In the midst of the global, sharing, experience, connection, innovation, gig economy-an economy by many names in the transitioning of economic epochs-those in positions of organizational and state leadership and power face surprising new pursuits and perils. In a world where celebrity status and social media activity have become almost reflexive metrics of leadership prominence and visibility, we examine how three exemplars-Musk, Trump and Zuckerberg-have navigated organizational and individual challenges and rewards specifically around the use of social media. We explore how the proliferation in the forms and usage of social media, both as related to lines of business and means of communication, enhances leadership interconnections with constituents and stakeholders, facilitating literally terabytes of information flows, while endangering strategic and ethical transparency. The increase in what can be termed off-piste social media posts-those posts deliberately shocking or provoking readers and deviating from the conventional or expected-has been noted, as has the increase in careful orchestration of highly groomed and curated online images. Analyzing pivotal blunders by each exemplar, we highlight the juxtaposition of social media and global renown, on the one hand, against solecisms in ethics and actions, on the other hand, as powerful leaders of global institutions confront series of dilemmas.