As software engineers we do trade-offs every day. We often need to pick between things like space vs time or budget vs scope. Or sometimes the amount of creative waste we can afford to have. And when we make the decision we need to be in full comprehension of both the upside and downside of a particular choice. In this talk we will discuss why our organization decided to move from Python to Java. We will go over each tradeoff we decided to do and the motivation behind it.