60 Deep Questions To Ask Yourself If You Want To Be Self-Aware

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Voltaire once wrote: “Judge a man by his questions rather than by his answers.”

There’s a lot of wisdom in that. A fulfilled life isn’t so much determined by what you know as it is by how willing you are to learn.

The most obvious way to learn is by asking questions. You do that every day without thinking about it. It’s the most direct way to access necessary information to get by, do your work, or understand your loved ones.

But what about your inner world? Are you as eager to get to know yourself as you’re curious about others?

If you are, here are some deep questions to ask yourself to increase self-awareness. No one else can answer these for you.

Asking self-reflection questions is like peeling an onion. Every time you think you found the answer, new questions arise. There’s always another layer to take off if you’re curious enough to see what’s underneath.

Self-awareness is a never-ending journey, and it’s also unique to you. The questions you’ll find in this post may not lead to definite answers. Instead, they’ll be a compass for navigating your self-discovery.

But before we jump to the questions, how about a short introduction?

What Is Self-Awareness and Why Should You Care?

Self-awareness is such a buzzword these days. We throw it around as if it was obvious what it means. But different people may have very different ideas about it.

On top, it’s easy to believe you’re self-aware even when you’re not. Tasha Eurich, who’s been researching this topic for decades, found that even though most people in her studies assessed themselves as self-aware, only 10-15% of them were right!

One reason this is so is that, according to Eurich, there are two sides of self-awareness. Often, people develop just one without concern for the other. Writes Eurich:

  1. “Internal self-awareness, represents how clearly we see our own values, passions, aspirations, fit with our environment, reactions (including thoughts, feelings, behaviors, strengths, and weaknesses), and impact on others.”
  2. “External self-awareness, means understanding how other people view us, in terms of those same factors listed above.”

Self-knowledge isn’t only about how you see yourself. It’s also being aware of how you come across to others. Only this way you’re able to form an accurate, complete image of who you are.

Daniel Goleman calls self-awareness the “keystone” of emotional intelligence. According to him, knowing ourselves is a prerequisite to navigating relationships, setting goals and regulating our emotions. Numerous studies confirm this — self-awareness seems to improve just about every aspect of your life.

Goleman says that self-awareness can be described as a conglomerate of these three competencies:

  • Emotional Awareness: Recognizing your emotions and the effects they have on yourself and others.
  • Accurate Self-Assessment: Seeing your strengths and limits from an unbiased point of view.
  • Self-Confidence: Having a strong sense of self-worth and competency which isn’t easily shaken by your circumstances.

Each of these competencies can be improved by asking yourself the right questions. You may then bounce your answers off of trusted friends, colleagues or family members. That’s how you ensure the “external self-awareness” component is also there.

But first, here are 60 deep questions to ask yourself. Self-knowledge has to start with you. So let’s begin to peel that onion, shall we?

60 Deep Questions To Ask Yourself

The self-reflection questions below are divided into three sets. I hand-picked them for you from a ton of self-improvement blogs, coaching sites and books to make sure they help to deepen self-awareness.

There’s one set of questions for developing emotional awareness, one for accurate self-assessment and one for building self-confidence. Together, they help you build the self-awareness triad as defined by Daniel Goleman.

Remember that there are no right or wrong answers to self-reflection questions. There’s only your unique answer - and that’s the only one that matters.

20 Deep Questions For Emotional Awareness

  1. Who are you most jealous of and why?
  2. How comfortable are you talking about your feelings and with whom?
  3. What upsets you about other people’s behavior — and what does that say about you?
  4. How do you handle difficult but necessary conversations?
  5. What demotivates you and what helps you regain motivation after you lose it?
  6. When was the last time you felt disappointed or hurt? How did you respond?
  7. What is your definition of happiness?
  8. In what ways are you preventing your own happiness?
  9. How do you typically feel just after waking up and when you go to bed?
  10. Has insecurity ever been useful to you? What about overconfidence?
  11. Are your actions mostly guided by love or by fear?
  12. Do people you surround yourself with lift you up or bring you down?
  13. How often do you treat yourself with love and respect?
  14. Is there someone who hurt you in the past and whom you still need to forgive?
  15. What regrets do you have about the past and what worries you about the future?
  16. What social situations make you uncomfortable?
  17. When you look back at the past month, what was the most joyful moment you experienced?
  18. When you can’t sleep at night, what do you usually think about?
  19. How do you feel when you see yourself in the mirror?
  20. What has the fear of failure stopped you from doing?

20 Deep Questions for Accurate Self-Assessment

  1. What positive qualities do you bring into your close relationships?
  2. What tasks and responsibilities do people at work trust you with?
  3. What skills do you want to learn in the next five years?
  4. In what ways are you contributing to your family, organization or community?
  5. What activities make you feel content, energized and fulfilled?
  6. What are your strategies for bouncing back after a failure?
  7. What threats and opportunities do you currently see in your life?
  8. What are you most likely wrong about?
  9. What could you give a 30-minute speech on with no preparation?
  10. Do you have any addictions? What are they?
  11. What do you spend too much time doing? What do you spend not enough time doing?
  12. What do you love about yourself?
  13. When people come to ask you for help, what do they usually ask for?
  14. When you ask others for help, what do you usually ask for?
  15. What do you think about when you’re alone?
  16. What are three questions you wish you had definite answers to?
  17. What is your biggest strength and your biggest weakness?
  18. If you could change one decision you made in the past, what would it be?
  19. How would you describe yourself in one sentence?
  20. What limiting beliefs do you hold about yourself and the world?

