Is it always better to take the initiative in political life and political struggle? Does it cohere with Machiavelli's advice throughout the book?

In my personal opinion, to take chances is always good advice. However, to just go out and make a daring political decision is simple ignorance, rather one should take bold action after thoroughly thinking out their course of action. For instance, a person hoping to become a politician in the American system shouldn't (and can't) go out and mindlessly campaign; buying expensive time slots in a market that isn't truly one's target audience, make boundary pushing remarks about another candidate or the state of the constituency. To do this would be a waste of time, money, and opportunity. Instead, a well thought out course of action might bring about great results for both the individual running for office, or already in office, as well as the constituency. If a potential politician were to recognize a target audience and their needs, figure out a potential solution to these needs, and readily address the issues and communicating the potential politician’s message effectively, there may be a chance at victory. This victory may lead to a change of the entire realm of politics or even society as a whole- for the better. Taking chances can be an extraordinary thing for a political individual to do, it can lead to their rise in power, a benefit for society, and a change in the world for future generations.

Let's say some of the most respected politicians in history never took chances, what would have been the resulting world? For example, what if Obama decided in his own mind that he was too young to win the presidency or that his skin color would impede his progress in the political world? Had Obama not run for office, the current political landscape could be drastically different. There might not be the public option, a completion of an auto bailout that has helped some of those companies keep and create jobs, no rethought on Don't Ask Don't Tell, etc.

However, I believe that this section of Machiavelli's The Prince is in some ways a parachute for the entirety of his book. If one were to argue against any notion Machiavelli made, using an example of certain leader in a certain nation he could say that they only succeeded because of good fortune. Furthermore, I think he included this part in an effort to flatter Lorenzo de' Medici, by alluding to Medici that he has good fortune and is thus destined to succeed.