108 Deep Questions to Ask Yourself (Backed by Experts)

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Career and executive coach Deepali Vyas shares her favorite questions to help you figure out what you want

Co-authored by Deepali Vyas and Annabelle Reyes

Last Updated: December 7, 2025 Fact Checked

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• Questions About Yourself
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• Emotions
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• Family & Friends
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• Love & Romance
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• Career
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• Philosophical Questions
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• Meaning & Importance of Introspection
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• Exercises for Introspection

|Show more |Show less

Are you interested in digging deep and really getting to know yourself better? If so, it may be time for some self-reflection and introspection! These skills are super important for personal growth, and they can even strengthen your personal relationships and help you thrive professionally. Luckily, we’ve compiled a thorough list of questions to ask yourself about your life, emotions, family, romantic preferences, career goals, and more. We’ve also included expert insights from career coach Adrian Klaphaak and life coach Tracey Rogers, so keep reading!

The Best Questions to Ask Yourself

Career and executive coach Deepali Vyas suggests asking yourself questions like “What do I actually want?” and “What does my ideal day look like?” Some more great questions to ask include:

• What do I value most?
• What are my strengths and weaknesses?
• What are my short-term and long-term goals?
• What brings me joy in my life right now?
• What am I most grateful for?
• What scares me the most?
• What is something that inspires me?

Steps

Section 1 of 8:

Questions About Yourself

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1. 
   Ask yourself questions about who you are to spark self-reflection. Rogers suggests taking an “internal inventory” to identify all the wonderful traits you have that you could cultivate more, as well as any negative traits that may be holding you back from being the best version of yourself. You can also ask yourself about your values, hopes, fears, and past experiences. Here are some examples:

   • What are my strengths?
   • What positive traits come naturally to me?
   • Do I have any negative traits I could work on?
   • What would I change about myself if I could?
   • How would the people closest to me describe me?
   • Am I more of an introvert or extrovert?
   • What are my moral and ethical values?
   • Do I live my life according to my values?
   • What acts of kindness have I done for others recently?
   • What do I find inspiring?
   • What am I most afraid of?
   • What is my most cherished memory?
   • What’s the hardest lesson I’ve learned so far?
   • What worries me the most about the future?
   • What would I do if I wasn’t afraid of failing?
   • What in my life do I take for granted?
   • What are the biggest challenges I face in life?
   • Am I true to myself, or do I hide parts of myself from others?
   • If today was the last day of my life, how would I spend it?
   • Do I push myself out of my comfort zone enough?
   • Do I care too much about what others think of me?
   • Am I holding myself back in any way?
   • What’s most important to me?
   • What do I desire most out of life?
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Section 2 of 8:

Questions About Emotions

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1. 
   After reflecting on who you are, reflect on how you feel. Being able to understand your emotions is an important tool in life. Emotional awareness helps you build better relationships, and it also helps you figure out how to effectively practice self-care. Here are some questions to ask yourself about your emotions:

   • What does “joy” mean to me?
   • What hobbies do I have that make me truly happy?
   • When do I feel most energized?
   • What do I love about life?
   • What makes me excited to wake up?
   • What inspires me?
   • When I’m feeling sad, what makes me feel better?
   • Is something standing in the way of my happiness? What can I do to change it?
   • Do I take care of myself enough?
   • Where in the world do I feel safest?
   • What makes me feel anxious?
   • What calms me down when I feel stressed?
   • Am I comfortable expressing my emotions? Or do I hide them?
   • Do I allow myself to cry when I need to?
   • Do I avoid my emotions or confront them head-on?
   • What negative emotion could I work on controlling more?
   • What positive emotion can I work on cultivating?
   • Am I good at putting my feelings into words?
   • Do I feel love for myself? How can I work on building self-love?
   • Do I enjoy my own company?

