I authored this book because dealing with intelligence, and the digital world is a passion for me and wanted to share my passion with you. In this book, I aim to provide compelling ideas and unique ways to increase, enhance, and deepen your digital intelligence and awareness and apply them to your organisation's digital journey particularly for modernisation and transformation initiatives. I used the architectural thinking approach as the primary framework to convey my message. Based on my architectural thought leadership on various digital transformation and modernisation engagements, with the accumulated wealth of knowledge and skills, I want to share these learnings in a concise book hoping to add value by contributing to the broader digital community and the progressing initiatives. Rest assured, this is not a theory or an academic book. It is purely practical and based on lessons learned from real enterprise transformation and modernisation initiatives taken in large corporate environments. I made every effort to make this book concise, uncluttered, and easy-to-read by removing technical jargons for a broader audience who want to enhance digital intelligence and awareness. Upfront, this book is not about a tool, application, a single product, specific technology, or service, and certainly not to endorse any of these items. However, this book focuses on architectural thinking and methodical approach to improve digital intelligence and awareness. It is not like typical digital transformation books available on the market. In this book, I do not cover and repeat the same content of those books describing digital transformations. My purpose is different. What distinguishes this book from other books is that I provide an innovative thinking framework and a methodical approach to increase your digital quotient based on experience, aiming not to sell or endorse any products or services even though I mention some prominent technologies which enable digital transformation, for your digital awareness, intelligence, and capabilities.