I always felt like productivity was a thing pushed by the CEO-Influencer complex and should not be taken seriously. My task tracking system was adding tasks in a checklist and breaking it down into sub-checklists where needed. I thought that should be enough.

Despite my simple system, I felt like I wasn’t getting done and neither was I happy with the impact of whatever I was getting done. Prioritising tasks was difficult because there I couldn’t capture the context about tasks that help in the prioritisation. I could move things around in my checklist but it was tedious. And I felt that it was because my checklist was not enough. I was conflicted about giving in to the discourse but things had to improve.

So I decided to give in and try Trello for some time. I preferred Trello because

1. I wanted a simple and customisable Kanban style board
2. Like most people working in the software industry, I only put up with Jira when I’m paid for it.

I wanted to address the problem of not being able to note down the context of tasks in a way that helps me prioritise those tasks. So I created labels like Hobby, Personal, Professional for my tasks. Two other kinds of labels I have is Deep Work and Urgent. So tasks can be categorised as Hobby + Urgent or Personal + Deep Work or even Professional + Deep Work + Urgent. So I would know to prioritise the urgent tasks first and then prioritise based on whether if it's a hobby, an errand or something related to work. The Deep Work label also was a visual reminder for tasks that required a large chunk of focus time. This is a prioritisation system that is not complex but captures enough information that helps me prioritise tasks by just skimming through the labels.

Another feature of Trello that I found useful was adding checklists to the tasks. But these checklists were more powerful than the checklists from my previous system. Each task in the checklist could be converted into its own task. Now I could add a detailed description for each task, subtask and also add labels to prioritise the subtasks.

This feature helped me in an obvious and also in a very subtle way that I only realised later. The obvious way it helped me was by having detailed subtasks that I could prioritise. For example, while trying to select what insurance policy to buy, I can create a task for comparing various policies. I may need to research the new insurance related terms I encounter on the way. So I could note down that information or context in that task without having to need another tool for it.

That is also the subtle benefit of this system that I realised only later. I was writing down my tasks and engaging with it much more deeply than in my previous system. I began articulating my thoughts about the tasks much more. It’s also convenient that articulating one’s thoughts for oneself is like riding a cycle with training wheels. And now I believe, any planning tool that makes one articulate one’s tasks and prioritise them is good. Maybe the tool itself, or Kanban might not be that important. The tool should allow the user to think and reflect on the task without getting in the way.