January 25, 2010

Task Management, or "Why I'm Neurotic And Inches From The Loony Bin"

I'm directly over the city of Columbus, Ohio, amidst a large amount of turbulence that would have spilled any drink I had, if only they had come around and brought me something. I'm also very frustrated, and I'll explain why over the course of this blog post, which is about my inability to find a task management system that has a foothold in even the 20th century. This will turn into something that most will skip with "too long, didn't read", but it's as much for my benefit as for yours. Who are we kidding, it's entirely for mine, I don't care about you.

I'm a list person. I need to write things down and capture them outside of my head or they simply won't happen. At one point in my life, I had a really great memory. It's still not so bad, but I can tell it's gotten a little worse as I've gotten older. Regardless, I have to write things down in order to organize them. This is the only way I'm able to execute on anything. It's also the act of writing things down that helps me remember them. I'm one of those people that learns best by taking notes, even if I never look at those notes again. None of this is up for debate, it's been proven time and time again to me through years and years and years of school, followed by work.

As an aside, I can barely read this as I type it because the screen is bouncing so much. Why? Because the plain is bouncing all over the sky, just north of Dayton, Ohio.

I used some task management software through college, but it was in grad school where I was really introduced to the joys electronic planning with my association with some research going on in the Graphics and Visualization Lab at Georgia Tech. They were doing work with the Apple Newton and I was able to procure one for daily use. That day my life changed.

Let me take a step back and introduce you to one of my neurosis and idiosyncrasies. I love office supplies: pens, highlighters, post-its, flags, folders, mechanical pencils, notebooks. If it's in an Office Depot, I love it. I can wander around a Staples for days and not get bored. I love them so much that I can't bear to see them spoiled by, well, using them. What if I mess up and have to scribble something out? What if I use too many and they're all gone? I have to force myself to unwrap post-it notes, let alone write on them. You can see this might make it difficult to organize my life with such supplies because doing so would mean I had to soil them.

Oh look, they turned off the fasten seatbelt sign.

With the Newton, everything was electronic. I could scribble out any mistakes, move things around on the fly, and never ever have to worry about unwrapping my precious stickies. It was as if a weight had been lifted from me. Most importantly, it was portable. Sure, my Mac had a stickies app, but I couldn't lug a PowerMac 6100/66 around to class in order to take down my homework or set up a study group. It was the best of both worlds in that I could write with my own handwriting (yes, it worked perfectly, regardless of what the press said) and I could take it anywhere. Life was good.

Right about the time I started working, Steve Jobs came back to Apple and decided that things had to change. Out went the Newton division and along with it my hopes and dreams. There was a new sheriff in town anyway, one that was taking over the PDA landscape: Palm. Sure you had to write with some arcane squiggles. Sure, it was tiny and you had to squint to see just about everything. But it was supported by everyone and had great desktop integration. That means I could use a desktop app at work and at home, but still be able to access and enter tasks/events on the road. For the most part, I was happy, but there was still something that left me wanting.

Remember that part about how I like to write things down in order to commit them to memory? The Newton allowed that, because I was really writing as if I was writing on paper. Doing any serious data entry on the Palm was a joke, so you just typed everything. In addition, the Mac desktop software was a joke, so I had to do most of it on my spare PeeCee at work and that made it difficult to do things at home. Also around that time, I was looking for something a bit more holistic in my life, something that would help organize not just remembering to do my TPS reports, but also help me make myself a better person.

About this time, I discovered Franklin Covey products. For those unaware, it's a methodology crafted around Stephen Covey's book about some habits and traits shared by highly effective people. He makes a lot of money on seminars and training, but that doesn't mean it's all schlock. There's some good stuff there, and it was the method I was after, not the religion. I was drawn to the "life-planning" aspect of FC, helping me to identify what and who was important to me, to set life-long goals and values, and to think about more than just TPS reports. It helped me evaluate who I was versus who I wanted to be and find a plan to unify the two. The approach of long-term and short-term planning, with frequent reviews, made a lot of sense to me and clicked very nicely. Day-to-day, it was a good system, and as part of a larger whole, it helped me to balance myself (or at least identify where I was out of balance so I could correct it).

