A collection of quotes for entrepreneurs curated in October 2025 around a theme of managing doubt, fear, uncertainty, and stress.

Quotes for Entrepreneurs Curated in October 2025

I curate these quotes for entrepreneurs from a variety of sources and tweet them on @skmurphy about once a day where you can get them hot off the mojo wire. At the end of each month I curate them in a blog post that adds commentary and may contain a longer passage from the same source for context. Please enter your E-mail address if you would like to have new blog posts sent to you.

My theme for this month’s “Quotes for Entrepreneurs” is managing doubt, fear, uncertainty, and stress.

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“You could not prevent a thunderstorm, but you could use the electricity; you could not direct the wind, but you could trim your sail so as to propel your vessel as you pleased, no matter which way the wind blew.” Cora L. V. Hatch in an 1859 lecture

h/t Quote Investigator: “We Cannot Direct the Wind, But We Can Adjust the Sales” I like this quote because it encourages entrepreneurs to focus on what’s under their control.

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“The engineering challenge is determining how much imperfection a system can tolerate and still function robustly. Perfect is impossible and near-perfect is expensive. Experienced engineers design reliable cost-effective systems out of parts that are allowed to be as imperfect as possible.” Peter Holst

Engineering is as much a craft or a practice as a science. Much of the challenge is estimating and managing uncertain quantities.

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“Stress comes primarily comes from not taking action on something you have some control over. If something is causing me stress, that’s a warning flag. It means there’s something that I haven’t completely identified that is bothering me, and I haven’t taken any action on it. I find as soon as I identify it, and make the first phone call, or send off the first e-mail message, or whatever it is that we’re going to do to start to address that situation — even if it’s not solved — the mere fact that I am addressing it dramatically reduces my stress. Stress comes from ignoring things that you shouldn’t be ignoring.”

Jeff Bezos in Academy of Achievement Interview May-4-2001

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“The uncompromising attitude is more indicative of an inner uncertainty than a deep conviction. The implacable stand is directed more against the doubt within than the assailant without.” Eric Hoffer in “The True Believer“

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“The success of most things depends upon knowing how long it will take to succeed.” Montesquieu

One failure mode I see some teams fall into is to ask if a plan is working well before any effects might be observed. “I sent him an email this morning and he has not replied,” or “we gave them a demo yesterday and they have not gotten back to us,” or “we have been at it for a month and have not made much progress.”

You must allow enough time for actions have effects that lead to outcomes. If you don’t let your actions ripen, you end up vibrating with frustration and give up too early.

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“Worry is a playground for those with enough time to visit it.” George Murray

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“There are two kinds of scientific progress: the methodical experimentation and categorization which gradually extend the boundaries of knowledge, and the revolutionary leap of genius which redefines and transcends those boundaries. Acknowledging our debt to the former, we yearn, nonetheless, for the latter.” Academician Prokhor Zakharov (character in Sid Meier’s Alpha Centauri game)

This message is shown when a player gains “Nonlinear Mathematics technology.”

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“Our doubts are traitors, And make us lose the good we oft might win By fearing to attempt.” William Shakespeare in Measure for Measure (spoken by Lucio in Act 1, Scene 4)

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“Beware of endeavoring to become a great man in a hurry. One such attempt in ten thousand may succeed. These are fearful odds.” Benjamin Disraeli

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“I’d rather see folks doubt what’s true than accept what isn’t.” Frank A. Clark

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“The virtue of prosperity, is temperance; the virtue of adversity, is fortitude; which in morals is the more heroic virtue. […] Prosperity is not without many fears and distastes, and Adversity is not without comforts and hopes. […] Prosperity doth best discover vice, but adversity doth best discover virtue.” Francis Bacon in “Of Adversity“

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“In estimating, it’s the tasks you forget that kill the schedule, not the individual task estimates being off.” Andy Cargile (cited in “Walter’s Laws“)

I blogged about this in “Seven From Skip Walter’s Laws Of Software Development” and suggested, “Implementing a ‘pipe cleaner’ version of the project, small but containing enough requisite variety to give you an understanding of the full problem, is one way to prevent these oversights. A waterfall approach may find itself in an unrecoverable situation if the task that was overlooked occurs late in the development process but requires preparation or support earlier in the process (e.g. testing a certain operating mode for the software or hardware).”

