For in writing the Discourses, Machiavelli discovered a basic paradox: When it comes to liberty, nothing fails like success. The freer a society becomes, the more prosperous and more arrogant it becomes as well. Like ancient Rome or Renaissance Florence, it sows the seeds of its own servitude. Although self-government and liberty are the highest forms of political life, Machiavelli revealed that human nature also makes them the most unstable.34