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I was recently mindlessly scrolling through social media (as one does...) when I came across a video post that asked a few questions that really struck me to my core.
These were not your typical "Where do you see yourself in five years?" or "What would you say to your younger self?" type of questions.
These were soul-stirring, heart-hitting, and emotion-triggering questions. The voice that was asking those questions sounded as if it was speaking to my soul. The next thing I knew, I was crying, thinking of the question, not even thinking about the answer, but the question! Nobody, including myself, has asked me those questions!
I paused and thought of an answer to a particularly deep question and I found myself diving deep into my emotions, pulling out answers from places inside me that hadn't been touched in the longest time. It was an emotional experience and quite frankly it took me by surprise. These were emotions that I had suppressed for a really long time. They were still there. I just never gave myself a chance to think, ponder and feel.
As we know it, we go through life wearing a lot of hats, we're a daughter, a sister, a mother, a girlfriend, a wife, a friend, a confidant, a colleague, a boss. Oftentimes, the real 'we' and all that 'we' encompass gets lost - and gets buried.
This whole experience made me wonder how often we allow ourselves to truly explore the depths of who we truly are and ask ourselves questions that reveal our true selves.
In this post, I've gathered 35 deep questions to ask yourself to help you uncover layers of yourself that have been, either, given the backseat or you might not even realize exist.
These are perfect for journalling or for moments when you feel like reconnecting with yourself on a deeper level.
35 Deep Questions To Ask Yourself
Have you ever experienced that? Deep questions that just stopped you in your tracks and made you pause to think and suddenly you're swelled up by all these emotions that you forgot were even there to begin with.
These 35 deep questions, once pondered over will force you to reach deep down and give attention to parts of you that you normally don't give attention to. They might emotionally move you and they might offer the clarity that you might be looking for.
These are definitely worth your time if you want to reconnect with yourself.
Who are you when no one’s watching?
This taps into the rawest version of ourselves. Our unfiltered, authentic traits and tendencies that we tend to keep guarded. This question reveals what we truly value, and who we are at our core once we put aside what we know society expects of us.
What are your most loudest, self-critical thoughts?
We all know how brutally critical our inner voices can be but acknowledging and identifying these thoughts and questioning them head-on allows you to recognize how they influence your self-worth.
What would you talk about if someone was actually listening?
Ever feel like you have so much to say, but no one’s really tuned in? This question gives you the chance to imagine a space where your words truly matter. What thoughts, feelings, or ideas would you finally share? It’s liberating to think about the things you keep bottled up inside, and this reflection can help you find your voice and the courage to express yourself. This question gives you the space to imagine a world where you can be truly heard—what would you finally say?
What's something you need to come to terms with?
Life can throw us some tough punches, and sometimes we hang onto pain or regret longer than we should. This question nudges you to confront those lingering feelings and find acceptance. Whether it’s a painful truth or a past mistake, acknowledging it can be a powerful step toward healing. It’s all about recognizing what you’ve been carrying so you can finally let it go.
What do you fear the most?
Fear has a way of controlling us from the shadows. By expressing what you fear the most, you give yourself a chance to face it. It could be failure, rejection, or even loneliness, but bringing it to the surface can be the first step toward overcoming it.
What parts of you do you hide from the world?
Whether we'd like to admit it or not, we do all wear masks, showing only certain parts of ourselves to the world. This question encourages you to dig deeper into the parts of yourself that you tend to keep under wraps. Why do you feel the need to hide them? Understanding the reasons behind those choices can help you reconnect with your authentic self and embrace all the facets that make you unique.
If you could vent to someone with zero judgment, what would you say?
Everyone judges - a lot or a little, they judge. Imagine a world where you could spill all your thoughts without a hint of judgment. How freeing would that be? Answering this question lets you release all the thoughts you keep inside, without the fear of judgment.
What's the most hurtful thing someone has ever said to you?
Words can sting, and sometimes they stick with us longer than we’d like and can leave lasting scars. This question helps you reflect on the painful words you've been carrying and maybe explore how that it has impacted you.
What's something you're holding on to that's still hurting you?
We all carry baggage, but sometimes we don't realize how much it's weighing us down until we confront it head-on. This question shines a light on the wounds that haven’t fully healed, giving you a chance to reflect on what you need to let go of.
What is something you feel guilty thinking about?
Guilt can be a heavy burden, especially when it’s tied to thoughts we don't want to admit. This question forces you to confront those hidden feelings and explore why they make you feel guilty.
If you could write a letter to someone you've hurt the most, what would the last paragraph be?
The last paragraph in any letter often carries the most weight. Writing a letter and focusing on the last paragraph, you're truly thinking about what you want that person to take away. It can be an apology, forgiveness, or some sort of closure.
What's one thing you wish you could say to your parents?
Sometimes, out of fear or respect, we often hold back so many things that we want to say to our parents. This gives you a chance to reflect on the things left unsaid and how it has affected your relationship with them.
When you look up at the night sky, what is it that you think about?
There's something quietly humbling about looking at the night sky. For a moment, you feel as if you're alone in this world. And this question allows you to reflect on your place in the universe and the thoughts you think about when you're looking at something as grand as the night sky.
What's one thing you wish you could forget?
There are some memories that linger and haunt us. These are memories we wish we could erase. Answering this question lets you bring these memories to the forefront and allows you to confront them and it may help you begin the healing process.
If you saw someone feeling the way you're feeling right now, what would you tell that person?
