A great piece by Joel Spolsky on calendar software, where he complains that all these online calendars don’t really offer very much, are half-baked and may just be efforts to attract buyouts from the big boys:

For all the Ajax calendars that are appearing, it’s a shame I can’t find one which really meets my needs. I tried out Trumba, Kiko, 30 Boxes, Yahoo! Calendar, and Spongecell. I couldn’t recommend any of them.
My needs are probably weird, but not that weird.

As Joel then goes on to point out, actually these calendars allow very little customisation, and surprisingly little basic functionality, such as alarms, events that don’t fit neat intervals (like flights) and making some events private.

I’ve tried a few of these offerings, and I’d tend to agree with Joel. All the calendars I’ve tried are basically reruns of offline software, but without many of its deeper functionality. There are some nice elements — Trumba’s way of showing events that span more than a day is quite nice — but most are small potatoes in the face of a much greater potential. Surely calendars, of all Web Apps, should be almost endlessly customizable, given that their job is to try to reflect as accurately as possible the endless weirdness and variety of our lives? When was the last time you met someone who had even vaguely the same kind of habits, schedule and needs as you? We’re all different and calendars, of all things, should reflect that.

Let me offer some suggestions, just in case you’re not following (and any of these calendar developers are listening):

• viewing options: If we’re going to go to the effort of entering all this data on your website, the least you can do is to offer us multiple ways of viewing said data. I’m not just talking boring day/week/month/listings, but color-coding time off, time on; how many 3–hour workday slots are still open in February; how many hours I’m spending in meetings with Client A; the best options for a long weekend where there are no, or few events on Friday or Monday.
• synchronize with other calendars, especially Outlook. How many people are going to spend time entering data into an online calendar but not have an offline one? (Trumba offers synchronization with Outlook but I must confess: I haven’t managed to make it work properly yet.)
• anticipate me: If I’ve entered a repeating event, say, notice it and ask me if I’d like to repeat it automatically. If I keep making the same trip figure this out offer to auto-fill the details next time I start entering that data in the calendar.
• minimise the clicks: Let me enter data, including labels/tags/categories into the calendar. I don’t like pop-up windows, and I don’t like moving between fields if I can help it. Let me just type “Meeting Bob Conference_Room 12:30 Tues” and let the calendar do the heavy lifting: “Meeting” gives the event a specific color and label, Bob is a name from my address book and so can be automatically filled in with family name and company affiliation, “Conference_Room” is clearly a place, and so can be assigned to that field, if it exists, while the time and the date/day are self-explanatory (why would it be anything other than the next Tuesday coming up?) This saves us time (which we don’t have much of; that’s why we’re using a calendar) and it also helps build a database to let us slice and dice our information later (when am next meeting Bob/using the conference room/having a lunch time meeting?) (30 Boxes and spongecell offer something like this feature, but there are still too many dialog or OK boxes inbetween, and spongecell’s syntax was eccentric at best.)
• move me: drag and drop, extending or shrinking events using the mouse should all be standard.

There are hundreds more ways that calendars could be more dynamic. I can hear the calendar developers already popping up and saying “You should check out this feature in our calendar” or “We’re working on just that feature in ours”. But my experience is that in fact most of these calendars don’t really have it. They may have one or two interesting new ideas, maybe even one that makes you go ‘wow!’, but there will always be some basic function that either isn’t there, or doesn’t work well. With calendars, it either works as a whole experience or it doesn’t work at all.

As Joel says, the trend these days is to get the stuff out there and add features later. That may work with other tools, because for the most part you can always switch to something else if those features are slow in coming. But a calendar needs to work well for you out of the box. After all, it is your life and you’re not in the mood to put it on hold for the promise of future features, future bug-fixes (how long are you going to stick with a calendar if it makes you miss an appointment?). As Joel puts it:

I’ve talked about this before — it’s the Marimba phenomenon — when you get premature publicity, lots of people check out your thing, and it’s not done yet, so now most of the people that tried your thing think it’s lame, and now you have two problems: your thing is lame and everybody knows it.

A calendar is the thing we build our lives around. Think hard about what you’re offering before you ask us to commit our daily schedule to it.