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How to Become a Really Good Pain in the Ass: A Critical Thinker's Guide to Asking the Right Questions

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In this classic guide to critical thinking, author Christopher DiCarlo provides you with the tools you need to question beliefs and assumptions held by those who claim to know what they're talking about. How to Become a Really Good Pain in the Ass provides timely solutions for today's world of misinformation based on timeless principles of logic and reason. These days there are many people whom we need to politicians, lawyers, doctors, teachers, clergy members, bankers, car salesmen, and your boss. This book will empower you with the ability to spot faulty reasoning and, by asking the right sorts of questions, hold people accountable not only for what they believe but how they behave. By using this book you'll learn to analyze your own thoughts, ideas, and beliefs, and why you act on them (or don't). This, in turn, will help you to understand why others might hold opposing views. And the best way to change our own or others' behavior or attitudes is to gain greater clarity about underlying motives and thought processes. In a media-driven world of talking heads, gurus, urban legends, and hype, learning to think more clearly and critically, and helping others to do the same, is one of the most important things you can do.

398 pages, Paperback

First published January 1, 2007

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About the author

Christopher W. DiCarlo

4 books10 followers

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5 stars
53 (19%)
4 stars
97 (36%)
3 stars
81 (30%)
2 stars
29 (10%)
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9 (3%)
Displaying 1 - 30 of 41 reviews
Profile Image for Brad.
220 reviews11 followers
September 24, 2012
There. Now it’s official. Rather than simply being accused of being a pain in the ass, I now have the requisite credentials to make it official. I feel emboldened now. Let the pain in the assing begin!

To be fair, the pain in the ass I have heretofore assumed I was is not the same sort as the pain in the ass training offered here. Previously, my pain in the assdom was related to the aspects of my personality that chose to use words like “heretofore.” The ass-paining training introduced here is essentially about honing one’s critical thinking skills, recognizing fallacies and inconsistencies in others position, and then tearing the argument the hell apart! Take that, small minded jerks!

Ok. So the concept that one is a “pain in the ass” because those whose brains are not as rational as yours will get so overwhelmingly frustrated by your superior thinking abilities is sorta condescending. I don’t think DiCarlo meant it as such; instead he inserts a light hearted approach with copious attempts at humor. That is where the title comes from. And sometimes his whimsical approach works; other times it falls flat. As a whole, the book is somewhat disjointed: the first third is the real ‘pain in the ass’ training and offers us the ABCDEs and Fs of critical thinking. At times it seemed too superficial (I would take Sagan’s Skeptical Toolkit from Demon Haunted World, personally, but comparing anyone to Sagan is cruel because he’s Carl Freaking Sagan) but I still found aspects rather useful.I particularly enjoyed F is for Fallacies. The second third on the history of Pain in the Asserdom was the weakest portion and the final third, using our newly honed critical thinking skills to answer life’s biggest questions, was the most intriguing.

I’m all for improving critical thinking – not only mine, but everyone’s. The tools to develop a critically minded approach to problem solving are, ultimately, what are lacking from contemporary discussions. So DiCarlo’s high spirited take is welcome. A quick and easy read and quite fun as well.
Profile Image for Bethany.
20 reviews
September 15, 2013
This book had three major problems for me.
1) The tone. DiCarlo writes this as if he is speaking to a classroom full of students, which isn't really a bad this, but as I am not a student, the tone comes off as a bit condescending/patronizing. I do not believe this is intentional, but it was still off-putting.
2) The graphics. 95% of the graphics in this book do not add anything to the text. They are there to show pictures. This would not be as much of an issue if DiCarlo did not refer to them in the text as if they would help the reader understand his point. Also, many pictures were drawn rather than shown as photographs, even when photographs are easily attainable. For example, when mentioning President Bill Clinton, he references a hand drawn sketch of the president, despite many pictures of said president in the public domain. Also, when talking about the straw man fallacy, instead of a graphic outlining said fallacy, there is a drawing of a straw man, which does not help the reader understand this fallacy.
3) Section 3. Section 3 does not add anything to becoming a better critical thinker. It merely answers five philosophical questions in the way of a "naturalist" or a "supernaturalist," clearly showing how "supernaturalists" have inferior critical thinking skills. Now, I am an agnostic, so if an author wants to poke a stick at religion, that's fine by me, but it is out of place here. DiCarlo could have taken any arguments and shown how one's reasoning is flawed in a variety of ways, but by adding this section, DiCarlo may have alienated many of his audience who want to learn these skills, but were not yet ready to apply them to religion. Start small, then work your way up.

