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Regardless of project/planning methodology, having a ever-growing checklist of less-obvious estimation items is a simple way to avoid forgetting to consider them. The book "Software Estimation: Demystifying the Black Art" [1] by Steve McConnell contains a number of these.

Some examples:

  - Team or company meetings
  - Team member sick days, holidays, vacations
  - Bugs in third party software
  - Maintenance of previous systems
  - Maintenance of build automation
  - Demos
  - Interviews
  - ...
... or your own list of whatever other items you have historically forgotten, or tend to forget when estimating.

In the painting example, the moving of the furniture was something I overlooked, despite having made the effort to carefully think of all tasks. A estimation checklist built up from previous painting projects could have triggered me to consider this task.

[1] http://www.amazon.com/Software-Estimation-Demystifying-Devel...



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