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20 Introspective Questions

  • Writer: Dani Jennings
    Dani Jennings
  • May 24, 2024
  • 2 min read

Inspired by We're Not Really Strangers, I had an idea to ask people around me (people closest to me as well as unfamiliar faces) the same set of twenty introspective questions to see how similar or different the plethora of answers would be. I love hearing about how others interpret questions, how their environments and experiences shape them and their perceptions, and if anyone shares the same opinions. I also just really loved reading the huge variety of answers without attaching them to anyone. It's fascinating to think how some of the people closest to you can have completely different opinions about the majority of these questions, yet your connection and bond is so strong.


The questions do not have a particular theme, except they ask you to reflect and be vulnerable. The purpose of this article is to showcase the similarities (and contrarily, uniqueness) we can have across various questions about life, including our perceptions, values, fears, what makes us happy, our insecurities, etc. As I was sorting through the answers, it made me feel simultaneously connected to others yet highlighted my individuality as I compared and contrasted the responses to my own.


My goal for people who read this article is to hopefully realize we're all simply human; we all have insecurities, dreams, fears... we all wish we understood something more, and we all have an ideal way to enjoy a sunny weekend. Whether or not our answers were identical is not important, our individual experiences will differ; however, the key takeaway is that we all deal with these questions at some point in our lives and that makes me feel more interconnected.


Below are the expandible questions and anonymous answers:


What are your biggest insecurities?

  • "It used to be more looks, but after college I grew out of it"


  • "Weight, teeth"


  • "I worry about my weight. I am critical of myself."


  • "My lack of jawline, my mental struggles and how I handle them sometimes"


  • "Verbal mishaps, people noticing my social anxiety"


  • "My toes lol"


  • "Adults judging me, doubting my decisions"


  • "Body"


  • "My weight and general appearance."

What is your dream career?

  • "NBA player"


  • "Professional drummer, auto designer/engineer"


  • "Professional musician"


  • "I would love to just be an artist and not have to worry about finances. to relax and enjoy my time and create meaningful pieces."


  • "School psychologist, clinical psychologist, psychology professor"


  • "College Professor"


  • "I don't dream of labor"


  • "It would be getting paid to be myself. Whatever art form whether that be modeling, speaking, guiding people in the audience.. something where I am using my voice/perspective & values to add to the lives of others."


  • "Radioing a family"

What do you love most about yourself?

  • "My confidence! Especially in my beliefs and my ability to stay headstrong even if I'm the only person in the room who thinks a certain way."


  • "I love the way that I see and understand people, and my sense of humor."


  • "I'm a great listener"


  • "Friendly to all"


  • "Sense of adventure"


  • " My smile"


  • "I love my humility. I know my heart and I know that I do not feel above anyone. I honor what it means to be a leader and observe myself when I slip into arrogance. Sometimes I wish I was more self-assured in the sense around confidence and just speaking my truth no matter what. Sometimes I don't want to stand out bc I don't want to be seen or judged."


  • "My humor"


  • "I love my genuineness, (sometimes) how deeply and how much I think, my loyalty to those closest to me, empathy, humor, wit. Also how I can get super passionate about certain things, and I'm not afraid to be honest."


  • "My adventurous spirit"

Are you afraid of death or dying?

  • "Yes"


  • "Dying painfully"


  • "I get curious about death a lot. Every time it inches closer in my life it unlocks something new to be grateful for, a new perspective, a new level of connection and love coming directly from that very scary and sad thing happening to another. It's interesting how in the presence of dying there is so much love."


  • "No, I am more afraid of important people in my life dying than myself dying"


  • "Both.. I have intrusive thoughts somewhat often about death and the process of dying. I get scared to lose my parents, pets, sibling, partner one day, best friends. It makes 0 sense how anyone could cope with that. I think that's called existential anxiety"


  • "Sometimes."


