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I would guess that most of us use a calendar tool of some sort, maybe you stick to paper calendars, but if you read this blog I would guess you use a digital calendar of some sort. The problem with digital calendars though is that they all suck, at least all the ones that I have tried.

The user interface of most calendar apps is set to mimic old day planners, failing to take advantage of the dynamic digital interface that is at their disposal. Further most digital calendars exist in their own bubble, much like PCs before networking was standard, no calendar program talks to the other (unless you have an expensive Exchange or iCal Server setup, which most people don’t and even then you are restricted to those using your server).

I spent a good three hours today driving around to and from various appointments, this gave me way too much time to ponder about the state of digital calendars. Luckily (for whom I don’t know) I came up with some ideas on how to fix calendar apps.

Getting Rid of Simulated Paper Views

First things first, all calendars suck at showing the data that we store in them. Who wants to see 30 boxes arranged in a grid with tiny text? Who wants to see only what they need to do today? Who needs to see the past days of the week when you use a week view? I would guess that for most of you these views are mostly useless, most useless is the seemingly more popular ‘list view’ where you get a list of upcoming events with times. Yeah, that isn’t very helpful in spatially planning your time, now is it?

Here is what my iCal looks like in the view I always look at it in, week view:

Here is the same view on the iPad:

And lastly the day view on the iPhone (because all the other view options suck):

Can anyone honestly tell me that those views work perfectly for them? Because I think they suck, actually I think they really suck.

Here is how I would like to see it (click for larger view):

You get ‘today’ a bit larger than the rest, since it is the most pertinent. You see the next three days, as I don’t plan a whole lot much more in advance, nor do I need to worry about it sooner than a fews days away. My reasoning for three days is so that on Friday you would be able to see Monday’s events in the view, thus helping those of us that work M-F. Additionally this doesn’t show you the past days, because really how often do you need to refer to your calendar to see what you did yesterday?

Additionally I used one column to show a list view of upcoming events. The idea behind adding this list view (even though I hate list views) is to help people see just how busy they are coming up, and as a quick point of reference when you are on the phone planning a meeting. If you are on the phone you wouldn’t have to switch from the current week to see your upcoming schedule instead you get an idea of what is going on and can click a link to add a future event.

I think this would be pretty sweet, but that may just be me.

Time to get Calendars Networked

I despise the refusal that calendar app creators have when it comes to getting all the clients talking to one another. Yes you can ‘invite’ someone to a meeting, but that is it. Unless you have iCal Server or Exchange you can’t see when they are free, or do a search for next available time everyone I want to invite has. It is 2010 and we have yet to figure proper scheduling, instead we waste time sending around 50 emails with 100 people CC’d and hitting reply all to figure out that everyone is free on Tuesday at 10.

Have you ever used iCal to invite someone to an event? Have you? It sucks. If the other person is using a Mac (which is not guaranteed) they get the option of Accepting or Declining. So if you happened to invite them when they are not free all the can do is decline, leaving you wondering if they don’t want to meet or if you just picked a bad time. If they are a Windows Outlook user forget about it, rarely does it work – often they have to manually reply.

If I send out an invite to three people all using Macs (let’s not ask for too much here) I should be able to immediately get automated responses letting me know if that person is not free, and if they are busy the computer should suggest 3 other times I can pick from that works for everyone – all without the end user ever having to see the request, yet. Once a time that works for everyone is seen we should then be asked if we want to attend, and given the option to add a custom response in – that way the communication is kept clear.

Why is it that I can’t attach a meeting agenda to the invite? That seems stupid, and trivial to do. Come on, I mean is anybody really trying to make a decent calendar program because I really get the feeling that I must be the only using a calendar at times.

Home Scheduling

Right now my household is just my Wife and I, and I can’t imagine how bad it will be scheduling things later in life when we add kids to the mix. Why is it that we can only subscribe to each others calendars? Why isn’t there just an option to make an event a ‘joint event’ where by one of us creates the event and it is automatically added to both our calendars, no acceptance needed. It would also immediately give an overlay of my calendar on hers when she goes to add a joint event so she can see if I am free (and vice versa).

Right now if we want to do something like this we have to use shared calendars (to make sure we are both free) and then invite each other to the events. How 1999 is that? Sure there are other web based options, but none that my Wife really wants to be using, if you want my wife to use it then it needs to be made super easy.

I’m Busy

I would also like to set times where the calendar app knows that I am busy (e.g. After 5pm before 7am and on weekends and holidays) and if I get an invitation during those times it is automatically declined with my pre-typed reason as to why. This is a tiny thing, but time savers like this really add up and keep you focused.

Location Aware

I figured we better hit on the hot topic of late, and I wonder why calendar apps don’t seem to know where things are. By that I don’t mean that they should know when I am at a particular place, but where things are in relation to one another. For instance if I set a meeting at 8a in Seattle, WA and another at 10a in Portland, OR shouldn’t my calendar program be smart enough to know that this is impossible. That is a 3+ hour drive, no way I can make it to both meetings.

I would like to see calendaring programs that take into account drive times. What if you could set a meeting to start at 10a, but remind you at 9:30a and block out the 15 minutes before the meeting as the needed travel time. How cool would that be? Then when you get an invite using the new invite system I devised above, the computer would be able to tell if that time is available and if you would even have time to get from one place to another. This is in the realm of possibility, so why isn’t any one doing it?

Money

As we all know this comes down to money, who wants to pay $50 for a good calendar app? I know I would, and a handful of others probably would, but enough people to make the product profitable? That is the real question, and the only way to find out is to try.