Checkpoints define moments of awareness and decision. Checkpoints help you pop your head up from what you are doing, and decide whether you should continue along your current path, or switch to a new one.

Checkpoints are pre-defined—you create them ahead of time—based on a trigger condition. To be effective, the trigger condition should be objective and easily recognizable.

Trigger Conditions

Common trigger conditions include:

  • Time
    When a specific time occurs, or after a specific duration.
  • Progress
    After a specific, measurable amount of progress has been made: words written, miles run, dollars earned.
  • Events
    At the start or end of a specific event.
  • People
    Once someone arrives, leaves or contacts you.
  • Resources
    After a resource runs out & needs replenishing: battery power, cash.

If the trigger is not easy to measure and recognize quickly, then it’s not an effective trigger. Subjective measures of progress, or resources whose level requires effort to calculate make poor triggers, since it’s unclear when they apply, and it’s hard to do quick checks to see if they’ve been triggered.

A Default Condition & A Question

An effective checkpoint has a default path. Checkpoints are not forks-in- the-road, where you are forced to decide the way forward.

When defining your checkpoint, decide on a default path and a question to ask yourself to decide whether you should deviate from this path.

For instance, the end time of a time block serves as a checkpoint, if you are not yet done with the task.

The default path is to switch to the next task. The question to ask yourself is: is the task I am currently working on more important than my next task?

If so, then deviate from your default path and continue working on your current task. Otherwise, follow the default path: put your current task aside and switch to working on the next task.

Forging a New Path

You don’t need to decide on your alternate path upfront, only your default path. Use checkpoints as a way to confirm your execution plan still makes sense, or whether you need to re-evaluate.

For example, if writing the first draft of a book, at the end of the chapter, you may set yourself a checkpoint: does the outline still make sense?

If so, continue writing the next chapter; otherwise, stop writing and return to the outline and decide how to change it.

Use checkpoints when you have a tendency to go down rabbit holes with a task, losing track of time or hitting the point of diminishing returns. They can give you enough awareness to stop yourself before you go too far.