A collection of quotes for entrepreneurs curated in August 2025 around a theme of insomnia, sleeplessness, and working all night.
Quotes For Entrepreneurs Curated in August 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 insomnia, sleeplessness, and working all night.
My birthday is this month so a few more quotes focus on mortality. I don’t mind growing old–especially as more of my friends stop doing so each year, but I do meditate on it more often than I used to.
“Entrepreneurs, the only people who work 80 hour weeks to avoid working 40 hour weeks.”
Lori Greine
Sleepless nights are another side effect of entrepreneurship.
“I find the nights long, for I sleep but little, and think much.”
Charles Dickens
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“Nothing cures insomnia like the realization that it’s time to get up.”
Anonymous
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“The hardest thing is to go to sleep at night, when there are so many urgent things needing to be done.”
Donald Knuth
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“Many creative minds overrate their most baroque works, and underrate the simple ones.”
Benoit Mandelbrot in “The Fractal Geometry of Nature” [Archive]
h/t John D. Cook; simple tools are easier and safer to re-use and have wider applicability. Even organizing theories or perspectives are most effective when they are straightforward.
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“I’m an insomniac, my mind works the night shift.”
Pete Wentz in “Gray“
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“It is better to sleep on things beforehand than lie awake about them afterward.”
Baltasar Gracian
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“Gary Kasparov: Are you saying that Trump has strategy?
George Friedman: I’m saying that he’s either the stupidest lucky man in the world or he knows what he is doing.”
Conversation in “The Storm Before the Calm” (Atlantic podcast transcript)
It’s a candid and insightful conversation that offers a realpolitik perspective on the current situation in Ukraine, Taiwan, Russia, and China. I profiled George Friedman’s book “The Storm Before the Calm” in “Entering 2025 as a Stranger in a Strange Land.”
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Replacing a healthy amount of sleep with just an extra cup of coffee.
h/t ADHD Memes; source TheDad
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“I’ve got a bad case of the 3:00 am guilts – you know, when you lie in bed wide awake and replay all those things you didn’t do right? Because, as we all know, nothing solves insomnia like a nice warm glass of regret, depression and self-loathing.”
D.D. Barant in “Dying Bites“
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“It is a common experience that a problem difficult at night is resolved in the morning after the committee of sleep has worked on it.”
John Steinbeck in “Sweet Thursday” [Faded Page]
Deidre Barrett used “committee of sleep” as the title for her non-fiction book that documented examples of artists, scientists, and engineers solving problems in their sleep.
“Dreaming is neither consistently wise nor consistently useless. The dream’s power lies in the fact that is it so different a mode of thought–that it supplements and enriches what we’ve already done while awake.”
Deidre Barrett in “The Committee of Sleep“
I have curated this quote twice before, in August of 2018 and November of 2021. The first was inspired by reading her book, the second was provided added context for a quote about Jeff Goldblum writing down his significant dreams as part of his morning routine. I noted then that in addition to the dream state there is hypnagogia or the act of falling asleep and the hypnopompic state of rational cognition and wakefulness after awakening. All three states can enable insight and creative solutions to problems. I keep a pad of paper by my bed to capture thoughts that occur as I am falling asleep or immediately after I have awakened. Sometimes I will remember something I should have accomplished–or need to do tomorrow–as I am falling asleep. Writing it down allows me to relax knowing I have captured. Other times I will wake up with an new approach to a problem or situation and write it down so that it survives my morning routine until I am ready to put it into practice.
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“Hello darkness, my old friend.
I’ve come to talk with you again
Because a vision softly creepingLeft its seeds while I was sleepingAnd the vision that was planted in my brainStill remainsWithin the sound of silence
Paul Simon in “The Sounds of Silence“
I think this song is about waking up from a disturbing dream at 3 am, unable to sleep. (One hint: the album is called “Wednesday Morning, 3 A.M.“) Disturbing dreams have awakened me a few times, leaving me unable to fall asleep. I think my “committee of sleep” had a violent disagreement, or decided they could not figure out whatever problem I was wrestling with and decided to throw it back to me because it was giving them headaches as well.
Here is one instance from three decades I remember vividly.
When Jeff Leader and I did the website for the Design Automation Conference in 1994, we hosted it in the San Diego Supercomputer Center. It was one of the few places that offered hosting in 1994. Two nights before the conference was to start, I had a vivid dream that I was in the passenger seat of a car with three other people. The driver was going too fast and misjudged a curve, plunging the car over a cliff on the seashore. I can remember the feeling of weightlessness as we plunged towards a rocky outcrop in the surf.
We were not flying, we were falling. As we were just about to crash, the scene changed, and we were now in a spaceship traveling through an asteroid belt; the rocks had become floating asteroids. This scene lasted only a second or two before I woke up in a cold sweat from my panic at falling from a height. I was filled with a strong sense of foreboding: something was wrong.
I sat up in bed, thought for a minute, and went to check on our web server. It was down. I sent emails to our contacts and went back to bed, worried we were going to let everyone down. It was an uncomfortable hour or so before I fell asleep again. The next morning, the server was operational, and we had no problems for the week of the conference. If the nightmare had not awakened me, I would never have known. Not all sleepless nights end as well.
