by Russell Newton

What Am I?

Riddles are phrases or questions framed in the form of puzzles that require all types of thinking to deduce its answer or some double meaning underlying its words. They employ several different patterns of thinking, challenging us to work with limited information in unique ways. No one style of thinking is better than the other. Each is useful in different situations, and we must grasp how to apply them correctly. This is exactly what riddles help us learn, since it involves many different thinking styles.

Everyone loves a good riddle. A riddle is a little hard to define, but we all know one when we see it: it’s typically a phrase or question that has some veiled or double meaning and which forces us to think really carefully about the answer. Riddles may seem like nothing more than child’s play (the last time you answered one may have been in childhood!), but riddles have a long and illustrious past.
Riddles are a “universal art” found in all cultures, and have been studied by linguists, anthropologists, theologists, and more to understand how and why human beings use these peculiar tales, questions, or puzzles. Want some proof? Here is a riddle mentioned in Greek antiquity, in other words, over two thousand years ago: Ares sent the Sphinx from her Aethiopian homeland (the Greeks always remembered the foreign origin of the Sphinx) to Thebes in Greece where she asked all passersby the most famous riddle in history: “Which creature has one voice and yet becomes four-footed and two-footed and three-footed?” She strangled and devoured anyone who could not answer. Oedipus solved the riddle by answering: “Man—who crawls on all fours as a baby, then walks on two feet as an adult, and then uses a walking stick in old age.”[9] By some accounts[17] (but much more rarely), there was a second riddle: “There are two sisters: one gives birth to the other, and she, in turn, gives birth to the first. Who are the two sisters?” The answer is “day and night.” (Both words—ἡμέρα and νύξ, respectively—are feminine in Ancient Greek).
Riddles seem to play with the flexible boundaries of language, showing us the intellectual conventions we didn’t even know we were using. Riddles lay bare our ordinary assumptions about the way the world works—and show us that things are not quite as they seem. They provide moments of surprise, shock, and even dumbfoundedness. They make us feel that we are not as bright as we would like to be, and that we are blind to the obvious.
On hearing the answer, we get a flash of insight and understanding, a little joke for the mind that’s like the equivalent of an optical illusion or an object that seems to change color completely when tilted in the light. Over time, riddles became a way of relating to others, and even the basis for philosophical questions, thought experiments, and methods of understanding the world around us. Riddles are more than simple wordplay, as this book will demonstrate, and can be used as tools for a range of purposes.
In this book, we’ll be exploring riddles for a few reasons, not least of which because they’re fun! Riddles can also be thought of as mini exercises for the conceptual mind, and a way to develop critical thinking and analytical skills, as well as strengthen the ability to think creatively.
“Out of the box” thinking may feel random and spontaneous in the moment, but in the chapters that follow, we’ll see how there are actually predictable formulas and techniques that can help us solve problems at a higher level than we’re used to. Riddles are a brilliant way to practice and learn about these different ways of thinking, if we know how to use them. You can read all you want about different types of thinking—it’s an important piece of the puzzle—but if you never apply them in a significant way, then all that knowledge will be for naught.
So first, let’s consider the mental tools we have at our disposal when approaching the task that is a riddle. In reality, this is about evaluating the problems and novel situations in our lives, and gaining better understanding and methods to navigate them effectively, quickly, and strategically.
Thinking Modalities

People seldom think of thinking as something they need to practice, develop, or strengthen. It’s almost as though we assume this skill is a given, and something that will run more or less on its own. Most of us are more focused on developing skills and what could be called crystallized intelligence—essentially knowledge and information. But can we develop muscles in the body without exercise? Can we use any tool at all without first understanding how best to use that tool? What can we actually do with the tool by itself, and no type of instruction manual for best practices?
This is how the vast majority navigate the world. But we can do better than that.
Thinking is an aptitude that is more fluid than we think—and more prone to bias, misconception, lazy assumption, shortcuts, weak hypotheses, and plain old habit. Realizing that your brain can (and should) be used to its full potential is like suddenly discovering that all along you’ve been using a precious and sophisticated piece of technology as a doorstop. Our brains can do so much more, but we have to deliberately give ourselves the opportunity to consider how we’re thinking in the first place, and then dedicate the time to improving it. Let’s take a look at some of the tools that will be in our arsenal at the end of this book.
Going Outside the Box

