The challenges of getting data and applications into the cloud are often not just technological, but also require changes in mindset and processes. This is because legacy procedures can produce legacy results, hindering digital transformation. To achieve success, it's essential to adopt new approaches and ways of thinking that allow for a smooth transition. Experience and perspective from experts like Mark Porter and Michael Ljung are crucial in guiding organizations through this process. By taking a step back and focusing on incremental delivery, automation, and agile methodologies, organizations can overcome the challenges of cloud migration and achieve digital transformation done right.