Quote Atlassourced quotes & context
20 quotations

Risk quotes

Explore Risk quotations through starting and direction, effort and consistency, setbacks and feedback. Compare how different writers frame the idea across distinct works and periods.

Start here

Four ways into this risk collection

20 shown
Source identified1
All warfare is based on deception.

“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 details

The Art of War, Chapter I 'Laying Plans,' section 18, Lionel Giles translation (1910), original scan leaf 62. 'All warfare is based on deception' begins Giles's section 18 before the examples of seeming unable, inactive, near or far. This remains translation-mediated ancient military strategy, not generic business, relationship or current operational advice.

Source identified2
At a great pennyworth pause a while.

“At a great pennyworth pause a while.”

Voice: Authorial persona / framed maxim · Poor Richard maxim, repeated through Father Abraham

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 details

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

Source identified3
The better part of valour is discretion.

“The better part of valour is discretion.”

Voice: Fictional character · Falstaff

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

Source details

Henry IV, Part 1, Act V Scene 4; reviewed against the 1917 Yale Shakespeare edition edited by Samuel B. Hemingway, printed page 110 / scan leaf 124. Falstaff says 'The better part of valour is discretion' after counterfeiting death during the battle and immediately boasts that this discretion saved his life. It remains comic fictional self-justification rather than a universal rule for courage or risk.

Source identified5
Tell the truth or trump—but get the trick.

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

Voice: Epigraph / fictional source voice · Pudd’nhead Wilson’s Calendar

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 details

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

Source identified6
Nothing noble can be performed without danger.

“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 details

Essays of Montaigne, Book I, Chapter XXIII, ‘Various Events from the Same Counsel,’ Charles Cotton translation edited by William Carew Hazlitt (1877); Project Gutenberg Volume 04 #3584 / Complete Essays #3600. Montaigne argues that excessive security-minded distrust can destroy the courage required for noble action; the reviewed direct evidence is the matching Wikisource chapter transcription.

Source identified7
The least outlay is not always the greatest gain.

“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 details

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

Source identified8
Many have been ruined by buying good pennyworths.

“Many have been ruined by buying good pennyworths.”

Voice: Authorial persona / framed maxim · Poor Richard maxim, repeated through Father Abraham

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 details

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

Source identified9
Few places in this world are more dangerous than home.

“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 details

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

Source identified10
men with common minds seldom break through general rules.

“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 details

Letters Written During a Short Residence in Sweden, Norway, and Denmark, Letter I; represented Cassell & Company 1889 text in Project Gutenberg #3529, preserving Wollstonecraft’s 1796 travel-letter work. After describing the customary maritime rule against sending out a boat, Wollstonecraft says that “men with common minds seldom break through general rules” while criticizing the captain’s reluctance to depart from convention. This is a first-person travel judgment about a particular situation, not a general empirical claim about ordinary people.

Source identified11
He will win who knows when to fight and when not to fight.

“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 details

The Art of War, Chapter III “Attack by Stratagem,” section 17, Lionel Giles translation (1910), printed page 24 / scan leaf 80 in the original Giles edition on Wikisource, cross-checked against Project Gutenberg #17405. “He will win who knows when to fight and when not to fight” is the first of five listed military essentials for victory; it remains battlefield-strategy judgment rather than a context-free maxim about every disagreement.

Source identified12
Happy is the man who learns from the misfortunes of others.

“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 details

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

Source identified13
The credit belongs to the man who is actually in the arena.

“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 details

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

Source identified14
The thinker has to decide, to choose; and there is always a risk.

“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 details

How We Think (1910), Chapter VIII, “Judgment: The Interpretation of Facts,” section 1, printed page 106, Project Gutenberg #37423. Dewey says the thinker must choose among candidate meanings for a perplexing situation and therefore accepts risk; the prudent thinker selects warily and remains answerable to later confirmation or frustration. This is part of Dewey’s historical educational/logical account of reflective judgment, not a modern decision-science finding.

Source identified15
It is hard to fail, but it is worse never to have tried to succeed.

“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 details

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.

Source identified16
We shall both be cautious and confident, and indeed confident because of our caution.

“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 details

Discourses of Epictetus, Book II, Chapter I, “That confidence (courage) is not inconsistent with caution,” George Long translation; 1877 George Bell & Sons witness on Wikisource, cross-checked against Project Gutenberg #10661. Epictetus distinguishes confidence toward externals from moral caution in the use of one’s own will.

Source identified17
There is a tide in the affairs of men which, taken at the flood, leads on to fortune.

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

Voice: Fictional character · Brutus

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

Source details

Julius Caesar, Act IV, Scene 3, in the 1919 Yale Shakespeare edition edited by Lawrence Mason. Brutus argues for marching to Philippi and compares opportunity to a tide that must be taken at the flood; the metaphor belongs to a disputed military decision inside the play rather than a context-free guarantee of success.

Source identified18
Our doubts are traitors, and make us lose the good we oft might win, by fearing to attempt.

