Last week, I shared the time management challenges that I’ve been experiencing, and my decision to migrate my time management approach and adopt a new piece of software.
This was a real-time update. I’ve been considering the decision to move for some time—and I’ve been avoiding it for an extended period as well, if I’m completely honest. When I wrote last week’s column, I had finished my research on potential solutions. I had just made a choice about OmniFocus. I was in the process of learning how the software worked, and figuring out how I wanted to use it.
At the time that I was writing, it was still very much the holiday season. Family and visiting obligations had passed. There was still a week until the new year started in earnest. My work commitments for the prior year were largely done. I was contemplating the start of the year, and actively working towards identifying my plans for the coming weeks and months. It seemed a reasonable time to make a move like this. Certainly, there was going to be no better time in the future.
We are now a week on, and as I write this the new year is nine days old. Work has recommenced, projects are advancing and there are expectations to deliver on. I’m still learning the software. And I’m still actively identifying all of my commitments and plans for the coming weeks and months.
Monday and Tuesday of this week were spent organizing and capturing commitments I didn’t want to—and realistically couldn’t—lose sight of. I was planning how I wanted to structure information and use the software. I was testing how to get information into the system itself. I was also figuring out how to reliably get information back out again because that’s the essence of a trusted system; it’s not about knowing that something has been captured, but also knowing it will be presented to you when it actually needs to be addressed.
By Tuesday evening, I was well into a transitional space between where I was and where I was going. I was living between a system that no longer worked and one that didn’t yet work the way that I had hoped. I had pages of notes of to-dos, actions and ideas that were as yet unorganized. And if I needed any proof of that, towards the end of the afternoon, I got an email reminder about a submission that I still had to get completed. A commitment that was due the next day.
An inherent challenge of meeting this obligation was that materials I needed were in my office in Toronto, and that was a good hour-and-a-half away from where I was. I also had other errands for Wednesday that needed to get done. So the day started with an odyssey of driving that I had initially hoped would wrap up by early afternoon. Courtesy of traffic and snowstorms, that extended well out into the afternoon, and I finally got home about 4pm. I still had an evening of activities ahead, a client workshop the next day that I still had to prepare for, as well as the submission to get ready.
If there was any question as to how I was feeling about all of this, know that the entire day was a stressful experience. I felt anxious, overwhelmed, frustrated and angry. I was on the verge of two full days of facilitating. There were other responsibilities and actions that were not yet addressed. My runway to get everything done was growing rapidly shorter and I had no idea what else was waiting in the wings to get done of which I wasn’t consciously aware. Overall, I was fundamentally questioning the decision to have tried to make any transition at all. It was sorely tempting to abandon the whole move to OmniFocus, and go back to what I knew.
Around mid-afternoon, several hours into driving, with this swirling vortex of emotions and unproductive thoughts in my head, I had two insights. Both of which arrived more or less simultaneously. Firstly, I had done this to myself. I owned the decision to move to a new approach to time management. I also owned delaying a move from a system that—as was clearly evident—was no longer working for me. And I chose now to finally make the move. There was no one else responsible for this state of being, and it would probably be useful and valuable to accept that.
Secondly—and more importantly—I came to the very conscious realization that this is what change genuinely feels like. I was experiencing the visceral and personal feelings that often accompany change. The raw emotions of stress, anger and frustration. The discomfort of not knowing how to function and what to do next. The loss of a place of familiarity and the struggling with a new and very different way of operating. The anxiety of not knowing what’s missing and what’s next.
It is easy to downplay what it takes to live through change; to forget how real and significant the challenge of change is. If we reflect even briefly on the word “change,” we see how abstract and anodyne a term it is. The dictionary offers a definition of “to make different in some particular” or “to give a different position, direction or course to” something. Even the interpretation “to make radically different from” doesn’t speak to the significant human impacts that underlie the transformation it contemplates.
The irony in all of this is that I theoretically embrace change. I enjoy the challenge of managing uncertain and difficult and complex strategic undertakings. I have spent a career consulting and advising others in how to do so well—or at least better. And while I may have more of a comfort level than many, that in no way minimizes the reality that I am human. I am subject to the same forces and emotional currents as the rest of the race. And I am more than capable of feeling the stress of being out of control.