  • "No"


  • "I don't want to die, but I don't think it's in my top fears. i can only hope that I have the chance to live a life I love before it happens. I do fear the people that I love dying."


  • "Dying, yes. Death, no."


  • "I was, because I was not at peace with my life, but now that I am, I am no longer afraid"


  • "I see it more as motivation to live life to the fullest"

Is there a piece of advice or saying you adhere to when going through hard times?

  • "This too shall pass"


  • ""What's meant for you always arrives at the right time." - so far in life, most of my hardships have had reasons for happening the way they did, even if I couldn't understand it in the moment. I remember my first heartbreak and how badly I wished it didn't happen. Once time passed, I became so grateful I had to go through that emotional pain to get me to this point in my life. On the other hand, for just unfortunate hard times that do not have a good reason (e.g., a loved one dying), my go-to thought is to think of not giving up. I imagine myself getting through the hard time and becoming stronger. But it is important to not suppress the pain."


  • "You choose to be here and to learn these lessons. There is nothing you can't grow through. You are always stronger than you think. Believe more in yourself."


  • "This too shall pass."


  • "I remember when I was sitting through one of my tattoos I kept repeating in my head, "this too shall pass." In life, when I find myself going through a rough time, especially if it's a really hard time, I remind myself that I've made it through all of my other hard times so far. So that even if in the moment things seem like too much, I've already made it this far and I can keep going."


  • "It could be worse. Or if you can get through this you can get through anything"


  • "The Serenity Prayer: Grant me the serenity to accept the things I cannot change, the courage to change the things I can, and the wisdom to know the difference."


  • "We grow through what we go through"


  • "There's no tuff times just tuff peoples"


  • "Times have been tough before, I've made it through, and then things got better. I know I'm not only capable of getting through it, but also I know these hard times are temporary."

What country do you want to travel to the most?

  • "Egypt"


  • "Greece."


  • "Australia and South Africa"


  • "Iceland"


  • "New Zealand"


  • "Antarctica"


  • "New Zealand"


  • "New Zealand or Russia"


  • "I want to visit Poland"


  • "Italy"

List your top 3 moments from the past year.

  • "Hiking Glacier NP with my boyfriend, when I moved to San Diego in July and knew nobody. It felt like a blank slate that I could do anything I wanted with and I felt so free and proud of myself! The third mem is visiting my parents in CO last summer"


  • "seeing old friends, when my boyfriend first said he loved me, seeing my friend get married"


  • "San Diego zoo with my daughter, Charlotte Hornets game with husband and son, meeting my daughter's boyfriend on FaceTime"


  • "Moving, promotion, new car"


  • "Swimming with sea turtles, my boyfriend throwing me a birthday surprise party, and visiting Sedona & the Grand Canyon"


  • "Traveling, going to friends' weddings, going to a sauna which was fun but out of my comfort zone"


  • "Glacier, Costa Rica, San Onofre"


  • "Visiting family, playing in reunion concert, vacation trip"


  • "Birthday dinner with dad, having all of my friends come to the Bucks game with me, Hanging Rock with friends for my bday"

What quality or trait do you wish you had more of?

  • "I wish I had more ambition."


  • "Empathy"


  • "Confidence"


  • "Patience"


  • "Patience."


  • "Unemotional judgement"


  • "Patience"


  • "Social skills"


  • "To speak up / stand up for myself with others."


  • "(Consistent) confidence, trust, patience."

What is something you wish people knew more about you?

  • "Nothing, I like to keep my life and thoughts at private as possible."


  • "I am a pretty open book"


  • "My patience and kindness are not unlimited."


  • "I wish people noticed when I needed extra kindness or help. I have trouble asking for help because my instinct is to be tough. I wish [people] could look at me and notice."


  • "I'm 56 but think like I'm 20"


  • "How accepting I am of others"


  • "Behind my skepticism and over-analyzing tendencies, there is a really sweet and trusting person who just puts up defenses to not get hurt. What's in my brain is not necessarily what's in my heart."


