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My Calendar Has Gotten Smarter In Really Dumb Ways

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When I travel to the East Coast, I sometimes feel like I’m living in a time warp, as my iPhone and Google Calendar keep notifying me about meetings that had happened three hours earlier.

I’ve already mentioned this problem on TechCrunch, in a post about the launch of smart calendar app Tempo, where I blamed the issue on “my apparently idiosyncratic way of dealing with timezones.” (In case you were wondering: I do my best to ignore timezones entirely, and if I’m traveling between zones, I put things on my calendar based on the local time of wherever I’ll be on a given day.) And I can’t deny that I’m pretty hopeless when it comes to using any productivity tool that’s more complicated than email.

But I also think there’s something telling about the fact that my Google Calendar gets so damn insistent about changing time zones when I travel. It’s always trying to cajole me into pushing my meetings three hours forward, and as a result, I feel like an idiot and yearn for a simple pen-and-paper planner. Ultimately, all I really want is a calendar that replicates the physical experience, but is accessible on any device, and without the messiness of writing stuff down and crossing it out. As for this crazy time-zone thing, I can figure it out without technological help, thank you.

But, you may be saying, calendars need time zones so that they can coordinate when people send calendar invites. To which I respond: Oh yeah, I kind of hate those, too.

For the most part, calendar invites are perfectly okay, I guess, though I do feel it’s slightly presumptuous when someone sends one without asking first. What’s more exasperating is the 1 percent of the time that something goes wrong and events disappear or pop up at the wrong time, and both parties scramble to figure out exactly what went wrong. Sometimes people send an email to make sure that the calendar invite came through correctly, which helps, but it also seems to defeat the purpose.

I mention both the time shifting and the calendar invites not just because I’m in a bad mood, but also because there’s something vaguely condescending about both of them. It’s almost as if, left to our own devices, we can’t be trusted to add items to our calendars correctly, so we need as much hand holding as possible.

The hope, of course, is that these features offload some of the basic mental work, so that we can focus on more important things. Sometimes that’s what happens, but sometimes it feels like we’ve replaced one kind of mental strain with another: Instead of remembering that New York and San Francisco are three hours apart, I have to decipher multi-step instructions from Google about how to swap time zones and attach multiple time zones to a single event. And then I have to understand how my Google Calendar syncs up with my iPhone calendar, and how that calendar syncs up with other apps. Hooray for technology!

And where do smart calendar products like Cue and the aforementioned Tempo fit in? They don’t actually set off my grumpy old man alarms in the same way. Maybe that’s because I haven’t tried Cue, and I’m still getting used to Tempo, so my impressions are still in the “hey, that sounds like a cool idea” stage. They’re untainted by the disappointment of using a real and inevitably imperfect product.

But the things that bug me about my calendar right now are the ones that, on a very low level, make me feel like I’m dealing with a particularly stubborn and dumb assistant. In the face of these frustrations, I could give up on the idea of an assistant, but maybe what I really need is a better assistant.

That’s what I’m hoping for, anyway. Otherwise I might have to give this pen-and-paper thing a try.