Our Tools Get In The Way, Too

We don’t really need any help on this front. We manage just fine on our own building strategies that get in our way. And yet, it’s not just our subconscious at work, generating fear, anxiety or doubt. Our conscious mind also wants control and certainty. It wants to know that we are on top of things, doing the work we need to do, and delivering on our promises and commitments. And our conscious and unconscious minds work in concert to add to the chaos when we fall out of control.

The more that we do and take on, the more balls we are juggling, the more that there is a risk that we drop something and it rolls away out of sight. And therefore the more that we feel the need—and arguably the important it becomes—to be on top of things.

At no time of the year does this pressure come more to the surface than now. The transition to a new calendar year—as arbitrary as that actually is in practice—is a point when many of strive to start out fresh. We are tempted to use the holiday downtime to catch up. We take our first few days back in the office to get organized. We clear our desks, organize our piles, and catch up on twelve months of filing. And we think about revising our time management approach.

Speaking personally, I am a graduate of more time management programs than I can think of. I’ve taken the courses, done the coaching, read the books, bought the planners. And the software. And more software. And yet a bit more software on top of that. You would think, at this point in my life, that I should be on top of this and have a system down to an art. Or a science.

I am as susceptible as anyone else to the thought, as we change over the calendar, that my time management needs some work. This is where our tools do very much get in the way because changing approaches and changing tools takes a cognitive toll. It takes work and effort. We are letting go of our previous approach in favour of a new strategy and a new system.

Very often, what we are changing to is a new system. In today’s reality, we don’t associate time management with the practices. We see it as a software problem. And when we want to change up our time management, we don’t go looking for new principles and approaches; we go shopping online for a new and better app by which to organize our lives.

This is a pressure that I have successfully resisted for a number of years but it has come back to the fore in a surprisingly forceful manner this year. And while I’m resistant, I suspect that’s about to change. To understand the reasons why, carry on. If you are one of the vary many others that get excited by new management systems—and if you are reading this, you likely are—then I suspect many of them may be relevant to you.

First, let’s discuss some fundamental principles. The whole objective of having a time management practice is to stay on top of our obligations. When I was young (meaning through high school into into university) I very successfully managed this with a small pocket notebook that had one spread per month, with each day represented by a tiny square. And that was just fine, thank you very much because that’s all I had to manage. However, times change.

The essence of time management is that everything is captured. This means we need a system that can scale to encompass everything we need to manage. David Allen, in his brilliant book Getting Things Done (and if you haven’t read it yet, I really do recommend it; I don’t use all of his system, but there are many ideas and concepts that I continue to find invaluable) talks about the idea of a trusted system. We need to know that everything has been captured. If we don’t trust that it has, we try to keep it all in our minds.

That’s why we wake up at 4am, our brains whirring with all manner of activity and ideas and actions. If we don’t have confidence that we have captured something in such a way that it will be available and accessible at the time that we require it, then we do not have a trusted system. Our subconscious keeps throwing them back at our conscious mind so that we don’t lose track. Instead, we lose sleep–with inevitable consequences.

What I have relied on has, at least in theory, stayed the same for about the last five years. I have been using a software package called Daylite for the Mac; it’s more than just time management, in that it is basically a stand-alone customer relationship management (CRM) tool. I like it in that it allows me to maintain all of my contacts in one place, and associate anything I do (email, action items and appointments) with who I do it for. It allows for some of what I look for in a time management solution, in that it understands projects, speaks of contexts and allows me to repeat activities that I perform on a regular basis.

I also rely on my notebook. Nothing particularly fancy; it’s a bog-standard, 5″ x 8″ notebook with a dot grid. (Leuchtturm 1917 if you are wondering about the particulars). Principally, I use it for notetaking during meetings, for planning, for capturing to-dos and commitments and for keeping track of my time.

What is an interesting reflection for me is that over the past three years, I have come to rely far more on my notebook for my day-to-day work, and far less on the software that theoretically drives how I organize. Part of that was prompted by a slow adoption of some of the techniques of bullet journalling.

My notebook was never particularly fancy, in comparison to many (search the #bulletjournal hash-tag on Instagram if you want to go down a rabbit hole of ornamentation and whimsy). My use has evolved to a pretty raw essence that allows me to capture what I need, and is far less than I documented last year around this time. I don’t pre-format anything. I start a new page, decide what it needs to be, and go from there.

