A RAINBOW PASS-IT-ON ICON CHALLENGE

This summer, I had two really big, multi-month projects at work I needed to make progress on and I noticed that (lacking any urgent deadlines for either of them other than "everything needs to be done by the end of the summer"), my natural inclination was just to work at a very leisurely pace and make extremely slow progress on them. This is exactly what happened to me last year, meaning that a lot of my plans to revamp my curriculum fell through and I needed to push them back a year to this summer. And this summer it was happening again!

I clearly needed to make short-term deadlines to give me a sense of being on-track or behind schedule. The issue, though, was how did I know what I needed to work on, and how long it would take me, and how to make reasonable goals, and how to rework my timeline and priorities if I fell behind where I expected? The projects I'm talking about here are BIG with a lot of different components that take an unknown amount of time. Short-term planning was difficult without some serious long-term planning.

Basically, I decided I might want to take a page from my software-engineering students' books and do some project management, like sprints and agile methodology and Gantt charts to make a rough, prioritized plan for these projects to make sure I was on track throughout, and be able to detect when I'm veering off track and replan as needed to make sure I'll still have the high-priority components done before the end of summer. But then as I set about doing some serious project planning work, one of my toxic traits immediately kicked in, which is that basically, before I had even been able to plan my projects in any detail, I instantly fell down a productivity tools research hole that lasted over a week where I spent all my time at work (AND all my free time over the weekend!) just trying out project-planning software and combing through documentation desperately trying to find a tool I liked that would help me with the project planning I wanted to do. Initially, I thought this task would take, IDK, maybe half a day at the most and then I'd move on to the other tasks I had planned out for the early project period. Instead, work entirely ground to a halt for over a week in early July as I spent all my time on this one task, and then another half a week or so actually using the tools to come up with a project plan. I had tackled the first/preliminary task -- only to find myself two weeks behind schedule already. Fun!

In my defense, I've had to try out a LOT of different software, and each one I've had to use for quite a while before I could figure out whether it actually had the feature set I needed, so that was quite the timesink. And the reason why it took me so long to figure out if the feature set was sufficient was basically due to non-transparent or -- in some cases -- broken functionality or unclear or missing documentation, so that's been frustrating.

In the end, for my particular needs (a one-person project; no internet connection or integrations into other software needed; need the ability to cover project planning at both a high-level/long-term scale (via Gantt charts) AND at a medium-length scale (through weekly, sprint-level kind of goals); being able to sort and color-code tasks coming from 4+ different streams of work, by the stream generating that task), I ended up picking Obsidian. (I'm also using TrackBear lightly just to make sure I'm putting in a reasonable amount of work into my important long-term projects each week.)

But along the way, I tried out and rejected: Monday.com, Microsoft Planner, GanttProject, Agantty, and ClickUp. I also looked into but ended up rejecting ProjectLibre, OpenProject, and TaskJuggler without trying them because they didn't look like what I needed or looked too difficult to install. I also had Asana, Wrike, and Notion on my list of things to look into, but they didn't seem particularly promising compared to the options I had already checked out, so I didn't get to those.

If anyone is interested in my adventures with and evaluations of various productivity/project management software...

( Obsidian )
( Monday.com )
( Microsoft Planner )
( GanttProject )
( Other FOSS software I rejected )
( ClickUp )
( Final options )
( TrackBear )
( Spreadsheets )