Theme for this month’s quotes for entrepreneurs is managing when you are “over your head.” How do you make realistic plans and what do you do when your plan is clearly not working.
Quotes for Entrepreneurs Curated in November 2023
My theme this month’s quotes for entrepreneurs is managing when you find yourself over your head.
“If you don’t know what you’re doing, don’t do it on a large scale”
Tom Gilb
This is a good rule of thumb for avoiding getting over your head. If you are walking in the dark room take slow small steps and listen carefully. I originally used this in my collection from May 2017.
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“You learn this–that if you’re ever going to take on a challenge, you’re going to take it on before you are ready.”
Robert Brault
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“Worry isn’t work. Being stressed out isn’t work. Anxiety isn’t work. Entertaining a sense of impending doom isn’t work.
Dan Pallotta in “Worry Isn’t Work“
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“We can’t absorb it all. We know too much, too quickly, and one of the worst effects of this avalanche of technology is the loss of compassion. […] Compassion is nothing one feels with the intellect alone. Compassion is particular; it is never general.”
Madeleine L’Engle in “A Circle of Quiet” (1972)
“A Circle of Quiet” is the first in a series of autobiographical “Crosswicks journals” that L’Engle wrote. One measure of getting “over your head” is a sense of being overwhelmed by information and a stream of changes in a situation. I think the loss of compassion, empathy, affinity for others is a significant marker for being overwhelmed.
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“Many of us feel stress and get overwhelmed not because we’re taking on too much, but because we’re taking on too little of what really strengthens us.”
Marcus Buckingham
Not doing enough to renew your gumption is a slow path to burn out. Not getting enough sleep render you ineffective in a matter of days, a lack of exercise takes longer. Another serious mistake is losing touch with family and friends.
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“A good product solves a specific problem in the minimum number of steps.”
Brian Norgard (@BrianNorgard)
The more complex the path to solving a problem, the more likely you will exhaust prospects with too much detail and the less likely they will adopt it. If their eyes glaze over when you demonstrate the solution path, this is a strong clue that it needs revision.
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“You don’t drown by falling into water. You only drown if you stay there.”
Zig Ziglar
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“Even in a last extremity, with neither money nor hope, a man seizes a deck of cards and tries to win at solitaire, to restore himself and taste the wine of luck.”
E. B. White in “Control” collected in “One Man’s Meat“
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“The greatest experience open to man then is the recovery of the commonplace. Coffee in the morning and whiskeys in the evening again without fear. Books to read without that shadow falling across the page.”
Peter De Vries in “The Blood of the Lamb“
The narrator’s daughter is experiencing a (temporary) remission from cancer and life returns to normal, accompanied by a hope for a normal life for her. In “Good Fortune” I wrote: “Before antibiotics and vaccines many parents would bury at least one child. You may not think seeing your parents die is good fortune, but you are wrong.”
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“There are so many things that we wish we had done yesterday, so few that we feel like doing today.”
Mignon McLaughlin
While my past failures to execute disappoint, my current distraction and inaction proves more acceptable. I try to “plan the work and work the plan.” I do the first part but fall down on the second. High performance is a habit I need to cultivate. It’s hard though, because developing self-discipline and follow-through requires self-discipline and follow-through. I find it hard to satisfy the initial conditions. I am less “over my head” than easily distractible and ineffective as a result.
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“Unconscious cognition leverages long walks, sleeping on it, and answers revealed in dreams.”
Gordon Brander (@goordonbrander)
Long walks and “sleeping on it” routinely increase performance and also work well as error recovery and insight generation techniques. Keep a pad of paper or index cards and a pen next to your bed so you can capture thoughts that occur as you are falling asleep or memories of dreams that offer insights.
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“Call it ‘the illusion of omnicompetence.’ When you know a lot about one thing, you spend a lot of time watching the less knowledgeable make elementary errors. You can easily infer from this that you are very smart, and they are very stupid. Smart, competent people” are not a generic quantity; they’re incredibly domain-specific. We like to think that being “smart and competent” makes you less likely to make mistakes. But when you’re out of your element, it may merely enable you to make more — and larger — mistakes.”
