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Enterprises are often confronted with the “Cloud Paradox” when they move workloads to a cloud service provider. This paradox occurs when the benefits of cloud adoption that initially made it a compelling strategy become the cause of spiraling costs, stifling innovation, and making it difficult to repatriate workloads from the cloud. Azul Systems have published a Cloud Adoption Journey chart to help technology leaders understand the various challenges and pitfalls of cloud adoption before they can realize the value optimization of cloud computing. This article outlines several initiatives that can help IT leaders avoid getting stuck in the Cloud Paradox and move further along the curve to realize the true benefits of cloud adoption.