Migrating databases presents both exciting opportunities and significant challenges, often taking longer than expected or resulting in incomplete transitions due to differing stakeholder goals. To navigate this process effectively, it is crucial to address five key questions: prioritizing between data consistency and availability, understanding each application's tolerance for downtime, deciding between an all-at-once or phased migration approach, determining the urgency of the migration timeline, and clarifying roles and responsibilities within the project. By tackling these considerations, organizations can avoid common pitfalls and achieve a smooth transition to a new database, potentially with the aid of specialized tools and expert guidance, such as those available for migrations to CockroachDB.