Dear Idiot Future Self,

Man, there are a lot of calendar apps out there–Rembember The Milk, 30Boxes, Google Calendar, Yahoo, Remind–but none of them can do very well the one thing for which my brain is totally useless and with which my GTD system struggles: reminding me of things exactly when I need to remember them.

The Ubiquitous Capture problem I have solved. I carry a hipster PDA (thanks, Merlin) and my trusty phone with Jott on the speed dial. At any time and place, my clever present self can delegate work to my idiot future self (IFS).

If that work happens to be time-sensitive, I have to rely on my IFS to check his reminders at the right time. Of course, my IFS will look at his actions list at some point and say: “Oh hey, there’s something I have to do later today. I totally have time to do this other thing first, though.” Naturally, my IFS will get lost in that other thing and completely forget about the time-sensitive action.

So, what I need is an application that includes all of the following:

• Allow me to not only delegate to my IFS, but interrupt whatever he might be doing. If he’s on IM, send him an IM. If he’s off IM, send him a text message by phone. If he forgot his phone, track him down with flying monkeys. Do not–I repeat, NOT–send an IM and an SMS and flying monkeys for every reminder. And don’t send reminders by email. If he were checking his email, he wouldn’t need a reminder. Please be smart about context.

• Allow me to add reminders from my phone, by talking. Integrate with Jott if possible.

• Allow me to add reminders without moving either hand from my keyboard (and/or my cup of Sulawesi as the case may be).

• Let my IFS see a calendar of things that are coming up, when he feels inclined to look (i.e. don’t keep the calendar in his face all the time). I want to give him a chance to prepare, and not catch him by surprise. Also let him see past events, to make sure he didn’t forget to follow up on something.

• Let me send messages to my IFS without putting anything on the calendar. These are messages that are relevant only on or after a specific day in the future, and I want to forget about them until then.

And lastly (this one might require a clever life-hack), remind my IFS to get the milk when he is in the car. Preferably just before he misses the exit.