I am arguing that before you continue your journey to embrace the latest and greatest apps in the ERP Cloud and the data in it, that each of you should ask yourself a series of key questions that are designed to test and challenge your assumptions before you make costly decisions about Big ERP, Big Data, AI, and the rest of it. And this should concern you whether you run a hospital, a university, an insurance company, or a manufacturing plant in China producing iPhones and MacBooks from a sea of parts sourced and made as cheaply as possible world-wide. So, let me present you with current-state situation statements and pose some questions to test your readiness to accept as dogma the latest marketing line pushed by Big Tech. If you like, you can think of what I am presenting as propositions that are intended to make you think; that are designed to give you pause before committing to a path that takes you into a land of no easy return-or perhaps, of no return at all.