Risk quotes

“All warfare is based on deception.”

Strategy depends partly on managing what an opponent believes about intentions, strength, timing, and position rather than revealing every fact directly.

Source note: The Art of War, Chapter I “Laying Plans,” Lionel Giles translation (1910).

“At a great pennyworth pause a while.”

An unusually cheap offer deserves scrutiny because apparent savings can still produce a bad purchase when the buyer has no real need for it.

Source note: The Way to Wealth, frugality section; Project Gutenberg #43855. The maxim introduces Franklin’s distinction between apparent cheapness and genuine value.

“The better part of valour is discretion.”

Courage is balanced with judgment here: avoiding a needless danger can sometimes be wiser than performing bravery for appearance.

Source note: Act 5, Scene 4; Falstaff reframes survival as a form of judgment.

“Fools rush in where angels fear to tread.”

The line warns that confidence without judgment can push people into situations that more thoughtful people approach cautiously.

Source note: An Essay on Criticism, Part III; Pope warns against reckless confidence and poor judgment in critics.

“Tell the truth or trump—but get the trick.”

The joke turns moral advice into card-table strategy, making the line funny precisely because truth and tactical winning are compressed into one impossible-sounding rule.

Source note: Pudd’nhead Wilson, Chapter I epigraph; one of the fictional Calendar maxims Twain places before the chapter.

“Nothing noble can be performed without danger.”

Avoiding every danger can also prevent worthy action; prudence needs to distinguish reckless exposure from risks that meaningful conduct sometimes requires.

Source note: Essays of Montaigne, Book I, Charles Cotton translation, in a discussion of distrust, security, and princely conduct.

“The least outlay is not always the greatest gain.”

Trying to minimize immediate cost can create a worse result when skill, care, or professional competence is what the task actually requires.

Source note: Moral printed after “The Widow and the Sheep”; the widow injures the sheep while trying to avoid the shearer’s expense.

“Many have been ruined by buying good pennyworths.”

A low price does not make a purchase beneficial when the item is unnecessary or when buying it leaves too little for more important needs.

Source note: The Way to Wealth, frugality section; Project Gutenberg #43855. “Pennyworth” refers to an apparent bargain and the warning is about false economy.

“Few places in this world are more dangerous than home.”

Muir uses deliberate provocation to challenge exaggerated fear of wilderness by comparing mountain risk with dangers accepted without notice in ordinary life.

Source note: The Mountains of California; the surrounding paragraph discusses hazards in the mountains and fear of leaving home.

“men with common minds seldom break through general rules.”

The travel reflection criticizes automatic conformity, suggesting that ordinary caution can keep people from testing whether a rule still makes sense in a particular situation.

Source note: Letters Written During a Short Residence in Sweden, Norway, and Denmark, Letter I; Wollstonecraft comments on a sea captain’s reluctance to depart from customary practice.

“He will win who knows when to fight and when not to fight.”

Judgment includes restraint: choosing the wrong contest can be as damaging as fighting badly once the contest begins.

Source note: The Art of War, Chapter III, among Sun Tzu’s listed essentials for victory.

“Happy is the man who learns from the misfortunes of others.”

Other people’s failures can become instruction when we pay attention to consequences before repeating the same mistake ourselves.

Source note: Moral printed after “The Lion, the Fox, and the Ass”; the fox changes his conduct after observing the ass’s fate.

“The credit belongs to the man who is actually in the arena.”

Roosevelt places greater moral weight on imperfect participation than detached criticism from safety.

Source note: Excerpt from the “Man in the Arena” passage, Paris, April 23, 1910.

“The thinker has to decide, to choose; and there is always a risk.”

Choosing among plausible interpretations necessarily involves uncertainty, so sound thinking requires a cautious selection that remains open to confirmation or correction by later events.

Source note: How We Think, Chapter VIII. The sentence concerns choosing the idea or principle relevant to a perplexing situation; the next clause says the prudent thinker selects warily, subject to later confirmation or frustration.

“It is hard to fail, but it is worse never to have tried to succeed.”

Roosevelt contrasts the disappointment of an unsuccessful attempt with the deeper loss of never attempting worthwhile work at all, making participation and effort more important than guaranteed success.

Source note: The Strenuous Life, speech before the Hamilton Club, Chicago, April 10, 1899; Project Gutenberg #58821. The sentence appears in Roosevelt’s opening argument for active effort and immediately follows his praise of the person who embodies “victorious effort”; it is preserved as historical motivational rhetoric rather than a promise that effort always produces success.

“We shall both be cautious and confident, and indeed confident because of our caution.”

Epictetus rejects confidence as recklessness: confidence becomes rational when caution is directed toward one’s own judgments and choices rather than toward externals that cannot be controlled.

Source note: Discourses, Book II, Chapter I, “That confidence (courage) is not inconsistent with caution,” George Long translation, Project Gutenberg #10661. The surrounding argument distinguishes confidence about externals from moral caution about how one uses one’s own will.

“There is a tide in the affairs of men which, taken at the flood, leads on to fortune.”

Brutus uses the tide metaphor to argue that judgment includes timing: opportunities can require action before circumstances change.

Source note: Julius Caesar, Act 4, Scene 3; Brutus argues for taking the current opportunity rather than waiting.

“Our doubts are traitors, and make us lose the good we oft might win, by fearing to attempt.”

Doubt becomes harmful when it stops useful action before reality has had a chance to test what might be possible.

Source note: Act 1, Scene 4; Lucio argues against letting fear prevent an attempt.

“Rapidity is the essence of war: take advantage of the enemy’s unreadiness, make your way by unexpected routes, and attack unguarded spots.”

Speed matters when it exploits a temporary opening; the point is timely movement into weakness, not haste without information or purpose.

Source note: The Art of War, Chapter XI “The Nine Situations,” Lionel Giles translation.

“October. This is one of the peculiarly dangerous months to speculate in stocks in. The others are July, January, September, April, November, May, March, June, December, August, and February.”

The list reveals that every month is dangerous, turning what sounds like seasonal financial advice into a satire on speculative risk and the false hope that timing alone makes gambling safe.

Source note: Pudd’nhead Wilson, Calendar epigraph; the stock-market joke follows the reflection on disagreeable people.