Pocket Revolutionary

This started out as a review of the new OmniFocus app for the iPhone. I was going to talk about it being the first time I can have powerful task management on my main computer and not abandon it at my desk. I was going to explain that I have always either tied myself to a solution that was too simple, but portable, or an awesome desktop app that was only truly helpful when sitting at my desk. Being too analytical, I started out by thinking out the history of my to-do list, and I realized that explained why I like OmniFocus better than my actual article. So, I present to you my (mostly) chronological evolution of to-do lists.

Day Runner

My first love…

My mom got me my first Day Runner when I was 13 (possibly younger). Really. I begged for it in the office supply store as only a future nerd could. She eventually gave in to my geekiness, and I got my first taste of organization. It seemed infinitely extensible, yet structured in a powerful “business professional” way. You’re thinking there was no way I thought about that when I was 13, but you could not be more wrong. I loved a fully-stocked planner, and I still kind of do. My wife replaced her Palm Pilot with a big planner last year, and she couldn’t be happier (although her iMac is replacing it). My problem? I write down way too much with my whole “ubiquitous capture” obsession, and I can kill many a planner.

Paper

…and then I couldn’t afford the refills.

Inevitably, at some point I wore out multiple planners and went through way too many refills. I realized that I could manage just as well with a good spiral notebook, and then I could stop crying quietly at night thinking about how much I was spending on that specially-formatted-just-because-we-can paper known as “refills”. Yes, I could have just printed my own refills, but that wasn’t nearly as easy/popular/economical in the olden days. I normally just ran out of the to-do list refills and ended up shoving a napkin with a project plan into the pocket.

Palm Pilot

Project management in my pocket.

I have had six different PDAs. I even had a Sharp Zaurus SL-5500, which gives me way too much geek cred. I used little project management apps like “progect” to organize my tasks. The thing I loved was that it was in my pocket all the time (seriously, all the time). I just ran my task list from my pocket, and never cared about syncing issues. This was good because I had Linux in the bad old “can’t-really-support-usb” days that involved modifying and compiling your own drivers (I did), and I tended to like Palm apps that could only talk to the ugliest desktop apps on the planet.

Paper 2.0

I guess I just need paper again.

At some point I realized that the un-sync-ability of my task apps made them about as “powerful” as pen and paper and less extensible. Obviously, my next step was to go back to paper with a vengeance. I mean, at least on paper I could organize things the way I wanted them, and I had started to work out my own GTD-like system with projects on one page, and today’s task list on another. I just had a great big list of tasks, and I narrowed that down to a smaller chunk every morning on a separate piece of paper. It was simple, but it didn’t always scale. Once my “big list” reached two pages, a lot of important projects got lost in the shuffle.

Palm Pilot w/iCal

Okay, I can kind of sync.

I had a brand new Powerbook, and it could sync! This didn’t really solve the scaling issue, but it was a start. I imported everything into iCal, and then I’d flag the top 5-10 tasks to work on each day. It was almost exactly like the paper system, but I could scan it faster and it could easily talk to my Palm Pilot. This worked great until my task list reached 265 (I’m now at 423). At that point, I lost perspective, got depressed, and started going on all-night organizational benders.

Kinkless GTD w/iCal

I can kind of sync, and I’m getting organized about it.

After taking a long weekend to “clear my mind” and “stop screaming at inanimate objects”, I found some great sites like 43folders.com that gave me enough tips to talk me off the ledge. I discovered Kinkless GTD, and then I read “Getting Things Done” by David Allen. I decided that GTD wasn’t “the way” or a cult, but it was a good place to start in actually, you know, getting things done. All of a sudden, life was a little bit easier. I had less stress. I could sync with— no, I could kind of sync with my Palm Pilot. I synced a couple times. One day, my iCal messed up it’s own records, synced with Kinkless, wiped out Kinkless, and then in “data seppuku” wiped itself out. I lost my 265 tasks into oblivion. This happened twice before I buckled down and bought Missing Sync.

iGTD w/iCal

I can kind of sync, and I have a GUI.

Unfortunately, I fiddled too much and got tired of pressing the sync button all the time. I completed something, so I pressed the sync button. I changed something, so I pressed the sync button. I forgot if I had forgotten to sync in a while, so I pressed the sync button. It was a natural result of Kinkless being a script, and you can’t blame Ethan for that. I wanted GUI goodness, though, and I tried iGTD. I used iGTD for quite a while, but I just couldn’t commit to it. I wasn’t managing my projects with the same top-down view I had grown to love. It was just built for people who think differently than me. At least I could still sync, though.

OmniFocus

I love my app, but I’m not mobile.

I joined the alpha testing for OmniFocus, and I loved it. It had more of the “big picture” views that I needed, and it even had some basic iCal syncing to tide me over. It wasn’t perfect, but it worked. It worked, at least, until I got my iPhone. I loved my Palm TX, but I just couldn’t resist the charms of the iPhone. I needed my task list, though, because I still have a few moments every day (maybe not today) that I’m not staring at my computer screen. I like to run errands, fix things around the house, and, yes, even help my wife cleaning the house. My big solution? To print an errands and housework list from OmniFocus or write it down in my notebook. Then, I’d check things off and “sync” it later by checking things off in OmniFocus. I always needed to add to my things to my inbox, and I got really good at emailing myself tasks. OmniFocus handled my emails with ease, but I still couldn’t actually edit tasks or plug my new tasks into just the right spot in the middle of a project. I was just sending myself reminders, basically, of things to organize later.

OmniFocus w/iPhone App

Bliss!

Here I am today, and I’m the happiest I’ve ever been with a total solution. This is sweet, sweet, synced bliss. I do my main organization, weekly reviews, new projects, etc. on my laptop in OmniFocus, and then it’s automatically in my pocket. I can even tweak, rearrange, defer, delegate, and create on my iPhone, and I’ll see it later on my laptop when I get back to work. I basically have a license to fidget with my system all the time, for better or worse. Okay, it’s not technically perfect. Sometimes the syncing is slow (like three-minutes-to-update-my-tasks slow) or I can’t sync at all, but that’s pretty much because of MobileMe’s widely-publicized growing pains. Even then, it’s still the best system I’ve had.

Addendum

Moleskine, you complete me.

Lest my pocket Moleskine and Pilot G-2 be offended, let me assure you that I’ve only abandoned paper for my to-do’s. My wife knows exactly how obsessive I am about my notebooks and pens. As an aside, if you haven’t read The Gel Dilemma on RandsInRepose.com, I highly recommend it. The only part where I differ with him is that he sees the retractable operation as a bad thing (which I know I used to), but I actually think it’s more convenient to getting my pen “ready to write” and never losing another cap.

Update: Thanks to an update in the OmniFocus iPhone app and a more stable iDisk connection, my syncs are nice and fast now. Thanks, Brian!