Section 3 of 8:

Questions About Family & Friendships

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1. 
   One way to understand yourself better is to reflect on your relationships. Analyzing your connections with your loved ones is a hugely important part of personal growth, Rogers explains. It helps you understand how you express affection and handle conflict, and what matters to you in interpersonal relationships. Try asking yourself these questions:

   • Would I consider myself a good friend?
   • Would I want to be friends with myself?
   • Am I putting enough effort into my relationships?
   • How do I show support to my friends?
   • What’s a kind thing I’ve done for a friend recently?
   • How would my closest friends describe me?
   • Which of my friends could I actually trust with my life?
   • What are the most important qualities I look for in friends?
   • Who do I go to when I need advice?
   • Who in my life do I look up to the most?
   • Who has had the greatest impact on me?
   • Which family member makes me feel happiest and safest?
   • Is there a family member I’ve grown apart from? Can the relationship be fixed?
   • What am I most thankful for about my family?
   • Do I feel supported and loved by my family?
   • Would I change anything about the way I was raised?
   • What’s one thing I really wish my friends or family knew about me?
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Section 4 of 8:

Questions About Love & Romance

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1. 
   Love and romance are important parts of many people’s identities. As a result, it can be helpful to ask yourself questions about your romantic preferences and desires. These insights can help you get a better idea of what you’re looking for in a partner, what you value in relationships, and what all of this says about you as a person.

   • How important is romantic love to me?
   • Am I comfortable being single?
   • Do I think it’s more important to love or be loved?
   • What qualities do I look for in romantic partners?
   • Am I willing to compromise in romantic relationships?
   • Do I maintain my sense of self even when I’m in a partnership?
   • How do I show love and support to my significant other?
   • What is my communication style in romantic relationships?
   • When I picture my ideal romantic relationship, what does it look like?
   • Is getting married an important goal for me?
   • Do I have any relationship or dating deal-breakers?
   • Do I enjoy dating around, or do I prefer monogamy?
   • What scares me about romantic love?
   • What is my primary love language?
   • What does “romance” mean to me?
   • Do I believe every person has one soulmate, or can people have many?
   • How do I handle conflict with a romantic partner?
   • What was my first love like? What did I learn from it?

Section 5 of 8:

Questions About Work & Career Goals

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1. 
   If you’re ready to level up in your career, self-reflection is a must. It helps you identify your strengths, and “when people align their work with their strengths, they are happier and more successful,” Klaphaak explains. Here are some questions to help you jump-start your reflection:

   • When was the last time you felt like you were in your element at work? What were you doing?
   • Which of your professional skills are you most proud of?
   • What professional achievement has meant the most to you so far?
   • What type of employee do you think you are?
   • How would supervisors or bosses describe you?
   • What motivates you to go to work every day?
   • What does “success” mean to you?
   • What is your "dream job"?
   • Who is your biggest professional role model?
   • Are you happy with the career path you’re on right now?
   • What are your short-term and long-term professional goals?
   • When you picture your ideal professional life, what does it look like?
   • Is there a goal I’ve given up on that I should revisit?
   • What’s worse, failing, or being too afraid to try?
   EXPERT TIP

   

   Adrian Klaphaak, CPCC

   Career Coach

   Adrian Klaphaak is a career coach and founder of A Path That Fits, a mindfulness-based boutique career and life coaching company in the San Francisco Bay Area. He is also an accredited Co-Active Professional Coach (CPCC). Klaphaak has used his training with the Coaches Training Institute, Hakomi Somatic Psychology, and Internal Family Systems Therapy (IFS) to help thousands of people build successful careers and live more purposeful lives.

   

   Adrian Klaphaak, CPCC
   Career Coach

   Ideally, your career should be an expression of who you are. Rather than thinking about what you want in your career, start by reconnecting to who you are. Define your values, strengths, passions, and purpose. Think of those core parts of yourself as an “inner compass” that points you toward a career path that fits.
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Section 6 of 8:

Deep, Philosophical Questions

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1. 
   To really dig deep, ask yourself some philosophical questions. These types of questions are great for boosting your critical thinking skills, and they can also help you understand the world (and your place in it) better. Here are some suggestions:

   • Do I consider myself more of an optimist or a pessimist?
   • What does it mean to be “a good person”?
   • What pieces of art have moved me and spoken to me the most?
   • Do I believe in karma?
   • Does religion or spirituality play an important role in my life?
   • Do I believe in a higher power?
   • Have I discovered my purpose in life yet?
   • If my life ended tomorrow, how would I want people to remember me?
   • What are your biggest questions about how the universe works?
   • If you could talk to your younger self, what would you say?
   • What makes me me?
   • Is fame a good thing?
   • Is social media more of a good influence or a negative influence?
   • Would I want to be able to see the future, or is it better not to know?
   • If you could change one thing about the world, what would it be?

