Can you think outside the box? Let’s find out! 

Here are 4 riddles to test your ability to think creatively and differently.


During a job interview, a guy was asked a tricky question:

“Let’s assume you are driving in your car on a stormy day and you pass by a bus stop noticing 3 people waiting there.

One is the perfect partner of your dreams.

Another one is an old friend of yours, who once saved your life.

The last one is an elderly person who looks very sick.

If you had only one seat available, who would you let sit in your car?  

Would you pick the elderly person because he is about to die?

Would you choose the old friend who saved your life to repay the favor?

Or would you go for the dream partner you might never see again”?

Before reading on to find an answer try to come up with your own.

If you cannot, consider the following hint, but don’t give in straight away; think unconventionally.

HINT: The interviewee doesn’t need to drive the car.

ONE POSSIBLE ANSWER: The interviewee gives the car keys to his old friend, and tells him to take the elderly person to the hospital. Then he waits for the bus with the partner of his dreams.


At a reception, guests drink poisoned orange juice contained in a jug.

Everyone dies except one man. 

How come?

Is the man immune to poison? No.

Is the orange juice always the same? Yup.

Is the poison already in the drink when the man drinks? Yup.

Does the man have an antidote with him? Irrelevant.

Does the man drink as much orange soda as everyone else? Yup.

Does the man drink first? Yup.

Can you figure out why the man survived when everyone else died?

Before reading on to find an answer try to come up with your own.

If you cannot, consider the following hint, but don’t give in straight away; think unconventionally.

HINT: Look at the image at the beginning. 

ONE POSSIBLE ANSWER: The poison is in the ice, therefore, the man who drinks the orange juice first does not poison himself because the ice has not yet melted.


A gentleman lives on the tenth floor of a building.

Every day, when he leaves the house, he takes the elevator to the tenth floor and goes down to the ground floor.

When he comes back home, however, he takes the elevator from the ground floor to the seventh floor, then climbs the rest of the stairs to reach his apartment.

That gentleman is not superstitious, he is not a sportsman and he hates taking the staircase. 

Why then does he behave that way?

Before reading on to find an answer try to come up with your own.

If you cannot, consider the following hint, but don’t give in straight away; think unconventionally.

HINT: Sometimes, when there are other people in the elevator and when it rains - and he has an umbrella with him - he arrives with the elevator up to the tenth floor.

ONE POSSIBLE ANSWER: The man is a dwarf and is unable to reach the button leading to the top floor. But, if it rains and he has an umbrella, he can reach the button to get to the tenth floor.


A man walks into a diner and sits down.

There's a new waitress he's never seen before.

When she comes to take his order, he says: "Just a cup of coffee, please".

A few minutes later the waitress brings the man his coffee and heads back to the kitchen. 

When the man notices that there is a fly in his coffee, he calls the waitress back. 

He asks her nicely to bring him another coffee. 

The waitress brings the man's cup of coffee back to the kitchen and returns with a new one shortly later.

"Here you are, I poured you a new cup of coffee, no-fly this time!", she says and hands him the cup. 

The waitress turns around and starts to head back to the kitchen.

She only takes a few steps before she hears the man shout out.

"Hey, this is the same cup of coffee, all you did was remove the fly"!

Assuming the coffee was still hot, and the cup was a different color and shape, how did the man know it was the same cup of coffee? 

Before reading on to find an answer try to come up with your own.

If you cannot, consider the following hint, but don’t give in straight away; think unconventionally.

HINT: The man knew it was the same cup after taking a sip.

ONE POSSIBLE ANSWER: The coffee was sweet. The man had added sugar to his coffee before noticing the fly. When the waitress brought him the "new" cup of coffee, he took a sip (to check whether it was in fact a newly poured cup of coffee) and noticed that the coffee was "already" sweet.


Did you come up with any innovative answers? If so, share them in the comment below.

You see, there are no non-creative people, there are only untrained minds. 

Creativity is not a virtue reserved for only a few people.

It is a skill that everyone possesses and that gets stronger with practice.

“Repetition is the mother of skill”. - Tony Robbins

Thus, you can also excel in thinking outside the box!


Well, because it is what separates you from the rest of the crowd.

Thinking outside the box frees you from the limitation that comes from thinking inside the box, giving you the freedom to think for yourself.

Thinking differently is what separates the people who live a dull life from those who live an extraordinary life.

"Don't just go do what someone says. Take interest in what someone says, then debate it, ponder it, and consider it from all angles". - Jim Rohn

Don’t take for granted that one person, your role models, or society have all the answers you look for.

Take their knowledge, but don’t take it as the only knowledge.

Make sure that what you finally do, is a product of your own conclusion, not someone else's conclusions.

Don’t buy into anyone else’s beliefs.

You shouldn’t fall for other people’s ways of thinking and seeing the world.

They may not be right!

As you collect knowledge, sort through it and find out what is valuable. 

Then you can develop your way of thinking and seeing the world.

In time, this will become your guidance system.

You were blessed with a brain, so use it!

All of us can bring something unique to this world if we just have the courage to bring it out of us and take the leap of faith without giving a f*ck about what people may think of us if we do not conform to the norm. 

“Is it so bad, then, to be misunderstood? Pythagoras was misunderstood, and Socrates, and Jesus, and Luther, and Copernicus, and Galileo, and Newton, and every pure and wise spirit that ever took flesh. To be great is to be misunderstood”. - Ralph Waldo Emerson

People should not hold onto old positions and beliefs merely because their elders held them.

As individuals, we should bring an evolution of new ideas - that is a source of creativity.

Would you like to start thinking outside the box and set yourself up to live an extraordinary life, but don’t know where to start?

Don’t worry, I wrote an article - HOW TO THINK OUTSIDE THE BOX AND LIVE WITHOUT LIMITATIONS - that can help you start.

You’ll learn strategies you can start implementing immediately to reawaken and beef up your outside-the-box thinking mode and live your life to the fullest.

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Christian Caliendo
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  1. Mikolaj Walczak

    The first one was really tricky. The solution is very clever, I couldn’t come up with anything.

    The orange juice – The man could have vomited after drinking it.

    The lift – The man may have a friend or a lover or somebody he helps living on the seventh floor and visit every day.

    The coffee – it could be a nasty man and a genuine waitress. Seeing that she was knew he could just drop a fly into his own coffee, call her so that everybody can hear and later make a scene so that she looks even worse in the eyes of others.

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