (personal and professional)?
2. How do I share my calendar with others (personal and professional)?
3. How do I find out about interesting events in my area (personal and professional)?

In addressing #1, I have seen two dominant approaches. The first (and most prevalent based on my unscientific research) is to just put everything on your work calendar. There are are a few reasons for this, I think.First, the office calendar environment is often the most full-featured application available. Second, because the employer is often the provider of the smart phone, an employee already has a synchronized version of his/her work calendar — adding personal appointments to the calendar is fairly painless. The second approach is to maintain two silos of appointments, personal on one device/application and professional on another. With people spending so much time at work and employers providing devices that synchronize calendars, my hunch is that more people will use their work calendar as the system of record than maintain two separate silos.

Question #2 is slightly more interesting, I suppose. Again, at work I think this is solved — anyone who has worked in a well-configured Exchange environment or used an equivalent program like MeetingMaker knows that calendar sharing is fairly easy to accomplish in a corporate environment. On the personal side, ti’s a lot harder. That being said, I don’t have a pressing need for this kind of functionality. I can imagine many use cases — coordinating family schedules, organizing little league practices, and things of that nature. I am just not convinced that the personal analog of calendar sharing is a huge opportunity. I am also not sure how you really build something defensible in this space.

The last question is the one that I think is the most interesting. I really like Upcoming.org as it usually points me toward events that are interesting. This is the one area of calendaring that I do think has real legs — there are far too many events out there for any individual to track and allowing users to post events is a good way to increase coverage. This is one type of functionality that I do think has legs. I don’t envision my Outlook calendar ever giving me the ability to do this. And it is the type of service that at least has the potential to create a dominant position as the place where people go to post interesting things.

Overall, I am curious to see if the consumer calendar sharing applications really take off, especially with more people having access to good calendaring applications at work and smartphone or web access to that calendar data at all times. For niches where shared calendaring is important, the value is clear.