I used to really admire Merlin Mann (I still do, but I used to, too). I was devoted to his vision of productivity. It was an organic and human approach that asked, “what do you have to do, to do your best work?” It was not about being productive in the corporate, widget-making sense; it was understanding and personal.
When Mann left the scene for good, it was after he had picked up a book deal, and then subsequently realized he had greater priorities: being available to raise his daughter. And while I understood the reasoning, and felt for him, a small part of me felt misled. How was it that the bastion of personal productivity could not even finish writing a book on the subject?
Regardless, I had fallen in deep with the rituals and markers of personal productivity. I was a devotee of Getting Things Done, and the hipster PDA, and OmniFocus. I’ve had the same OmniFocus database for nearly ten years, and I’ve used it as a launchpad for my whole life, at the 50,000 foot view, with varying degrees of success.
GTD did not cleanly make the leap into the modern world. Written at a time when access to the web, one’s phone, and one’s filing cabinet were all separate and unique things (contexts, in GTD parlance), David Allen’s system for keeping track of everything in your life often feels clumsy and bureaucratic. Despite that and other difficulties, I’ve held fast, and have worked diligently to make my OmniFocus database my single source of truth for my entire life.
I prided myself on “universal capture”—being able to pin down specifics of every request made of me, and everything I wanted to accomplish, in precise detail. I would collect notes during conversations, process everything into tasks, or research, and keep those tasks around long after everyone else had forgotten about them.
And then, in secret, I would agonize about everything I had put on my plate, and discard countless to-dos in regular pruning sessions. Projects I had painstakingly described in my GTD system simply dropped off the radar as I decided they were not important, or worth doing. Each time this happened, the sense of dejection I felt at Mann’s frustrating, self-imposed exile from the world of personal productivity returned. Was any of this worth doing? Was this a question of garbage in, garbage out? Was I being scrupulous or pedantic? Was this making an impact on my life? Could I point to the exact improvements of maintaining this eclectic system? Was I in thrall to my own ideas of what it meant to be productive?
At the start of every year, I review my successes and failures of the last one, and consider what I can change, or what needs fixing. Every year I ask myself if I should continue doing this whole GTD, maintaining my OmniFocus database; my second brain, and source of truth about my priorities, even if it occasionally became stale or painful to keep up. Every year, life grows a little bit more complicated, and I use that as an excuse to sally forth and continue the good fight against apathy, boredom, and listlessness.
Last year, I barely looked at my OmniFocus, even though it occupied valuable real estate on my lock screen, and my phone’s home bar, and was permanently open on my desktop. I grew more frustrated that I couldn’t use it for sensitive and proprietary work tasks, for which I had to maintain a completely separate system.
Here’s a project about exploring and learning about the city I recently moved to. It has tasks to go to museums, read historical books, spend time identifying plants and trees in the local parks. None of it got accomplished, and now it lingers, a disappointing reminder of lofty goals waylaid and ignored. Is it still important? Well, I want to do those things, still. But I haven’t. And on top of that, it just makes me feel guilty that the project hangs around, asking to be done, for a status update, in reviews that are meant to be weekly but usually end up sporadically.
It’s useful to consider the existential question, even if it’s disconnected from life on the ground: am I being productive when I do these things, and am I being unproductive when I fail to? How much of that failure is mine, and how much of that is the various impedance mismatches of the system? I mentioned contexts and filing cabinets earlier, but there are other holes: GTD has no good way to articulate deep work and research, tasks with vague goals and deliverables.
This train of thought has had no satisfying end for me. The fundamental goal of all this, for me, is to never have to worry about if I’m doing what I want to; to, at a glance, know exactly what I should be spending my time on, based on the goals I set myself, and what I want out of life. In practice, the system is stuffy and onerous, inflexible and grating and a pain in the ass to maintain, and it rarely, if ever, reflects my true desires and ambitions. And if I need a reminder to go grocery shopping, then I can just put that in a fucking to-do in Reminders.app.
For years I’ve felt the system cannot fail, it can only be failed. It was a question of rigor, of constant upkeep, of nurturing. For years I’ve considered a change of pace, a move to a different tool. I’ve fiddled with my contexts and rearranged projects and tasks, but the end result is strangely consistent: things fall off the radar, the right priority isn’t put in front of me at the right time, and I continue to be bombarded with requests and obligations that simply don’t make it into this supposed single source of truth.
If you’re hoping for a neat wrap-up to this, you’re going to be disappointed. This is more of an airing of grievances, a personal reminder that something is rotten in the state of GTD. Every year, the whole labor of love gets closer to the chopping block, and more information escapes the system to reside somewhere else. But I can’t bring myself to perform the execution. Not yet. As we enter 2018, I’m resolving, again, to do better, to try harder, to articulate my goals, plan them out, and make them a reality, despite reality’s plans for the contrary.