Estimates, especially for software projects, are highly inaccurate due to various challenges and laws of nature. It is difficult to provide confident estimates for tasks as simple as a person's age or as complex as the number of bugs in a project. Parkinson's Law and the Student Syndrome mean that people will naturally procrastinate and not finish work on time if given too much time. Estimates also become less accurate the more granular they are due to exponential aggregation error. Instead of relying on estimates, it is better to measure progress using techniques like story points, cycle time, and cumulative flow diagrams, and to break work down into smaller chunks with clear requirements.