Like January, I would consider February a success in all important ways.

Outcome of Goal 1 (Backlog System)

I am very happy with where this ended up. In February I spent somewhere in the range of 5 hours thinking through my desired task management properties, doing research, trying out different tools, settling upon a workflow, and migrating everything to it. In the end I was able to land on one that seems to have served me well for the rest of the month - an outcome I estimated at (70%) at the time the goal was formulated.

My system is built upon Trello. Trello allows you to create lists with items in them, move items between lists, tag items with colorful markers, add notes, set deadlines, search for tasks, and archive, among a variety of other less important features (to me). An image is worth a thousand words, so an example of my system is shown below (click here for full-size). embedded trello screenshot

I have an “inbox” list for items that I think about and want to quickly track, without having to try and prioritize them. Trello has good mobile support, so I can quickly add items from my phone without navigating a bunch of menus. Tasks themselves are organized into lists by an estimate of value-per-unit-time I expect from working on that task (V0 is the highest, V2 is the lowest, anything lower than V2 doesn’t deserve to be tracked). They are tagged with a color indicating the “urgency” (from U0-U3), which is an estimate of how quickly the potential value of the task will go down as I leave the task undone. More details in the original goal.

Trello allows setting mobile push reminders when due-dates hit (or beforehand if you prefer), which I use as a configurable notification system. If I want to be reminded of a certain task on a certain day, I can add a due-date. It also allows for tracking due-dates in the more standard way (of when the item is actually due), but I usually navigate that by setting a due-date for the time when I think I should next work on the item, rather than setting a due date for when it should be complete. This system is all about helping me pick what tasks to work on when, so I find that more useful.

If there are no further actions I need to take on a specific task right now, but I want it to come back on my radar in the future, I put it in the “awaiting” list. This is a list for items that have no next action, but have a due-date (this task is “awaiting” some trigger before it becomes re-activated). When the date hits I am reminded to deal with it appropriately. I use this for recurring time-based tasks such as weekly laundry reminders, as well as reminders about upcoming appointments or meetings. I also often use this for periodic check-ins, for tasks whose next step is of the form “see if there are any new developments, and if not extend the due-date”. This makes it easy to send out pings or reminders if other parties are involved.

And of course there is a column for recently-completed tasks, which I periodically archive. I could archive the tasks directly after completing them, but this lets me track which archived tasks were completed versus those who were archived for other reasons, such as deprioritization. And it just feels nice to add completed tasks to a growing list.

After landing upon this system, I migrated all my old backlog items from my various storage places into it. I tried to lower every item’s value- and urgency-ratings as much I could tolerate, as I tend to naturally look at everything and think “oh, this could be important”. The tasks ended up with a fairly even spread among value and urgency, and many tasks were deprioritized altogether in this process, which I consider a success. I still have a lot of work to do in improving my intuitive ratings for value and urgency. Right now my “value” ratings tend to naturally include a lot of weight on how urgent something feels, and I have to put in a lot of effort to explicitly try and separate those. It feels like I’m a bit better than I was, so that’s at least somewhat encouraging.

Since creating this system I’ve found it very helpful. For one thing, the reminder system has felt very powerful and has many times successfully reminded me to revist a task that had completely fallen off my radar. For another, whenever I finish something and am looking for the next task, this will help me prioritize, and I often find myself deciding upon tasks that didn’t even come to mind in the few seconds I normally allow myself to make those decisions. When I look at the board of tasks, my attention is generally spent almost completely on a triangle in the upper right corner, focusing naturally on tasks that are both valuable and urgent. Note that oftentimes, when I start a work block there will be some obvious task that I should work on, usually because I’m already in the middle of it. In these cases I don’t check the system at all, and just get right to the obvious next thing.

I initially predicted (70%) likelihood that I would make some significant change after using the system for a while, and it turns out that I did. My first iteration of the system involved a trello tool that allowed for duplicating tasks on a timer, for instance allowing me to create a new laundry task every week. This very quickly led to lots of clutter, and I had some problems with being unable to stop cards from endlessly duplicating. After thinking about it for a bit, I realized I didn’t actually need different cards, I could just reset a due-date reminder on the existing card, which gave way to the “awaiting” list. This system feels much nicer, and the “awaiting” list turned out to be useful for a variety of other use-cases.

Outcome of Goal 2 (Pay Down Debt)

I predicted a 70% chance that I would clear out the top items on my priority list, which in order were the two large tasks mentioned earlier, deciding upon and drafting March goals, setting up the task management system from goal 1, writing the January retrospective post, and writing this February retrospective post. I successfully cleared all but the last one by the end of the month (as you can probably tell by the date attached with this post). I did spend at least 80% of my time working on these tasks, as predicted.

In goal 3 I predicted a 60% chance that I would finish the January retrospective and march goals draft, which is a lower probability of only completing a subset of these items. I think that was a more reasonable estimation, and I underestimated the number of things I was committing to by saying “all high-value and high-urgency tasks up to and including writing this blog post and the January retrospective”. I did not meet the 70% prediction, so I should update downwards a little bit. (Note that this is a failure of prediction, I don’t think there was anything wrong with how I spent this month).

Outcome of Goal 3 (Carry Goals Forward)

This also went well overall. I continue to make use of my accountability structures and send out documents outlining my monthly goals in a timely fashion. I continue to do my work blocks on weekday mornings on the bus. I continue to go to the library every weekend to get that work block done - with the exception of one weekend, in which I had a full 2-day commitment. In that case I got my work done in a bunch of small ~30-minute increments where possible, but didn’t go to the library. I consider that a good way to navigate situations like that.

My cross-training wasn’t as regimented but I still mostly stuck with it. After doing it for 2 months I think I’m coming up on some diminishing returns, and will probably not continue committing to this goal. I may bring it back sometime in the future if I decide I want to do another cycle.

As I mentioned in my last parting thoughts, I don’t plan on continuing to explicitly call out this carry-forward goal every month. That being said, I would still like to write up any retrospective notes if anything didn’t go as planned.

Other Takeaways

I am once again surprised and encouraged by how well this monthly-goal system seems to be working. In terms of improving my future ability to get personal work done, I feel like the progress in this month has improved my capabilities, though not nearly to the extent of January. I feel like the hardest part of ingraining this new monthly-goal system is now over, but I have to continue being somewhat vigilant in the next couple months to make sure it stays that way.

I once again did better than my probability estimates indicated, so I should once again update my confidence upwards a bit.