How to Be More Interesting

In one sentence

To be interesting, you must move from "automatic" thinking—which relies on clichés and social scripts—to "active" thinking, which deliberately explores alternative perspectives and unconventional connections.

Why read this (for who it's for)

Most people believe being "interesting" is about having a high-status life, exotic experiences, or a unique set of hobbies. De Bono argues that being interesting is actually a cognitive style. This book is for anyone who feels they have "nothing to say," who finds themselves stuck in repetitive small talk, or who wants to become a more creative thinker in their professional and personal life. After reading this, you will be able to generate original thoughts on demand by systematically breaking your own mental habits.

The big idea

De Bono argues that the reason we are often boring is that our brains are designed for efficiency, not for novelty. We use "mental shortcuts" to navigate the world: we rely on clichés, common knowledge, and the "expected" response. While these shortcuts help us survive, they kill our ability to see the world uniquely. To be interesting, you must consciously override these shortcuts.

The core thesis is that interestingness is the byproduct of a creative mind. If you can see a situation from a different angle, you will naturally have something unique to say about it. Therefore, the goal isn't to "perform" interestingness; it is to cultivate a mind that is capable of generating original thoughts. You do this by practicing "lateral thinking"—the ability to move sideways, to look for what is not there, and to challenge the "obvious" conclusions of our daily lives.

Key ideas

The Trap of Automaticity

What it is — Our brains operate on "automatic" modes to save energy. In conversation, this means we often wait for our turn to speak rather than listening, and we rely on pre-packaged stories rather than spontaneous observations. Why it matters — If you rely on automaticity, you will always say what everyone else is thinking. You become a mirror of the crowd rather than a source of original thought. In the book — De Bono illustrates how we often "prepare" our response while the other person is still talking, meaning we aren't actually processing their unique input.

The Definition of Interesting

What it is — Interestingness is the ability to provide a new perspective or a "different" way of looking at a common thing. It is the opposite of "common" or "expected." Why it matters — It shifts the goal from content (what you say) to process (how you think). If you change the process, the content becomes interesting automatically. In the book — He argues that an interesting person doesn't just tell a "cool" story; they offer a perspective that makes the listener see a mundane object or situation in a way they hadn't considered before.

Lateral Thinking vs. Vertical Thinking

What it is — Vertical thinking is the logical, step-by-step progression of a known path (A leads to B). Lateral thinking is the "sideways" jump to a new path (A leads to C). Why it matters — Most people try to be interesting by thinking harder about the same old ideas (vertical). To be interesting, you must think differently (lateral). In the book — De Bono uses the analogy of a maze: Vertical thinking is trying to find the fastest way through the existing paths; Lateral thinking is looking for a way to jump over the walls or find a hidden door.

The Power of "What If?"

What it is — A fundamental tool for generating new ideas is the "What if?" question. It forces the brain to abandon the current reality and explore a hypothetical alternative. Why it matters — It breaks the "common sense" barrier. Common sense is often just a set of social rules that prevent us from seeing what is actually possible. In the book — He encourages readers to ask "What if" about mundane things, like "What if chairs were illegal?" or "What if gravity worked in reverse for ten minutes a day?"

Challenging the "Obvious"

What it is — The "obvious" is the enemy of the interesting. To be interesting, you must identify what everyone assumes to be true and then question it. Why it matters — If you agree with the obvious, you are redundant. If you challenge the obvious, you provide value and novelty. In the book — De Bono suggests looking at a common object (like a pencil) and asking: "Why is it this shape? Why is it this material? What would happen if it were liquid?"

Frameworks & tools

The "Alternative Perspective" Protocol

Use this when you find yourself stuck in a boring conversation or a stagnant thought process.

1. Identify the "Common" View: What is the standard, expected answer to the current topic?
2. The "Opposite" Test: What would the exact opposite of that answer look like? (Even if it's absurd).
3. The "Different" Test: What is a third option that isn't the opposite, but is still not the "common" view?
4. The "Why" Drill: Ask "Why is it this way?" three times in a row to peel back the layers of assumption.

The "What If" Expansion

A tool for generating creative content for writing, speaking, or socializing.

1. Pick a Subject: Choose a mundane object, a social rule, or a daily routine.
2. Apply a "What If" Constraint: Change one fundamental rule of that subject.
3. Explore the Consequences: If that rule changed, how would the world/object/routine change?
4. Share the Result: Describe the new reality to the other person.

