For most people, a someday/maybe list is simply a shadow inbox. It’s a place to collect (but not process) the cruft of your wishful but unwilling mind.

If you’re someone that keeps up with someday/maybes, you probably do it in a text file, OmniFocus, or any of the hundreds of other electronic task systems available.

Good luck with that.

Someday/maybes don’t fit well in linear task systems because linear task systems flow top to bottom. They presuppose order and priority.

In every other corner of my linear system (OmniFocus), projects and single actions have clear entry and exit points. Someday/maybe items rarely lend themselves to entry, exit, or even action. (If they did, they wouldn’t be on a someday/maybe list.)

And so by listing non-actionable, single points of thought in a linear fashion, I’ve found that there’s little chance I’ll ever act on them.

Someday/maybes need help before they can morph into projects. They require a special type of processing that involves introspection and, especially, a creative, pattern-seeking mindset.

You’re talking. Listen.

The veins of gold in someday/maybes are the invisible connectors between the data points dropped by your restless, wanting mind.

Instead of keeping a someday/maybe list in a linear task management program like OmniFocus, I maintain someday/maybe mind maps.

I find that it’s much easier to uncover patterns and relationships when I can rearrange ideas and see how they form a mosaic of my mind’s wants.

Individual pieces of written thought on a someday/maybe list are less important than the why behind their existence. It’s the difference between looking at single data points and the story those data points tell in a chart.

Someday/maybe mind maps are simply a means of listening to the story you’re trying to tell yourself. They’re a cognitive bridge.

When you focus on stories instead of syllables, you’ll probably discover that your someday/maybes can be executed in batch. Perhaps that trip you’ve always wanted to take to Paris can be combined with a goal to learn French, write more, or take cooking classes.

Look for ways to bundle ideas, and try to mix the fun stuff with the business stuff.

Tools for cognitive cartography

iThoughts is still my favorite mobile mind map app because it uses Dropbox to stay in sync between my iPad, iPhone, and Mac. The interface of iThoughts is awesome, but it’s really the ubiquity of my maps via iThoughts that make it such a useful app.

After using Freemind on my Mac for some time now, I've started warming up to Mindnode Pro, which feels snappier and more agile on the screen. Mindnode works well regardless of window size, but full screen view in Lion is truly its sweet spot, in my opinion. The visual elegance is inspiring in itself.

Whatever system you use to manage someday/maybes, it will work best if it’s

  • nonlinear,
  • doodle-friendly,
  • portable,
  • visited often,
  • easy to use, and
  • fun to use.

You can still use OmniFocus (or other) inbox to collect items for your someday/maybe maps. Remember that step 1 is still get it down.

But the next time you find something in your inbox that seems like an action but is too abstract or forward-looking to act on, try putting it on your someday/maybe map. It could be the data point you’ve been waiting for.