As professionals, we forget this at our peril. Whether we are managing projects, executing strategy or facilitating change, we are fundamentally taking people out of their comfort zones and moving them someplace different. And that different place is—by definition—not comfortable. It is unfamiliar, frequently unpleasant and often unasked for. We are taking people from what they know—as inefficient or ineffective as that might be—and moving them into a place that is unknown.
The experience of working through that transition is enormously challenging, particularly on an emotional level. It is a place of anxiety and stress. Asking people to work and operate in a different way is taking them from a place of competence to one of incompetence. We are creating confusion and sowing doubt in them about their own skills and ability to function. People are going to react to that with frustration and resentment and anger. And that’s normal. It’s to be expected. It needs to be planned for, allowed and supported.
The other thing we need to be careful of is dismissing or downplaying the magnitude of the change that we are contemplating, or advocating for. Again, this is easy to do in the abstract. On a surface level, we look at a solution as replacing like for like. We are dealing with concepts we already understand. We are just changing how those are presented, or structured, or managed—or the tools by which we organize them.
I’ve been managing commitments all my professional life. I’ve worked through and adapted many of the constructs of Getting Things Done, along with a variety of other concepts, approaches and strategies. That’s resulted in an approach to organizing that been mostly stable and has served me (relatively) well for close to 15 years. My presumption when I started this transition was that it would be straightforward and that I simply needed to learn what buttons to push and I would be able to carry on pretty much intact.
The reality has been very different. I’ve actually gone through a review and revisiting of my practices. I’ve re-read a surprising amount of Getting Things Done, and have identified a number of things that I could be doing differently or better (and that I arguably used to do, and let slide). I’ve been rethinking my overall approach, which has also led to a questioning of how that approach gets managed in the software.
The software has its own assumptions. I know this in theory, but again managed to overlook that truth in practice. OmniFocus—like many other solutions—has been developed based on the developer’s interpretation of Getting Things Done, and their judgement of how to operationalize it. There are options about how to apply the software, certainly; but that has led to different judgement calls about how to structure information and use the system.
Projects are a really good example of this. My normal habit has been to equate a project in my system with a specific customer engagement. I’ve then worked to manage the details through an organizing structure of indents and numbering within the overall project. OmniFocus can work that way, but prefers not to. The preferred tendency of the software is to organize higher level commitments and initiatives into folders, and have projects be something very granular and concrete inside of those folders, where each project then has a number of actions to be accomplished. In this world, each deliverable—for example—becomes a project, rather than each customer engagement.
That’s a bigger shift to think and work through than one might presume. What is changing here is mindset and habit and familiar approach. It is a different way of both thinking and doing. We’re undoing what used to work, and replacing it with something different that we hope works better. But until we fully transition from one state to the other, we are muddling about with an ill-formed practice that needs constant conscious thought to make work. At this stage, we are a long way from habit.
When we work through situations like this, we feel adrift and anxious. Stress grows, because the familiar doesn’t work and there are a number of open loops and outstanding questions about how to move forward that are unresolved. The consequence is confusion and lack of clarity, which can often manifest itself into an overall sense of incompetence. Something that should be simple and easy and familiar no longer is any of those things. When everything is fuzzy, we scramble for a hard edge that we can hang on to and keep in our grip.
The tough thing to remember in this middle place is that it’s temporary. We are letting go of one approach so that we can land on a new and better one. And the amorphous fuzziness in the middle is actually beneficial; it means we are genuinely willing to let go and transition, rather than force fitting old ways of thinking into new approaches and practices.
Ultimately, the concepts coalesce. New ideas form. New structures emerge that make more sense and lend themselves more effectively to what we are trying to do. We figure out what does work, and how we want to move forward. Most importantly, we build a sense of how to connect idea to action. We come out the other side, better off—but different—than when we went in.
What is essential to remember is that this feeling is universal. We aren’t alone. That’s true of transitions that we are making on our own. It’s also very true of those changes that we inflict on others.
For the changes that we lead, we need to keep in mind that we’ve already worked through our own transition and come out the other side. What we are asking others to do is to make their own transition. We are asking them to take on the stress and challenge and difficulty of finding a new way through. It is essential that we remember how fraught with anxiety that journey can be. Most critically, we need to build time, space and support for that journey to occur.