First off, happy new year to everyone who reads this blog. It’s a bittersweet delight to see 2020 fade in the rearview mirror, knowing that we have a bit more of the same still to endure in 2021.
This is not to say that we shouldn’t—each of us—try to make the very best we can of 2021. That will be a challenge, and the nature of that challenge isn’t terribly evenly distributed. We each have different issues to face. Some might be personal, others professional, for some it is social and family, and for more than a few it is “all of the above.”
Last year around this time, I shared the saga of switching up my approach to time management. I had also advised against the appeal of shiny new tools, processes and approaches: “If what you are doing now is working for you, then keep doing it.” My challenge then was that I had progressively come to appreciate that my current strategy wasn’t working for me, and hadn’t been for some time.
In an ideal world, what got implemented in its place would be working amazingly, and all my time management problems would be solved. While I would love to say that, I would be lying. I will acknowledge that I got progressively further along in the implementation process (after an uncomfortable transition period). Nonetheless, I’m nowhere near time management nirvana, and it will be some work yet before I could consider myself even encroaching on its suburbs.
As I mentioned last year, the solution I moved to was a Mac-based time management solution called OmniFocus (and for those that cry out, “but I’m on Windows!”, know that I feel your pain. If I was, I’d likely be endeavouring to implement Todoist). My primary reasons for selecting it at the time were several:
- It understands Getting Things Done. While I’m not a loyal adherent to the philosophy of GTD, I have borrowed some of the concepts that do work for me (notably the use of contexts), and I’ve continued to pervert David Allen’s definition of projects in a way that works for me
- There are robust versions of the software that work not just on the Mac, but also on the iPad and on my phone. The phone capability was a particular issue, because it’s the device that I have with me most. It was this, more than anything, that was what caused the falling-out of my last solution. For want of portability, I’d reverted almost exclusively to planning in a paper journal.
- It has a lot of flexibility and power under the hood. In particular, you can scale OmniFocus up or down as you need to, and it theoretically comes along for the ride.
Astute readers will have noticed the insertion of the word “theoretically” in that last point. That would be the crux of my challenges in terms of migrating to OmniFocus. Yes, it scales, but there are some biases built in. There’s a lot of flexibility, a huge potential for both automation and nuance, but there is also a lot of detail that can be managed along the way.
For anyone that has been down this road (and I suspect that’s most of you), you will have had reinforced over and over again the value of a trusted system. A trusted system is what prevents our brains whirring away at 4am with actions, to-dos and project plans. It provides the reassurance that what we would otherwise repetitively review is captured in a place where we will be reminded of what we need to do at the appropriate time.
The idea of a trusted system is awesome. The promise of it is huge. At the same time, the actual attainment of knowing what you need is captured, and will be available when you need it, is daunting. Implicitly that means that everything needs to be in there. This is the whole idea of the “collection” process in Getting Things Done; everything, everywhere—in every file, drawer, pile, nook or cranny—gets filed, actioned, flagged or chucked.
Accomplish this, and you will have a very long to-do list indeed. This was the first of the challenges I encountered in implementing OmniFocus. I got to a very large, very detailed, very comprehensive list of all the outstanding things that at some point my brain had decided it would be a good idea to accomplish.
For a period, this detail was useful. Early on in the year, I was stage managing (and set designing, and lighting designing, and then accidentally set building) a theatrical production. There are a great many moving parts in such an undertaking. Not only are there the various things that I need to get done personally, but there are a great many more that involve the coordination of others.
During this period, the power and detail of OmniFocus was amazing in keeping on top of things. In terms of structure, I had three levels of work breakdown and a mess of to-dos and action items at the bottom. Most days involved crossing as many as 30 things off the list. I knew where I was, I was on top of what was outstanding, and I was able to follow up on the commitments of others in a way that might have seemed vaguely intimidating.
Shortly after this, however, the pandemic struck. While my very active work and volunteer lives came screeching to a fairly immediate halt, OmniFocus lumbered on, unconcerned and uncaring. I found myself confronting a long list of to-dos that, for a time, I didn’t have a particularly compelling interest in getting done. There were days where it felt like my to-do list was driving me, rather than reflecting the most important things that I cared about doing.
This brings us headlong into the other challenge of having a trusted system: the confidence that we’ll be reminded of things when we need to see them. This is unquestionably the part of the system that I haven’t fully come to terms with. While everything gets captured, what comes back out again is currently less filtered and focussed than it should be. I was being confronted by all the things, all the time, rather than the critical actions that needed to be addressed.
