What’s The Point Of Planning?

Planning is supposed to be good for us. Deliberate choices are favoured over haphazard randomness. Proactive is preferable to reactive. Thinking it through is preferred to winging it.

At the same time, there are so very many quotes that seem to undermine the very idea of planning. “The best laid plans of mice and men oft go awry.” “No plan survives first contact with the enemy.” “Life is what happens when you are making other plans.” The deeply philosophical and mildly esoteric, “The psuedoscience of planning seems almost neurotic in its determination to imitate empiric failure and ignore empiric success.” And the vaguely hopeful but still also disparaging, “I have found plans to be useless, but planning indispensable.”

I was thinking of this as I was working through my to do list the other day. As usual, it is extremely long. More than a little ambitious. Actually, if truth be told, relentlessly and unattainably aggressive. But hopeful. Ever, ever hopeful.

On good—and astonishingly productive—days, my to-do list is wonderful helpful. It guides me as to priorities and commitments, and gives me that lovely little hit of dopamine reward when I tick something off as done. On bad days (or weeks, or months) I ignore it almost completely. Oftentimes the urgent and critical things still get done. But also, other things that I consider important don’t get any progress or attention whatsoever.

This usually results in a painful hour spent every week or three reviewing the list. Project by project and item by item I work through it, acknowledging what is done, cringing about what is not, and typically punting the whole thing a few weeks into the future. Things that didn’t get done in April optimistically get scheduled for June. May’s activities are grudgingly shifted to July. The odd thing gets flagged as ‘someday’ to avoid the necessity of in the future rescheduling it for a fourth or fifth or eighteenth time. And the rare—very rare—action actually gets deleted off the list as being hopelessly impractical and unattainable.

If I was wanting to be euphemistic about this and put a positive spin on it, I would call this my weekly ‘collection’ process. That’s the term that David Allen uses in his book Getting Things Done for making sure that you’ve got everything you want to accomplish in a trust system. Really, though, that’s not the problem. I’m actually quite good about the process of capturing to-dos, whether they are single tasks, bite-sized projects or full on engagements. It’s the getting them off my list again that is more challenging.

This is not to say that I’m lazy. Many have argued in the past—and some still do—that I’m a workaholic. I certainly enjoy my work most days, although sometimes I find it overwhelming. It’s more an acknowledgement that I have more ambition than I have time to deliver on it. And that from time to time I like to indulge in having moments, days and weekends in which I’m not assiduously thinking of what I am doing, what I should be doing and what needs to happen next.

But it does raise some fundamental challenges about how we think about plans, and how we think about planning. Interestingly—but perhaps not unsurprisingly—our thinking processes are decidedly fixed in nature. In the larger symphony of human experience, to-do lists play the same note over and over again, and in the same way.

A case in point would be how we think about project plans. I’ve been supporting a few organizations of late in evaluating and selecting potential project management software packages. I also did a recent webinar on what constitutes state of the art. I’m genuinely excited at this point in time, in that we seem to be—for the first time in a very long time—on the verge of some very different ways of thinking about our work and our projects. There are solutions that are fundamentally trying to upset and reinvent how we think about project organizing.

The vast majority of traditional project management software—and a surprising number of current products—have a single, dominant view. Open the application, and you are presented with a view of the Gantt chart. Just like every single writing application leverages the dominant metaphor of a type writer, just about every project management application focusses on activities represented by lines spread along a linear calendar.

While the Gantt chart can be considered a useful representation in some contexts, that’s not to say that it is universally relevant. More importantly, it brings some assumptions to the table that aren’t always operative. Every activity presumes to have a clear start and end date. Within the activity, there are resources assigned, ideally with hours of effort that they will expend. Dependencies are firmly drawn from the hard completion point of one activity on to the start of the next.

Actual reality is different. Activities are often more fuzzy and indeterminate suggestions of work, in which we might wrestle with a problem, figure out some workable alternatives and continue our explorations from there. The actual effort required is often nebulous, shifting from no more than a productive morning to days or weeks of interminable slog. Activities don’t have clearly defined boundaries on their beginning and their end; we explore and consider what we need to do, and we often progressively evolve, review, revise and finalize the results until we are satisfied with them. We don’t wait until activities are fully complete, so much as start thinking about the next thing while we are wrapping up and bringing to a close what we already have in flux.

