Okay, I admit it. I’ve grumbled about iCal on and off since it came out. It’s one of those things in life that makes you nuts with how it almost works. The alarm choices are amazing but there’s no way to have them added automatically. The shared calendars are great, but only one person can make changes. The snoozing sucks, notifications magically disappear, and some days, the “moist Jolly Rancher” design motif makes me want to barf pink. Hrmph. But (and it’s a big but)…

The truth is, iCal works great with kGTD (mostly of course), and once you make your peace with the perplexing stasis of its feature set, there are some not-bad hooks and affordances hiding in its pastel, roundy corners. Here’s a few I like.

Calendar Groups

Yes, I’ve mentioned these repeatedly, but they’re just so great. The killer trick here is the ability to nest contexts/calendars in a way that supports either “Areas of Responsibility” (if you use calendars as projects) or — my preference — grouping related contexts into “Super Contexts.”

So, for example, I’ve put “email,” “web,” “design,” “print,” “google,” and “buy online” tasks into a group called “Computer.” When I’m planning for a time when I won’t be at the computer, I deselect one box, and a couple dozen tasks I can’t possibly do anything about just disappear. Print that list, and off I go.

Remember: whether or not you’re doing GTD, it’s valuable to always know what you don’t need to be thinking about at a given time. Think about it.

Work the notes field

I use the crap out of iCal’s various extra fields — esp. for appointments.

• Phone calls - paste the number you need to call in the notes field, so you have it right where you need it when you need it
• Meeting and call agendas - When you set an appointment, paste in the contents of the email where the meeting’s raison d’être was laid out. Or just type in 3-5 quick bullets on what you’ll need to cover. You’ll thank yourself when the notification pops up three months from now and you’re thinking “Status meeting about what?!?!”
• “Homework” assignments - When I send coaching clients an iCal invite for a call or appointment, I use the notes field to remind them what they’ll need to prepare, read, or bring along before we meet. Easier and much more convenient than a separate email.
• Attendees - Definitely use the “Attendees” field even if you don’t send an invitation. As we’ll see below, the print-out of your calendar can be set to include the phone numbers of everyone involved. Super useful when you’re stuck on the train and want to let ‘em know you’ll be ten minutes late.
• Address & Directions - I always drop in the address of the offsite location and usually include a link to the Google map for the location (invited attendees love this). When you get the morning alarm for an afternoon meeting, print out the map and drop it in your bag (or, be really cool: print it out the day you schedule the meeting, and put it in your tickler file)
• From/To times - Yes this is a weird suggestion, and I’ll own that. My friend Dennis taught me to make appointments at “odd times.” Think about it: if you tell someone “I’ll pick you up at 7:08” they’re much more likely to see it as a time certain rather than the squishy quarter-hour SWAGs by which most of us schedule our world.

Print it out

Although it could benefit from a few more printing options, iCal’s current print capabilities are actually pretty smart and can be used to great ends.

• Calendars on or off - It’s really handy to be able to say which calendars/contexts you want to see on your print-out. Having a day where you can’t afford to fiddle around? Print a to-do list with a focused subset of “calls,” “email,” and “to-schedule” and then turn off all your “productivity” crap. Have a “vertical day” where you only work on stuff for one project. Let self-imposed constraints give you a little extra focus.
• Travel light - Before you head out for the day, print an updated copy of your calendar for the next 3 months and stick it in your bag. It’s a fast way to glance your availability on the road (without needing to truck a laptop around). Scribble changes on the calendar over lunch, and when you get home, enter the new events into iCal.
• Daily agenda - I love printing out a List view for the day before I hit the road. Appointments (with, as above, phone numbers), plus a list of my current to-dos all in one place.

Random tips

• Running dashes - If you could benefit from a few procrastination dashes, make sure to expose that right in the task. If you want to spend five fast minutes drafting a letter, create an item called “05dash - Draft letter to Anil.” To show only tasks like this that are quickly “dash-able” do a search on “dash.” Bingo.
• Backup - It only takes a minute to back-up iCal “File > Back up Database” and it might save your ass some day. Do a backup every week and every time you think of it.
• Rerrange to-dos manually - If sorting your to-dos by “Calendar,” “Date,” “Title,” or “Priority” doesn’t do it for you, try dragging them around “Manually.” It’s buggy and will probably lose its order if you click around (or sync with kGTD) but this manual shuffling is a fast way to reconfigure your per-day focus on the fly.

Got a great iCal tip? What cool stuff are you doing with iCal?