Section 7 of 8:

What is introspection, and why is it important?

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1. 
   Introspection means looking inward, and it helps you understand yourself better. It involves asking yourself questions about your beliefs, values, desires, and feelings and reflecting on these things in an in-depth way. Introspection is important for your mental health because it helps you identify and understand your emotions, which in turn helps you manage them better.

   • Self-reflection also involves identifying your strengths and weaknesses, and this awareness can lead to more professional success.
   • Self-reflection fosters healthy relationships as well. When you’re more in touch with your emotions, you’re better at sharing them with others, which can help you grow closer to people and handle conflicts in a healthier way.
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Section 8 of 8:

Introspection & Self-Reflection Exercises

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1. 
   1
   Take a “fear Inventory.” When Rogers has clients who are looking to engage in some self-reflection, she suggests an exercise called a fear inventory. “It’s an exercise where you keep track of anxieties, insecurities, or doubts that come up for you when you’re trying to make an important change in life,” she explains. You can keep track of these things on a piece of paper, in a journal, or even in your notes app on your phone.

   • In doing this exercise, you’ll usually be able to pick out a common thread that’s held you back at different points in your life.
   • “It’s a powerful moment when you understand, ‘Oh, this is my pattern,’ or ‘This is a fear that I continue to come back to.’ And when you can name it, it’s easy to change it,” Rogers says.
2. 
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   Identify what’s in your control and out of your control. When you start a journey of self-reflection and personal growth, “It’s important to know what we have control over and what we don’t,” Rogers explains. “So if a client came to me and said, ‘I really need to make some changes, and I need to do some reflection on where I am and where I wish to be,’ I would ask the client to identify some things that they can change, and some things that they may have to surrender along the way.”

   • For example, Rogers gives the example of a client who wants to lose weight. “I would say, ‘What are some things you can do for yourself to change your physical health? And what are some things that you need to surrender, that you don't have control over, and therefore shouldn't be too focused on?’”
   • “And so their answer might be, ‘Well, I can go to the gym, I can create an exercise routine, those are things that I can change for myself. I can't change how quickly the weight falls off, and I can't control how much weight will fall off.’ That kind of exercise can really be helpful in a very realistic practical way,” says Rogers.
3. 
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   Have an internal dialogue with yourself. “One other exercise that's fun is called a voice dialogue,” Rogers says. “It's basically having a conversation with two different voices in your head that may be in conflict with each other. For example, say someone wants to make important changes when it comes to navigating family dynamics. On the one hand, they know that they need to put up better boundaries, but on the other hand, they feel really guilty about it. It'd be a conversation between these two voices,” Rogers explains.

   • You can imagine this back-and-forth dialogue in your head or write it out in a journal. Rogers has even had clients who take more creative approaches to the exercise.
   • “I've had clients pull out sock puppets. I've had clients create a screenplay. It's a really fun exercise, and it's just for the sake of understanding what it is that’s blocking you, where you feel conflicted,” Rogers says.
4. 
   4
   Identify times when you were “in the flow.” If you’re hoping to grow professionally, Klaphaak recommends looking back and identifying "the moments when your innate strengths were coming through." According to Klaphaak, these are examples of being in the flow. "They don't have to be big flashy achievements— they could be small things that went unrecognized, like supporting a friend through a challenge in their life,” he explains. “What's important is that you felt like you were in your element, at your best, doing something that came naturally to you.”

   • Klaphaak suggests writing a reflection about each of the experiences you identify.
   • “Ask yourself what strengths you used in these experiences, and notice which strengths show up repeatedly - those are likely to be your core strengths, the ones that you want to make sure to use in your career,” he says.
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