What is Letter 28 About?

Letter 28, written on December 4, 1903, addresses a disagreement about personnel selection: John Jr. wants to promote Roger to a position of major responsibility, while Rockefeller firmly opposes this decision. Rather than merely vetoing his son’s choice, Rockefeller uses this moment to articulate a comprehensive philosophy about the true determinant of capability—not knowledge, credentials, or experience, but the quality and creativity of one’s thinking. Through the story of testing Roger with an impossible-seeming question about abolishing prisons, he reveals how a person’s mental approach to problems—whether they seek solutions or enumerate obstacles—determines their ultimate value and potential. The letter represents Rockefeller’s most concentrated exploration of thinking quality as the fundamental differentiator between those who achieve breakthroughs and those who merely maintain status quo.

The Personnel Disagreement

The Context

Rockefeller opens with direct disagreement: “I do not agree with your point of view, of letting Roger take on the heavy responsibility and face the music alone.”

This establishes the stakes: John Jr. wants to promote Roger to significant position with substantial autonomy (“face the music alone”). Rockefeller has attempted persuasion but failed: “In fact, with regards to this, I have worked hard, but the result was quite disappointing.”

The fundamental issue: “My principle of employing people is that those who are entrusted with important tasks are those who can find ways to do things better.”

The criterion for promotion isn’t loyalty, experience, or credentials—it’s demonstrated capacity to improve upon current methods.

The Disqualification

“But Rogers is obviously not qualified, because he is a lazy person.”

This “laziness” isn’t about physical effort but mental effort—Rogers doesn’t actively seek better solutions, doesn’t question existing approaches, doesn’t push boundaries of what’s possible.

The letter will reveal that this intellectual laziness—accepting limitations rather than questioning them, enumerating obstacles rather than finding solutions—represents fatal flaw for anyone aspiring to leadership or significant responsibility.

The Roger Test: A Revealing Conversation

The Impossible Question

“Before I started working with Roger, I tested him with a question. I said, ‘Mr. Roger, what do you think the government can do to abolish all prisons in thirty years?'”

This question serves multiple diagnostic purposes:

Tests creative thinking: Can he imagine radical alternatives to current systems?

Reveals mental flexibility: Can he entertain seemingly impossible propositions?

Assesses problem-solving approach: Does he seek solutions or enumerate obstacles?

Demonstrates attitude toward limits: Does he accept constraints or question them?

The question deliberately proposes something that seems impossible, forcing respondent to either:

• Creatively explore how it might be accomplished despite apparent impossibility
• Defensively explain why it cannot be done

The response reveals fundamental mental orientation: solution-focused or obstacle-focused.

The Defensive Response

Roger’s reaction was defensive confusion: “He was confused when he heard it, and suspected that he had heard it wrong. After a while of silence, he began to refute me.”

Rather than engaging creatively with the challenge, Roger:

1. Assumed mishearing: Couldn’t believe such a question was serious
2. Remained silent: Couldn’t generate initial thoughts
3. Began refuting: Focused on impossibility rather than possibility

His response: “Dear Rockefeller Sir, do you mean to release all the murderers, robbers, and rapists? Do you know the consequences of doing this? If that’s the case, we will not have peace. In anyway, there must be a prison.”

This reveals several problematic thinking patterns:

Literal interpretation: Assuming “abolish prisons” means “release all criminals”

Catastrophizing: Immediately imagining worst-case scenarios

Binary thinking: Either prisons exist as they are, or chaos results

Defending status quo: “In anyway, there must be a prison”

Missing the question: Not engaging with “how could this be accomplished?”

The Redirection

Rockefeller attempted to redirect Roger’s thinking: “Roger, you only said the reasons why the prison cannot be abolished. Now, try to believe that the prison can be abolished. Assuming it can be abolished, how should we proceed?”

This brilliant reframing:

• Acknowledges his response: “You only said the reasons why…”
• Redirects the task: Not “can it be done?” but “how could it be done?”
• Requests belief suspension: “Try to believe that the prison can be abolished”
• Makes assumption explicit: “Assuming it can be abolished…”
• Focuses on method: “How should we proceed?”

