Jumping Around

Overall, I think that I’m able to do a lot of things if I can set my mind to it. Once I get started I can hold my focus and learn new technologies and techniques for solving problems, design systems and machines, and pore over blog posts, books, and articles to understand a topic of interest more deeply. What is it then that causes so few of my projects at home to get done?

Certainly part of it is akratic tendencies on my part: When I get home after work I’d generally rather have a beer on the couch and watch a show than try to marshall whatever brain power remains for my projects, regardless of how much I’d like to have them done[1]. That doesn’t entirely explain it though. I’ve put in enough time over the past few years that it seems like something should have resulted from it; at least one large project should have been completed at this point.

I think in large part my tendency to jump ship to new projects when existing ones get boring is to blame. As it turns out, I can be easily distracted by shiny ideas and fancy new tools; I’d rather spend time playing around with something new than chugging through my backlog. This isn’t uncommon and it’s certainly not new - a lot of talented folks have this same problem. The internet certainly doesn’t help either because while it’s an invaluable tool for gathering information that’s useful for your current focus it’s also a bottomless distraction machine.

Focus over the medium term is the missing ingredient. This isn’t to say that one should never abandon a project or create a new one; there are times when a project just isn’t interesting at all, and it should be mothballed. The difference is between proactively choosing to not work on something because your time is better spent elsewhere and being led by your distractability to pursue new and shiny side paths.

As usual I think that a combination of self awareness and tooling support is the likely solution to this problem, at least in the short to medium term. Having a global overview of current work-in-progress can be extremely helpful. Unfortunately I haven’t yet discovered a working system for myself, but here’s what I’m using at the moment.

Trello is the first thing that comes to mind when I think of a “global view” into a project. The kanban-style boards give you a very easy at-a-glance view of a project’s state. It falls a little short on the global view because the “boards” overview doesn’t give you any indication of how many cards there are, but it can let you see the projects you have in progress.

For personal task management I’ve been using Todoist, primariy due to its ease of capturing new tasks on a variety of platforms (having native apps on the phone and a web app helps a lot here). It works well for small one off things, but falls short on larger projects in part because it relies so heavily on the “list of tasks” paradigm. Tagging and sub-projects alleviate this somewhat, but it’s not ideal.

I have a somewhat lukewarm relationship with Evernote, mainly because while I value its native applications and presence on my phone it feels clunky for a lot of what I would like to use it for. Text entry and editing in the interface isn’t great (but I’m an Emacs user, so I’m somewhat particular about my text editors) and I wish it supported Markdown for faster input. For keeping track of tasks, you have to decide between keeping tasks as bullet points in a note (hard to scale, and hard to capture quickly) or keeping them as notes in a notebook which gets unwieldy quick. Because of these shortcomings, I primarily use Evernote as an archive for checklists and scanned files.

To my mind a tool which would support my ideal personal project management system would have these qualities[2]:

  1. Present on my phone and the web, for easy capture
  2. Provides breakdowns of task load by project, and within projects
  3. Highlight projects that haven’t been worked on recently
  4. Provide some method of tagging tasks and viewing them by context
  5. Support markdown or some other form of plain-text entry

Maybe someday I’ll find it. Until then, I’ll do my best with what I have.

  1. To an extent this can be alleviated through judicious use of commitment contracts and self-tracking, though it does still require some self discipline to actually work on the projects.  ↩

  2. Of course, hacking productivity systems is one of the surest ways to avoid doing actual work; part of my struggle is the varying levels of “just accept that it’s not perfect and go do something” that I can muster.  ↩