That said, the first two sections of the book had helpful information, and could go a long way towards creating more critical thought in the world, which can only be a good thing.
Profile Image for Todd N.
361 reviews263 followers
January 15, 2023
Really interesting book and useful overview of techniques for thinking critically and making cogent arguments. I only read section 1 about arguments/critical thinking and section 2 about Socrates and the Skeptics. The latter parts about the Big Questions felt less useful.

Although the book was published in 2011, 12 years ago, it comes from a more innocent time when people weren't being besieged by a constant barrage of bad faith arguments from the left, the right, social media, news, editorials, parents, children, pets, spouses, advertising, corporations, HR departments, click-thru agreements, and cookie pop-ups to name a few off the top of my head. In this environment, reading this book feels more like a defensive act than self-improvement.

Prof. DiCarlo writes as if the biggest threat to critical thinking is "supernatural thinking," religion, mediums, and woo-woo ideas. If only. Honestly, I never saw the huge conflict between the two, as long as everyone stays in their lane. I can be both billion year old carbon and having to get back to the garden.

I went through the first sections a second time, and this time put the main points into an Apple note so I can review it later. I'm especially interested in the false syllogisms and logical fallacies. By the way, I think the killer app for social media would be some sort of code that points out logical fallacies. Imagine if Facebook comments were tagged with something like "Warning: this post contains ad hominem and tu quoque fallacies. Click here for more details."

Recommended, even if just to flip through for the parts that you find interesting.
87 reviews69 followers
March 4, 2017
I loved the book but some parts of it looked a little biased. But anyway, we all have our biases. Overall the book is well written and very interesting and more so if you have some background in logic theory and mathematics.
Profile Image for Jennifer.
1,678 reviews63 followers
September 3, 2012
DiCarlo's work is really more like two books in one: Part One, How to Become a Really Good Pain in the Ass; Part Two, Let's Watch Christopher diCarlo Be a Really Good Pain in the Ass. Frankly, I found the former far superior to the latter (possibly because I like truth in advertising), full of loads of tips and tricks that I plan to practice on poor, unsuspecting people throughout the duration of the campaign season. The second half isn't bad, per se, just... anticlimactic. Extra points given for wildly random things dropped into extremely serious discussions ("Thou shalt sodomize squirrels on the Sabbath" was priceless).
124 reviews18 followers
December 22, 2020
'Critical Thinking' is a phrase that gets thrown around often but it is rare that a hear a good definition of what it is. This is the BEST book I've ever read on the subject which breaks down epistemology, the theory of knowledge. It covers structured logic (the logic forms of argumentation), logical fallacies, how we are biased not simply by our environments but also by our biology, deductive/inductive reasoning and the differences in views between naturalistic (rational + empirical thought) thinking and thought influenced by a predilection for the supernatural. One of my favorite books for illustrating reasoning and valid knowledge.
Profile Image for Mathew.
26 reviews
May 19, 2013
Very much enjoyed this book. I'm not a philosophy major but appreciated all this book covered. It helps you understand where people are coming from and what they're influenced by. I didn't read this to learn to be a pain in the ass so much as to learn how to formulate a solid argument or position and this book covers that.

I did find some of the topics a little hollow and overly lengthy but the author knew what he was trying to share so I'll just go with it.

Profile Image for Blakely.
207 reviews6 followers
September 25, 2013
If your college Philosophy class was a three course meal this is a nice light snack. Quick, easy to read and to understand, but still pretty good. This contains probably the best description of the Socratic Method I've every read.
Profile Image for Bruce.
19 reviews
January 9, 2012
Good roadmap to a way of thinking about your views of the world. It provides terminology, rationale and comparison for multiple views. A good starting point for a more formal entry into skepticism.
196 reviews1 follower
August 28, 2022
I can't remember offhand exactly how I heard about this book, but it's been quite a few years since I purchased it originally. In fact I believe I have the first edition as opposed to what is currently on sale because the cover is different.

The title in itself is quite intriguing shall we say, and while it might offend some people it is extremely relevant to the contents of this book. The fact that students today are not taught any, or at least very few critical thinking skills is a shame. This book goes a long way to correcting this shortsighted component of our educational system.