20 Deep Questions for Building Self-Confidence

  1. What compliment do you like to hear the most and why?
  2. What challenges have you faced in the past that you’re proud of overcoming?
  3. What is the mistake you learned from the most?
  4. When do you say “I can’t” most often — and is that actually true?
  5. When was the last time you did something that made you feel scared or uncomfortable?
  6. What difficult problems have you solved that you initially thought were unsolvable?
  7. When was the last time you said “no” and felt good about it?
  8. What one thing would you do if the success was guaranteed?
  9. If you could offer advice to your teenage self, what would you say?
  10. What would you do differently if you knew nobody would judge you?
  11. Are you on the right path in life? How can you tell?
  12. What accomplishments are you most proud of?
  13. When it’s all said and done, will you have said more than you’ve done — or vice versa?
  14. What changes have you undergone that you thought impossible five years ago?
  15. When was the last time you felt empowered?
  16. What do you need to tell yourself today?
  17. What will you never give up on?
  18. What is the best decision you’ve ever made?
  19. What was the best thing you did for yourself today?
  20. When was the last time you surprised yourself?

How To Answer Deep Questions To Access Insight

Asking yourself deep questions is just the first part of the equation.

By picking a self-reflection question, you set a process of self-discovery in motion. You cut into one layer of the onion. To peel it and see what’s underneath, you need to make a serious attempt to answer that question.

How you answer it also matters. There are a few ways of doing it and each may result in slightly different outcomes.

It’s entirely up to you how you choose to answer those deep self-awareness questions. Below, I’ll give you some options and describe what’s likely to happen as a result.

Talking to others

This may be the most challenging way of answering deep questions. You can either bring them up yourself, or ask a friend or family member to ask them to you. Then, let them witness you reflecting on the answer.

By voicing your response in front of somebody, you can find extra dimensions of self-awareness. It’s not just about what you say — but also, how. Do you feel nervous or insecure? Do you feel proud of what you’re saying? Are you anticipating a certain reaction? Such observations can provide extra insights about yourself.

Additionally, you can then ask for feedback about your answer. This way, you add to the external self-awareness that Tasha Eurich talked about.

Recording a voice message

Recording your answers in a form of an “audio journal” can be an interesting way to answer self-reflection questions. You still get to say your answers out loud — but without the pressure of other people listening.

It can be interesting to hear yourself talk when no one’s around. My guess is that you don’t do that very often. Taking a deep question and recording your answer can be a revealing experience regardless of what you say.

Another great thing about it is that it’s efficient. When you talk, you can express yourself faster than when you write. Then, there’s also the advantage of accessing the recording later on and reflecting on it.

Journaling about it

When it comes to answering deep questions, journaling is your friend. 

By writing about your experiences, you relate to them differently. Your thinking changes when you put words down on paper. Because writing by hand is relatively slow, your mind is also forced to slow down and select words more carefully.

Answering self-reflection questions in writing will produce different outcomes than when you talk. To access valuable insight, don’t censor what you write. Allow yourself to journal freely, without editing a single word.

Once you finish, I recommend taking a few hours break before you read your answers. This way, you get to look at them with fresh eyes and a new perspective.

Meditating on it

Another way to answer deep questions about yourself is through meditation. The idea is to ask the question — and then, remain open to the answers without “thinking about them.”

This is different from journaling or talking. Rather than actively producing the answer, you remove yourself from the process. You ask the question and let your unconscious mind do the work behind the scenes.

This requires you to let go of what you think you know about yourself. Be prepared for surprises.

To answer your question in this way, you don’t need to sit in a formal meditation (although you certainly can). You may also ask the question and go for a walk, do some mindful exercise or take a shower. Meanwhile, observe the thoughts your mind is producing without pushing for a particular outcome.

The answers may come when you least expect them.

In a dream or after waking up

One way of working with your unconscious mind is asking deep questions just before you go to bed. This way, you plant an idea and let your brain work on it while you sleep.

This is a technique the world-class chess and tai-chi champion Josh Waitzkin uses for solving big life questions. He calls it MIQ: Most Important Question. Shortly before your bedtime, Waitzkin recommends asking the question that’s important for you right now. Then, you let it go and fall asleep.

This way, your unconscious mind gets to work on the question without any effort on your side. The answer may come in a dream or just after waking up. The next morning, you can use your journal to free-write about the insights you received during the night. 

Write them down first thing after waking up and let yourself find the most important answers: yours.

Closing Thoughts

A huge part of your life depends on how self-aware you are. If you know what makes you tick, what your fears and desires are, which events trigger what emotions, and so on — then you’re way ahead of the pack.

You make better decisions and spend time on the right things. That’s because you understand the consequences of your actions.

To reach higher levels of self-awareness, there are many deep questions you can ask yourself. The more you ask and look for answers, the more you’re able to learn.

You keep peeling consecutive layers of the onion even when other people claim there’s nothing new to learn. But you know better. You know that answering deep questions usually leads to… more questions.

And, you’re comfortable with that.

The deeper you go into this journey, the more you accept that you may never fully know yourself. And that’s okay.

After all, it’s not the answers that matter most. It’s the process of self-discovery that creates a sense of wonder and joy. It’s the search itself that creates meaning. That meaning can change from moment to moment, as you keep asking questions.

As Victor Frankl said:

“The meaning of life differs from man to man, from day to day and from hour to hour. What matters, therefore, is not the meaning of life in general but rather the specific meaning of a person's life at a given moment.”

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