There is nothing more difficult to take in hand, more perilous to conduct, or more uncertain in its success, than to take the lead in the introduction of a new order of things.

Machiavelli makes this observation in the early chapters of *The Prince* while discussing “new principalities” and the hazards faced by a ruler who tries to found or reform a political order. Writing after the upheavals of late‑15th- and early‑16th‑century Italy—foreign invasions, shifting alliances, and the fall and restoration of regimes in Florence—he had seen how reforms provoke entrenched interests. The line reflects his practical, unsentimental analysis of power: innovators face resistance from those who benefit from the old order, while potential beneficiaries of the new order often support it only weakly until success is assured.

The quote argues that initiating systemic change is uniquely dangerous because it creates enemies immediately and allies only conditionally. Those invested in existing arrangements will fight to preserve their advantages, while those who might gain from reform hesitate, doubting whether the reformer can prevail. Machiavelli’s point is less moral than strategic: the reformer must anticipate hostility, uncertainty, and the fragility of early support, and must therefore rely on decisive leadership, force, and institutional consolidation. The line has become a classic statement about the political and organizational costs of innovation and reform, emphasizing that “better” ideas do not automatically translate into stable outcomes.

1) “There is nothing more difficult to plan, more doubtful of success, nor more dangerous to manage, than the creation of a new system.”
2) “It must be considered that there is nothing more difficult to carry out, nor more doubtful of success, nor more dangerous to handle, than to initiate a new order of things.”
3) “There is nothing more difficult to execute, nor more dubious of success, nor more dangerous to administer, than to introduce a new order of things.”