Kubernetes has evolved from a buzzword to a standard platform for microservices, prompting many organizations to consider migrating from legacy systems to this cloud-native technology due to its scalability and flexibility. This article delves into the initial stages of planning such a migration, emphasizing the importance of defining clear goals and outcomes to avoid common pitfalls. A successful migration begins with a thorough assessment of existing technologies and an understanding of the organization's readiness for change, including budgetary considerations and knowledge gaps. Organizations must decide whether to perform a lift-and-shift, refactor, or completely re-architect their systems, factoring in the complexity of existing homegrown tools. The article highlights the significance of preparing for the learning curve associated with Kubernetes and suggests leveraging external advisors and resources to ensure a smooth transition. Defining key performance indicators (KPIs) and benchmarks is crucial to measuring the success of the migration project, which will be further explored in subsequent posts focusing on practical implementation steps.