Entrepreneurship & Strategy

Lateral Thinking: Abandon the Wrong Well, Generate More Ideas, and Leave Room for Disorder

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#得到頭條20260304 (Dedao Headlines course script), with Robin’s closing comments

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Collected in Robin Shen’s Field Notes · Content type and attribution are shown above

English translation of the Chinese post originally published 2026-03-04. Translated 2026-11-06 with AI assistance. Historical figures and claims have not been updated or independently verified. 中文原文

Reading guide

Three points about lateral thinking: rational abandonment matters more than stubborn persistence (the well-digging analogy, illustrated by Bettger dropping third and subsequent sales calls after analyzing his records); quantity matters more than quality (force yourself to generate ten ideas, with Dyson’s 5,127 prototypes as an example); and some disorder matters more than perfect organization (add constraints, bring in outsiders, and stay open to surprises). Robin closes by urging curiosity, openness, and alertness.

Key points

  • The well-digging analogy: abandon a location once you find it is wrong; test new directions with small bets
  • With one answer, the brain chooses the safest; forcing ten ideas helps later ones break habitual patterns
  • Constraints, outsiders, and openness to surprises can break fixed patterns of thought
One clear path continues into the distance among several branching routes, suggesting choice and focus.
Entrepreneurship & strategyThematic illustration · AI generated

