10 Bizarre Questions You Need to Understand Yourself

Understand yourself

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Understand yourself with these 10 bizarre questions.

Sometimes the quest to understand yourself can become tiresome. In particular, the same old “self-discovery” questions can become tiresome.

You’ve heard them before, you haven’t found them insightful, and you feel an involuntary sigh coming when they’re put in front of you.

It’s kind of like when your mother-in-law makes you lasagna for the fifth straight family dinner. Perhaps the lasagna was okay the first couple times (and you felt terrible saying that lasagna didn’t work for you because you’re not supposed to admit that).

But by the fifth dinner, you’re dreading the walk to the kitchen where you will find please-not-again-don’t-be…yup! It’s lasagna!

The repetition (and ricotta cheese) is not the only thing killing your ability to understand yourself better.

Your brain is also staging a series of biases to get in the way of your self-discovery.

If you’ve been following our series, you also know that the scarcity mindset is also inhibiting your cognitive ability.

Just like Isaac Newton needed that apple to fall on his head to make a breakthrough with gravity, you need new questions to dislodge your brain and make a breakthrough in self-awareness. (Okay, maybe not just like Isaac Newton, but close enough).

For this reason, I’m giving you 10 questions that you’ve never heard of to gain insights you never knew. Get ready to understand yourself.

I’m Calling You Out: You Probably Won’t Actually Answer These Questions

I’m not naive. I know that most of you will skim through the questions without stopping to answer them.

Perhaps you’ll pause to consider their genius originality (toot toot… that was my own horn).

But that doesn’t mean you’ll take the time to think about your answers.

Based on my research and personal experience, I can tell you a few reasons why this is. It’s your habit to skim rather than engage, and it’s difficult for us to establish new habits.

You’re probably locked in the scarcity mindset and feel like there isn’t enough time, so you think you need to move onto the next thing quickly (there is enough time!).

You’re interested in the topic, and you want to understand yourself better, so clicking on the link made you feel like you were doing a good thing. However, you don’t actually want to put the work in.

You want these questions to be quick and easy because we live in a world that makes quick and easy feel like the expectation.

Finally, you don’t really see the purpose of answering these questions, so you aren’t motivated to do so.

Don’t get me wrong – I’m not criticizing you. I’m mostly describing my own behavior here, to be honest.

But I will say this: there is a purpose.

By understanding yourself better, you will open yourself up to a whole new frontier of happiness and meaning in your life.

I’m proof, other people are proof, and you can be proof too.

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10 Bizarre Questions that Will Change How You Understand Yourself

1. If you created a new town, what would its motto be?

I fell in love with Portland, Oregon the first time I visited it. Every store seemed to have a declaration of human rights, and every house had an “In Our America” sign in its yard (which I have since ordered and put in my yard in New Hampshire).

The only way I could describe the feeling was, “It made me soul happy to be there.”

We are deeply impacted by our environment, but often we do not get to choose it. Not completely, anyway. But what if we could?

If you could create an entirely new town, what would its motto be? What message would you want to give to the outside world? To the people living within its boundaries? Who would you want to attract to your town?

Imagine if an entire community could genuinely live by this motto. What do you care about in your town? What way of living would make your soul happy?

What would you want to put on a sign in your yard?

Your answer doesn’t need to inspire you to move (nor should it make you feel bad about your current home). Instead, it should help you realize what’s important to you and what your values are.

Your town motto can help you understand yourself.

Town motto values

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2. If you had to tell four people to get into a lifeboat with you, and everyone else in the world would cease to exist, who would you tell to get in?

This scenario probably makes you uncomfortable, because we try so hard to make room for everyone in our lives. But, as painful as it would be, how quickly could you decide?

No lifejackets, no alternative boat, no bullshit: who would you tell to get in the boat?

Humans are social creatures, and as such, we spend much of our time creating and fostering bonds with the people around us.

At times, we even judge our self-worth based on these relationships and how many we have.

