The Search for the Perfect Task Manager

Personal Information Management has been on my mind for years. There’s never a time when I’m not striving to improve the way I organize “bits of daily information” like my calendar, phone numbers, etc. In fact, a number of close friends and I have been experimenting with some of the (life) organizational techniques in the (slightly cultish) book Getting Things Done by David Allen.

Being a Mac enthusiast, I’ve embraced the Apple PIM (personal information management) offering, which consists of the Address Book, Mail, and “iCal” calendar application. One other very important addition is Mac’s iSync application which, at the cost of $100 per year for a .Mac account, allows me to effortlessly synchronize my Address Book and Calendar between all my Macs (my desktop and laptop) and my Palm Pilot and my Razr mobile phone. It also allows my Safari (the Mac web browser) bookmarks to be synchronized between the desktop and laptop.

iSync was the must-have application which locked me into Mac’s Address Book and iCal—and by extension, the Mail program which I really like anyway. Keeping contacts between the laptop and desktop was simply impossible and trying to do so drove be bonkers. I also hate hand-programming (and updating) phone numbers in my mobile phone. I revel in not being stuck when my phone dies, I change providers, or just want to upgrade it.

But this total buy-in has locked me into using iCal, whose “todo list” management is it’s weakest link.

I would go as far as saying that iCal’s task management downright sucks. If you’re keeping track of the top-ten things that you have to remember to get done, okay it’s fine. But the moment you really want to organize with it, you’re screwed. The use of iCal calendar associations (the closest thing you have to “categories”) allows only the loosest of grouping. Your only application view of tasks is squished in a side-bar on the side of a calendar. And finally, there’s no good way to print out a view of tasks. Yes, iCal has a task printout, but it’s barely customizable and you simply can’t get a decent “simple table” display.

It just bites.

MS Entourage 2004

I’ve toyed with MS Entourage—the Mac Microsoft Office PIM parallel to MS Outlook. The Entourage 2004 has an interesting implementation of tasks with an additional organizing concept of “Projects”. The most recent version upgrade adds Spotlight searching and (ta da!) sync support. The sync support is interesting because it first syncs Entourage contacts and calendar events and tasks/todos with Apple’s Address Book and iCal and then lets those applications do the iSyncing between computers and phones and PIMs.

So I dropped the big chunk of change to upgrade my (six year old) MS Office X. for the 2004 version. Of course, that meant moving to Microsoft’s mail client—which I find ergonomically “cluttered” and not nearly as nice as Mail—and moving to the Entourage calendar (abandoning the multiple-calendar concept of iCal) and its address book (no complaints now due to the new syncing support).

I spent an afternoon creating “Projects” and adding all the todo items and adding categories and cross linking relevant mail messages and contacts and calendar events, etc. And now I see some glaring problems.

1. Although I can sync todos and calendar events between my desktop and laptop, the Categories and the Projects and the links are all missing. That means I have a single monolithic list of dozens of task/todo items on my laptop that have no grouping information.
2. Projects can’t be printed!If you view a Project the printing icon just goes gray! Two years after the product release I’m floored they didn’t add this feature in a fix-patch.
3. There’s no “group by” view of tasks. I can sort by category (which breaks down a bit since tasks can have multiple categories) but that really doesn’t help out. I could create dozens of “custom views” but it still makes it impossible to do a single, comprehensive printout. I’ve read a number of blogs where people bemoaned this missing feature.
4. Some bug in Entourage actually prevents me from printing tasks or calendars at all! Every time I try I get the “spinning rainbow beach ball” for about 2 minutes, the application sucks up about 1.5 gigs of memory and then I get an unspecified error! It’ll print on my laptop, but unfortunately (as I already mentioned) none of the categories are preserved there. Bad buggy Microsoft software!

Well, that was a mammoth waste of time and money. (And now I have to decide whether to back-out completely to return to my Mail/iCal applications or stick with a non-printable Entourage. Grrr!)

Other Task Managers

I’ve also thought about abandoning iCal’s tasks and using a stand-alone task manager. There are a number of applications (and a few OmniOutline extensions) that offer some alternatives, but there are two big problems:

1. It’s really rather nice to have some integration between a calendar and a task list.
2. It’s important to be able to move between my desktop and laptop readily. (Sync is important.)

Granted, there are some solutions that store everything in a text file that I could keep on my iDisk, although the iDisk has an annoying habit of causing long delays as it tries to sync information with the online volume, and any application file that updates the file constantly becomes unusable because of this.

Murray’s Pet Project

So I’ve been bandying-about an idea for that “first great Macintosh application” that I’ve been wanting to write for about a year. I’ve always known enough Cocoa programming to get through some book examples, but I’ve never had a chance to write a Real Life application. I know the exact app, and I think it would be a killer.

Essentially, I would love to write an application that extended the pre-existing iCal todo items to add the necessary functionality. The application would have its own todo-centric view. It would manage some additional information for the iCal todos, but iCal would still manage the major cross-computer/mobile phone/PIM syncing. The thing that it would do that MS Entourage doesn’t is have its own additional iSync module that would synchronize the “extended information” across multiple computers.

I also have in my mind a project-map of how I could first build and test the most fundamental framework components and then continue on to add features piece-by-piece with new versions. The 0.9 version would have no real interface or just a skeletal one, but would provide all the functionality as AppleScript-able components. This makes sense because the iCal integration would be using AppleScript. The 1.0 version would provide a basic tabular task view much like Entourage or Outlook. The 2.0 version would add the grouping concept of “Projects” much like Entourage has then. The 3.0 version (or maybe a “Pro” version) would extend the application to act more like MS Project with the whole GANT chart perspective.

Another layer of features could involve some of the ideas introduced in Getting Things Done. Among them:

1. Have a grouping concept of “domains” (my term) which refer to where you would be doing the todo item. The book suggests you keep lists of “things to do when your sitting at the phone” or “things to do when you’re off running errands” or “e-mails to write when you’re at the computer” or in my case “things to do that require a chunk of time at the computer” like programming projects or web research.
2. Implementing a “tickler file” where some todo items are hidden from view and drop into place at a certain date. (In other words, deferring the item until a later date or after some event has happened.) This keeps unnecessary clutter from taking your attention. The feature could also allow repetitive things like “take out the trash on Monday night” to show up on the task list on Monday morning. I’ve seen people do all sorts of “hacks” to provide themselves this functionality, but it’s always messy.

The big thing I like about this (hypothetical) application is that it doesn’t force the user to use it as an “all or nothing” solution: it’s an extension of something that already comes on all Macs. (I hated that using Entourage really meant locking into its calendar and e-mail program as well. Okay, I didn’t have to use it’s e-mail program, but you get the idea.) And the other important thing is the iSync capability. I just can’t live without it.

So am I going to write this application I’ve been mulling over in my head for over a year? Well, right now I’m pretty darned busy with the job hunt (although as Shareware it could hypothetically bring in some revenue) and things like finding a roommate, getting the Stonewall Democratic Club’s new website up and running, and other volunteer obligations, but I might just parcel out this project.

I really have always loved the idea of being a (paid) Mac programmer. The Cocoa environment is such a joy to work with. In my little hypothetical pipe dream I would spring the cash to go up to San Francisco in August to the big Developers Conference with my newly-sharpened programming skills and network until I found some work in the L.A. area…

Anyway, that’s what’s been on my mind recently.