Paradoxes are an inevitable part of life. The relationship between paradox and the paradox of inquiry is presented. Next, the role of chaos is analyzed, as also documented through an experiment that chaos instigates creativity. Comparing two firms, one orderly, the other in chaos, it appears that, paradoxically, the chaotic firm had more patents and published more papers than the stable one. These chaos-to-order inspirations prompted leaders to facilitate connections, colocation, inclusion, and working together. Dee Hock, the founding CEO of Visa International, coined the name “chaordic era”. Chaos and synchronization are closely related. The paradox is that probably only unorganized, chaotic systems can generate higher-order synchronization (e.g., blinking fireflies, self-organizing V-shaped flocks of birds, or strangers in an audience eventually catching a common clapping rhythm). Artificial intelligence (AI) paradoxes are mentioned (e.g., Moravec’s paradox: for AI, the hard problems are easy, and the easy problems are hard). Other examples: On the one hand, AI aims to increase automation; on the other hand, it also requires more human involvement to reflect on the insights generated (automation paradox). AI generates job losses; however, it also creates new jobs (e.g., providing the support systems for those newly unemployed: the transition paradox)