While my notebook structure has simplified, it has also become something I am far more dependent upon. Simply put, it’s my everything. If I were to lose my notebook, I would be at a complete and utter loss. Action items, plans and commitments start there. As does my time tracking (which the essence of me as a consultant being able to bill my clients). While they may migrate later to other systems, the foundation lies in my notebook.

At the same time, my life has become slightly more chaotic. As I’ve implied in previous posts, I’m now actively involved in my local community theatre. And by active, I mean that as production director I look after all of the technical facilities of the theatre; I was also lighting designer of their adult Christmas show and I am stage manager, lighting designer, set designer and possible construction lead of their current show. And that’s not all my volunteer commitments; I serve on two other boards of directors, and I am also the program lead for a national conference in 2021. Not to mention having a real job as a consultant that occupies many waking hours already, and involves numerous commitments for several clients.

As you can imagine, I’ve been wrestling with how to manage all of the chaos that is my existence. And my notebook has been holding it together, but only barely. Sitting beside me are my two previous notebooks, which collectively represent my past year. There are still ideas and action items in every single one of them that I haven’t dealt with, brought forward or captured anywhere else.

The inclination at the start of the year was to rethink my system (as you do) and question whether or not I should do something else. And the temptation this year was very, very strong to do something else. That’s not a new temptation; as I acknowledged at the outset, it’s a common feeling at this time of year. But it is one that I have resisted so far.

The reason I’ve resisted changing systems is that I have learned by experience that this rarely works in isolation. It’s not the system, it’s the habits and the practices that drive the system. Fix those, and as long as you have the essential functions in place, you bend many different systems to your will. I have repeatedly invoked David Allen’s principle of relying on a trusted system. As long as you trust the system, you’re good.

And the problem, at this point, is that I don’t trust my system. I can find the same to-do written down at several different points in my notebook. Sometimes those appear in my software package as well; very often they do not. But what I lack, and that I am very consciously wrestling with, is that I currently have nowhere to step back and assess all of the commitments on my plate. There is no way to survey the overall projects and plans, and be able to meaningfully and humanly plan out my week and month in a way that allows me to get it all done and still get a good night’s sleep.

And while I’ve gotten away with it so far, that’s not likely to continue going forward. So something has to change. That change should be relying on Daylite more, in that it theoretically does most of what I want it to do. And the problem is as long as I’m in front of a computer, it does. And as soon as I am not (which is most of the time) it gets ignored. Yes, there are app for my iPhone and iPad. And I find them functionally useless for viewing the to-dos I have, let alone capturing any new ones.

That is why, I believe, I’ve come to increasingly rely on my notebook. It is with me more than my computer is. And while I always have my phone, it’s far easier to write something down on paper currently—so I don’t lose sight or thought of it—than it is to try to enter it in the app I have. This means that I don’t currently have a trusted system; while I might record things, they aren’t necessarily coming back up into my awareness when I need them (as evidenced by now consulting three notebooks, not one).

And so, after very many years of resisting, I’m actively considering the migration of my personal time management to a new system. Daylite has its uses still, but this isn’t one I will rely on or trust it for going forward. I’ve spent several days research and pondering on this. Firstly, I’ve been assessing whether I should make a change. And secondly, and no less significantly, I’ve been extensively researching what I should think about changing to.

Having reviewed a number of potential solutions—all of which are in the Mac ecosystem—I’ve landed on OmniFocus. I’m a fan of the Omni Group, and this is the only one of their software packages that I don’t currently use. I considered Things (I’ve used it before) and while tempting, decided it doesn’t give me the flexibility I need right now. ToDoist was another strong contender. What ultimately tipped me over the edge was the flexibility in planning and viewing, given the many horizons that I’m currently managing my time across.

I’ve not committed yet, but I’m leaning that way (I’m currently in the land of free trials, putting it through its paces and seeing if OmniFocus can fill the gaps that my current system is experiencing). My initial impressions are favourable, but the test will be how it works in the field. In particular, that depends on the degree to which it allows me to be confident that it can not just capture what I need to do, but also provide the reminders of what is required when they are needed. That’s still my test of a trusted system. I’ll keep you posted on if this gets me there.

Side note: if a post on what I evaluated and why I chose OmniFocus would be interesting to you, leave a note below or send me an email and I can devote a future post to my thinking and evaluation process.