Getting Organized, Staying Organized

This is probably the kind of article that most people would expect to be published around the turn of the new year. As we transition to a new year, shiny resolutions at the ready, “getting organized” seems like one of those purposeful self-improvement activities we should be engaging in. And yet life doesn’t always work like that. At least, my life doesn’t always work like that.

There are a number of reasons why this is a subject that’s top of mind for me (because if I’m honest, it’s a subject that never quite goes away). The first, and probably the most significant, is that I’ve just spend much of a holiday weekend doing exactly that.

I am at a point of transition right now, on a number of fronts. Not big, cosmic, life-altering transition, but transition all the same. The past several months (since about March) have been a whirlwind in many ways. Our condo flooded (and not the good kind of flood, if there can be considered to be such a thing). My wife broke her leg. I had a massive number of customer commitments, which involved a considerable amount of travel. There was, to put it mildly, a lot going on.

Throughout this period, I was proud of the fact that I managed to stay on top of all of the urgent commitments. Deliverables got done, deadlines were met, workshops happened, meetings and phone calls were held. Around the edges, reconstruction of both the condo and my wife’s leg progressed. In other words, all of the urgent things that needed managing got managed.

This shouldn’t be overly surprising, in that I tend to be quite good at managing urgency. It’s one of the reasons, I suspect, that I was attracted to a career in project management in the first place. If there are deadlines attached to something, the deadlines get met. If the deadline is unrealistic or unattainable, then expectations get managed. Give me something to do with a date attached, and it most assuredly will get done.

Where it tends to go a little more sideways is on the important things. Stephen Covey distinguished between urgent and important in his landmark book, The Seven Habits of Highly Effective People. Intersecting urgency with importance, he noted that the vast majority of energy gets expended on what he termed Quadrant 1 activities (urgent and important). Precious little time gets spend addressing Quadrant 2 (important, but not urgent).

The work of Quadrant 2 is where much of the helpful and useful work of improvement and strategic growth live. It’s where we invest in us. We learn new skills, develop new ideas and concepts, consider new opportunities and build new capabilities. All very useful, valuable and—indeed—important. Work that we should care about doing, and investing time in doing.

The challenge with attending to the important-but-not-urgent work of our lives is that, well, it’s not urgent. It doesn’t need to be done right now. What more, there are frequently any number of urgent demands on our time (not all of which are important) that do want to be done right now. What isn’t urgent can be done later. The problem is that, for many of us, the definition of ‘later’ tends to be in terribly close proximity to ‘never.’

If we want to do the things that we care about, we need to do something to make them happen. If they truly are important to us, and will make a meaningful and helpful difference in our lives, then we should be finding the time for them to occur. That means carving out the time that is necessary, and choosing to do now work that we could reasonably justify still putting off until later. And that is pretty much where we came in to this post.

A book I’ve mentioned a few times in recent weeks is Getting Things Done, by David Allen. It’s an awesome book, and one I have a great deal of admiration for (in fact, I really wish I’d written it). And I mention it as often as I do because I’ve found its concepts regularly and personally useful.

One of Allen’s key principles is that our minds won’t let go of things until they are in what he refers to as “a trusted system.” We hang on to to-dos and follow-ups, and go over them in our minds again and again, because we don’t feel that we have put them somewhere where we know we will find them again. Getting Things Done (or GTD) is all about designing a trusted system to capture the things your brain is worrying about, so it can go off and be awesomely productive doing something else.

There’s a lot of truth in that. One of the reasons that we feel satisfaction when we finally clean up our desk, our workspace or our files is that we feel there is order. We know where things are. We can find them again if we need to. And that’s what we are also needing to do with our projects, our commitments, our action items and our reminders.

The problem lies in figuring out how to manage the important-but-not-urgent things that define Covey’s Quadrant 2. The reading that we want to do. The writing that we want to accomplish. The projects we want to get done, whether those are around the house, around our careers or around our relationships. Systems that have been designed around GTD (and there are a LOT of them) often have an ability to set a due date of ‘Someday’ to capture this.

The theoretical usefulness of ‘someday’ as a due date is that it avoids scheduling something with a specific due date that is nothing more than an arbitrary deadline. When we do that to ourselves, we often wind up triaging and focussing on what is still most urgent and ignoring what is less so. Then we wind up moving and re-scheduling activities that didn’t get done, over and over again. Alternatively, we accumulate an insurmountable list of unaccomplished activities that inspires nothing so much as guilt, dread and the desire to hide under the covers.

There is also a challenge with NOT attaching a date to an item on our to-do lists, however. When we schedule something for ‘someday,’ we again push it out into the elusive and abstract future, when we might be better prepared to dealing with it. In practical reality, however, someday typically never comes. Unless there is some regular review of what we have put off to tomorrow, and a conscious deciding to move some of those items into our more immediate plans, they are unlikely ever to occur.