What do you know about creativity? Do you imagine that it’s something a bit like a flash of light from nowhere, something that only the rare gifted person has access to? Perhaps you think it’s a “left brain versus right brain” phenomena and that some people are just born better able to create and think up new ideas.
We’ll abandon these conventional ideas for one reason: they’re limiting and limited. Instead, we’ll look at creativity with curiosity and try to understand what it is. What is a creative person actually doing when they bring something completely new into the world? In understanding the function and nature of creativity, we can then learn to practice it ourselves (more on this later, when we explore riddles). In time, we will be able to systematically become more creative. It sounds like an oxymoron, but most things in this world can be trained and cultivated, and very few things are dependent on raw talent and luck.
Divergent thinking is the name given to the kind of intellectual activity that explores and expands on as many solutions or alternatives as possible. Quick—think of a simple iron nail. How many uses can you think of for a single iron nail? The activity that your brain engages in to do this is called divergent thinking.
Being flexible and open, the idea is to “brainstorm” and open the field right up. This kind of thinking, crucially, needs to be removed from goal-oriented, convergent thinking—it works best when you suspend judgment (i.e. telling yourself, “that’s a stupid idea”) and simply let ideas flow as they will. This is the kind of opening-up, rather than narrowing-down, kind of thinking.
The type of thinking to solve riddles is, you guessed it, almost purely divergent. When three of the most obvious descriptions of assumptions fail, where do you go from there? You must start to think outside your conventional boundaries and diverge. Without it, you will be running your head into the same wall repeatedly.
Lateral thinking is also a term you may be familiar with. In contrast to “vertical thinking,” which is step by step and rather predictable, lateral thinking seems to take a step to the side, into a new dimension. It makes you ask how you get from Point A to Point B, and attempts to detach from the current scenario. Lateral thinking is the act of mentally manipulating factors and situations.
We’ll see plenty of examples of lateral thinking in the riddles that follow later in the book, and it’s this kind of thinking that is best for problem solving or generating truly novel ideas. Imagine a classic maze printed on a piece of paper, with an IN and an OUT. You’re given a pencil and told to solve it. You might go about drawing a line from IN to OUT, winding along the paths of the maze.
Or, if you were thinking laterally, you might simply draw a long line outside the maze, bypassing the entire thing—you’ve still solved the puzzle, only not on its own terms. In doing so, you’ve found the solution at a different level of thinking than the problem was created. Going even further, you could solve the problem in an even more outlandish way: by curling the paper in on itself, you can bring the IN to the OUT in three dimensional space, allowing your pencil to make the tiny jump from one to the other.
You’ve solved the problem again, by now completely breaking the rules of both previous solutions (you might then pull a Matrix-style trick and claim, as your final solution, that “there is no paper”). The point of this thought exercise is to expand your mind and imagine “what if” rules didn’t exist.
Systems thinking is similar in that it is the ability to see and comprehend the “bigger picture”—as well as how all its components fit inside it. Understanding large-scale interrelations is sometimes enough to solve a problem creatively.
Connecting the dots, synthesizing separate ideas, seeing the whole, and perceiving relationships and connections are invaluable for those problems in life that are “greater than the sum of their parts”—i.e., most of them! As an example, you may be dealing with a difficult person and unsure how to get them to see your point of view. But really, you can fix things by seeing their point of view. When you understand who their boss is, what their objectives and motivations are, and all the complex links that connect you to them, you can better understand their position—to your benefit.
By zooming out, you add context and dimension to the situation, and act accordingly. Many of us have the problem of getting caught in the weeds—for another analogy, not being able to see the forest through the trees. Systems thinking implores you to see the clues and hints that inevitability exist in every situation, and expand on what they could mean for you. It may not appear to be a type of creative thinking at first glance, but if it’s something that forces a different perspective, it counts!
Finally, inspirational thinking is also a kind of creative thinking, and can be best described as receiving insight or inspiration from somewhere else entirely. Take an entirely different activity, mindset, discipline, or field, and force-apply this to your current situation. For instance, generating ideas that must start with each letter of the alphabet. This gives you twenty-six ideas, as well as fitting an intentional constraint.
This results in a sudden explosion of understanding or a peak experience—a lightbulb switching on in your head. It can seem like this flash of creative insight is unpredictable (a freebie from the mythical muses?), but people who have these insights often lay extensive groundwork and actively court those insights one way or another.
Salvador Dali, for example, was known to drift off to sleep with a spoon deliberately held loosely in his hand, balanced above a china plate. As he began to dream, his grip would loosen and he’d drop the spoon; the clattering on the plate would wake him up instantly. He’d then reach for his notepad nearby and scribble down all the images that had come to his half-awake mind. He called this chasing hypnagogic sleep, as he wanted to play in the area of consciousness between waking and sleep.
In a similar way, August Kekule is reported to have had a dream about a snake biting its own tail, and in a flash, understood the ring-like structure of the benzene molecule—a puzzle that had filled his waking hours. Others receive this inspiration from altered states of consciousness (like dreams), mystical experiences, or even profound moments during meditation or time spent in nature.
We can access this state by simply stepping away from the problem at times and letting our unconscious mind do the work for us. The more varied and different your experiences are, the more mental models you can try on for size and apply to different situations.