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How to Become a Really Good Pain in the Ass

How to Become a Really Good Pain in the Ass

A Critical Thinker's Guide to Asking the Right Questions
by Christopher W. DiCarlo 2007 398 pages
3.59
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Key Takeaways

1. Become a "Pain in the Ass" to Question Beliefs and Assumptions

The purpose of this book is to provide tools to allow you to question beliefs held and assumptions made by others who claim to know what they're talking about.

Empower yourself. Being a "really good pain in the ass" isn't about being obnoxious; it's about using critical thinking tools to challenge unfounded claims and hold people accountable for their beliefs and actions. This skill is vital for navigating a world filled with confident assertions, from politicians and experts to friends and family.

Question everything. Just as Socrates challenged Athenians to examine their deeply held beliefs, you can use questioning to reveal faulty reasoning and inconsistencies. This process helps clarify your own ideas and understand opposing views, fostering more meaningful discussions.

Be prepared. Challenging others' views can be uncomfortable for them, as people often dislike having their beliefs questioned. While this path can be lonely and may lead to conflict, it empowers you to think more clearly and confidently about important issues affecting everyone.

2. Arguments Provide Structure for Your Ideas

To have an argument, you need at least one premise and one conclusion.

Build your house. Think of an argument like a house: the conclusion is the roof (your main point), the premises are the walls (your reasons), and the assumptions are the foundation (underlying beliefs). A strong argument requires sturdy walls supported by a solid foundation.

Deductive vs. Inductive. Arguments use different types of reasoning:

  • Deductive: Guarantees the conclusion if premises are true (like solving Clue). Forms include Modus Ponens (If A, then B; A; therefore B) and Modus Tollens (If A, then B; Not B; therefore Not A). Validity is about structure, not content.
  • Inductive: Provides probable or likely conclusions based on evidence (like scientific generalizations). Conclusions are warranted, not guaranteed.

Clarity is key. Structuring your ideas as arguments increases the chance of being understood, even if others disagree. Diagramming arguments helps visualize this structure, distinguishing conclusions from supporting premises and underlying assumptions.

3. Understand How Biases and Context Shape Perception

To ignore context is to ignore a very important aspect and dynamic of critical thinking and reasoning and argumentation.

Filters of information. Biases, both biological (genetics, neurochemistry, emotions, sex, health) and cultural (memes, ethnicity, family, religion, geography, education, friends, media), act as filters through which we interpret information. Recognizing your own biases is the most difficult part of critical thinking.

Circumstances matter. Context includes time, place, surroundings, and circumstances. Information taken out of context can lead to unfair judgments and hasty reactions, as seen in media manipulation or misinterpretations of events.

Play fair. Understanding context and acknowledging biases are crucial for fair play in critical thinking. This involves:

  • Acknowledging your biases.
  • Gathering enough facts and understanding their context before judging.
  • Being open to revising your position based on new information.

4. Evaluate Claims Based on Evidence and Criteria

Extraordinary claims require extraordinary evidence.

The Sagan principle. The strength of a claim dictates the level of evidence required to support it. Simple claims need little evidence, while extraordinary claims demand compelling proof. Believing something on insufficient evidence is irresponsible.

Types of evidence:

  • Anecdotal: Personal experience (often unreliable on its own).
  • Legal Testimony: Sworn statements in court (can be biased).
  • Intuition: Gut feelings (least justifiable, hard to measure).
  • Scientific: Empirical data gathered through systematic methods (most reliable for natural world).

Criteria for good evidence. Evidence should adhere to standards:

  • Consistency: Avoids contradictions (aligned with Laws of Thought: Identity, Noncontradiction, Excluded Middle).
  • Simplicity: Favors less complicated explanations (Occam's razor).
  • Reliability: Comes from trustworthy sources with proven track records.
  • Relevance: Directly supports the conclusion.
  • Sufficiency: Provides enough support for the claim's strength.

5. Identify and Avoid Common Errors in Reasoning

A fallacy is an error in reasoning.

Inconsistency weakens arguments. Fallacies are flaws in the structure or content of an argument that make it unreliable. They often stem from inconsistency, whether in stated reasons or between beliefs and actions (hypocrisy).

Common fallacies to spot:

  • Ad Hominem: Attacking the person, not the argument.
  • Ad Ignorantiam: Arguing something is true because it hasn't been proven false (or vice versa).
  • Appeal to Authority: Relying solely on authority without evaluating the argument itself.
  • Ad Populum: Claiming something is true because it's popular.
  • Begging the Question: Assuming the conclusion in the premises (circular reasoning).
  • Confirmation Bias: Seeking only evidence that supports existing beliefs.
  • Post Hoc: Assuming causation because one event followed another.
  • Slippery Slope: Arguing one action will inevitably lead to a terrible outcome.
  • Straw Man: Misrepresenting an opponent's argument to make it easier to attack.