The redirection tests whether Roger can shift from obstacle-enumeration to solution-generation when explicitly asked.

The Ultimate Failure

Roger’s final response revealed complete incapacity: “This is too hard for me, Mr. Rockefeller, I can’t believe it, and it’s hard for me to find a way to abolish it.”

This admission contains multiple failures:

Belief limitation: “I can’t believe it”—inability to suspend disbelief for creative exploration

Method poverty: “It’s hard for me to find a way”—lack of creative problem-solving capability

Surrender: “This is too hard for me”—giving up rather than persisting

Self-limitation: Accepting mental constraints rather than pushing through them

Rockefeller summarizes Roger’s approach: “This is Rogers’s method—no way.”

The person whose default response is “no way” disqualifies himself from positions requiring innovation, breakthrough thinking, or transformative change.

The Predictive Conclusion

Based on this conversation, Rockefeller reaches firm conclusion: “I cannot imagine how he will use all his talents to actively react when he is given a heavy responsibility, or when an opportunity or a crisis hit.”

The logic: If Roger can’t creatively engage with hypothetical question in low-pressure conversation, how will he perform when facing actual high-stakes crises requiring innovative solutions?

“I do not trust Roger; he will only turn hope into hopelessness.”

This harsh assessment reflects understanding that the person who cannot think creatively about possibilities will convert every opportunity into impossibility, every challenge into insurmountable obstacle.

The Philosophy of Creative Problem-Solving

The Fundamental Principle

Rockefeller articulates his core belief: “Finding out a way to do things better is the guarantee of being able to complete anything.”

This establishes creative problem-solving as prerequisite for achievement. Without capacity to find better methods, improvement becomes impossible; without improvement, competitive disadvantage accumulates until displacement occurs.

The Belief Requirement

“This does not require superhuman wisdom, the important thing is to believe that things can be done, and to have this belief.”

This democratizes creative capability by locating it in belief rather than innate genius:

Not required: Exceptional intelligence, extensive education, rare talents

Required: Belief that solutions exist and can be found

The mechanism: “When we believe that something is impossible to do, our brain will find various reasons for us not to do it. However, when we believe—really believe that something can be done, our brain will help us find various ways.”

Belief determines whether the brain functions as obstacle-generator or solution-generator.

The Creative Enabler

“Believing that something can be done will provide us with creative solutions and bring out our various creative abilities.”

This describes how belief unlocks creativity:

1. Belief that solutions exist → Mind searches for solutions
2. Solution-seeking activates creativity → Novel connections and approaches emerge
3. Creative capabilities manifest → Solutions actually get found
4. Found solutions validate belief → Belief strengthens for future challenges

Conversely, disbelief blocks this entire process before it begins.

The Destructive Alternative

“On the contrary, not believing that things can be done successfully is tantamount to shutting down our wisdom in creative problem-solving, which will not only hinder our creative ability, but will also destroy our ideals.”

The damage is comprehensive:

• Shuts down wisdom: Prevents using intelligence creatively
• Hinders creative ability: Blocks access to innovative thinking
• Destroys ideals: Eliminates aspirational goals as “impossible”

“The so-called aspirational element turns out to be the foundation of creation and achievement, but that is it.”

Without aspirational belief that things can be better, the entire creative and achievement process collapses at the foundation.

The Organizational Implications

The “Impossible” Taboo

“I hate my subordinates saying ‘impossible’. ‘Impossible’ is a term for failure.”

This prohibition isn’t arbitrary but reflects understanding that “impossible” declarations prevent the creative thinking necessary for breakthrough solutions.

“Once a person is dominated by the idea of ‘it is impossible’, he can produce a series of ideas to prove that he is right.”

This describes confirmation bias in service of limitation:

1. Person declares something impossible
2. Mind searches for supporting evidence
3. Evidence found confirms impossibility
4. Confirmation strengthens original belief
5. Cycle continues, making impossibility self-fulfilling

The “impossible” declaration becomes self-validating prophecy as mind generates endless reasons why the impossible claim is correct.

