Gall's law says that all working complex systems evolved from simpler systems that also worked. Containers and, in the following more significant step, Kubernetes, apply this law, growing sometimes complex systems over time. Yet, there are realistic chances of failing this evolution. So in this talk, I will share our lessons learned from many projects with different customers and industries and how we overcome over-engineering and manage technical debts. We will dig down on the natural appearing steps from container to container orchestration, how to take on uncertainties, tell you how you will fail for sure, and give you helpful tools and techniques on your hand to be successful.