Be vigilant. Recognizing fallacies in others' arguments and your own is crucial for sound reasoning. While avoiding them entirely is difficult, awareness helps limit their impact.

6. Learn from Socrates: The Power of Questioning Ignorance

...for the unexamined life is not worth living...

The Socratic method. Socrates used feigned ignorance and persistent questioning to reveal inconsistencies in people's beliefs, demonstrating how little they truly knew about concepts like piety or justice. This often frustrated those who thought they possessed wisdom.

The gadfly. Socrates saw himself as a "gadfly," stinging society (a lazy horse) to provoke critical thought. He was executed for challenging the status quo and encouraging youth to question authority and traditional beliefs.

Reflective vs. Blind Ignorance. Socrates distinguished between:

  • Reflective Ignorance: Knowing that you don't know (Socrates's position on supernatural matters).
  • Blind Ignorance: Believing you know when you don't (the dogmatists).
    Being a good pain in the ass involves helping others see their blind ignorance, fostering humility and a more responsible approach to knowledge.

7. Embrace Skepticism: Suspend Judgment on Absolute Truth

The Greek term skeptikos means 'inquirer' or 'investigator.'

Beyond doubt. Skepticism, or Pyrrhonism, is not just doubting but actively inquiring. Ancient Skeptics, like Pyrrho and the Academics, questioned the possibility of attaining absolute truth (Big T Truth), especially regarding supernatural matters.

The Reality Measuring Stick. Skeptics argued that without a universal criterion or "Reality Measuring Stick" to objectively measure truth, particularly supernatural claims, we are in the dark (like the "gold in the dark room" analogy). Different perspectives (species, individuals, senses, circumstances) conflict, and there's no way to definitively say which is "truer."

Modes of Inquiry. Skeptics developed "modes" to demonstrate the relativity of perceptions and the flaws in dogmatists' proofs:

  • 10 Modes: Highlight conflicting appearances and observations.
  • 5 Modes (Agrippa's): Attack proofs based on discrepancy, infinite regress, relativity, hypothesis, and circularity (the Münchhausen Trilemma).

Practical living. Despite questioning absolute knowledge, skeptics lived practical lives (the Practical Criterion), relying on appearances, bodily drives, laws, and skills. They distinguished Big T Truth (unknowable) from little t truth (practical, provisional understanding).

8. Distinguish Natural and Supernatural Ways of Knowing

The most basic form of natural response is common sense.

Two realms. The book frames answers to the Big Five (What can I know? Why am I here? What am I? How should I behave? What is to come of me?) through two main lenses:

  • Natural: Observable, testable phenomena governed by knowable laws (science, common sense).
  • Supernatural: Above or beyond nature (deities, spirits, paranormal activity).

Testability is key. While natural claims are open to empirical and rational scrutiny, supernatural claims often invoke insulation strategies (like Russell's teapot) to avoid testing. However, any supernatural claim that purports to intervene in the natural world is, by definition, open to scientific investigation.

Criteria differ. Natural knowledge relies on criteria like consistency, coherence, and empirical evidence, leading to provisional, probabilistic understanding (little t truth). Supernatural claims often rely on faith, revelation, or tradition, lacking a measurable standard for absolute certainty (Big T Truth).

9. What We Can Know Is Limited and Probabilistic

No assertion without assumption.

Inherent limitations. From a natural perspective, our knowledge is limited by historical facticity (the tools and language of our time) and the need to make assumptions (every assertion rests on presuppositions). Absolute certainty about Reality is unattainable.

Complex systems. The Onion Skin Theory of Knowledge (OSTOK) illustrates the vast, complex interplay of Natural Systems (RNS - physics, biology, etc.) and Cultural Systems (RCS - family, politics, etc.). Understanding causal clusters within this network is key to natural knowledge.

Probabilistic understanding. Natural knowledge is provisional and probabilistic, not absolute. Science builds a self-correcting, cumulative understanding of the natural world, constantly revising models based on evidence. Supernatural claims, lacking measurable criteria, cannot demonstrate absolute knowledge.

10. Our Origins Are Rooted in Natural Processes, Not Necessarily Design

Our ancestry lies in the primordial oceans of a very young Earth.

Natural origins. A natural response to "Why am I here?" and "What am I?" points to cosmic, geological, and biological evolution over billions of years. From quantum fluctuations and star formation to the emergence of life in primordial oceans and the evolution of Homo sapiens from earlier hominins in Africa, naturalism offers a detailed, evidence-based account.