I don’t mean to minimize the connections you have with people, nor dissuade you from making new ones. But I do think it’s vital for you to realize who you value most in your life.

At the end of the day, we only have so much time and energy to give out. You need to be able to identify who in your life you couldn’t live without.

These four people are who you should be concentrating your energy on. To understand yourself, you should know who they are.

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3. What would $10 million give you that you don’t have now, and how can you incorporate that into your life?

Have you ever played the “What would you do if you won the lottery game?” Of course, you have – you’re human.

It’s fun to fantasize about a giant check and all the purchases you could make (even though science has proven that more money doesn’t actually lead to happiness).

When we play this game, we like to think in terms of new possibilities.

I want you to take the question a step further: what do these possibilities say about what you want in life, and why do they need to be tied to more money?

This will require you to think beyond material things. No, you probably can’t find a way to buy that yellow Lamborghini you’ve been drooling over on Grand Theft Auto. But I dare you to look at the motivation behind why you want it.

For example, $10 million would give me more opportunity to travel.

If travel is important to me, how can I incorporate it into my life now?

Ten million dollars would also give me more opportunities to spend with my family, as I’d be less busy with my current job. While I can’t give up my employment, I can look at where I can plan on more family time in my life, either through texts, calls, or visits home.

If you think $10 million would drastically change your life happiness, think critically about what it would give you that would make you happy.

Then question why you can’t do those things now.

understand yourself and your motivation

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4. If you were sent to live in outer space for five years, what would you miss the most?

Warning! I’m about to get morbid, but stay with me.

After someone dies, how often do you hear their loved ones express the little things that they missed the most? The small, seemingly insignificant moments that created a person’s existence?

As you work to understand yourself, I don’t want you to think about your death here.

Instead, I want you to think about the seemingly insignificant moments that you take for granted every day.

If you were sent off to live in outer space for five years, what would you miss the most? Upon your return to planet earth, what would you be most eager to do?

Hopefully, a list of people come to your mind when you think of this question. After reuniting with your loved ones, however, what else would you want to do?

Think past the initial binge of food, drink, and whatever other immediate pleasure you want satisfied.

What parts of your routine would you miss? What moments or activities would you want to experience again?

It can be tough for us to understand these emotions fully within a hypothetical question, but thinking about this question can shed light on things you take for granted.

It can also help show you what’s important to your happiness.

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5. If your life was turned into a movie, what big moments would make it into your story?

Movies do a great job of letting us see into a character’s life. We can watch them grow and change. If the story is told well, we’re also able to see what experiences caused them to develop the way that they do.

Not only does this instill empathy in us, but it allows us to consider how big situations in their life affected them. Whether they are battling an evil villain or going through an unfortunate break-up, an emphasis is placed on their story.

Imagine if your life was a story depicted in a movie. Fight your immediate reaction of, My story isn’t interesting enough to be a movie.

Firstly, your story is interesting because it’s real, and it’s your story. It inherently holds importance in the world.

(Secondly, if they can make a two-hour movie depicting two people moving at a colossally slow pace around a spaceship, they can certainly make a movie about your life. Seriously, how did people sit through that??)

As they introduce who your character is to the viewers, what snapshots of your childhood would they show? What interactions would reveal your character?

What significant moments in your life would make it into the movie? What would the main conflicts be? How would the changes in you be depicted to the viewers?

I know I just threw a lot of questions at you, but seriously: imagine your life as a movie. In doing so, you might gain a little bit more clarity about who you are as a person.

Not only will you understand yourself better, but you also might develop a bit more empathy for yourself.

Understand yourself

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6. What is the exact opposite of you? Which qualities do you like, and which qualities do you not like?

Frequently we find ourselves thinking about who we want to be and how far we are from this fantasized version. For this question, I want you to dismiss these wistful desires. Instead, I want you to imagine the exact opposite of you for everything.