  • "Just because I can sound stupid doesn't mean I'm not smart"


  • "I'm very open so people know everything about me haha"


  • "I wish people knew the depth of my heart but I realize that's only for me to know. So maybe I wish people knew how fly I actually am lmao. Shouts to bball."

Name an influential person in your life right now (they can be a personal connection or someone you don't actually know).

  • "My son."


  • "My grandmother"


  • "My mentors - some who I have not met yet but mostly to those who are in my life that guide me spiritually - shouts to Daniel who is in person and Blu who is not yet in my life. Then I feel like I also connect deeply with certain podcasts."


  • "My boss"


  • "Sophia Bush!"


  • "Don't have a specific person per say, so reading about or watching people's stories who have overcome hard times. Or, my friends"


  • "My manager is amazing"


  • "I would say each other my friends in a different way"


  • "Though both parents are deceased, I've learned valuable lessons from them. Mom - be accepting of all kinds of people, love yourself so you can love others unconditionally. Dad - don't sweat the small stuff, a sense of humor makes life fun."

Tell me an honest hot-take or controversial opinion.

  • "Sports fans are just cosplaying professional athletes"


  • "Hmmm idk if this qualifies but I believe women should live together rather than w their partners. I see sisterhood being the ultimate transcending experience & to be amplified by other WOMEN who believe & see you .. I feel like that gives more strength than the potentially fleeting support from a man."


  • "Being an influencer/content creator is not a career and should not make money. The amount of new unwarranted information and content I've ingested in the last few years due to the influx of this "profession" is scary. Society has let teenagers from TikTok become more influential and richer than educators, scientists, physicians, humanitarians, etc. Also, the amount of hate and false, misleading info online for clickbait/interactions nowadays is crazy... "Doctors don't want you to know this", or "(I don't have any formal education or background in nutrition or science but-) Here's how I fixed my gut health!" What r u even talking about??? lastly why do we worship celebrities... ok that's it I say as I'm scrolling Insta"


  • "Go vegan. For the planet, the animals, and your health."


  • "Body positivity promotes poor health by telling people it's okay to be morbidly obese."


  • "Rolling Stones > Beatles"


  • "Mushrooms can be more helpful than actual therapy"


  • "Queen doesn't have a single good piece of music. It's all overplayed garbage."


  • "College education is overrated"


  • "Adults should get a license to be allowed to be a parent, not everyone should be one"

What is currently your biggest fear?

  • "My parents dying"


  • "Being heartbroken / something tragic unexpectedly happening to myself or someone close to me, settling in life (aka not fulfilling things on my bucket list or making the most out of my life and doing what I want to do)"


  • "Suffering from advanced pancreatic cancer"


  • "Regret. Getting older and regretting what I've done with my time here. I always remind myself that it's impossible to actually regret my choices because I say "I made the best decision I could with the knowledge I had then"."


  • "Losing those I love."


  • "Any medical problem"


  • "Being single and working a crappy job for the rest of my life and not being able to start a family"


  • "Losing employment"


  • "Rejection"


  • "alage eaters/suckerfish (the ones that clean your fish tank). but more seriously, I have a deep fear of abandonment. this has manifested itself through issues or breakups with close friends, romantic relationships, or even casual friends (when I was more emotionally vulnerable)."

  • "Biggest fear - being seen / heard"

Describe a time in nature that left you in awe or feeling deeply connected.

  • "Amazon rainforest after a big rain we climbed up to a viewpoint of the jungle. While we were in at the top, I saw a rare eagle and a rainbow. I cried at the beauty!"


  • "In Bali overlooking so much untouched nature that way incredibly massive and went on further than I could see. Beautiful powerful oceans and rock crashing & crash created a rainbow. I also love watching other people be in awe of nature. We are the only species on this planet that stops and stares at the sunset because somewhere along the way we believed to be separate from it. The birds don't stop, the fish keep doing their thing etc. but we humans get captivated by the beauty not realizing we are looking at ourselves through the vastness, abundance, depth and beauty that surrounds us in our natural world. Mother Nature and that is our human nature."