The Roger Mistake

“Roger made this mistake. He is a traditional thinker, and his mind is numb.”

The “traditional thinking” pattern:

• Precedent-worship: “This has been practiced for a hundred years, so it must be a good way”
• Risk-aversion: “It must be kept as it is, so why risk it”
• Change-resistance: Questioning “why change?”

“In fact, it can often be achieved only through thinking about the reasons diligently.”

The very solutions Roger declares impossible could be discovered through sustained creative thought—which he refuses to invest.

“‘Ordinary people’ always hate progress.”

This harsh assessment recognizes that resistance to creative problem-solving and innovative thinking is ordinary; embracing it distinguishes the exceptional.

The Knowledge-Experience Trap

The Insufficiency of Learning

“People believe that it is impossible to find the best way to do anything. The best way is to have as many creative ideas.”

This challenges knowledge-accumulation as primary strategy. Collecting existing ideas and methods, while useful, proves inferior to generating novel creative ideas.

“Nothing grows on ice and snow. If we let traditional ideas freeze our hearts, new ideas will grow out of nowhere.”

The metaphor captures how traditional thinking creates conditions hostile to innovation—like frozen ground where nothing can sprout.

Knowledge as Limitation

Later Rockefeller elaborates on knowledge’s paradoxical danger: “Everyone needs to know that all knowledge will be transformed into preconceived notions, and the result will be one-sided conservative psychology, thinking that ‘I understand’, ‘I understand’, and ‘society is like this’.”

This describes how knowledge creates rigidity:

1. Knowledge acquired → Develops understanding of how things work
2. Understanding solidifies → Becomes “preconceived notions”
3. Notions harden → Creates “conservative psychology”
4. Psychology manifests → “I understand” attitude closes mind to new possibilities
5. Closure persists → Lost interest in questioning, learning, innovating

“With the prejudice of ‘understanding’, there will be a lack of interest in knowing, and if there is no interest, it will lose the motivation to move forward, and only boredom is left waiting.”

Knowledge paradoxically breeds ignorance by creating false confidence that current understanding is complete.

The Value of “Not Understanding”

“Therefore, not understanding will lead to success.”

This counterintuitive claim reflects insight that ignorance of how things “should” work can enable breakthrough thinking that expert knowledge would prevent.

The expert knows all the reasons something won’t work; the naive person, unburdened by this knowledge, sometimes discovers it will work through unexpected approach.

The Ego Problem

“However, under the control of self-esteem and sense of honour, many knowledgeable people always find it difficult to ‘don’t understand’, as if asking others for advice, saying that they don’t understand is a shameful thing, and even regard ignorance as a sin.”

This identifies ego as obstacle to learning:

• Self-esteem prevents admitting gaps in understanding
• Sense of honor makes “I don’t know” feel shameful
• Intellectual pride treats ignorance as moral failing

“This is trying to be smart, and they will never understand this great motto—every opportunity that we don’t understand will become a turning point in our lives.”

Each acknowledged ignorance creates opportunity for learning; each pretended knowledge closes that opportunity.

The Smart-Fool Paradox

The Definition

“A person who is smart is a fool, and a person who knows how to play a fool is really smart.”

This paradoxical formulation distinguishes:

Being smart(foolish): Displaying knowledge, showing expertise, demonstrating competence

Playing fool (smart): Acknowledging ignorance, asking questions, remaining open to learning

The mechanism: Appearing smart satisfies ego but prevents learning; appearing foolish enables learning that creates actual competence.

The Practical Application

“If smartness is regarded as a criterion for reaping benefits, then I am obviously not a fool.”

Rockefeller then illustrates through personal example of securing a $50,000 loan when seeking only $15,000:

A banker approached offering the loan. Rather than accepting eagerly (which would reveal desperate need and weaken negotiating position), Rockefeller “pretended” not to be interested: “That’s it… Can you give me twenty-four hours to think about it?”

This “playing fool” by not immediately accepting enabled negotiating “terms that were the most favourable to me.”

The appearance of not being desperate (playing fool about his need) created negotiating leverage that appearing smart (showing eagerness) would have destroyed.

