| Summary: | The purpose of this article is to explore the fascinating similarities that can be found between the Renaissance era and nowadays. In both moments in time, the ways of doing of the era before, were no longer valid for the new challenges the world was having at that moment, and completely new solutions were required. There is an analysis of the Renaissance and Machiavelli and his leadership learnings about appearance, influence, honor and self-ambition, gloria or public recognition, structure and flexibility and about chaos as a trigger for change. Study on modern leaders like Barack Obama and Steve Jobs shows that there are important similarities between their leadership styles and Machiavelli’s learnings. However, where Machiavelli leaned on hierarchical power, modern leaders need to enhance his learnings with an orchestrated leadership style rather based upon Influence than power, more suitable for today’s environment. Nowadays, like at the beginning of the Renaissance, we appear to be again in a chaos situation marking a turning point to a new era, the transition to which demands increased flexibility carefully balanced with existing and new structures, until a new status-quo is created.
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