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If you were born perfectly cunning and ruthless, you may be a psychopath. Like any other skill, cunning is something that most people have to work at. Some people are naturally more cunning than others, while others are more gullible. Regardless of your starting point, know that you can always improve your ability to be cunning through practice. Try to find low-stakes opportunities for practice so that you're well-prepared when the time comes to be cunning in a serious situation. Performing good-natured pranks and practical jokes are a good way to build many of the skills you'll need to be cunning without exposing yourself to much risk. For example, many pranks require you to act, lie, suppress your emotions, and ascertain others' true motives if you want the prank to go off without a hitch. {"smallUrl":"https:\/\/www.wikihow.com\/images\/thumb\/f\/fa\/Be-Cunning-Step-7Bullet1.jpg\/v4-460px-Be-Cunning-Step-7Bullet1.jpg","bigUrl":"\/images\/thumb\/f\/fa\/Be-Cunning-Step-7Bullet1.jpg\/aid3021566-v4-728px-Be-Cunning-Step-7Bullet1.jpg","smallWidth":460,"smallHeight":345,"bigWidth":"728","bigHeight":"546","licensing":"<div class="mw-parser-output"><p>License: <a rel="nofollow" class="external text" href="https:\/\/creativecommons.org\/licenses\/by-nc-sa\/3.0\/">Creative Commons<\/a><br>
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<\/p><\/div>"} Cunning people are skeptics at heart. Never accept the information you're supplied with or the impression someone gives you without thinking about it first. Constantly ask yourself whether the people you interact with seem genuine. Look for ways that these people may be distorting the truth or outright lying in order to advance their agenda. Investigative journalists routinely cut through mountains of lies and pretense to get to the truth. If you're looking to sharpen your skeptic's eye, you probably don't need to go to journalism school, but you may benefit from researching and watching how journalists coax facts from their subjects in one-on-one interviews. {"smallUrl":"https:\/\/www.wikihow.com\/images\/thumb\/c\/c1\/Be-Cunning-Step-8Bullet1.jpg\/v4-460px-Be-Cunning-Step-8Bullet1.jpg","bigUrl":"\/images\/thumb\/c\/c1\/Be-Cunning-Step-8Bullet1.jpg\/aid3021566-v4-728px-Be-Cunning-Step-8Bullet1.jpg","smallWidth":460,"smallHeight":345,"bigWidth":"728","bigHeight":"546","licensing":"<div class="mw-parser-output"><p>License: <a rel="nofollow" class="external text" href="https:\/\/creativecommons.org\/licenses\/by-nc-sa\/3.0\/">Creative Commons<\/a><br>
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<\/p><\/div>"} The great British Prime Minister Winston Churchill was noted for his cunning wit, among many other things. He had a reputation for crafting clever, biting quips and one-liners out of thin air. In fact, because of a speech impediment, he actually crafted most of his witty responses beforehand by trying to consider every possible objection he might face. Take Churchill's success to heart. Before important situations, take time to imagine every possible way the situation may play out and have your responses planned. The worst case scenario with this approach is that things will turn out in a way you didn't anticipate. However, in the rare occasion that this happens, you won't be any worse off than if you hadn't considered any outcomes at all. Even the most experienced swindlers get caught every once in a while. If you're looking to become confident, you're bound to make eventual mistakes. Your schemes will be uncovered, you'll be embarrassed, and you may have to apologize. Use your failures as learning experiences. Make note of exactly when and how your plans went wrong, then try never to make that mistake again. The French theologian Pierre Charron once famously said, "the easiest way to be cheated is to believe yourself to be more cunning than others." A cunning person should certainly be able to find others' strengths and weakness, but it's almost as important that she also be able to find her own. Give yourself a brutally frank evaluation. What are you good at? What are you bad at? What makes you nervous? When are you most confident? Be honest with yourself about your abilities. If you are, you'll know which of your strengths you should play to and which of your weaknesses you need to work on.
Practice, practice, practice. Never take anything at face value. Consider all possible outcomes. Learn from your mistakes. Know yourself.