Full text — English translation

Verification notes (2026-10-30): 1. Bettger's figures come from How I Raised Myself from Failure to Success in Selling. This site found only excerpts and reading notes (secondary sources), not the full book. Those excerpts say 70% of sales closed on the first meeting, 23% on the second, and 7% on the third or later, with about half his time spent on that 7%. The post says he “exceeded a million dollars for the first time” after abandoning those calls. A source for that claim in Bettger's work was not found; this site retains it without verification. Another measure cited in the excerpts is the value of each call rising from US$2.80 to US$4.27. That is not the same figure as the post's and is provided only for comparison. Sources: https://tuningjohn.com/book/selling/ https://sobrief.com/books/how-i-raised-myself-from-failure-to-success-in-selling 2. Dyson's own account says he made 5,127 attempts (prototypes) before producing a bagless vacuum cleaner. Source: https://www.theglobeandmail.com/report-on-business/careers/leadership-lab/yes-its-ok-it-took-me-5127-attempts-to-make-a-bagless-vaccuum/article19992476/ 3. The term “lateral thinking” is associated with de Bono, who published The Use of Lateral Thinking in 1967. The “well-digging analogy” and the ten-idea procedure (1 + 4 + 5, then select three), among other claims here, are the course script's account of de Bono. They were not separately checked against his original work and are treated as the speaker's statements. Source: https://ci.nii.ac.jp/ncid/BA04689051 ---- When a direct approach fails, can we try another angle? This way of changing angles has a name: lateral thinking. Put simply, lateral thinking means not solving a problem head-on or focusing on a single vertical line, but looking sideways for alternatives. Proposed as early as 1967 and continually developed since, it has become a cornerstone of the broader system of innovative thinking. Edward de Bono, the scholar who introduced it, later became known as the “father of innovative thinking.” A few key points about lateral thinking. First, rational abandonment matters more than stubborn persistence. “With enough effort, even an iron rod can be ground into a needle.” That certainly makes sense. But in studying lateral thinking, Edward de Bono proposed another view: the “well-digging analogy.” Suppose you want to dig a well. You choose a spot and keep digging. The deeper you go, the more you invest and the harder it becomes to stop. Even after a long time without water, you tell yourself, “Water is just ahead. Persistence means victory.” But what if you chose the wrong spot in the first place? De Bono says lateral thinking means decisively abandoning the site once you discover it is wrong, and finding another. Not “persistence means victory,” but “decisively abandon the wrong well.” Take Frank Bettger, a legendary figure in American insurance. He worked several times harder than his colleagues, but his performance would not improve. Then he analyzed a full year's work logs. He found that 70% of his business came from customers who bought at the first meeting, 23% at the second, and only 7% at the third or later. Yet that 7% consumed roughly half or more of his working time. In other words, he was wasting enormous time on the “wrong well.” Bettger made a decisive choice: forgo that 7% and free up time to develop new business. As a result, his new insurance business that year exceeded a million dollars for the first time. How can you tell whether a well is wrong? Are time and effort severely out of proportion to returns? Are you repeating the same actions while expecting different results? Is your reason for continuing that you see hope, or that you cannot bear to give up the costs already incurred? If the answers are all “yes,” you may have encountered a “wrong well.” What next? De Bono suggests not immediately going all in on a new direction, but setting an “exploration period.” Give yourself, say, a month to test a new direction cheaply, using small bets. Abandoning the wrong well means testing more possibilities at lower cost, not changing direction blindly. Nor does it mean quitting whenever things get difficult. It means remaining alert to your direction. If the direction is right, move to the second point: quantity matters more than quality. Do not “find the one correct answer”; force yourself to produce more ideas. Some might find that strange. Shouldn't quality matter more than quantity? De Bono's logic is this: when you allow yourself only one answer, your brain automatically chooses the safest, most conventional one, because you fear it might not be good enough. Force yourself to generate ten or twenty answers, however, and although the first few may be conventional, eventually you must break habitual patterns and consider ideas that are strange, wild, yet genuinely valuable. In other words, forcing more ideas helps you break habitual patterns and reach real innovation. James Dyson, founder of Dyson, reportedly spent five full years developing his bagless vacuum cleaner, building 5,127 hardware prototypes. The first 5,126 all failed; only the 5,127th succeeded. De Bono's specific suggested procedure is to write down your first idea, usually the safest and most conventional. Then force yourself to add four more. This feels somewhat difficult, but manageable; the four may differ a little while remaining conventional. Next, generate another five. This is the crucial step: with conventional answers exhausted, you must start thinking of seemingly “implausible” ideas. Finally, select the three most interesting of the ten for deeper thought. The valuable ideas may be hiding among those last five “implausible” ones. What if you cannot come up with any? Two techniques can help. One is “extreme assumptions.” Ask: what if the cost were zero? What if time were unlimited? What if it had to be finished in one day? Such assumptions force you beyond conventional frameworks. The other is “reverse thinking.” Ask: what would I do to ruin this? List every way to make it fail, then reverse the question. Avoiding those pitfalls may reveal the right path. AI now makes this process easier than ever. AI generates many options; people confirm the direction and make selection decisions at critical points. In other words, AI handles quantity, people handle quality. In practice, though, plans often fail to keep up with change. That brings us to the third point. Third, a degree of disorder matters more than perfect organization. Many think doing something well requires everything to be orderly and methodical. Sometimes, however, a degree of disorder, unexpected constraints, and heterogeneous groups can break fixed patterns of thought. When everything is orderly, the brain goes on autopilot. You know the next step and how things will unfold. You need only execute, not think. New ideas struggle to emerge in that state. When something unexpected happens—a sudden constraint, or a new teammate with an entirely different background—the brain must reconsider: the old method no longer works, so what should I do? Disorder and constraints can sometimes catalyze innovation. How do you apply this? Add constraints. When solving a problem, ask, “What would I do with only half the budget?” Or, “What if I had only a third of the time?” Such limits force you beyond conventional approaches. Try this in a meeting: require every proposal to fit on one page. This forces you to discard unimportant details and retain only the core logic. Bring in outsiders. When building a team or seeking advice, do not look only for people with backgrounds like yours. Deliberately seek people from different fields and experiences. They may offer angles you have never considered. Stay open to surprises. When plans are disrupted, do not rush back to the old track. Pause and ask: could this surprise create new possibilities? What problem has it exposed—insufficient resources, the wrong direction, or a flawed goal? Sometimes a surprise is telling us the original plan has holes. This is not a call to create chaos deliberately, but to stay open to the unexpected. To borrow de Bono's words: lateral thinking is not about proving yourself right or wrong, but finding more possibilities. Lateral thinking does not merely teach a specific technique. It helps us remain alert to direction, open to possibilities, and sensitive to the unexpected. #得到頭條20260304 ---- Robin: “Stay curious, stay open, and stay alert.”

These articles are personal notes, book excerpts, and collected reprints. Figures and events reflect the time of the original publication, are not current information, and do not constitute investment advice.

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