And I mean for everything. Personality traits, beliefs, behaviors, values, relationships, characteristics, strengths. Go through category by category, if that’s easier to consider.

But you need to think of the complete opposite. I’m talking walk through a closet door, land in a parallel universe, and stumble upon your alter-ego opposite.

For example, I’m extremely organized and on top of things (some might call it a Type A personality). The opposite of this would be a laid-back, disorganized, Type B personality, if you will.

Additionally, my opposite would be introverted, largely unmotivated, more relaxed, mostly negative, more relationship-oriented, and uninterested in the world.

After you identify some opposites, I want you to consider your list. Which qualities do you shudder at? Conversely, which ones do you like?

I certainly don’t want to give up my drive or positive outlook, but I could use to be more relaxed and relationship-oriented in my life.

It’s essential to keep in mind that there are many different characteristics, none of which are better than others. This question isn’t designed to make you feel inferior or superior.

Instead, it’s meant for you to examine which qualities you are proud of and which ones you might want to change.

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7. If someone you cared about changed lives with you right now (mind, body, and all), what would you warn them about?

We are often much kinder to our closest friends than we are to ourselves. You might have heard the question, “How would you talk to your best friend if they were in your position?” This strategy is meant to improve our self-talk.

For example, you might be critical and call yourself a cotton-headed ninny muggins, but you’d never be that harsh (by Elf’s standards) to a friend.

I want you to take this line of thinking beyond self-talk. Imagine if a close friend or relative was going to wake up tomorrow in your life as you. I’m not talking Freaky Friday style, in which you simply trade bodies.

Instead, this person will adopt all of your fears, desires, habits, and emotional patterns.

What would you warn them about, and what advice would you give?

When I think about this question, I imagine my younger cousin stepping into my life. I would warn her about my need for control and how it can manifest itself in unhealthy ways.

I’d give her the heads up about my struggles with vulnerability (I mean, who doesn’t struggle with vulnerability?), as well as the harmful coping mechanisms that I’ve adopted to combat these fears.

As for advice, I’d send her with a metaphorical suitcase full of the practices I’ve learned that help me.

It would be filled with mantras that guide me to let go of unimportant things, breathing exercises that calm me down, and behavioral tells that help me realize something is bothering me more than I understand.

After you answer this question and understand yourself, try carrying this metaphorical suitcase around with you more often (you can even get it monogrammed).

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8. Choose one person from each stage of your life whom you had the most significant impact on (good or bad). If all of these people got together for a dinner party, what would they say about you?

It can be tricky to understand the impact our behaviors have on others. It can be even more challenging to consider the overall impact our life has on others.

First, before you dive into this question, prepare yourself to be both open and forgiving. We are continually maturing and changing. The only thing to be ashamed of, perhaps, is when we stop growing.

So if you bullied your second-grade classmate for his outrageous bowl-cut, it’s okay – let it go. Guilt won’t serve you any more than his haircut served him.

You can define “stage of life” with whatever standards you want (by location, by job, by decade). The important thing is that you consider the people whom you most affected.

If each person were to describe you, what would they say about you? Would the other people at the dinner table be surprised by their stories? What commonalities would arise?

This question not only makes you consider your impact on others, but it also allows you to examine your growth over the years.

Furthermore, you might find that your impact differs in different spheres (i.e., I was super supportive to my colleagues, but I was somewhat critical of my friends).

All of this information can be useful as you develop how you understand yourself and decide who you want to be moving forward.

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9. If you had to choose a fruit that best represents who you are as a person, what would it be?

Amidst the sea of questions like, “Who are you?” and “What defines you as a person?” sometimes you need to ask a question outside of the box (or outside of the fruit platter, if you will).

While this question may seem silly, it can reveal quite a bit. To accurately answer it, you first need to contemplate what part of your life you want to focus on.

Will you try to match up a fruit that is similar in appearance (I’m looking at you, cucumber)? Or perhaps, choose a color that you think embodies your spirit (omg, am I a red apple or a blueberry?)?

