Overcome the Planning Fallacy

• The next time you find yourself struggling to estimate, ask: How much time and effort have similar tasks required in the past?
• Schedule buffer time: Keep in mind that there will always be factors outside of your control, and moreover, you may very well be overestimating your capabilities.
• Commit early and publicly: Give yourself a little bit of external commitment pressure in order to not leave all of your work to the last minute.
• Assume the worst: Start by imagining what will go wrong before it actually does. By doing so, you’ll be better able to foresee potential (if unlikely) issues. And you’ll be equipped to develop a suitable backup plan as a preventative measure.

Research shows that we often underestimate the time and obstacles involved in completing a task even when it directly contradicts our past experiences.

This can be explained by our optimism bias — our natural tendency to believe that the future will somehow be be...