The book itself gives an extremely in-depth but easy to read introduction to critical thinking, arguments, how arguments are structured, scientific reasoning, the rules of reasoning, and much more. It does this with excellent examples, that should be relevant to any reader.

At the time of writing Dr. Carlo was a professor at University of Ontario Institute of technology, and now according to the internet is at the University of Toronto. I assume, although it's not stated that this book is based on his lectures to undergraduate students.

I believe this would be an excellent book for every undergraduate student in the sciences and liberal liberal arts to read as it gives it a very good background to critical thinking, something that every student should be aware of and be fluent in.
Profile Image for Bethany.
1,183 reviews20 followers
February 19, 2021
I thought this book was going to make me armed and dangerous in a debate. Instead I got a delightful discourse on philosophy, physics, anthropology, genetics and religion.

This guy would have been my favorite professor. I always appreciate finding someone who can so eloquently articulate my own beliefs.

Bonus points for working in a conversation about fellatio into a chapter on fallacies.

My 5 question answers:
What can I know?
A lot about a little or a little about a lot, but a fraction of everything either way

Why am I here?
To contribute, to dissipate energy, to improve

What am I?
A human, who likes my kids and pets, to read, to explore

How should I behave?
As a productive contributing member of society

What is to come of me?
I will die. Some people may remember me. My energy will reabsorbed into the universe.
Profile Image for Vlad.
4 reviews1 follower
March 24, 2020
It was an alright introductory book. The author does a great job explaining logical laws and concepts. The historical background of the skeptics & other followings were also very insightful. However, the last half of the book which addressed the 'big 5 questions' were easily skippable and added nothing, in my opinion.

There were so many useless pictures; they added nothing whatsoever. I vividly recall a simple drawing of a ruler, just because rulers were mentioned.
Profile Image for Marius.
11 reviews
October 20, 2024
Kitab sübut edir ki, Vikipediya ondan qat-qat yaxşıdır. Məntiq səfsətələrini detallı və düzgün öyrənmək üçün kitabı seçmişdim. Amma görünür ki, akademik kitab seçməməkdə səhv etmişəm. Məntiq səfsətələrini öyrənmək üçün kitab çox səthidir. Qeyd etdiyim kimi, Vikipediya bu baxımdan daha yaxşı izahlar verir. Ayrıca, kitabı yarısına qədər oxumaq lazımdır. İkinci hissə kitabın əsas müzakirə obyekti olan beş böyük suala fövqəltəbii və naturalist baxışlar arasındakı fərqi izah edir.
84 reviews
June 20, 2019
First and second part where okay, nothing i havent read before. The drawings didnt add anything to the book imo, good easy page turner.
Profile Image for Stacie.
45 reviews
September 27, 2019
Pretty darned good! It's an easy read and has some great techniques on forming rational arguments for debate.
Profile Image for JM.
22 reviews4 followers
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January 10, 2023
I refuse to read Socrates for Dummies.
Profile Image for Sarah Clement.
Author 3 books119 followers
February 6, 2013
This would be a really great book for teaching critical thinking to high schoolers. The writing is clear and easy to understand, and it covered the most basic and important aspects of critical thinking. It's systematically written, and it's very clear where diCarlo is taking you. However, the style of writing wasn't for me, as it seemed more like an essay for university than one with a compelling, interesting narrative. It was almost robotic at times, then he would throw in a pretty decent joke, so I don't think he's completely humourless! I just think his personality doesn't come through in the writing, and even though it's a book about a serious topic, I think a more compelling narrative would have made the book much better. His paragraphs are also unbearably long in parts, mainly because they cover more than one point. This not only makes it more difficult to read, but it doesn't make sense given how clear he is in most of the book. He also has a habit of repeating the same points over and over again. In several places he actually has almost an identical sentence written with slightly different wording, right in a row! The only reason I can think of for this is that he teaches undergraduates, and he must be used to having to flag his point really obviously and repeatedly to make sure it gets through. I'm a very slow, careful reader, however, so this drove me insane.

