All courses of action are risky, so prudence is not in avoiding danger (it's impossible), but calculating risk and acting decisively. Make mistakes of ambition and not mistakes of sloth. Develop the strength to do bold things, not the strength to suffer.

A prince, therefore, must not mind incurring the charge of cruelty for the purpose of keeping his subjects united and confident; for, with a very few examples, he will be more merciful than those who, from excess of tenderness, allow disorders to arise, from whence spring murders and rapine; for these as a rule injure the whole community, while the executions carried out by the prince injure only one individual. And of all princes, it is impossible for a new prince to escape the name of cruel, new states being always full of dangers.

...it behooves us to adapt oneself to the times if one wants to enjoy continued good fortune.

Rome remained free for four hundred years and Sparta eight hundred, although their citizens were armed all that time; but many other states that have been disarmed have lost their liberties in less than forty years.

Nevertheless, he must be cautious in believing and acting, and must not inspire fear of his own accord, and must proceed in a temperate manner with prudence and humanity, so that too much confidence does not render him incautious, and too much diffidence does not render him intolerant. From this arises the question whether it is better to be loved more than feared, or feared more than loved.

One should never allow chaos to develop in order to avoid going to war, because one does not avoid a war but instead puts it off to his disadvantage

In truth, there never was any remarkable lawgiver amongst any people who did not resort to divine authority, as otherwise his laws would not have been accepted by the people; for there are many good laws, the importance of which is known to be the sagacious lawgiver, but the reasons for which are not sufficiently evident to enable him to persuade others to submit to them; and therefore do wise men, for the purpose of removing this difficulty, resort to divine authority.