Digital transformation is creating a world where businesses must test new, exponential strategies while maintaining incremental business functions to keep the lights on. How can we manage this balance between old and new, and choose which path to modernization is right for us? To be prepared to lead our companies into the future, we need to increase our digital fluency. If we don’t, we risk becoming obsolete or worse, making critical mistakes that harm real people. We have to be digitally fluent so that we can speak and translate the language of the technologies—and technologists—shaping our livelihoods and organizations.