Who Organizes the Organizers?

When my husband and I first met he was crazy about a Britcom SciFi series called Red Dwarf. I have visceral memories of an early date, struggling to swallow cheese pizza while we watched a character’s space-flu-swelled head explode yellow mucus all over sick bay.

My favorite character on Red Dwarf was Rimmer, an intolerable, stuck-up, incompetent hologram who, in his human life, failed exams over and over again. Rimmer couldn’t understand what went wrong. He devoted countless hours to making intricate study time tables, organizing his highlighters and pens, making color coded, tabbed binders for his notes. When the day of the exam came around he’d spent so much effort organizing that he never read or learned anything.

Perhaps Rimmer’s cautionary tale made me hesitant to spend much time on my organization tools. For years the only tool I would use was OmniFocus. I resisted trying alternatives and didn’t want to waste time picking out todo apps. I just wanted to get stuff done.

Problem was, I didn’t get stuff done.

My OmniFocus accumulated a cruft of unaccomplished tasks. Some tasks were one month, two months, three months past due. Repeating household chores clogged my past due list. Abandoned projects hid in folders, some so buried I forgot they existed. At some point the shame of these undone todos got too heavy. I came to dread opening OmniFocus so much that some days I didn’t check it, resulting in a few unfortunate dropped balls.

I still use OmniFocus. It’s a beautiful, cross platform app that lets me forward emails to my inbox, gives me great views of what needs to be accomplished, and grabs my attention for the critical stuff. But OmniFocus is no longer my only organization app.

I spent some of my valuable, I should-be-accomplishing-something time, researching chore reminder apps. Chore Checklist was the easy winner. This awesome app is made especially for the work we all have to do around the house: dusting, scrubbing the toilet, taking out the garbage. Tasks are sorted in time interval lists. There things I need to get to every week (laundry), things I do every two weeks (mopping), every month (clean the fridge). I can program a task to grab my attention, so I never forget garbage day, but the default for repeating chores has no reminder. When I have an hour to work, I fire up Chore Checklist for an instant priority view: chores due are orange, chores left undone for too long are red.

By deleting all the repeating chores from OmniFocus and switching to Chore Checklist, our home is cleaner and my todos are usually done. With fewer past due tasks screaming at me in OmniFocus, I’m willing to go the extra mile to check everything off for the day. And Chore Checklist keeps me on priority without making me feel like I’m so far behind I might as well give up.

Using the right tool for the right task made such a difference that I began investigating tools to help me organize the other morass of shame in my OmniFocus: creative projects. Creative project organization needs to provide a place to dump my hopes, dreams, brainstorms, cherished darlings, and abandoned ideas, without clogging up my todos. For my first pass in creative organization, I hacked the Ulysses writing app on my Mac. Ulysses allowed me to create my own file and folder structure. I set up an inbox to collect flashes of insight and ideas. Later I drag those ideas into “blog post ideas”or “short story ideas.” There are folders for rough drafts awaiting editing, for posts posted. My evolving writing snippet moves from folder to folder, keeping track of its progress. I even coordinated Ulysses with Daedalus, the companion app for the iPhone, so when an awesome story idea comes to me while I’m brushing my teeth or walking to yoga, I can capture it and send it to the Ulysses inbox.

This process works great for capturing brainstorms, writing short shorts, and tracking blog posts. For more complex projects Ulysses doesn’t feel like the correct tool. Since my instinct was to drag items from folder to folder, I’m trying out Trello Task Management, which uses the model of dragging an index card from column to column as parts of a project move through their phases.

I don’t want to end up like Rimmer, lost in color coding my Trello cards instead of doing my work. On the other hand, I have to say that color coding Chore Buster was a life changer. Creepy soap scum on the shower door? Gone.

Finding the balance point of how much organizational structure supports, not distracts, is pretty personal, and varies based on what you do and your personality. From my recent experience, it’s worth the time to push the balance toward a little more organization, so long as you mindfully observe whether or not the effort results in more productivity and more ease.

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