So, back to my transition period. As I write this, at the beginning of August, I’m starting what will at least be a few weeks of not travelling for work. I still have customer commitments to manage, but they are of the somewhat less urgent variety. Perhaps most importantly and exciting, I actually have some time to spend focussing on personal projects that I care about doing, but that I simply haven’t had the bandwidth to do. I can tackle some of my important-but-not-urgent goals. Of which there appear to be a surprising number.

This is perhaps the other challenge of putting things off to ‘someday.’ Let enough time go by, have a fertile enough imagination, and actually commit your future plans to paper or some other trusted note taking system, and you wind up with quite a list of things to consider. Having too many choices can be entirely more intimidating and debilitating than having few or no choices.

The idea of a trusted system that captures ideas and possibilities is useful, if only for psychological well-being. At the same time, being able to organize and manage those ideas when the opportunity presents itself is critical. What I’ve come to appreciate is that the systems that manage the urgent work of every day living and consulting are not, and cannot, be the systems of managing the important work of the future. Calendars and to-do lists are focussed on priorities and deadlines, and they are brilliant at doing so. The ability to flag something as needing to be done ‘someday’ notwithstanding, they are not great at managing the possibilities and might-bes of tomorrow.

The challenge is that future-oriented might-dos are unstructured in nature. They vary in size from new books to write, products to develop and ventures to launch to books to read, music to listen to and wines to try. Being able to capture, explore, sift and separate out these ideas is a very different organizational challenge that then usual day-to-day of meetings, tasks and phone calls.

This past weekend has been about figuring out ways to tackle this problem, in a way that works for me. I’ve tried numerous systems in the past. Some of those I have liked, some I have loved and others have had far more promise in concept than they’ve delivered on in reality. An early favourite (and this goes back some) was Lotus Agenda. It was perhaps the first attempt at creating a free-form, unstructured organizer that could conceptually capture, link and associate ideas. Ahead of its time (the technology and character-based interface couldn’t deliver on the promise) it nonetheless was a kernel of what became Lotus Notes.

A favourite for a period of time, and all the more useful because of its simplicity, was a product called Note Studio. Developed by an Australian company now focussed on games development, it was a straightforward and unstructured list and hypertext manager. It survived for an impressively long amount of time, but eventually was unsupported and unsupportable on my computer.

Since then, I’ve captured all sorts of lists in all sorts of apps and notebooks, and that’s really been the challenge. The system is no longer trusted, because it’s too chaotic, haphazard and fractured. I have some things in one place, other ideas in another and still more somewhere else. What is most critical at this point is to assemble it altogether in something meaningful, useful and relevant.

What I’ve landed on is an eco-system of four separate applications. None of them talk to each other (much), but none of them overlap in terms of functionality, either. Each is designed for one express purpose, and each purpose means something in terms of how I organize and structure my work, my time and my daydreaming and development:

  • My calendar application manages just my calendar. I don’t use it to show to-dos, and I don’t carve out special appointments with myself. If something appears in my calendar, it’s because there is an actual event on an actual date and time that I am supposed to be at.
  • I use an application called Daylite to manage my work projects. It’s billed as a customer relationship management tool, and I find it particularly useful as it integrates my contacts and to-dos with my emails. I can capture notes, emails, action items and documents and associate them with my various customer projects. The to-do part of the application is quite well designed, and it manages to keep me on top of the urgent parts of my life.
  • The unstructured what-ifs, possibilities and future projects are finding their way into a new application called Tinderbox. It’s the first application that I’ve found that comes closest to what Lotus Agenda wanted to be twenty-five years ago. The technology, the software, the interface and the sheer processing power have now caught up, where the possibility is now a reality. What’s awesome is that it truly is unstructured and flexible. I can envision taking an idea through to the structuring and development of a project, all within the same application.
  • The last piece of the puzzle is how I manage and collect the writing of others, and it’s been one of the hardest problems to solve. Years ago, I had filing cabinets full of articles and references that I wanted to be able to refer back to and reference. Then I had files on my hard drive, followed by files in DropBox, so that I could at least get access to them anywhere. The challenge was again in search-ability and making connections. Too often, it was easier to go out and find an article all over again rather than hunting through my files for a dimly-recalled reference. Devonthink is a rather clever piece of software that collects articles and documents. It lets me tag and organize them, but it also has the smarts to index and make connections across articles that go beyond what my grey matter can recall.

Setting up all of the above has taken time and effort. It has been one of the important but not urgent activities I’ve been carrying around for a while now. I’m still not done getting organized, but I’m making progress. The real benefits, though, won’t come until I continue to use and manage them on an on-going basis. But finding the right place for each thing has been a critical turning point in designing a trusted system for me. I’m now at the point where when something goes in, I have a reasonable level of confidence that it will come out again. Now I just have to use it.

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