Evidence abounds. This natural narrative is supported by converging evidence:

  • Radiometric Dating: Measures the age of Earth and the universe.
  • Fossil Record: Documents the history and lineage of life, including hominins.
  • Genetics: Traces human migration out of Africa via DNA analysis (e.g., Genographic Project).

Implications of African origins. Accepting our shared African ancestry highlights human interconnectedness and challenges socially constructed ideas like racism. It suggests we are products of chance and natural processes, not necessarily divine intention.

Supernatural creation myths. In contrast, supernatural responses offer diverse creation myths (Eskimo, Egyptian, Abrahamic, etc.) and rational proofs (ontological, cosmological, teleological). These often lack empirical support, rely on question-begging, and struggle with logical inconsistencies (e.g., the problem of a caused cause or arbitrary divine will).

11. Ethical Behavior Stems from Social Needs and Harm Reduction

There is nothing more frightful than ignorance in action.

Natural ethics. From a natural perspective, ethics and morality evolved from the needs of social species, particularly humans, for group survival and cooperation. Rules emerged to manage behavior related to survival and reproduction (fight, flight, food, procreation).

Constraints and control. Human behavior is influenced by complex natural and cultural constraints (OSTOK). This raises questions about free will and accountability – how much control do we truly have over our actions? Science is increasingly revealing the causal factors behind behavior.

Common principles. Despite complexity, some ethical principles appear across cultures and belief systems:

  • The Golden Rule: Treat others as you wish to be treated.
  • The No Harm Principle: Avoid causing unnecessary or unwanted suffering.
  • Tolerance-Harm Inverse Proportion (T-HIP): Tolerance for beliefs/actions decreases as the harm they cause increases.

Supernatural ethics. Supernatural responses often ground ethics in divine commands or karmic systems, linking behavior to eternal reward or punishment. While some supernatural moral principles overlap with natural ones (Golden Rule, No Harm), the motivation (divine approval/afterlife reward) and justification (untestable divine will) differ significantly from a naturalistic focus on practical benefit and harm reduction.

12. What Comes Next Remains Unknown, Emphasizing This Life

I don't believe in the afterlife, although I am bringing a change of underwear.

During life. A naturalist sees life's trajectory influenced by complex, often random causal factors (OSTOK, epigenetics, luck). While we manipulate systems to our advantage, our control is limited. Supernaturalists often attribute outcomes to divine intervention or prayer, despite lack of empirical evidence and logical inconsistencies (e.g., divine plan vs. miracles).

After death. Regarding what comes after death, the naturalist position is "I don't know." Based on evidence from neuroscience and analogy with other species, the most likely outcome is nothingness – the cessation of consciousness. While some speculate about physical continuance in unknown dimensions, this relies on the argument from ignorance.

Fear of nothingness. The prospect of eternal nothingness is terrifying for many, driving a strong metaphysical yearning for meaning and purpose beyond this life. This fear fuels belief in diverse afterlife concepts (heaven, hell, reincarnation, etc.).

Untestable claims. Supernatural afterlife claims, however, lack empirical or rational proof and conflict with each other. Near-death experiences (NDEs), often cited as evidence, have plausible natural explanations (brain activity during oxygen deprivation). Without a Reality Measuring Stick, these remain matters of faith, not verifiable knowledge.

Value of this life. For the naturalist, accepting the possibility that this is the only life we have places immense value on the present. It emphasizes the importance of how we treat each other and the planet, making this life everything.

Last updated:

Review Summary

3.59 out of 5
Average of 100+ ratings from Goodreads and Amazon.

How to Become a Really Good Pain in the Ass receives mixed reviews, with an average rating of 3.59 out of 5. Readers appreciate the book's introduction to critical thinking, logical fallacies, and philosophical concepts. Many find it humorous and accessible, particularly for beginners. However, some criticize the unnecessary illustrations, repetitive content, and biased tone, especially in the later sections. The book is praised for its historical overview of skepticism and its approach to addressing "big questions," but some readers feel it becomes less engaging in the latter half.

Your rating:
4.37
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About the Author

Christopher W. DiCarlo is a Canadian philosopher, author, and educator. He has taught at the University of Ontario Institute of Technology and the University of Toronto. DiCarlo is known for his work in critical thinking and skepticism, with a focus on naturalistic approaches to understanding the world. He has written extensively on topics such as epistemology, logic, and the intersection of science and philosophy. DiCarlo's writing style is often described as accessible and humorous, aiming to make complex philosophical concepts understandable to a general audience. His work emphasizes the importance of rational inquiry and evidence-based reasoning in addressing life's fundamental questions.

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