Building complex systems often requires simplicity in components—a lesson the Istio project has learned throughout its seven(plus)-year journey. Although Istio offers a lot of powerful features for application networking, crucial for many organizations, the path to maturity and broader adoption was fraught with challenges. In this talk, we explore the key mistakes made during Istio's development, including its initially complex architecture, an overload of features, premature release of version 1.0, difficulties faced by contributors, and delays in joining the CNCF. We will discuss the impact of these mistakes, how these missteps were addressed, and how they have positioned Istio as a leader in the service mesh market. This presentation will detail how Istio's evolution reflects a shift towards simpler, more modular components that together offer effective solutions for managing APIs and service-to-service communication regardless of platform.