The messy reality of actual project life defies the presumed orderly, systematic and very hierarchical structure of our Gantt charts. But the software doesn’t know what to do with it. If we were accurately representing projects, Gantt charts would progressively fade out the further in the future they extend. Activities would be represented with varying degrees of sharpness and precision, ebbing and flowing with understanding and insight. Dependencies would give a range of options from ‘sort of started’ to ‘when you have a clear grasp of things’ to ‘mostly finished.’

Frankly, we have the same problem in our personal lives, and in planning our own personal commitments. Which is why I go back and forth over my to do list, revising, updating, shifting and extending as required. Not every activity, project or commitment has the same level of clarity, importance, relevance or urgency. In defining activities, though, we have no options to reflect that.

For example, my customer commitments tend to be pretty hard and fast. Not exclusively, mind you, in that many of the projects I work on are uncertain, conceptual, require a great deal of input and often involve learning and evolution. But once I have committed to a date—for a workshop, a meeting, a deliverable or a review—the work pretty much gets done when I say it will. Around that, other work evolves. I am far more firm with my customer commitments and far more flexible with the commitments I make to my self. I also tend to be more committed to promises made to my wife, my larger family and my friends. That’s not to say what I want is unimportant and takes a back seat, necessarily. It just means I’m most flexible with the things that matter only to me.

Defining a to-do in my planner, though, provides for none of that vagueness or uncertainty. The activity is defined, a priority might be set, I assign it a context and am prompted for a due date. That can be a specific date, it can be today or it can be someday. That’s it. There are no other options. I’d like to be able to say “sometime this week.” Or “towards the end of next month, when I have bandwidth, free space and the energy.” But that kind of conditional schedule doesn’t exist in software.

It does, however, exist in my head. And that’s why I don’t really resent my shifting relationship with my to-do lists. There are days when I need it. Today, for example, it has been front and centre; I’ve had one focussed day in which to follow up and take care of a number of important, small pressing commitments. For the next seven days, I’m already pretty tightly scheduled, and my to-do list may or may not get much of a look. I will check in with it from time to time to make sure the essentials get taken care of. I’ll see where I am next week, what’s been done and what needs to change. Some things will be accomplished, new actions will have been added and yes, some activities are going to once again get punted forward to the future.

There are some people who would likely be driven to distraction by my approach to planning (particularly knowing that I make my living as a pretty well-respected consultant who guides organizations on the defining and executing strategy). Some of you may be sitting, mouths agape, gripping your heads in horror even as you read this.

That raises an interesting question about how each of us relates to our work, our plans our activity. For some, the to-do list is all about the deadline. Once fixed, it becomes immovable. Make a promise, even if to yourself, and not delivering on it is a failure. I don’t think that way. For me, what is important is not the deadline, but the reminder. My system reminds me of what is important, and the things that I want to do. I use my to-do list to focus my attention, certainly, but there is a sliding scale of commitment, priority and focus. That’s partly driven by who the work is for, partly shaped by how much energy and focus I can bring to bear and partly compromised by what other opportunities are presenting themselves to me in the moment. My to-do list is a shifting list of opportunities that ebb and flow based on what I have to do, what I want to do and what I hope to do.

In a perfect world, my system of planning and organization would keep up with me and I wouldn’t need to manage it quite so proactively. I genuinely don’t enjoy moving to-dos forward in time. I just don’t beat myself up about doing so. And given that no software package that exists—or is likely to exist in the coming years—can appropriately make choices for me of where I should or will spend my time, it’s up to me to keep track of what I’m doing now and what I hope to accomplish in the future.

There are those that will tell you that failing to plan is planning to fail. Peter Drucker was certainly on the side of committed deadlines with his quote, “Unless commitment is made, there are only promises and hopes; but no plans.” For me, I’ll take Gloria Steinem’s viewpoint: “Without leaps of imagination or dreaming, we lose the excitement of possibilities. Dreaming, after all is a form of planning.”

My ambitions are unlikely to recede. Life is going to continue to happen. New opportunities are going to present themselves, and yet I will still work to deliver on my current commitments. I will inevitably continue to make the best of it, planning what I can get done and moving what I cannot. After all, it’s not really about finally clearing the list. And I still have some time in August that looks free.