The Dual Benefits

“Playing stupid brings you many benefits. The meaning of pretending to be stupid is to stay a low profile and become humble, in other words, to hide your cleverness.”

The advantages:

Strategic: Prevents opponents from recognizing your capabilities and preparing countermeasures

Social: Humility attracts support; arrogance repels it

Learning: Appearing unknowing enables gathering information

Positioning: Underestimation by others creates opportunities to exceed expectations

“The smarter the person, the more necessary it is for them to play stupid, because as the saying goes—the more mature the rice, the more they sag.”

True capability manifests as humble willingness to learn, not proud display of knowledge.

The Aspirational Instruction

“Son, only after having hobbies can you then do it with ease. Now, start to love acting like a fool!”

This concludes the theme by advocating deliberate cultivation of “playing fool” as valuable capability enabling:

• Continuous learning
• Strategic advantage
• Social effectiveness
• Genuine wisdom development

The Integration: Thinking Quality as Determinant

The Complete Framework

Letter 28 presents comprehensive model where success depends on:

Not primarily:

• Knowledge accumulation
• Educational credentials
• Experience length
• Intelligence level

But primarily:

• Quality of thinking
• Creative problem-solving capability
• Belief that solutions can be found
• Willingness to question assumptions
• Openness to learning (“playing fool”)

The Roger Counterexample

Roger presumably possessed:

• Relevant knowledge
• Appropriate credentials
• Adequate experience
• Reasonable intelligence

Yet he failed Rockefeller’s test because he lacked:

• Creative thinking capability
• Belief-based problem-solving
• Willingness to suspend disbelief
• Openness to impossible-seeming ideas

His knowledge, credentials, and experience proved worthless because his thinking quality was poor.

The Promotion Criterion

Rockefeller’s principle for advancement: “Those who are entrusted with important tasks are those who can find ways to do things better.”

This focuses entirely on creative problem-solving:

• Not: Maintaining current operations efficiently
• Not: Executing existing plans competently
• But: Finding better methods, improving processes, discovering innovations

The person qualified for increased responsibility demonstrates capacity to improve upon status quo, not merely maintain it.

The Practical Implications

For Personnel Selection

The letter suggests testing candidates’ thinking quality through:

Impossible-seeming questions: Like the prison abolition challenge

Observation of response patterns: Do they seek solutions or enumerate obstacles?

Assessment of belief flexibility: Can they suspend disbelief for creative exploration?

Evaluation of learning orientation: Do they “play fool” to learn or “be smart” to impress?

The person’s response to such tests reveals more about their potential than credentials or experience can.

For Self-Development

For those seeking to develop superior thinking quality:

Cultivate solution-focus: Train mind to seek ways rather than obstacles

Develop belief-based thinking: Practice believing solutions can be found

Question assumptions: Regularly challenge “that’s how it’s always been”

Embrace “not understanding”: View ignorance as opportunity rather than shame

Practice “playing fool”: Ask questions, admit gaps, remain open to learning

Resist knowledge-rigidity: Don’t let existing knowledge close mind to new possibilities

For Leadership

Leaders should:

Ban “impossible” language: As Rockefeller did, prohibit defeatist declarations

Reward creative thinking: Promote those who find better ways

Challenge traditional thinking: Question precedent and status quo systematically

Model belief-based problem-solving: Demonstrate that solutions can be found

Encourage “playing fool”: Create culture where admitting ignorance enables learning

The Deeper Philosophy

Thinking as Foundation

Throughout the letter, Rockefeller treats thinking quality as foundational to all achievement:

“Learning itself is not very good. Learning must be used to make it work. To become a person who can use what you have learned, you must first become a person with practical ability.”

Knowledge without quality thinking remains inert; quality thinking converts knowledge into capability.

The Ability Source

“So where does the ability to practice come from? In my opinion, it is hidden in hardship.”

This connects thinking quality to experience, particularly difficult experience: “Walking a difficult road—a road full of hardships, misfortunes, failures and difficulties will not only build our strong character, but also the ability to implement great things that we rely on will come into being.”

