Monitoring systems have not changed significantly in 20 years and has fallen behind the way be build software. Our software is now large distributed systems made up of many non-uniform interacting components while the core functionality of monitoring systems has stagnated. Furthermore, it is often people without expert knowledge of systems under observation that are responsible for monitoring and operating them. In this talk, we will explore how our current monitoring capabilities are failing us and discuss how we can build systems that are both reliable and observable while making our lives (or the lives of the people responsible for their operations in production) easier.