Megan McArdle in “Obamacare is no Starship Enterprise“
I quoted this in “The Illusion of Omnicompetence: Smart and Competent Are Domain Specific Adjectives.” Overestimating your competence in a particular problem domain is a frequent precursor to getting over your head. I am particularly cautious when I say, How hard could it be?” for a category of problem I have not encountered before. It’s also dangerous to scale up a solved problem by more than a factor of two or so and assume you can keep it under control. I think Derek Sivers’ advice about scaling up your startup is on point here:
“Prepare to double: have a plan for what would happen if the business doubled.
‘More of the same’ is never the answer.”
Derek Sivers in “Anything You Want“
I referenced this in “Anything You Want by Derek Sivers.” For planning purposes this is a reasonable stress test for a business operating plan. Figure out what will break and what’s now possible with twice as many customers, with twice as much revenue, with twice as many employees (note that ratios between customer count, revenue, and headcount may not remain constant).
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“Often in life you have to fail small to achieve large.”
Robert Brault
A scale model or prototype can often capture critical elements of a situation that allow you to explore one or more ways that your business or product concept may fail. But you fail in a fraction of the time at a fraction of the cost and, therefore, in a much more recoverable manner. Instead of aiming for a plan that cannot fail, build prototypes that will fail safely.
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“The person who lives ethically always has a way out when everything goes against him; when the darkness of the storm clouds so envelopes him that his neighbor cannot see him, he still has not perished, there is always a point to which he holds fast, and that point is–himself.”
Soren Kierkegaard in “Either/Or: A Fragment of Life”
I originally curated this in June 2016 but have recycled it because it was apropos this month’s theme. If you cannot be true to yourself in times of trouble you compound your difficulties.
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“Character is a strange blending of flinty strength and pliable warmth.”
Robert Shaffer
To survive and manage the rich variety of situations we encounter in this life you need a range of strategies you can employ effectively. I like Shaffer’s suggestion that we need to combine hard strength with encouraging support as the situation requires. When you find yourself over your head or in a survival situation you will need to be able to try different approaches to persevere.
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“Scientists discover the world that exists; engineers create the world that never was.”
Theodore Von Karman
I originally curated this in March 2018, I am recycling it because sometimes you have to design or invent your way out of challenges. The solution is not something you can look up in a book or repurpose from another problem but something new that you have to create.
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“Those whom the Gods would destroy, they first call promising.”
Cyril Connolly in “Enemies of Promise“
I originally curated this in 2009, but I thought it represented another important reason entrepreneurs find themselves over their heads. Unfortunately, various media players must find a hot new trend every month, and you can be the unwitting beneficiary. If paying customers tell you they are incorporating your product into future plans and essential infrastructure, I think it’s safe to believe them. People you pay directly or indirectly (e.g., consultants, employees, coaches, etc.) have a perverse incentive to cheerlead. Be cautious about your own “press.” Good founding teams hold each other accountable and help maintain a more accurate shared assessment of capabilities and deficiencies that must be addressed.
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“A day can really slip by when you’re deliberately avoiding what you’re supposed to do.”
Bill Watterson
I’ve learned from long experience that postponing unpleasant obligations is unfortunately an all too easy way to find yourself over your head.
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“Cheetahs can also swim, but a dolphin does it better.”
Derek Sivers
If you are in water over your head you have to at least float, swimming is better. More context:
“But I guess we all have a nature. A way that comes, I was going to say comes easiest to us but maybe our nature amplifies certain ways. We can do things that are against our nature. But if we do things that are in line with our nature, then those things are really supercharged, right? Because that’s just our nature. Cheetahs can also swim, but a dolphin does it better.”
Derek Sivers in June 2020 Interview
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“A person who has not done one-half his day’s work by ten o’clock, runs a chance of leaving the other half undone.”
Emily Bronte in “Wuthering Heights” [Gutenberg]
More context
“You shouldn’t lie till ten. There’s the very prime of the morning gone long before that time. A person who has not done one-half his day’s work by ten o’clock, runs a chance of leaving the other half undone.”
Emily Bronte in “Wuthering Heights” [Gutenberg]
Michael Bowen offers a similar perspective
“An early start beats fast running.”
Michael Bowen (@mdcbowen) “Cobb’s Rules“
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“The best proof you are still capable of learning is that there is something you recently unlearned.”
Robert Brault