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

Voice: Fictional character · Lucio

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

Source details

Measure for Measure, Lucio to Isabella. The retained modern locator is Act I, Scene 4; the represented 1623 First Folio witness, reviewed through the 1910 Methuen facsimile transcription on Wikisource, labels the same scene Act I, Scene V (Scena Quinta). Lucio urges Isabella to test her ability to plead for Claudio rather than let doubt prevent the attempt. This is fictional dramatic speech, not Shakespeare speaking autobiographically or a universal psychological law.

Source identified19
Rapidity is the essence of war: take advantage of the enemy’s unreadiness, make your way by unexpected routes, and attack unguarded spots.

“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 details

The Art of War, Chapter XI 'The Nine Situations,' section 19, Lionel Giles translation (1910), original scan leaf 178 / printed page 122. 'Rapidity is the essence of war' introduces the instruction to exploit unreadiness, unexpected routes and unguarded positions; it remains historical battlefield strategy, not current operational guidance.

Source identified20
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.

“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.”

Voice: Epigraph / fictional source voice · Pudd’nhead Wilson’s Calendar

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 details

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

Topic guide

A quick guide to risk

Achievement language is strongest when it connects motivation with specific behaviors: starting, practicing, persisting, choosing standards, and learning from results.

Reading lenses

Starting and directionEffort and consistencySetbacks and feedbackStandards, patience, and useful work

How to use this page

Use the quotations to compare approaches to effort rather than as guarantees of success. The useful question is what a line changes about the next decision, not how intense it sounds.

Choose the lens that matches what you are looking for, then open a quotation for its source and context.

Browse by reading angle

Choose a way into these risk quotes

These routes are drawn from the quotations loaded on this page and are meant as starting points, not extra topic labels.

Short & memorable

Concise lines for readers who want the core idea without a long passage.

  1. “All warfare is based on deception.” — Sun Tzu · The Art of War — Laying Plans
  2. “At a great pennyworth pause a while.” — Benjamin Franklin · The Way to Wealth
  3. “The better part of valour is discretion.” — William Shakespeare · Henry IV, Part 1
  4. “Fools rush in where angels fear to tread.” — Alexander Pope · An Essay on Criticism
  5. “Tell the truth or trump—but get the trick.” — Mark Twain · Pudd’nhead Wilson’s Calendar

Reflective & philosophical

Quotations connected with deeper interpretation, perspective, philosophy, or sustained thought.

  1. “All warfare is based on deception.” — Sun Tzu · The Art of War — Laying Plans
  2. “The better part of valour is discretion.” — William Shakespeare · Henry IV, Part 1
  3. “Fools rush in where angels fear to tread.” — Alexander Pope · An Essay on Criticism
  4. “Tell the truth or trump—but get the trick.” — Mark Twain · Pudd’nhead Wilson’s Calendar
  5. “Nothing noble can be performed without danger.” — Michel de Montaigne · Essays of Montaigne — Book I

Practical & action-oriented

Lines connected with action, discipline, effort, habits, work, or perseverance.

  1. “Nothing noble can be performed without danger.” — Michel de Montaigne · Essays of Montaigne — Book I
  2. “He will win who knows when to fight and when not to fight.” — Sun Tzu · The Art of War — Attack by Stratagem
  3. “The credit belongs to the man who is actually in the arena.” — Theodore Roosevelt · Citizenship in a Republic
  4. “It is hard to fail, but it is worse never to have tried to…” — Theodore Roosevelt · The Strenuous Life
  5. “We shall both be cautious and confident, and indeed confident because of our caution.” — Epictetus · Discourses of Epictetus

Growth through difficulty

Material about failure, adversity, recovery, resilience, or learning from pressure.

  1. “Nothing noble can be performed without danger.” — Michel de Montaigne · Essays of Montaigne — Book I
  2. “He will win who knows when to fight and when not to fight.” — Sun Tzu · The Art of War — Attack by Stratagem
  3. “Happy is the man who learns from the misfortunes of others.” — Aesop · Aesop’s Fables — The Lion, the Fox, and the Ass
  4. “The thinker has to decide, to choose; and there is always a risk.” — John Dewey · How We Think
  5. “It is hard to fail, but it is worse never to have tried to…” — Theodore Roosevelt · The Strenuous Life

Earlier sources

Older works represented in the collection, useful for comparing how the topic changes across time.

  1. “All warfare is based on deception.” — Sun Tzu · The Art of War — Laying Plans
  2. “At a great pennyworth pause a while.” — Benjamin Franklin · The Way to Wealth
  3. “The better part of valour is discretion.” — William Shakespeare · Henry IV, Part 1
  4. “Fools rush in where angels fear to tread.” — Alexander Pope · An Essay on Criticism
  5. “Tell the truth or trump—but get the trick.” — Mark Twain · Pudd’nhead Wilson’s Calendar
Authors and sources

Who speaks here, and which works are represented?