Analogue Journey — Part 1: The Digital Catalyst

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About four months ago I declared bankruptcy -- of a sort. It was a kind of technological bankruptcy. This is the the tale of that decision but to find its roots I need to take you back to a time before I'd come to this realization. A time when, for me, technology could solve all of my problems. This goes back years -- though I'm not sure how many at this point.

For some time I've been battling my way through the jungle of productivity tools. Apps, sites, systems, tricks, life hacks, thought technologies, and anything else you can imagine. Early in 2016 I committed to picking a tool and sticking with it.

The app I chose was Todoist. This was far and away the best tool I'd used because it was simple. One screen, all my tasks, and it told me what was coming and when it was due. And it had filters, so I could build custom lists by project and tags so I could group things... and it had Karma.

Over several months I used it constantly. But as time moved forward and I became more and more entrenched in the system I began to find that I was spending far too much time concerned with the app and the system. I was managing my work almost as much as I was doing my work. This would not do.

I began to slip in and out of using Todoist. My frustration with it causing me to abandon the tool that had gotten me organized. The longer I went without checking the more cognitive stress built up because I knew there was incomplete work sitting in there and I couldn't remember what it all was. The longer it was left getting more and more out of date the more useless it became. The system and the tool had become more and more work and I didn't like it. I didn't have a solution at the time but I knew something would have to change.

For the next few months I continued to slip in and out of using Todoist, trying to simplify it and spend less time with the management of the work. This was, after all, the tool that had gotten me out of the quagmire of work that I had built up over years of "seat of the pants" organization. People around me began to notice a change -- things were less likely to get missed or forgotten, and I was generally more organized and on top of things. These were not small benefits and I didn't want to abandon the tool. But I wasn't happy. This would not do.

To be continued...