Sometimes, we are our own harshest critics. By imagining someone else feeling how you do, you might find yourself offering advice or comfort that you’ve been denying yourself. It can also provide you with clarity and comfort to deal with what you're feeling.
If you were to write a book about your mom and/or your dad, what would the title be?
Titles are powerful—they are a window or a glimpse into the whole story. By imagining a book title for your mom and/or your dad, you're acknowledging the role they have played in your life, whether it’s one of strength, sacrifice, or love.
What do you need to forgive yourself for?
Have you ever wondered why it's always easier to forgive others rather than forgive ourselves? The reality is that self-forgiveness is tough because we are often tough on ourselves with endless negativity and self-criticism. Identifying what you're holding against yourself and allowing yourself forgiveness can actually help you move forward.
What is one thing you wish people would understand about you?
Misunderstandings can create distance between us and others. By expressing what you wish people knew about you, you can start to bridge those gaps and bring more authenticity to your relationships.
What's something you'd do if you weren't afraid?
Fear is often the biggest obstacle that comes between us and the lives that we want to live. Confronting your fears and imagining how your life would be without them, you can get more clear on your true hidden desires and dreams.
If you could write a book about your mom, what would the title be?
We often get attracted to a book by its title. Titles are powerful and are basically the essence of a story. Taking time to come up with a book title about your mom reveals the role that she has played in your life. It can be of strength, sacrifice, or love. You'd think this would be easy but once you really think about it, it's harder than you think - you might just end up with titles for a book series!
What's something your parents did to you that you will never do to your kids/future kids?
We all have things we’ve experienced growing up that we’ve sworn we’ll never repeat with our own children. This question prompts you to reflect on those lessons and how they’ve shaped your parenting ideals.
What’s the most difficult truth you’ve had to face?
The hardest truths are the ones that we often don't want to come to terms with but these are also the ones that bring us the most growth. Confronting our difficult realities allows us to heal and learn from it. They also might be a contributing factor in shaping the person you are today.
What do you need to get off your chest?
Let's face it —we carry a lot of things and for far too long. Emotions, thoughts, regrets. Giving this question enough thought gives you the opportunity to lighten the emotional burden you carry with you by acknowledging what they are and releasing them.
What's one thing people assume about you?
Ever wonder what people assume about you? This question gets you thinking about those little (or big) judgments others might make, whether they’re spot-on or totally missing the mark. It’s a chance to reflect on how these assumptions shape the way you see yourself, and maybe even uncover any hidden truths—or misunderstandings—about how you’re perceived.
What are the challenges you're facing right now?
What's weighing you down right now? This question is all about bringing those challenges to the surface so you can see them clearly. Once you name them, it becomes a little easier to face them head-on and start finding a way through them.
What's one thing you needed as a child but never received?
Childhood wounds often linger into adulthood. This question allows you to reflect on the unmet needs of your younger self and how they’ve shaped who you are today.
What’s standing in the way of you and happiness?
Happiness can feel elusive, especially when there are obstacles in the way. This question pushes you to examine what’s blocking you from experiencing true joy and fulfillment.
What’s the best part of being you?
This question is a reminder to celebrate what makes you special. It helps you shine a light on the parts of yourself you’re proud of—the things that make you, you.
What’s the one thing you'd want people to remember about you?
This question helps you think about the mark you want to leave and the impact you hope to have. It’s a chance to reflect on what truly matters in the life you’re living.
If your heart could talk, what would it be saying right now?
Sometimes we push those deeper feelings aside, but this question gives you a moment to just pause and listen. It’s like checking in with yourself, letting whatever’s really going on inside come up, with no filter, no judgment.
What would you do differently if you knew nobody would judge you?
Imagine what life could be like if judgment wasn’t holding you back. This question lets you picture a version of yourself that’s free from other people’s opinions and expectations. It’s a chance to think about those dreams, choices, or little quirks you might embrace if you weren’t worried about anyone else’s thoughts. Sometimes, we keep parts of ourselves hidden, so imagining life without that weight can be eye-opening.
Beyond the titles that others give you, who are you?
We spend so much time being someone’s friend, parent, or co-worker that we often lose sight of who we really are underneath it all. This question pushes you to step out of those roles and think about what truly makes you, you. It’s about looking past the labels and reconnecting with the parts of yourself that might get overshadowed by everything else.
What are you most proud of yourself for?
We’re so quick to downplay our own achievements, but this question asks you to give yourself a bit of credit. Think about the moments that make you proud—whether it’s something big or a small, quiet win that only you know about. It’s a chance to really honor yourself and acknowledge the things that make you feel accomplished, however small or big they may be.
What do you believe is the purpose of your life?
This one’s all about getting to the heart of what drives you. We’re not talking about career goals or checking things off a list, but really digging into what gives your life meaning and what you hope to bring to the world. It’s a big question, but it helps you explore what makes you feel fulfilled and connected, and what legacy you hope to leave behind.
When did you last tell yourself, "I am enough"?
How often do we give ourselves that little reminder? This question nudges you to check in on how you truly feel about yourself and whether you’re embracing your own worth. It’s about letting go of any need for outside validation and realizing that, just as you are, you’re complete. It’s a powerful moment of self-compassion that we don’t often take the time to feel.
You don't have to answer these questions all at once and they are not meant to be easy. You'd have to truly dig deep and be truthful to yourself.
Whether you answer them through journaling or simply thinking about them, the point is to explore the parts of you that you don't always give attention to.
So, what question resonates with you the most? Let me know in the comments if you feel like sharing—I’d love to hear your thoughts!
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