The illustrations in this book are weird. They are often of everyday objects, and it's difficult to find the method in the madness behind how these were selected. When there are relevant illustrations that are useful, they sometimes just threw me off. In his discussion of the "Onion Skin Theory of Knowledge" for instance, he is actually talking about pre-existing theories that many authors before him have discussed. Using systems theory to explain the relationship between natural and cultural systems is not new, and I found it a bit odd that he didn't reference any of these authors. There are entire disciplines devoted to this sort of perspective! (e.g. human ecology)

At the beginning of the book he asks you to answer 'the five big questions' and then you're supposed to answer them at the end. They were interesting, but it would have been better if he had either phrased the questions more accurately or set them up better. I personally misinterpreted a few. For instance, "why am I here?" was actually "why is the universe here?" and "what am I?" is actually "where did humans come from?" or something to that effect. If he had explained that this was to get a sense that this was about whether you believe in natural or supernatural origins of life, that would have changed my thinking, but I thought the questions were more about ontology and epistemology.

All that said, I am giving the book a fair rating because I think it's a really good guide to critical thinking, and I think it will be a useful book to keep around as a reference. I recently heard an interview with diCarlo, and I must say I am looking forward to his next book which is on free will. But I think with that book I will have a look through before buying to see that it's written in a style that is...well...more my style.

Profile Image for Bob.
35 reviews2 followers
April 25, 2013
When I started this book I was unimpressed by the accompanying diagrams -- they seemed totally unnecessary. And the first part of the book is really a primer for those unacquainted with the tools of critical thinking but it is well written with a certain self-deprecating humor. The author frames the book in terms of the Five Big Questions that most humans attempt to answer in some form or another either through a natural or a supernatural approach. It is designed for anyone who would like to know more about how to think of such things in a way that is honest and practical and meaningful.

The middle part of the book reviews early critical thinkers (it would have been a blast to have a further historical survey, but this was not part of the author's intention) and, again, is a good primer on the (written) origins of rationalism.

Having answered the big five as requested in the first part -- and anticipating that my answers wouldn't change -- I didn't expect much from the third section, where the author explores both the rational approach and the supernatural approach to answering these primary questions. But he really hit his stride and systematically broke down each of the ways we can arrive at answers to these questions.

Along the way he effectively gives a concise summary of the big bang, evolution, quantum mechanics and other scientific ideas that are top-notch. By the end of the book, I was energized and enthused by his methods and can readily recommend the book to the newly skeptical or to the open-minded believer both.
112 reviews15 followers
August 9, 2012
This is an excellent and accessible introduction to formal logic as well as an interesting discussion on philosophy. The first section deals with formal argument, including different structures of arguments as well as many fallacies common in Logic. The book itself has a definite bias towards a naturalist alignment, but does well to make attempts to emphasize the suspension of judgement towards the supernaturalist points of view. In the third section of the book, diCarlo makes a strong argument for taking the naturalist position when it comes to five of the most important questions of the human condition (the Big Five he calls them). He reminds the readers that we are subject to what he calls historical facticity, meaning that just because we can't quantify things like God, soul, and other supernatural entities, doesn't mean that they might not someday develop the means to empirically measure the soul (Newton would not have been able to discuss formal Quantum Mechanics, for example, the discourse of his particular milieu would have prohibited it--the knowledge had not yet been discovered). I would recommend this to anyone is looking to springboard into philosophy and logic, and is open to having ideas like faith, truth and knowledge examined closely. It is also ideal to those who took a 100-level philosophy course during their undergraduate career and wants to brush up on argument and reasoning skills.
Profile Image for Jay C.
393 reviews53 followers
April 1, 2012
Probably more like a 3.5 stars rating would be appropriate. Sort of a textbook on critical thinking and skeptical thinking as a PROCESS, rather than how it is more often viewed in the world at large as "not believing in anything." Definitely worth reading. It made me wonder/marvel at the fact that kids in school are not taught the tools of rational, logical thinking. Why is that, anyway?

One somewhat petty annoyance I found in the book was the inclusion of a lot of unnecessary or superfluous "illustrations" or "figures." DiCarlo discusses at one point how a squirrel may run across the road as you pass over him with your car and yet not be struck, and that this is not "miraculous" but rather a function of luck and timing of that particular "dash" the squirrel makes. When he mentions the squirrel, he parenthetically notes: "see figure x" which is a photograph of a squirrel sitting on a feeder. Really? Did that enhance my reading experience? No. I found it odd...
Profile Image for Fotis Chatzinicolaou.
79 reviews15 followers
July 3, 2014
Υπέροχο βιβλίο!

Μέσα αναλύονται όλα τα εργαλεία για να γίνει κάποιος a pain in the ass, ή για να το πω πιο light, ένας ορθολογιστής.

