Scary, Monstrous, Overwhelming Deliverables

Deliverables are powerful monsters. Deceptively so. Pay attention to them, and they are as docile and affectionate as kittens. Unwatched, they become ferocious and feral with astonishing speed, exponentially expanding in size, significance and scariness.

As a consultant, a great deal of what I produce is writing in one form or other. I create nothing so much as words and ideas designed to shape perceptions and perspectives. The form these take varies—reports, white papers, presentations, speeches and more. But the means of production is pretty standard: me in front of a keyboard, typing furiously away, in whatever locale I find myself.

The advantage to this is that I can work just about anywhere. My office, certainly. But coffee shops, hotel lobbies, airport departure lounges, client meeting rooms and convention centre presentation halls have all been productive work environments. Even airplanes, as long as there is a reasonable guarantee of enough space so that the seat in front of me won’t descend with sufficient force and speed as to crush my laptop.

For all that I write on a regular basis, getting the writing done is a perennial challenge I’ve frequently struggled with. I talked last week about getting organized, and it’s a state that I relish, but don’t always enjoy as my actual state of being. While most productivity coaches, self-help gurus and time management experts will say that the best work comes from pacing and steady attention, that is not my normal work experience. When I develop a deliverable, it is usually as a result of fevered and focussed attention over a finite period. Often with a looming deadline attached.

There is admittedly a benefit to working this way sometimes. There is a coherence that is possible by producing something in a tight timeframe that is harder to maintain when an activity stretches over an extended period. Particularly on a large deliverable, the focussed attention that is paid to the overall work means that all of the moving parts and their interaction are able to be kept in closer harmony. And, truth be told, it gets the work done faster, if only in terms of duration.

There is also a decided downside to working this way. For starters, it’s exhausting. There is an emotional toll associated with that much focus and vigilance being exercised over the course of a few narrow days. It takes a great deal effort to apply a single-minded level of attention to one thing, and to work to get it produced.

The larger potential compromise is in the quality of what gets produced. If you are—like me—someone that values doing their best work, there is always a level of anxiety in getting things done in a compressed period. There is a fear that it might be substandard, or that it doesn’t live up to the potential of what you are capable of. There is a gnawing suspicion that more time, more reflection and a more relaxed pace may be able to produce something better. This hasn’t generally been true for me, at least not very often. The deliverable I have been working on over the last few days is emblematic of that. I had begun working on it a few months ago, in May, and had done a fair bit of work in developing the outline and defining the early, foundational sections. The challenge was that, prior to this current session of work, I haven’t touched it since May 23.

That’s not to say that it hasn’t been in my consciousness. In fact, I’ve thought about it a great deal. I’ve reflected on my hopes and aspirations for what the finished product will be. I’ve set goals in terms of accessibility, understandability and readability. Recognizing that I am writing for an audience with a very broad range of skills and abilities today, I have thought hard about how to make complex ideas simply and straightforward. I’ve noted ideas about how to approach this document while I’ve been having discussions in other contexts about other deliverables.

All of that has been working away in my mind, and much of this reflection has been of value. I’ve noted before that until a deliverable is ready to come out, I typically can’t force it. Once gestated, however, it pretty much comes out full form. The first book I wrote, of which I was a co-author, had four years of research and thinking go into the shaping of it. At the same time, almost every word that appears in it was crafted in an intense two-week writing retreat in the mountains of British Columbia. We had nothing committed to paper when we arrived. Virtually all of it was in a final draft form by the time we were done.

All of this is to say that I have a complicated relationship with deadlines and work. Conceptually, I would like to work at a more leisurely, refined and relaxed pace. But I seemingly can’t or won’t do so. And that’s a challenge. For all of the positive and constructive thinking I’ve done about my current deliverable in the past few months, there has also been a much larger level of cognitive grinding away that was less positive and less constructive.

Specifically, the more time that has passed without actually making meaningful progress in writing, the greater the mounting sense of dread and foreboding I’ve had about doing the work. In actual reality, the deliverable is the same size and scope that it was three months ago. Perceptually, though, it had become absolutely massive and overwhelming. While my conscious mind squirmed uncomfortably about the thought of what I still had to do, my unconscious mind managed to turn it into an absolute horror show of angst, torment and suffering. By the time I had the bandwidth to returning the work, the work appeared massively epic and insurmountable.

This is arguably neither healthy or productive. Dreading work is not a really great way to spend your career (and I still claim most days to genuinely enjoy what I do). And in reality I don’t actually like working this way, even if it seems to still happen on a not-too-infrequent basis. Given that my demeanour during these periods can best be described as intensely focussed—and more honestly reflected as surly—it’s not something the people around me enjoy enormously either.

Managing it takes work, and my current experience demonstrates that this continues to be a work in progress. Countering the overwhelming nature of my current assignment, for example, was an exercise in reorienting myself to what had to be done, when it needed to be done and the work that would be required to deliver a quality final result. The hour spent going over what was already completed and planning what was remaining managed to defuse a significant amount of dread. The planning that had already been done was solid. I had developed far more than I remembered and I had a clear and relevant outline for what still needed to be done.

The existential dread that I had experienced—building up the deliverable into something unmanageable and unworkable—was a product of not having the time to spend working on it, not taking the time to review where I was and what was already done, and extrapolating from there the impossibility of successfully completing it in the time that I had left. Consciously paying attention to where I was and what was required to finish did a lot to undermine that dread.

The larger management challenge is being able to proactively address circumstances like this before they actually become monstrous and overwhelming. And that’s where the work of getting organized comes back to the fore.

The hard truth is that for all my current experience has been frustrating and challenging, it is now far less frequent than it used to be. I’ve gotten better in recent years at managing my workload and commitment level. For the most part, I am able to do the work, and do the work well, while maintaining a much more reasonable and sustainable pace. Occasionally, circumstances lead me to get overwhelmed, but they are rare. Thisis good for me, not to mention infinitely better those around me.

Keeping control of my overall workload is the value of getting organized that I discussed last week. And while I have been successful over the last few months in tackling the urgent, there are still a few important commitments that I have allowed to slide down the list. It’s those remaining obligations that I am tackling at present. While there are only a few deliverables that remain, they are relatively large and significant, which is what makes them challenging. And they’ve only grown larger as they have feasted on my unconscious anxieties while barely being allowed to nibble at my conscious attention.

For many of us, the monsters that lurk in our subsconscious have a lot to do with the work that we do. The larger they grow and the more they loom, the more intimidated we are and the more unproductive we become. Managing our demons, though, in a lot of ways involves managing ourselves. Attention, focus and a realistic sense of our workload and its attainabilty is what helps to maintain perspective. It’s also what starves the beasts and shrinks them down to size.

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