Hardship builds practical capability by forcing creative problem-solving in high-stakes situations where theoretical knowledge proves insufficient.

The Character Connection

“Those who climb out of the midst of suffering know what it means to find ways and means to save themselves.”

This reveals that creative problem-solving capability isn’t purely intellectual but involves character—the determination to find solutions when circumstances demand it.

The Primacy of How You Think

Letter 28 establishes thinking quality—specifically, creative problem-solving capability grounded in belief that solutions can be found—as the fundamental determinant of potential and achievement.

The letter’s enduring insights include:

First, the ability to find better ways of doing things matters more than knowledge, credentials, or experience. Roger’s disqualification despite adequate background demonstrates this principle.

Second, belief determines whether the brain functions as obstacle-generator or solution-generator. Believing something is impossible causes mind to produce reasons supporting impossibility; believing solutions can be found causes mind to discover them.

Third, the “impossible” declaration is self-fulfilling prophecy. Once someone declares impossibility, confirmation bias generates endless supporting evidence, making the declaration true.

Fourth, knowledge paradoxically creates rigidity by generating “I understand” psychology that closes mind to new possibilities. The expert often cannot innovate because knowledge creates false confidence of complete understanding.

Fifth, “playing fool”—acknowledging ignorance, asking questions, remaining open—proves smarter than “being smart” through displaying knowledge and expertise. The former enables learning; the latter prevents it.

Sixth, creative thinking capability can be tested through impossible-seeming questions that reveal whether someone seeks solutions or enumerates obstacles.

Seventh, hardship and difficulty build practical capability by forcing creative problem-solving in high-stakes situations where theoretical knowledge proves insufficient.

The letter’s message to John Jr. regarding Roger’s promotion is unambiguous: do not advance people to significant responsibility based on credentials, knowledge, or loyalty if they lack creative thinking capability.

Roger’s inability to engage creatively with the prison abolition question revealed fundamental limitation that would manifest as failure under actual responsibility. Better to recognize this limitation through harmless hypothetical question than discover it through costly real-world failure.

For all readers, the framework is transformative:

Your achievement will be determined less by what you know than by how you think.

Develop belief that solutions can be found→ Mind searches for solutions

Cultivate creative problem-solving→ Discover better methods

Question assumptions systematically→ Challenge limitations others accept

Embrace “not understanding”→ Create opportunities for learning

Practice “playing fool”→ Remain open while gathering information

Resist knowledge-rigidity → Don’t let expertise close mind

The person who develops superior thinking quality—who seeks solutions rather than obstacles, believes in possibilities rather than impossibilities, questions assumptions rather than accepting them, embraces ignorance rather than hiding it—will outperform those with superior credentials but inferior thinking.

Rockefeller’s principle for advancement—”those who can find ways to do things better”—applies universally. In any domain, at any level, the person who discovers improvements and innovations proves more valuable than the person who merely maintains status quo, regardless of how competently they maintain it.

The deepest wisdom: human potential is constrained less by external circumstances or innate limitations than by internal thinking patterns. The person who believes things cannot be done will find endless confirming evidence. The person who believes solutions can be found will discover them with remarkable consistency.

Roger failed Rockefeller’s test not because he lacked intelligence or knowledge but because his thinking quality was poor—he defaulted to impossibility, defended status quo, and couldn’t engage creatively with challenging questions. This thinking pattern would have manifested as failure at every level of increasing responsibility because the pattern itself, not merely specific knowledge gaps, was the limitation.

The invitation Letter 28 extends is to examine and transform thinking quality:

Are you solution-focused or obstacle-focused? Do you believe better ways can be found or defend current methods? Do you question assumptions or accept them? Do you “play fool” to learn or “be smart” to impress? Does your knowledge enable creativity or create rigidity?

The answers determine not just whether you deserve promotion but whether you’ll achieve anything genuinely significant. Superior thinking quality, sustained over time, produces breakthrough achievements that superior knowledge alone cannot. This is why Rockefeller insists on thinking quality as the criterion for advancement—and why Roger, despite adequate credentials, must not be trusted with major responsibility.