  • "Anytime I get to gaze at the stars, specifically in areas far removed from light pollution."


  • "Calm days on the lake"


  • "Swimming in billionaires bay in Antibes, France"


  • "I feel this when I'm at the beach alone at night. sometimes I'll go there when I'm having a lot of feelings. there's something about staring at the water, and the moon or reflection of the moon on the water. The ocean is such a powerful force and I feel it so deeply at night; like it somehow knows my secrets without me having to say them aloud. it knows my pains and says it's okay."


  • "Doing mushrooms at a beach in CR"


  • Hiking at Mt. Rainier. Growing up in a NJ suburb I never went hiking at national parks. Mt. Rainier is such a magical place with wildflowers everywhere and majestic views."


  • "Sooo many times but the first memory that comes to mind is in Glacier NP in Montana. After backpacking a bunch of muddy, cold miles we set up camp on this huge, beautiful, quiet lake. At night there were thousands of visible stars in the park - ones you cannot see in San Diego. It started snowing too!! I felt super isolated from society yet immensely interconnected with myself and nature."


  • "Seeing fog pass through Appalachian mountains"


  • "Arizona sunsets, or seeing ocean life in clear waters on the beach."

What is one word that describes your aura/essence?

  • "Honest"


  • "Engaging"


  • "Productive"


  • "Personable"


  • "Loyal"


  • "Inviting"


  • "Analytical"


  • "Bubbly"


  • "Humility / Calm / Soft"


  • "enigmatic"

What is your most ideal way to spend a sunny weekend day?

  • "Any way that makes me happy and the sun is on my face"


  • "Wake up early, farmer's market + coffee + long morning walk, exercise outside and see friends, eat healthy good food, sunset + photoshoot, watch a movie or sports in the PM and have deep talks."


  • Long morning walk in the sun. Big pancake breakfast! Then a beach day with friends. Including swimming in the ocean, reading, paddle boarding, and playing games. We must stay at the beach to watch the sunset."


  • "Beach day or hiking."


  • "Outside with friends."


  • "Outside"


  • "As silly as it sounds I would love to slightly sleep in, run a couple errands maybe, then spend some time in the sun (but not too much to make me tired). to make things perfect it would be nice to spend some time with friends at a brewery outdoors."


  • "Basketball + boxing + weight training + sleep"


  • "Sunday market ! I get to buy fresh products as well as try new foods or just browse and talk with people"


  • "By the beach, reading a book, w chai tea, meditating, yoga, then meet a friend for a stimulating convo, then cuddle with my imaginary bf - thanking and loving life. Then I go out for yummy and healthy food that gets cooked for me while I chiiilll."


  • "Swimming laps by myself at a tropical island"



If you could quickly master a new skill or hobby, what would it be?

  • "Music theory"


  • "Piano. I would love to create music in this way. It sounds so elegant and peaceful."


  • "Would love to know how to make pixel art"


  • "I would like to play piano. When I was younger I was told I had "piano fingers," but I never learned any musical instruments."


  • "Dancing or being fluent in multiple languages. Dancing because it's so much fun and I would love to actually be skilled at it. Languages would help me travel and communicate with more people."


  • "woodworking, I like to build stuff, from tables to small trinkets like chess pieces"


  • "Bodybuilding so I could sculpt myself however I wanted easily or guitar/singing so I could jam to every song I love without sounding like a dying hyena"


  • "Yoga, because the process of getting more flexible and building strength is so difficult, but the payoff of better physical/mental health is worth it."


  • "Playing double bass drums and reading sheet music. As a kid, I took drum lessons for a short time, I was impatient and didn't want to learn how to read music. I've got good rhythm and miss playing."


