This week's email draws from a conversation I had with my Dad, a mechanical engineer, about project estimations.

When I was learning the challenges of time estimates as a software engineer, I came across the tactic of "make a good faith estimate, then double it." I loved it. It made my estimates more reasonable and I found joy in acknowledging the chaos of our day to day lives.

During a holiday visit home, I shared this technique with my Dad and he raised the bar. He mentioned the "Rule of Pi" used in his work: multiply any estimate by 3.14. My mind was blown, first because it drove home that humans have always struggled with estimates no matter the work, second because tripling an estimate is... a lot (though I respected the more scientific vibe).

Fast-forward a bit, I found myself in a large and vague planning project at Trulia. We were told, "the deadline can be flexible, but delivery has to be precise." I pulled π out of my pocket.

Of course, "flexible" turned out to have its limits. It was nerve-wracking being the one providing the longest timelines for work. We had a massive whiteboard with every team's deadlines, and my team's dates were in months and everyone else's were in weeks.

This sparked some productive conversations around confidence and a project filled with unknowns. Ultimately, these discussions were beneficial, and we found a reasonable footing, despite initial discomfort. The big win though was that the ice was broken with the "Rule of Pi" and I'd seen what it could do.

Bargaining is inevitable in planning. Setting the initial anchor healthily can alter the planning discourse and the eventual perception of success. The same outcome can be viewed as a total failure or resounding success based on the context.

The ending to the Trulia story is that the entire project got totally changed halfway through, and none of that planning actually mattered. Can't win them all.