As parents, we want to teach our kids how to be good thinkers. But “thinking” isn’t just about memorizing facts; it’s about how you approach a problem. The most powerful, and rarest, thinking skill is “Lateral Thinking.”
This is the art of solving problems by challenging your own assumptions and attacking the problem from a new direction. And the single best way to teach it? Riddles.
Here are 5 classic riddles and the “lateral thinking” lesson each one teaches.
Thinking Sideways
Four riddles to challenge your assumptions and spark lateral thinking.
Riddles aren’t just for fun; they are a powerful workout for the brain. They are a fun, engaging way to teach your family the real-world skill of “lateral thinking.”
If you enjoyed these 5, our book Riddles for the Family and Smart Kids will help you all become master lateral thinkers. This book is a collection of 187 riddles with illustrated answers. Their purpose is to make think and enhance your perspective. It is for the family because the different pictures can guide the answers. If you don´t know the answer, every part has a collage of images to give you a clue! Of course, the answers are in the back of the book. But you must try to find the correct picture first.
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Solving riddles is excellent practice, but it is only one specific type of cognition. To build a more robust mental toolkit, you need to broaden your approach by learning How to Think Smarter, which covers logical fallacies and mental models that apply to everyday decisions.
1. The Assumption Riddle
The Riddle: “A man is in his car. He sees three doors: a red door, a blue door, and a green door. Which door does he open first?”
The Answer: The car door.
The Lesson: This riddle is brilliant. It immediately makes the listener assume the “red, blue, or green” doors are the only options. It teaches kids to question the very premises of a problem. Before you try to solve for “X,” make sure “X” is the real question.
2. The “Multiple Meanings” Riddle
The Riddle: “What has many keys but can’t open a single lock?”
The Answer: A piano.
The Lesson: This riddle teaches that words are slippery. We hear “keys” and our brain locks onto one meaning (“a key for a door”). “Lateral thinking” is the ability to break that first, obvious association and ask, “What else could ‘key’ mean?” It’s a lesson in flexible, creative vocabulary.
3. The “Properties” Riddle
The Riddle: “What is full of holes but still holds water?”
The Answer: A sponge.
The Lesson: This riddle forces us to think about properties. Our brain hears “full of holes” and “holds water” and sees a contradiction. We assume “holes” lose water. The lateral thinker ignores that assumption and just searches for an object that has both properties. This is the core of scientific, “out-of-the-box” thinking.
4. The “Wordplay” Riddle
The Riddle: “What can you catch, but not throw?”
The Answer: A cold.
The Lesson: Similar to the piano, this riddle plays on the different meanings of a verb. We get stuck on the physical act of “catching” and “throwing” a ball. The answer requires a mental leap to a completely different context. It teaches us to “zoom out” and consider all possible meanings.
5. The “Red Herring” Riddle
The Riddle: “You’re in a dark room with a candle, a wood stove, and a gas lamp. You only have one match. What do you light first?”
The Answer: The match.
The Lesson: This riddle is a masterclass in misdirection. It floods your brain with “red herrings” (the candle, stove, lamp) to make you focus on the wrong part of the problem. The lateral thinker ignores the noise, identifies the first, necessary step, and solves the problem instantly.