Μέσα θα βρείτε μια αναφορά στον Σωκράτη και αρχαίους Sceptics (το θεωρώ αστείο που τόσα χρόνια στα σχολεία, έμαθα τι είχε κάνει αυτός ο Σωκράτης χάρη σε ένα άσχετο βιβλίο), βασικούς κανονες για επιχειρηματολογια,διαστρεβλώσεις, πως να κοιτάζετε το περιεχόμενο σε διάφορες περιπτώσεις, πως να αξιολογείτε αποδείξεις και άλλα.

Το βιβλίο επίσης ξεκινά και τελειώνει με 5 ερωτήσεις όπου καλείστε να απαντήσετε στην αρχή, πριν διαβάσετε το βιβλίο και στο τέλος, αφότου το έχετε διαβάσει.

είναι ενδιαφέρον να βλέπει κανείς πως διαφοροποιούνται οι απαντήσεις αφότου έχεις διαβάσει το βιβλιο.

Είχα απορία για το πως θα μπορούσα να εισάγω κάποιον στην λογική του ορθολογισμού, και αυτό το βιβλίο είναι σίγουρα recommended material ^_^
Profile Image for Paul Lunger.
1,317 reviews7 followers
May 17, 2012
Canadian columnist, Christopher DiCarlo, in his first novel presents a rather humorous & yet interesting look at the process of critical thinking & how arguments are formed. Across 12 distinct chapters & over 300 pages, he takes a look at the unique characteristics of how biases are formed in arguments & also how to deconstruct things to find the truth within them. Each chapter builds upon successive themes whether they're in current terms or historical & the recaps of each chapter make this even more successful. What helps is that you the reader get a chance to answer the questions he poses & then use them to relate to what the book states. Overall one of the better self help guides in recent memory.
Profile Image for Romeo Verga.
81 reviews
April 17, 2017
This book discusses very interesting philosophical questions that many have thought of already. Readers should be aware some book shows of the extreme standpoints (ie extreme left and right) in arguments which may just be for illustrative reasons. In contrast, some of the book shows more of a balanced point of view.
In my opinion, there is too much fluff in this book when it goes too much in depth in scientific topic which I found very unnecessary to go into the level of detail that this book went through to support philosophical questions and thought processes.
Regardless, this book is very insightful and I recommend this book highly.
Profile Image for Ryan.
117 reviews5 followers
June 18, 2015
I'd probably give this 3.5 stars. It's a very solid--and funny!--intro to logic and some philosophy ("intro" being the operative word there: if you've taken deductive logic or Philosophy 101, you probably won't get much more than a review out of this). Fun though it was, there were times where DiCarlo could have fleshed some things out a bit more and added some stronger arguments for and against the supernatural positions that he picks apart. Still, this is a fun, informative and quick read that would work really well for a book club. Recommended.
10 reviews2 followers
November 11, 2015
I agree with the previously reviews and I couldn't have put it better. If you want to get good at arguing about religion, here's your bible, pun intended. If you want to be better at arguing in general, don't get your hopes up, but don't give away the book just yet.
Liked:
-Part 1 and 2 - I actually felt like I learned things about myself reading this.
-I do like the casual tone of the author, but I agree, especially by the end of the book, it's condescending. That being said - quick, easy read for 300+ pages.
Disliked:
-All of part 3.
-The illustrations. Completely pointless.
2 reviews
January 21, 2018
I'm obviously biased but I do believe it has more to offer than the usual/typical book on Critical Thinking. Focusing on the Big Five most important questions humans have asked themselves; and then to draw on the history of ancient skepticism as a precursor to scientific inquiry; and finally, to answer the Big Five questions in both natural and supernatural responses - demonstrates a focused fairness we don't often see today.
10 reviews
May 20, 2012
Great book for learning how to be a critical thinker. The book explains some interesting steps in how to break down the arguments of others, dissect their ideas and reveal their bias, hypocrisy and inconsistencies.

I do however would like to pose a warning to those who strongly believe in religion. This book focusses on arguing against religion. So if you don't like to be challenged or consider any questioning of "faith" blasphemous, stay away.
Profile Image for Matt.
2 reviews5 followers
May 21, 2012
I'm pretty new to the science and philosophy behind critical thinking. This book provides a great overview of both before diving into some thoroughly enjoyable natural and supernatural answers to the authors big five philosophical questions.
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