Even in the depths of a pandemic lockdown, there are things that need to be taken care of. Groceries need to be purchased. Garbage needs to get taken out. Furnace filters need to get changed. Subscriptions and licenses need to get renewed. Getting prompted on those is helpful and useful. Getting prompted by the several hundred other things on your list—when you have no intention of tackling them—is not only less helpful, but it is also more than a little bit demoralizing. By the summer, my list had become a depressing reminder of the many things that I had ambitions to do that I was not getting done.
What this speaks to is the very real challenge of defining—and then managing—priorities. It is arguably where the vast majority of time management solutions fall down. By the time everything gets collected, compiled, coded and cross-referenced, what you wind up with is a long and undifferentiated list of all the things you have to do, want to do, should do, might do and would like to get reminded of some day.
Failing to get any meaningful traction on priority, the tendency is to default to doing everything that falls into quadrant one of the Eisenhower matrix (you know the one); days become an obsessive challenge of crossing all the urgent and important off the list. That goes on for as long as possible, until you collapse in exhaustion on your quadrant four sofa with Netflix, takeout food and a large and comforting glass of wine. The consequence is that you find yourself right back where you started, with a slightly-more-organized list of all the things, in a shiny new piece of software.
Where I had arrived by the time I hit the end of the year and began the development and piloting of Strategy Making was that OmniFocus was where all of my day-to-day minutiae got managed. For everything that was a priority, however, I was back to managing in a (slightly larger) journal. There was some method to this madness, in that I was proving out and revisiting concepts that I was reinforcing in the workshop. At the same time, I felt that I was very close to where I had come in at the start of the year: valuing time management, but stuck between systems that weren’t quite working for me.
I haven’t wholly abandoned OmniFocus, or the idea of getting everything in a trusted system that actually works for me but doing so has required more work and thinking. The challenge is a not-insignificant one: accepting that there are granular things that we simply need to get done, while keeping our focus and attention on the essential priorities we care most about accomplishing. This is precisely the problem that I built Strategy Making to address. Ironically, it took developing the workshop to recognize where—for all of my previous efforts—I was still falling down.
Moving forward into 2021, I’m restructuring how I am using OmniFocus to allow it to encompass both the details and the priorities. Part of what is enabling that is a slightly more creative use of contexts. Think about what happens when you are focussed on a priority, and something shiny, new and useful presents itself. Depending on your impulse control, you might either embrace the new squirrel and start playing with it, or maturely say “not now.” Both create a challenge: you have one priority to pursue, and one to defer.
What approaches like “Getting Things Done” advocate for is using a context of “Someday” to push out beyond the horizon those things that we would like to consider but are not prepared to tackle currently. There’s a problem with this, of course. Someday never comes. The only way those items are coming back over the horizon is because we remember them, or we actually have a disciplined review process that consciously assesses and moves someday into something more committed. In our comprehensive trusted system, however, there are going to be a lot of “somedays” out over the rainbow. We lurch once again back to our problem of prioritization.
Rather than “someday,” I’m working to be a little more specific. To keep my to-do list from overwhelming me with detail, what moves me forward on my priorities (and what I was using my journal once again to manage) I’m tracking with a context of “Priority.” This is reserved for the things that are important for me (rather than those that are urgent to everyone else). For the focussed hours that I’m trying to move projects forward, those are the only actions I see.
For the shiny objects that I’m moving out into the future, I’m also being more specific about where in the future they go. Where something is appealing but my attention is currently elsewhere, I might flag it to consider “After Current Project.” Where it is more time-specific (things I might like to do in the summer, for example) it might get flagged “Summer 2021” instead. Or “After Covid.” I’m resisting using “Someday” as a context, unless it is truly a “might like to try it someday, but no idea when, where or how.”
Organizing is a challenge for the best of us. I am as guilty as the next person of starting with good intentions, and then getting dragged sideways. While I strive to continue to get better about how I organization, manage and focus, I also recognize that I am human (and more to the point, I’m not a machine). Structuring my work, my wishes and my wants in a way that is responsive to me continues to be a work in progress. My goal continues to be having the tools work for me, rather than the other way around.
If you are working to get focussed on your priorities—and you are determined to make 2021 your best year yet—then you will want to check out Strategy Making. Now that we are through the pilot, I’m working hard to get it formally launched. I’m excited to share it with you; get on the waiting list to be the first to know when it is available.