Want to know the single biggest problem with every single GTD system in existence? They don’t enforce specificity when defining a task. Tasks, (unlike checklists which can be semantically reduced to a single word  – “milk”), require, demand, beg for as much specificity as you can muster.

What catches most people, most of the time, is that our To Do lists are a mix of things we’ve done countless times before and already know how to do because we’ve internalized their details, and things we’ve never done before.

  • clean house.
  • take out garbage cans.
  • add Twilio to mySuperDuperWebApp.
  • SuperBowl prep.

We hit Item 3 like a mountain bike hitting a tree as high speed. Thud. Item 3 is like just about every single one of hundreds of startup tasks – is not something we’ve done before. We need to query it and break it down into things we do have experience with:

  • clean house.
  • take out garbage cans.
  • add Twilio to mySuperDuperWebApp by
    1. Reread Twilio API,
    2. Review Twilio Rails examples:
    3. Review this Rails example:
    4. Check StackOverflow for questions tagged with ruby-on-rails or ruby-on-rails3 and Twilio.
    5. Setup a testbed app
  • SuperBowl prep.

Whether you do that breakdown into things you do know how to do when you make your list or when you’re doing your list is up to you. But you’ll find the process easier if you mark those items (I use !!!) when you’re creating your tasks – to remind you that here there be dragons.