  • "Omg there are so many things. Speaking multiple languages fluently, being able to long distance run, learn piano, learn how to make more complex/intricate canvas art"

What is something seemingly small that never fails to make you happy?

  • "Hugs."


  • "Head scratches."


  • "The beach / ocean"


  • "Grocery store sales on my favorite items"


  • "Finding a great new song"


  • "Chicken wings"


  • "Cats purring"


  • "hugs, a small supportive comment, seeing pretty flowers, seeing dogs (esp pugs)"


  • "A good basketball game or good workout"


  • "noticing the small things about nature, like the way the sun hits so perfectly, the color of leaves, the color of the sky or the shape of clouds. but also, just sweet interactions with little kids."

What is a must-do one day in your life?

  • "Get married, travel a lot more, complete most of my all-time bucket list, own a house"


  • "Safari in Africa"


  • "Travel to Greece."


  • "Family together in one place"


  • "Visit Antarctica before it is gone/melted"


  • "Pole dancing & goin ATTTT ITTTT"


  • "See favorite bands"


  • "Backpack Macchu Pichu"


  • "Visit Yellowstone"


  • "I feel like my response over time would be constantly changing. I would really like to solo-travel again."

What is something you wish you understood more, or related to more?

  • "Charisma"


  • "Others' insecurities"


  • "I wish I understood more about climate change and what common people can do to help reverse it."


  • "Being optimistic or positive constantly"


  • "Narcissistic personality disorder"


  • "I wish I understood other cultures' ways of life and mindsets. I'm curious about other cultures' (primarily non-Westernized) views towards the world, what it's like living where they do, their values. It's so interesting how some people view the same topic so differently (e.g., in the U.S., it is typical to want to move out of your parents' house as soon as possible because we value independence that way... but other cultures have moral obligation and long-standing customs to live with your parents basically forever)."


  • "I want to learn more about the heart & brain coherence. I wish I understood more about space. I am currently learning about human design and astrology which is super interesting."


  • "Mental health challenges. Luckily I haven't experienced mental health challenges in my life, but the majority of the population has. I wish I understood better so I could better support friends/family."

Share a favorite quote of yours - whether it's an uplifting mantra, or something funny from a movie.

  • "My biggest struggles are also my greatest lessons"


  • "This too shall pass"


  • ""Be the reason why someone feels welcomed, seen, heard, valued, loved, and supported.""


  • "There's no need to be a hero. You don't need to force yourself just to make people acknowledge you. When you do that, you end up blaming yourself, blaming other people...and feeling jealous of everyone... But still...it doesn't have to be like that. Even if people don't acknowledge you, you just have to be someone that you can be proud of! Cuz...you yourself are your biggest supporter! If you can learn to love yourself... That love will continue to support you for the rest of your life."


  • "Whether you think you can, or you think you can't, you're right."


  • ""I was warmed by the sun, rocked by the winds, and sheltered by the trees ..." - Geronimo"


  • ""When I was a child I sometimes experienced these moments - moments of pure liveliness, pure presence. Moments in which it felt like the power of life itself was rushing through my veins and that would stick in my brain as memories forever. Sounds kind of spectacular, right? But all these moments actually happened in the most random and normal situations. Riding a bike home from seeing a friend on a warm summer evening. Waking up to a cool, foggy morning. Touching a horse. Looking out of a train window. Every time I suddenly got this warm, cozy, fulfilled feeling in my heart, making me shiver and feel deeply connected. The opening up of all my senses for everyday magic. The longer I'm here, the more I realize that these moments don't have to be an exception from our daily struggles, but can actually be a state of living. Wherever you are, whatever you're doing, remember to build your circle so you can always feel safe enough to experience life so presently.""


  • ""If you bring forth what is within you, what is within you will save you. &. If you do not bring forth what is within you, what is within you will destroy you.""


 
 
 

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