Almost 18 years have passed since Nassib Taleb conceived the Black Swan event. The Black Swan is a random event that lies outside the realm of expectation and has a significant impact and a surprising, and often deleterious effect. Black Swans can explain many consequential events in our world, while human beings tend to rationalize explanations of a Black Swan event after the fact. In recent years, Black Swans have increased due to globalization, digitization, and arising interconnectedness, interdependence, and complexity. Continuous news coverage of events around the world and information at our fingertips often amplifies information in ways that may lead to contagion or hysteria. The focus of this chapter is to develop better insights into Black Swan events in work environments. The COVID-19 global pandemic swiftly impacted many aspects of people’s lives globally. Geopolitics and violent hotspots have destroyed human lives, and economic systems. In technology, artificial intelligence continues to disrupt our world in real time. This chapter examines Black Swans in work environments and viable options for mitigation of their impact through building resilient organizational architectures, adaptation, responsiveness, and innovative risk management strategies.