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“Colocation facilities allows organizations to place their physical servers and networking equipment in a data center environment that provides power, cooling, security, and bandwidth. Think of it as specialized daycare.” Paul Kedrosky in “Data Centers“

Excerpt has been condensed for clarity. Colocation offers risk reduction in the same way that daycare does.

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“Design is the rendering of intent.

What we intentionally design can delight someone. It can also frustrate them.

We can change our rendering, with the intention to create more delight & less frustration.

When we do that, we’re designing the user’s experience.”

Jared Spool in a May-4-2018 tweet

This is a summary of Spool’s article “Design is the Rendering of Intent” (Dec-2013)

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“Nothing in life is to be feared. It is to be understood.” Marie Curie (1867 – 1934)

I have included it in this month’s roundup because it’s a good reminder to examine your doubts and fears and try to understand the mechanisms and causes behind events or outcomes you want to avoid or prevent. I cannot find an exact cite but have found it published as early as the 1940s in the The National Underwriter (1940), Ladies Home Journal (1944), Reader’s Digest (1944), The Camping Magazine (1945), and The Journal of the Indiana State Dental Association (1948).

“The road to perseverance lies by doubt.” Francis Quarles

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“We demand guaranteed rigidly defined areas of doubt and uncertainty.” Douglas Adams in “The Hitchhiker’s Guide to the Galaxy”

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“90% of the things I worry about never happen. Worrying works.” found on Reddit Anxiety Memes

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‘If I see the very same beginnings which have commonly ended in great calamities, I ought to act as if they might produce the very same effects. Early and provident fear is the mother of safety; because in that state of things the mind is firm and collected, and the judgment unembarrassed.” Edmund Burke in a speech on the petition of the Unitarians, House of Commons, May 11, 1793.

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“Strategy is the art of being temporarily wrong in pursuit of being eventually and surprisingly right.” Joe Burns

This reminds me of a quote by Neal Stephenson I collected in “Quotes For Entrepreneurs–May 2012”

“Any strategy that involves crossing a valley—accepting short-term losses to reach a higher hill in the distance—will soon be brought to a halt by the demands of a system that celebrates short-term gains and tolerates stagnation, but condemns anything else as failure. In short, a world where big stuff can never get done.” Neal Stephenson in “Innovation Starvation“

I shortened the Stephenson quote to: “Strategy is crossing a valley: accepting short-term losses to reach a higher hill in the distance.” Hill climbing is a tactic: take the gains that are in front of you.

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“In law, nothing is certain but the expense.” Samuel Butler

I cannot find a citation but it’s too good to leave out.

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“People prefer the certainty of misery to the misery of uncertainty.” Virginia Satir

“The certainty of misery is better than the misery of uncertainty.” Walt Kelly (From his comic strip Pogo).

I cannot find a citation for either but in my experience this is a very good rule of thumb. I think there is a corollary that applies to opaque solutions from AI tools. People would rather live with problems they understand than solutions that they don’t.

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“You find yourself away out in the midst of a vague dim sea that is shoreless, that fades out and loses itself in the murky distances; for you cannot discern the thin rib of embankment, and you are always imagining you see a straggling tree when you don’t. The plantations themselves are transformed by the smoke, and look like a part of the sea. All through your watch you are tortured with the exquisite misery of uncertainty. You hope you are keeping in the river, but you do not know. All that you are sure about is that you are likely to be within six feet of the bank and destruction, when you think you are a good half-mile from shore.”

Mark Twain “Life on the Mississippi” [Gutenberg]

More context:

“From Cairo to Baton Rouge, when the river is over its banks, you have no particular trouble in the night, for the thousand-mile wall of dense forest that guards the two banks all the way is only gapped with a farm or wood-yard opening at intervals, and so you can’t ‘get out of the river’ much easier than you could get out of a fenced lane; but from Baton Rouge to New Orleans it is a different matter. The river is more than a mile wide, and very deep—as much as two hundred feet, in places. Both banks, for a good deal over a hundred miles, are shorn of their timber and bordered by continuous sugar plantations, with only here and there a scattering sapling or row of ornamental China-trees. The timber is shorn off clear to the rear of the plantations, from two to four miles. When the first frost threatens to come, the planters snatch off their crops in a hurry. When they have finished grinding the cane, they form the refuse of the stalks (which they call bagasse) into great piles and set fire to them, though in other sugar countries the bagasse is used for fuel in the furnaces of the sugar mills. Now the piles of damp bagasse burn slowly, and smoke like Satan’s own kitchen.