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“For better or for worse, I’ve left Twitter. The platform was my reading aggregator for the last ten years to find information-dense articles. In 2023, that function completely broke down. Elon’s algorithm changes have deprecated tweets that include links, which drive perfectly sane people not to share their source, writing instead “link in bio” or “link at bottom of thread.” And after Twitter removed headlines from articles, it became much more difficult to figure out what I could be reading. What is Twitter anymore? Not the platform for surfacing information-dense articles, but rather mostly shouting and videos.”
Dan Wang (@DanWang)) 2023 Letter
It’s a mistake for forums to ban or penalize outbound links. They benefit from providing a high signal to noise ratio and links provide substantiation of claims and context for remarks. LinkedIn also penalizes links that are “off platform.”
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“It was that sort of sleep in which you wake every hour and think to yourself that you have not been sleeping at all; you can remember dreams that are like reflections, daytime thinking slightly warped.”
Kim Stanley Robinson in “Icehenge“
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“If you can’t sleep, then get up and do something instead of lying there and worrying. It’s the worry that gets you, not the loss of sleep.”
Dale Carnegie
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“A good laugh and a long sleep are the best cures in the doctor’s book.”
Irish Proverb
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“Without enough sleep, we all become tall two year olds.”
JoJo Jensen in Dirt Farmer Wisdom (2002)
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“The people who change things aren’t at the parties, they’re at home obsessed with problems everyone else finds tedious. It’s nothing glamorous, just steady incremental progress over a long period of time.
Exceptional looks boring until suddenly it isn’t.”
Shane Parrish in “Exceptional Looks Boring“
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“Nothing slows design more than the lack of a clear, evidence-based decision-making process. Few organizations have this.
Nothing slows gathering evidence to inform your decisions than not knowing what you need to know.
More tools or data won’t speed anything up if you aren’t asking the right questions for the right reasons.
Clarity is the real accelerant.”
Erika Hall in “I continue to see so much nonsense justified activity” (edited for clarity)
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“We don’t always realize how many people it takes to create a successful company, because we think about who received a paycheck or invoice payment.
Wrong. Both Smart Bear and WP Engine would have been impossible without my wife, yet she never worked there.”
Jason Cohen (@aSmartBear)
See also “Treat Your Spouse as an Investor.”
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“The future is an opaque mirror. Anyone who tries to look into it sees
nothing but the dim outlines of an old and worried face.”
Jim Bishop in New York Journal-American, March 14, 1959
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“The best bridge between despair and hope is a good night’s sleep.”E. Joseph Cossman
This is sometimes credited to Matthew Walker because Walker uses this quote in his book “Why We Sleep.” Cossman bought the patent for spud gun and made a fortune selling it and many other thingamajigs–not to be confused with a thingamabob, doohickey, whatsit, whatchamacallit, whatnot, or a doodad–including the ant farm via mail order.
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This reminds me of
“Embrace the ‘fertile void’ of sleepless nights. Lots of creativity can occur then.”
Cecily Drucker
Part of a longer excerpt in “Cecily Drucker’s Startup Secrets.” I used this graphic as an illustration in “13 Tips for Getting Up Early and Arriving Early” and curated the quote and image together in my April 2016 roundup. I also used the Cecily Drucker quote in “Productive Larks and Creative Owls” and “Use the Cult of Done Manifesto to Avoid Procrastination and Perfectionism.”
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Breathe deep the gathering gloom
Watch lights fade from every room
[…]
Cold-hearted orb that rules the night
Removes the colors from our sight.
Red is grey and yellow white,
But we decide which is right
And which is an illusion.
Late Lament by Graeme Edge of the The Moody Blues
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“One hour’s sleep before midnight is worth three after.”
George Herbert in Jacula Prudentum (1651).
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“Experience of the world may be looked upon as a kind of text, to which reflection and knowledge form the commentary. The advice here given is on a par with a rule recommended by Pythagoras, to review, every night before going to sleep, what we have done during the day. We should, therefore, be careful to preserve the memory of our thoughts at important points in our life; and herein lies the great advantage of keeping a journal.”
Schopenhauer in Maxims
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“I fall asleep with the TV on. I wake up at some nameless hour and watch the colors of the screen spill across the ceiling, and remember how I’d fall asleep to the TV sometimes when I was little, when I was home sick, and I’d wake up in the middle of the night to the Star-Spangled Banner and some old film of a flag blowing in the wind, telling you the day was over and it was long past time to go to bed. That was back when days used to end, before CNN and infomercials, before all our days bled right into each other.”
Michael Montoure (1970-2023) in “Cold Season” collected in Slices
I can remember watching TV until station sign-off. I can also remember getting up early enough to see the signal test pattern replaced by the start of Farm Report.
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“The problem facing the U.S. is not simply the short-term: the real problems will arise in the 2030s and beyond. Semiconductor manufacturing decision-making does not require nimbleness; it requires gravity and the knowledge that abandoning the leading edge entails never regaining it.”
