One of the biggest “oh noes” in the book for me is when estimations are wanted for work that already has a timeline and scope seemingly out of my control. All to often these kinds of projects feel doomed to fail, or at best a gamble. After reading a stream of different view points on this topic I decided to stop and reflect on myself. Why do I feel this way when a project takes this form?

The first thing I thought to myself is this pattern has failed in the past; however, that alone didn’t feel like the true heart of the issue. After digging more into my thoughts I realized it’s the feelings of defeat that accompany the failure. I have experienced plenty of defeating moments in the past, and none of them ever seem to feel as terrible. Why?

I believe it’s because during these estimations you begin to convince yourself into having a solution to resolve any disconnect between the scope and timeline given. As work progresses and the solution you had in your mind begins to reveal things you hadn’t planned for you can start to feel trapped. Shamed by missing these holes in your plan you begin to work harder, and longer at getting done in time. At the end, when and if the work misses it’s deadline you’re left believing it was solely your own fault for not being able to make it happen.

I hope in the future to remember this and not become a victim of my own optimism.