There was some desktop software (PC only, of course) and accompanying Palm software (remember, everyone supported it). I used this for a while, but while the system was great, the desktop software was shit. Unadulterated shit. It did about half of the system very well, but the other half barely worked. It's as if the FC developers didn't even understand the system for which they were building software. The poor customer support people on the forums were overrun with complaints and eventually stopped responding. Updates were slow to nonexistent and didn't address the obvious bugs people would routinely complain about. After all this, I started to doubt what I could get out of this system. I made a temporary switch over to LifeBalance because it had a Mac client, but it never really worked right either.

Then one day I decided to take the software out of the equation entirely. If it was the software that was the barrier, the solution seemed obvious. I invested a couple hundred dollars in a nice leather binder, a year's worth of planner pages, all the inserts, pages, goal planners, etc and started my journey down the path people had been traveling for centuries: pen and paper. With pen and paper, I was free to organize myself exactly how I wanted and could adapt the system to my needs. There were no rules to follow because I controlled the horizontal and the vertical. What could go wrong?

I've lived with a paper planner for close to 10 years now and clearly it wasn't a bad solution. It allows me the tactile learning which I require by writing in my own hand, and it's portable. There are some problems though, which should be obvious. Remember my neurosis about not wanting to mess up? Yeah, well, I still have that. Crossing things out still makes me bleed internally. It's distracting, and always seems to happen right after a 3-day weekend when I write everything off by a day. In order to use the system properly, I need to write goals and assign them tasks. That means opening up my package of goal sheets and scribbling on them. This too makes me bleed internally because I know that once I put pen to virgin paper, the magic is gone. What if I write things in the wrong order? What if I make any number of mistakes? It's too much, and so I don't do it. There's also the problem that my paper-based system isn't on the Interwebs anywhere. If I don't have my planner, I can't capture anything. I generally have my planner, but not always. The last annoyance is the cost. The pretty pages aren't cheap, and you have to keep buying them year in and year out. At $65 a year (that's just for the yearly pages, there may be other pages I need to get too), you can see how much money I've spent in the last decade on this stuff. I could argue that being this organized has allowed me to be in the position I'm in and the system has clearly paid for itself in that regard, but it's still a bitter pill to have to swallow every year.

So come this New Years, I thought to myself I would try to find a solution that was up to the standards of the 21st century in which I'm a citizen. There are a few requirements to head back into the digital domain. First off, it has to run on a Mac (duh, but this means no iPhone-only solutions) and have a way to access it from my iPhone via something other than the built-in calendar app. Second, I must be able to have first-class viewing/editing from both home and work machines without resorting to lugging around a laptop or requiring the use of my iPhone at one or the other. As I split my time about equally working at home and the office, I need something that syncs between both sets of work machines. I do not want to have to have a separate laptop open at all times that I must carry to work in order to access my life. This much is firm. Finally, it's gotta cost less than the paper planner pages I already use, though this isn't really a problem.

Scanning the Mac desktop landscape, there are really only two players: Things and OmniFocus, and thankfully each comes with a 14-day trial. I downloaded both and played around with them, as well as took the temperature of their online communities in the forums (support is important). Here's the gist of what I came away with.

Things is a beautiful application. It's a lot like an iApp in that it doesn't have complicated inspectors for everything, nor is it cluttered with buttons and UI thingamabobs that probably serve some purpose if only I could figure out what it was supposed to be. A lot of time was spent on the visual design, as well as the work flow, and it shows. It's a very good example of a well-designed, user-centric application. The ability to put multiple tags on items harkens back to the planner software I used in college that's long gone the way of the dodo. It's very flexible and comes with lots of awards for both it and its iPhone app.

There are some downsides, however. Multi-machine sync is something you have to hack with Dropbox and seems easy to mess up if I forget to quit the app before I go to work or come back home. The developers have promised it for forever, but it's still not here (they're a pretty small shop). Being a small shop, new features and bug fix releases are few and far between. Now, I run a rag-tag open-source project with limited to no resources so I understand what they're going through, except my app is free. We don't get paid. I don't make real dollars (or euros) on every user, money they could theoretically use to hire some more developers. I've also seen complaints that the software doesn't scale particularly well (performance of single-file database, no nested projects, etc) and If I'm going to invest in a system, I'm not going to invest in another one in 6mo because it can't keep up with me. That would be unfortunate, and it gives me pause.