Memorable examples & stories

The Pencil Example

De Bono asks the reader to look at a pencil. Most people see a tool for writing. He challenges you to see it as a "stick of graphite encased in wood." By changing the vocabulary, you change the perspective. Lesson: Changing your words changes your thoughts.

The "Why" of Chairs

He explores why chairs are designed the way they are. Most people take the chair for granted. By asking "Why is it this height? Why does it have four legs?", he shows how to find interest in the mundane. Lesson: Interest is found in the details of the familiar.

The "Obvious" Trap

De Bono describes how we often stop thinking the moment we find an "obvious" answer. If someone asks, "How can we improve this?" and you say, "We need to work harder," you have stopped thinking. Lesson: The "obvious" answer is a dead end for creativity.

Key quotes

"Interestingness is not a matter of what you know, but how you think." (Paraphrased) Why it matters: It shifts the focus from accumulation of facts to the quality of mental processing.

"The enemy of the interesting is the obvious." (Paraphrased) Why it matters: It identifies the specific mental habit (common sense) that kills original thought.

"To be interesting, you must be able to see what others miss." (Paraphrased) Why it matters: It defines the ultimate goal of lateral thinking as a social and intellectual superpower.

How to apply it

This week

• The "Why" Exercise: Choose one object in your house every day (a toaster, a shoe, a spoon). Ask "Why is it designed this way?" and come up with three alternative designs.
• The "Opposite" Response: In a low-stakes conversation (with a friend or family member), when someone asks for your opinion on a common topic, briefly consider the exact opposite of your first thought before speaking.
• The "What If" Journal: Write down three "What if" scenarios before bed. Example: "What if humans could see infrared?"

Ongoing

• Break the Script: When someone asks "How are you?", instead of "Fine," give a specific, slightly unusual observation about your day.
• Active Listening for "The Gap": When listening to others, listen for what they aren't saying or the assumptions they are making.
• Practice Lateral Thinking: Whenever you face a problem, force yourself to come up with three "bad" or "impossible" ideas before you allow yourself to think of a "good" one.

Common pitfalls

• The "Performance" Trap: Many readers try to act interesting by telling "cool" stories. De Bono warns that this is just a different form of automaticity. You must change your thinking, not your acting.
• Over-complicating the "What If": You don't need to solve world problems. The goal is to practice the muscle of lateral thinking, not to produce a Nobel Prize-winning invention every time you look at a chair.
• The "Expert" Fallacy: Thinking you need to be an expert in a field to be interesting. You don't. You just need to be able to look at the field from a new angle.

Connects to

• "Thinking, Fast and Slow" by Daniel Kahneman: Explains the "System 1" (automatic) thinking that De Bono wants you to override.
• "Big Magic" by Elizabeth Gilbert: While more about the feeling of creativity, it complements De Bono's mechanics of creativity.
• "The Art of Thinking Clearly" by Rolf Dobelli: Helps identify the cognitive biases that lead us toward the "obvious" rather than the "interesting."

If you remember only three things

• Interestingness is a cognitive skill, not a personality trait.
• The enemy of interesting thought is the "obvious" (automatic thinking).
• Use "What if?" and Lateral Thinking to see what others miss.

Internalize it

• Reflection questions

  • When was the last time I had a thought that was truly original, rather than a recycled opinion?
  • What "obvious" truths do I accept every day without questioning?
  • How would my daily routine change if I applied a "What if?" constraint to my morning coffee?
  • Can I describe a common object (like a door) in a way that makes someone see it differently?

• Flashcards Q: Is being interesting a personality trait? A: No, it is a cognitive skill based on how you process information. Q: What is the "enemy" of interesting thought? A: The "obvious"—the automatic, expected responses our brains use to save energy. Q: What is Lateral Thinking? A: Thinking "sideways" to find new paths rather than moving "vertically" through known logical steps. Q: What is the primary tool for generating new ideas? A: The "What if?" question, which forces the brain to explore hypothetical alternatives. Q: How does De Bono suggest we look at common objects? A: By breaking them down into their basic components (e.g., a pencil is a "stick of graphite encased in wood") to see them as new. Q: What is the difference between "performing" interestingness and "being" interesting? A: Performing is using a script of "cool" stories; being is having a mental process that generates original perspectives.

Fidelity note

This summary is based on Edward de Bono's core principles of lateral thinking and his specific application of these to the concept of "interestingness." I am highly confident in the distinction between vertical and lateral thinking and the "What if" framework. Because De Bono's work is often a series of conceptual exercises, the "stories" are often mental experiments rather than historical anecdotes. Readers should verify the specific "What if" prompts in the text to find more variety.