It ought to be remembered that 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
Written byNiccolò Machiavelli1469–1527 · Florentine diplomat, historian & political theorist
This is genuine Machiavelli — The Prince, chapter VI, written around 1513 and first printed in 1532, five years after his death. The exact English wording you are quoting is W. K. Marriott’s 1908 translation, confirmed word-for-word in the scanned Marriott edition on Wikisource and in Project Gutenberg’s text of it.
“It ought to be remembered that 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” Niccolò Machiavelli, The Prince, ch. 6, trans. W. K. Marriott (1908); Italian original c. 1513, first published 1532. · Verbatim: “And it ought to be remembered that 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.”
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Provenance
The source
Work
The Prince (Il Principe)
Chapter
Chapter VI — Concerning new principalities which are acquired by one’s own arms and ability
Written · published
Composed c. 1513 · first published 1532
Translation
W. K. Marriott, 1908 (J. M. Dent & Sons, London; E. P. Dutton, New York)
And it ought to be remembered that 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. Because the innovator has for enemies all those who have done well under the old conditions, and lukewarm defenders in those who may do well under the new. This coolness arises partly from fear of the opponents, who have the laws on their side, and partly from the incredulity of men, who do not readily believe in new things until they have had a long experience of them.
Chapter VI
Note the opening word. Machiavelli’s sentence begins “And it ought to be remembered…” — the circulating quotation drops the conjunction. The Italian behind it reads “non è cosa più difficile a trattare, nè più dubbia a riuscire, nè più pericolosa a maneggiare, che farsi capo ad introdurre nuovi ordini.”
The Italian original of the sentence sits in chapter VI and reads “non è cosa più difficile a trattare, nè più dubbia a riuscire, nè più pericolosa a maneggiare, che farsi capo ad introdurre nuovi ordini” — Italian Wikisource, Il Principe, Capitolo VI ↗.
The familiar English is William K. Marriott’s: the Wikisource index for the scanned edition ↗ records the translator (1847–1927) and the year 1908, and the proofread chapter VI carries the sentence word for word.
Machiavelli’s Italian text, first published in 1532, has been in the public domain for centuries. The rights question that actually matters here is the translation: this exact English wording is W. K. Marriott’s, first published in 1908 ↗ — comfortably before the 1931 United States cutoff — so the translation is public domain in the US, and Project Gutenberg distributes it on that basis ↗. A modern translation of the same sentence would not be free to reuse.
Rights status is our research, not legal advice — and copyright varies by country and edition. For commercial or published use, confirm with the rightsholder. See terms.
Fact-check
What goes wrong with this one
The rare case where a famous Machiavelli line is genuinely his. What travels badly is not the attribution but the wording, the date, and the missing first word.
✕
The EnglishWhichever translator you are actually quoting Translation
Machiavelli wrote in Italian. The sentence you see quoted is one translator’s English — W. K. Marriott’s, published in 1908 — rendering “non è cosa più difficile a trattare, nè più dubbia a riuscire, nè più pericolosa a maneggiare” ↗. Other English editions in wide circulation say “carry out,” “dangerous to handle” and “doubtful of success” instead. Quoting the words as Machiavelli’s own is a small fiction; they are Marriott’s.
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The missing first wordQuotation collections Clipped
The sentence in the book begins “And it ought to be remembered…” — it continues an argument rather than opening one. The scanned Marriott text ↗ carries the conjunction; the circulating quotation almost always drops it.
By associationMachiavelli’s wider reputation Context
Machiavelli is a fake-quote magnet: “the end justifies the means” and “keep your friends close, and your enemies closer” are both catalogued among things he did not write ↗. This passage is not one of them — it is on the page, in the book.
✓The thought and the sentence are genuinely Machiavelli’s, in The Prince, chapter VI — and the exact English you are quoting is W. K. Marriott’s 1908 translation ↗.
Context
Why the line stuck
Chapter VI is Machiavelli’s chapter on rulers who took power by their own ability rather than by luck or inheritance — his examples are Moses, Cyrus, Romulus and Theseus. The famous sentence is not a warning against ambition; it is a piece of arithmetic. Anyone imposing a new order inherits, on day one, every enemy the old order made comfortable, and gains only allies who are not yet convinced the new thing works.
That asymmetry is why the passage escaped political theory and became the standard epigraph for change management, product launches and reform programmes. It reads like modern strategy writing because it describes a structural problem rather than a Renaissance one — though it is worth remembering that Machiavelli’s solution in the same chapter is armed force, which the boardroom versions tend to leave out.
The innovator has for enemies all those who have done well under the old conditions, and lukewarm defenders in those who may do well under the new.
How many English versions are there?
The Prince has been translated into English many times, and this sentence is one of the passages where translators diverge most visibly. Marriott’s 1908 “take in hand … perilous to conduct … uncertain in its success” is the version that dominates online quotation; other widely circulated renderings say “carry out,” “dangerous to handle” and “doubtful of success,” and looser business paraphrases replace “a new order of things” with “a new system.”
All of them are the same Italian sentence: “non è cosa più difficile a trattare, nè più dubbia a riuscire, nè più pericolosa a maneggiare, che farsi capo ad introdurre nuovi ordini.” Which English words you attribute to Machiavelli therefore depends entirely on which translator you are actually quoting.
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1469–1527 · Florentine diplomat & political theorist
Machiavelli served the Florentine Republic as secretary to the Second Chancery and to the Dieci di Libertà e Pace, the council that ran diplomacy and war. When the Medici returned to power in 1512 the republic collapsed; he was dismissed, falsely implicated in a conspiracy against them, tortured, and released under a papal amnesty. The Prince was written around 1513 in that enforced retirement and was not published until 1532, five years after his death — so the most quoted political book in Europe is one its author never saw in print.
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Cite this
Cite this source
Niccolò Machiavelli, The Prince, trans. W. K. Marriott (London: J. M. Dent & Sons; New York: E. P. Dutton, 1908), chap. 6. Italian original composed c. 1513; first published 1532.
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Quotle.info. “Who really said ‘It ought to be remembered that 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’?” Last verified 6 Aug 2026. https://quotle.info/who-said/it-ought-to-be-remembered-that-there-is-nothing-more/