60 Hard Questions to Ask Yourself and Unlock Your Life

hard questions to ask yourself

60 Hard Questions to Ask Yourself

July 5, 2020


It’s one thing to answer fun and silly questions about yourself. It’s quite another to tackle the hard questions. Many of us run away from these hard questions with the determination of an eight-year-old running from cooties.

The truth still stands. You can only grow when you’re willing to ask yourself the hard questions.

Oh, and you have to answer them, too.


Skip down to the different categories of hard questions to understand yourself better:


Questions Improve Our Self-Awareness

We all lack self-awareness in some capacity. As such, we have trouble finding purpose in our lives. We get caught up with false cultural narratives, troubling emotions, and faulty thinking.

(Want to learn more about what’s holding us back from knowing how to answer questions about yourself? Read my posts about false cultural narratives, troubling emotions, and faulty thinking.)

This can make it super challenging to understand ourselves and what we need.

We’re also terrified of any hard questions to ask yourself. After all – what might we find? What might our answers reveal about our current status in life?

We must find the courage to dig in, dig deep, and ask ourselves the hard questions.



When Tackling These Hard Questions About Yourself

Some of you will skim over this list, consider a few questions for 1-2 seconds, and then happily click to another page. (Yes, I’m calling you out. Not even 2-3 seconds??) Others might pull out a journal, roll up the sleeves, and get down to business.

The more effort you put in, the more you’ll get out of these questions about yourself. If you’re worried about holding yourself accountable, find an accountability buddy or break it down into simple steps.

When tackling these hard questions, be kind to yourself in the process. Adding a layer of judgment to your answers isn’t going to help anyone. Nor is denying what you actually find. (“No, that’s not a good answer. Kara, please choose a different one, thanks.”)

Part of being vulnerable is accepting your authentic self. After you accept yourself, you can learn how to share it with the world.


Hard Questions to Ask Yourself

Hard Questions About Your Childhood

  1. What is something that happened in my childhood that still bothers me?
  2. What hopes and dreams did I have as a child that I have given up on?
  3. What primary coping strategy did I develop as a child that I still use today?
  4. What messages did I receive about what I needed to do to receive love?
  5. How did my upbringing shape my view of what I wanted for a healthy family? A relationship?
  6. What lesson from childhood has stuck with me the most?
  7. Who had the biggest influence on me as a child?
  8. What communication patterns did I develop as a child? Are they effective or ineffective?
  9. What did I not like about my childhood that I want to change for my adult life?
  10. What did I feel most ashamed of as a child? How might this shame still be affecting me now?


Hard Questions About Your Challenges and Failures

  1. When have I failed in life?
  2. How did I handle each failure in my life? What was my reaction to failing?
  3. How was failure treated in my upbringing?
  4. When in my life have I repeated the same mistakes over and over again?
  5. What do I feel most shameful about in my life?
  6. What is one of my biggest regrets? What did I learn from it?
  7. What challenges in my life defined me the most?
  8. What is my attitude when facing a challenge?
  9. How comfortable am I asking for help when I’m faced with a challenge?
  10. What is my most harmful pattern when faced with stress?


Hard Questions About Your Happiness

  1. What gives me a deep and profound sense of joy?
  2. What do I lose track of time doing?
  3. What do I feel most proud of?
  4. If I could map out a perfect day, what would it consist of?
  5. What helps me recharge my energy levels?
  6. How do I define happiness? Do I understand what’s needed for happiness?
  7. Can I identify what limiting beliefs get in the way of my happiness?
  8. When do I confuse my own happiness with the happiness of others?
  9. Do I understand what universal elements are needed for a happy life?
  10. When do I prioritize what makes me happy? When do I neglect it? Why?


Hard Questions About Your Relationships

  1. What relationship gives me the most meaning?
  2. How much energy do I put into the relationships that are most important to me?
  3. What relationships in my life make me feel worse about myself instead of better?
  4. Who in my life am I my most authentic self with?
  5. When have I hidden my true self because I was afraid of what others would think?
  6. What are the most important qualities for me in a relationship? Friendship?
  7. How can I be a better friend/partner/family member? Where do I fall short?
  8. What do I need to feel trusted in my relationships?
  9. When do I feel lonely in my life (even if I’m surrounded by people)?
  10. How connected do I feel to a community? What communities do I feel connected to?


Hard Questions About Your Growth

  1. How am I a different person now than I was five years ago? Ten?
  2. What am I most afraid of?
  3. What do I have trouble trusting about myself?
  4. How often do my emotions interfere with what I want for myself?
  5. Where in my life do I feel like I’m not living up to my full potential?
  6. What am I most grateful for in my life?
  7. If I evaluate the narrative I create for my life, is it more negative or positive?
  8. If I could go back and change something I said, what would it be?
  9. What causes me to feel the most out of control?
  10. How often do I feel lost or purposeless? What causes these moments?


Hard Questions About Your Purpose and Impact

  1. What day-to-day tasks fill me with purpose?
  2. How do I define a purposeful life? How is my definition influenced by others?
  3. What percentage of my time is spent on things that give me meaning? Things that don’t?
  4. What am I adding to the lives of others? To the greater world?
  5. If I die next week, what would people say about me? What do I want them to say?
  6. Who is greatly influenced by my day-to-day actions?
  7. Who looks up to me in life? Who do I look up to?
  8. When do I make other people’s lives more difficult?
  9. Where in my life can my actions help improve the lives of others?
  10. How has my purpose – and what gives me meaning – changed throughout my life?



These deep questions to ask yourself are just that: hard. Don’t expect yourself to know or embrace the answers right away. Instead, give yourself time to really consider these questions about yourself and what they mean for your life.

The more self-aware and vulnerable you can be, the more you can design a purposeful life for yourself.

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