So I decided to check out the 800-pound gorilla, OmniFocus. If Things is simple and clean like Camino, OF is like Opera. Sure, you can do tons and tons with it, but, um, do I really want to? The inspector dialog for editing tasks is daunting. I feel a large learning curve coming on, and I'm not sure I want that, as I'll get to below. OF does a great job of multi-machine sync without any hackery and that's a huge benefit for me. Clearly OmniGroup is supportive of this software, they make good and solid products, and they have the resources to continue developing it for a long time to come. It seems we have the requirements met, thus I popped over to their forums where I found them full of happy users and OmniGroup employees answering questions and providing support. Upon further reading, however, I found something I wasn't actually expecting. The forums are chock full of Getting Things Done (GTD) zealots whose beliefs about how the software should be used are clear.

GTD, for those who don't know, is a different system for managing your life. There's nothing wrong with it, I have nothing against people who use it. However, I don't really care to follow GTD (I have my own system, thanks), and it seems that OF was built specifically for GTD. If you want a feature or behavior that's not part of core GTD, don't even bother asking about it, as you'll be met with stiff resistance from the community who will not so gently point out that you're doing it all wrong. I don't need this stress in my life, nor do I want to set out using software in a manner at odds with its design philosophies. Down that road lies madness, and I'd rather avoid it altogether. OF may be awesome, but I just don't want to use it.

Then someone at work suggested a cloud-based solution such as Remember The Milk. I hadn't even though about a web-based alternative, but the benefits were suddenly obvious. Multi-machine sync was entirely a non-issue, and I always have a web browser open for Gmail. After some searching around, I found Toodledo which, astoundingly, was free (let me say that again, free!) for just about all of its functionality. Not only that, it did more than just about every other cloud-based task manager (who, again, demanded yearly payments). It followed GTD, but didn't force anything down your throat and even had several non-GTD features that appealed to me (tags, priorities, etc). It also has a 3rd party API so there are multiple iPhone apps to choose from. Being able to open any laptop in my house, or any computer I come across and see my tasks is liberating, even in just the one night I've been playing with it (laptop batteries kept dying). Perfection, right? What could be wrong now?

For starters, the web site's UI is ugly and mildly confusing. Yes, it's powerful, but it takes a lot of getting used to and navigating to get what I want. There's also a bigger problem. In theory sending any of my daily work tasks up to a 3rd party server is bad bad bad. In practice, I work on an open source project and the majority of my tasks are for things in my home life. However, now I'm concerned about any strategy that isn't pen and paper since every multi-machine sync solution requires a third-party server. That said, my binder could get stolen on a trip, and it's clearly not encrypted, so it could leak just as much. The only truly safe solution would be to use a single work laptop with disk encryption and lug it everywhere, which violates requirement number two. This has my stomach in knots, enough so that I'm thinking about going back to Things and manually copying around folders.

One thing that I'm still searching for is a solution for calendaring. Tasks are just one aspect of organization. I still have to get to my appointments on time. It would be nice to have one program to be able to check calendar and tasks, especially on the iPhone where context switching is expensive. There's a phone app called Pocket Informant that duplicates/replaces the calendaring functionality of the built-in calendar app. It sync with Google Calendar as well as Toodledo. In that respect, it's perfect. However, it's really really complicated and clunky. It also doesn't support Toodledo's tags, and in a day of using it it's already corrupted itself once. That's fine, i just reset and did a re-sync (this is really why life in the cloud is awesome) and it's fixed, but makes me hesitant to spend the money on the software. Toodledo has its own iPhone app, but it lacks calendar, so I'd have to get the built-in calendar to behave with calDav, something it only wants to do begrudgingly. For example, I got it to see my work calendar, but only the first calendar. I guess when I get off the plane I'll try some hacks I've found to get it to see others. These are things I don't have to do with PI.

Congratulations if you made it this far. You're one of probably four (one of them is my beautiful wife, I love her dearly and have no clue why she puts up with me; that leaves you and two others). Where am I in all this task nonsense? I'm still not sure, though I don't have my binder with me this week on travel. I guess I'll have to find make something work, sink or swim.

Update from somewhere over Nevada: I decided to play some more with Things while I had my laptop and some time to kill. I went and entered all the tasks and projects that I had put into Toodledo just to ensure that Things could fit my workflow and something surprised me. It was so much easier using Things than the clunky Toodledo web UI that I'm almost ready to plop down my credit card. I'll be stuck with the poor sync hackery, but it might almost be worth it. I want to live in the cloud, I want to believe that there is no need for desktop software and that everything can be done on the web, but I don't think I can in this instance. At least the calendar side can mostly be online.

Posted by pinkerton at January 25, 2010 7:23 PM | TrackBack