Next, you need to choose a fruit that best represents this critical aspect of you.

Turns out, there are over 2,000 kinds of fruit in the world, but the western world only sees about 10% of those. That’s a lot to choose from.

Fruit to understand yourself

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10. What do your choosing process and final choice say about you?

What was your reaction to the previous question about fruit, and what does this say about you?

Did you build an elaborate metaphor for your likeness with a pineapple, intrigued by the challenge of comparing yourself to a fruit? You’ve probably got a creative mind and enjoy tackling abstract questions.

Did you click on the link to learn more about the thousands of kinds of fruit? You’re most likely someone who enjoys learning new information and expanding your knowledge.

Or did you scoff at the fruit question, displeased with its childish, pointless nature? If so, you’re probably someone who likes to think in terms of concrete examples and real-world answers.

As with all of our questions, there is no right or wrong answer. The purpose of these questions is not to work toward a single truth.

Instead, they are meant to build your ability to understand yourself better.

Whether you’re a pineapple, an exotic and rare rambutan, or an I-don’t-give-a-flying-f*ck-what-fruit-I-am, you can learn about yourself by considering how you view the question and ultimately, how you view the world.

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Conclusion

Self-awareness is a hugely useful skill to possess, but it can be challenging to come by for multiple reasons. And while there are simple ways to build your self-awareness, sometimes you might find yourself feeling like the questions and actions are tired and overused.

Sometimes it takes something new to shake your brain loose and get you out of your typical thinking patterns.

I urge you to take the time to consider these 10 bizarre questions (and I mean actually take the time… what about five minutes per question? Okay, fine, 90 seconds. Fine, one minute each, ten minutes total. *she continues to barter with no one*).

Ten minutes of your life to understand yourself ten times better is a pretty sweet deal.

How about this. I’ll reply to your comment (promise it won’t be about fruit unless you want it to be) if you choose one of the ten questions and post your answer in the comment box below.

  1. If you created a new town, what would its motto be?
  2. If you had to tell four people to get into a lifeboat with you, and everyone else in the world would cease to exist, who would you tell to get in?
  3. What would $10 million dollars give you that you don’t have now, and how can you incorporate that into your life?
  4. If you were sent to live in outer space for five years, what would you miss the most?
  5. If your life was turned into a movie, what big moments would make it into your story?
  6. What is the exact opposite of you? Which qualities do you like and which qualities do you not like?
  7. If someone you cared about changed lives with you right now, mind, body, and all, what would you warn them about?
  8. Choose one person from each stage of your life whom you had the greatest impact on (good or bad). If all of these people got together for a dinner party, what would they say about you?
  9. If you had to choose a fruit that best represents who you are as a person, what would it be?
  10. What was your reaction to the previous question about fruit, and what does this say about you?

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FOLLOW-UP QUESTIONS

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Comment below with answers, ideas, and more questions, or contact me to collaborate on a future post!

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EXPLORING YOURSELF

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Which of these ten questions stood out to you the most?

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How did considering these questions make you feel?

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Which question gave you the most trouble to answer? Why do you think that is?

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EXPANDING YOUR WORLD

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How does the location of where someone lives affect them?

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How much control do humans have over their personal characteristics?

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Why do so many people who win the lottery go bankrupt?

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1 thought on “10 Bizarre Questions You Need to Understand Yourself”

  1. “If you were sent to live in outer space for five years, what would you miss the most?“

    Mars Farmer reporting for duty…

    I am sure this will pain the extrovert, but after family, I’d want to just be at home. I love the safety and silence of it. Even after doing anything you can think of on (or off) this planet, we all just want to go home to our bed, our kitchen, our toilets, or the warm embrace of a naturally buff 5’8” companion. As boring as it sounds, I’ll never take it for granted.

    Great Twitch stream, again. As always, Moose and Clive Club forever.

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