An embankment ten or fifteen feet high guards both banks of the Mississippi all the way down that lower end of the river, and this embankment is set back from the edge of the shore from ten to perhaps a hundred feet, according to circumstances; say thirty or forty feet, as a general thing. Fill that whole region with an impenetrable gloom of smoke from a hundred miles of burning bagasse piles, when the river is over the banks, and turn a steamboat loose along there at midnight and see how she will feel. And see how you will feel, too! You find yourself away out in the midst of a vague dim sea that is shoreless, that fades out and loses itself in the murky distances; for you cannot discern the thin rib of embankment, and you are always imagining you see a straggling tree when you don’t. The plantations themselves are transformed by the smoke, and look like a part of the sea. All through your watch you are tortured with the exquisite misery of uncertainty. You hope you are keeping in the river, but you do not know. All that you are sure about is that you are likely to be within six feet of the bank and destruction, when you think you are a good half-mile from shore. And you are sure, also, that if you chance suddenly to fetch up against the embankment and topple your chimneys overboard, you will have the small comfort of knowing that it is about what you were expecting to do. One of the great Vicksburg packets darted out into a sugar plantation one night, at such a time, and had to stay there a week. But there was no novelty about it; it had often been done before.”

Mark Twain “Life on the Mississippi” [Gutenberg]

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“Calamity, n. A more than commonly plain and unmistakable reminder that the affairs of this life are not of our own ordering.”

Ambrose Bierce in The Devil’s Dictionary

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“There is something basically healthy about being confronted with an unflattering version of yourself and your worldview from time to time; to be asked to think of yourself or people like you as the bad guy.” Conor Fitzgerald “The Devil You Know“

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“The most believable opinions are those of people who

1. have repeatedly and successfully accomplished the thing in question, and
2. have demonstrated that they can logically explain the cause-effect relationships behind their conclusions.”

Ray Dalio in “Believability Weight Your Decision Making“

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“We must learn to love in the absence of illusions. We must try to live a just life in an unjust world. We must be willing to go on caring even when we are helpless to change things. Our best may not turn out to be good enough. Still it will have to do.” Sheldon Kopp in What Took You So Long? (1979)

This reminds me of the Stockdale Paradox:

“You must never confuse faith that you will prevail in the end—which you can never afford to lose—with the discipline to confront the most brutal facts of your current reality, whatever they might be.” James Stockdale

I devoted my April 2022 roundup of quotes for entrepreneurs to it. Here is a A more optimistic take (originally curated in August 2023)

“My son, everything works out in the end. If it didn’t, it’s because it hasn’t come to an end yet.” Fernando Sabino recounting a conversation with his father in “The Checkerboard”

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“We must not, in trying to think about how we can make a big difference, ignore the small daily differences we can make which, over time, add up to big differences that we often cannot foresee.” Marian Wright Edelman in “Families in Peril“

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“Focus on the look and feel of the setting. The way the light lays across things. Take it in like a shot from a movie. Notice the movement and speech of people or animals, the soundscape and overall ambiance. It’s just a little corner of the world where things are unfolding, and you’re not here. Maybe nobody is. When you do this, you might notice a certain lightness or simplicity arising. Things are more poignant. Everything seems less complicated, because it’s just stuff happening, not stuff happening to you.”

David Cain “How To See Things As They Are“

More context:

“I’m in the back room of a coffee shop right now, switching between writing and another mental exercise: pretending I’m not here.

I don’t mean I’m wearing a disguise, or hiding behind a potted plant. I’m doing a perspective-shifting practice that I’d recommend to anyone: now and then, wherever you are, look at the scene in front of you as though it’s happening without you.

From any seat, or standing spot, anywhere—in an office, a breakfast diner, a public square, a waiting room—see your surroundings just as they’d be if you weren’t here to see them.

Focus on the look and feel of the setting. The way the light lays across things. Take it in like a shot from a movie. Notice the movement and speech of people or animals, the soundscape and overall ambiance. It’s just a little corner of the world where things are unfolding, and you’re not here. Maybe nobody is.

When you do this, you might notice a certain lightness or simplicity arising. Things are more poignant. Everything seems less complicated, because it’s just stuff happening, not stuff happening to you.”

