Risk is action’s price.
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 - (The Prince)
Safety is an illusion, Machiavelli suggests, so the wise person stops trying to escape risk and learns to weigh it. Every path, including standing still, carries a price, and someone who refuses to choose has only picked a danger they can't see. Prudence becomes a skill of judgment: study the odds, accept the lesser evil, then commit instead of dithering. The preference for bold mistakes over timid ones echoes the late chapters of The Prince, where he argues that fortune tends to favor the daring over the cautious. The wording here is a modern paraphrase of those themes rather than a single verbatim sentence, so it is best read as a summary of his outlook.
It rests on his habit of looking at the world as it is, not as we wish it were. Hoping for a risk-free road is a comforting fantasy, and he distrusts comforting fantasies.
Today, imagine someone stuck in a steady but stagnant job who dreams of changing careers. Waiting for certainty means the years slip by quietly. Following Machiavelli, they would calculate: save several months of expenses, talk to people in the new field, take a course, set a date. Then they would actually apply, accepting that staying put was a risk too.