Ben Thompson in US Intel
There are compounding effects from investment in capability development that can be hard to overcome. This reminds me of an observation by Michael Bowen:
“An early start beats fast running.”
Michael Bowen (@mdcbowen) “Cobb’s Rules“
I like this Bowen quote and used it as a section title in “Labor Day 2014: Knowledge Work Productivity,” a closing quote in “Start with a List of Customers and Problems that Build on Your Experience and Relationships” and curated it in “Quotes For Entrepreneurs August 2014” and “Quotes for Entrepreneurs Curated in November 2023.”
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- A List of Initiatives is a Strategy
- You can Prove that Your Strategy is Correct
- Analytically Strong People are Better Strategists
- Strategy is a Zero-Sum Game
- Strategy is Formulated at the Top & then Executed Below
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“Starting a few years ago, I became aware that I was moving into the final period of my life, when I had to really think about whether a particular project–a book, say–was worth investing some of the limited number of professional years I have left.”
Glenn Reynolds in “Report From The Other Side–Of the calendar, that is.“
I had a similar epiphany in 2011 when I was hospitalized for twice with a serious infection.I felt like I had really hit an inflection point in my life, that it was now clearly finite with an end point likely between 2031 and 2051. I resolved to work on things that would make a difference. I had to make my efforts count, to work while I had the light.
“Work while you have the light. You are responsible for the talent that has been entrusted to you.”
Henri Frederic Amiel in his Journal
See “Connect With Your Purpose” for an obituary I wrote in case I looked the wrong way before stepping off a curb.
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+”Reputation is the quiet echo of persistence. Each time you endure, follow through, or resist the easy exit, the slow sediment of persistence settles into place, layered not in your memory but in the memory of others. Persistence transforms us into the kind of beings who can endure.”
Colin W.P. Lewis in “Persistence Over Talent“
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L’esprit d’escalier
notepad as i am falling asleep
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In restless dreams, I walked aloneNarrow streets of cobblestone‘Neath the halo of a street lampI turned my collar to the cold and damp
Simon sounds of silence
sleepwalking as a child
find quote from an entirely other day
driving home from Full circle connections, falling asleep on the highway
bumps
work camp story – don’t turn the heater on
fell asleep driving in first Full Circle Connections
fell asleep in meetings at Cisco with Lou
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-> watch for this on your team, also in yourself,
take breaks don’t stay at work, don’t let work expand to fill the time available, don’t let your startup eat yoru life
rules of thumb for when to power on through and when to take a break, when to go home and sleep
something to look forward to should pull you out
the need to let go to sleep
Schopenhauer’s maxims https://www.gutenberg.org/files/10715/10715-h/10715-h.htm
chaap 12 Schopenhauer’s maxims https://www.gutenberg.org/files/10715/10715-h/10715-h.htm
The sight of things which do not belong to us is very apt to raise the thought: Ah, if that were only mine! making us sensible of our privation. Instead of that we should do better by more frequently putting to ourselves the opposite case: Ah, if that were not mine. What I mean is that we should sometimes try to look upon our possessions in the light in which they would appear if we had lost them; whatever they may be, property, health, friends, a wife or child or someone else we love, our horse or our dog—it is usually only when we have lost them that we begin to find out their value. But if we come to look at things in the way I recommend, we shall be doubly the gainers; we shall at once get more pleasure out of them than we did before, and we shall do everything in our power to prevent the loss of them; for instance, by not risking our property, or angering our friends, or exposing our wives to temptation, or being careless about our children’s health, and so on.
chap 14
39 If you want your judgment to be accepted, express it coolly and without passion. All violence has its seat in the will; and so, if your judgment is expressed with vehemence, people will consider it an effort of will, and not the outcome of knowledge, which is in its nature cold and unimpassioned.
Schopenhauer’s maxims https://www.gutenberg.org/files/10715/10715-h/10715-h.htm
43 Money is never spent to so much advantage as when you have been cheated out of it; for at one stroke you have purchased prudence.
Schopenhauer’s maxims https://www.gutenberg.org/files/10715/10715-h/10715-h.htm
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How do you “stand beside yourself” and see if you are contributing to the problem (“are your lights on”)
donnella meadows – leverage points
KGB quotes https://www.kgbreport.com/cgi/searchkgbquote.cgi
How do you tell if you are moving too slowly?
strategy https://rogermartin.medium.com/the-five-deadliest-strategy-myths-7331995f68fd
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get relationship diagram from keeping the joint running
Bob Lewis https://issurvivor.com/archives/
also first ten hires to 60 fractional relationships
team size / innovation / relationships
hunting party – complementary skills
different silos have different incentives and different currencies. How well can you tailor your efforts to meet their needs so you can their support in a peer to peer / quid pro quo / “market model instead of
top-down / command and control
cultivate and coordinate
Pareto optimal
to Stumble over something you have to be moving
H– catechsim OLE
https://groups.google.com/g/lean-startup-circle/c/r1fWsJumUQc/m/7THJx7zYmg8J
https://groups.google.com/g/lean-startup-circle