David Cain “How To See Things As They Are“

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“The decisive fact of 2025 is no longer AI’s plausibility–we know it works–but its consequences. Systems that we didn’t elect are now shaping what we see, what we decide, how fast we discover, and how our institutions manage uncertainty.

The urgent question is, “What novel forms of public good and public risk appear once it does?”

Colin Lewis in Turing 75 Years On

This has been true for any significant invention: the moldboard plow, water wheel, clock, printing press, steam engine, etc. They are transformative but bring mixed blessings: there is no gain without loss.

I am coming to the view that AI is a misnomer. Computers provide tireless clerical labor, simple rules applied on demand.

An algorithm getting a “better idea” rarely, if ever, ends well unless it’s reviewed and approved by a human in the loop. And yet everyone wants to be the sorcerer’s apprentice, ignoring how poorly that worked out for the hapless novice.

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“No human being is constituted to know the truth, the whole truth, and nothing but the truth; and even the best of men must be content with fragments, with partial glimpses, never the full fruition. […]

Only steadfastness of purpose and humility enable the student to shift his position to meet the new conditions in which new truths are born, or old ones modified beyond recognition.”

William Osler in ‘The Student Life” (1905)

I really like the warmth and practical insight of Osler’s approach to medicine and to life. His advice is still applicable today, as science and technology continue to give birth to new truths and transform established practices beyond recognition. I don’t think we are required to abandon our values to embrace the instrumentality of an insect colony, but we need to maintain a humble appreciation for how things change.

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“It is not always by plugging away at a difficulty and sticking to it that one overcomes it; often it is by working on the one next to it. Some things and some people have to be approached obliquely, at an angle.”

Andre Gide in his Journal entry for October 26, 1924 translated by Justin O’Brien (1951)

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“All gardeners live in beautiful places because they make them so.” Joseph Joubert

A more positive version of “when life hands you lemons, make lemonade.” Find ways to work with what you have and improve where you are. It beats worrying about what you don’t have.

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“To educate myself on startups, I like to read books about expeditions where half the people die.” Michael Mayer (@mmay3r)

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“There was an odor of trouble, an indefinable wrong. It was like playing chess and making a bad move and not knowing why but knowing instinctively that it was a bad move. The instincts were yelling. As they used to do long ago at night in Indian country. He gazed out into the black. The stars were obscured. It was the blindness that bothered him.” Michael Shaara in “The Killer Angels“

Longstreet is lost in thought the evening of Monday evening, June 29, on the eve of the Battle of Gettysburg. The two armies have had a small skirmish but neither side has any real knowledge of the size or disposition of the force they are facing.

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“Hope is not a strategy, but it is an awfully good tactic.” Seth Godin in “More of a Realist“

Originally curated in December 2015. I think this leverages Virgil’s observation, “they can because they think they can,” a short quote I have curated more than a dozen times since 2006, starting with “Lighting the Way for Your Competitors.”

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“I was seldom able to see an opportunity until it had ceased to be one.” Mark Twain in “Autobiography of Mark Twain” Volume 1 (2010)

Doubt, fear, and stress can create uncertainty that clouds our ability to recognize either threats or opportunities.

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“Fear cannot be banished, but it can be calm and without panic; it can be mitigated by reason and evaluation.” Vannevar Bush in “Modern Arms and Free Men“(1949)

See Vannevar Bush on “Modern Arms and Free Men” on his insights into how the US leveraged its scientific and engineering talent for World War 2.

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“Doubt can only be removed by action.” Johann Wolfgang von Goethe

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“Many people assume they are bad at writing because it is hard. This is like assuming you are bad at weightlifting because the weight is heavy. Writing is useful because it is hard. It’s the effort that goes into writing a clear sentence that leads to better thinking.” James Clear

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“Information is the resolution of uncertainty.” Claude Shannon

Your probability estimate for the likelihood of an event represents your state of information about it. To the extent that exploring your own doubts and fears about a situation and comparing them with those of others yield insights into real risks and actions you can take to mitigate them, it’s a useful exercise in constructive pessimism.

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“Discipline is the scaffolding of greatness and the quiet architecture of progress. The ambitious mind builds freedom through structure, knowing that mastery is born from repetition refined by intent.” Ivanka Trump birthday tweet

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