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60 Deep Questions To Ask Yourself To Create “Aha” Moments

Deep questions are powerful. They force answers.

Deep and compelling questions force us to think profoundly and examine ourselves. Sometimes they challenge our beliefs about what we “know” to be true.

I use deep questions to help my life coaching clients elicit insights, uncover buried beliefs, and reach conclusions about who they are and what they want for their lives. Often I will ask a deep question, and the first comment is one of surprise — “Wow, that's a great question. I've never thought about that.”

Then they have to ponder the question, which often leaves an uncomfortable silence, requiring them to articulate what comes to mind. In that uncomfortable space, the subconscious mind goes into action, and often small breakthroughs and “aha” moments are the result.

You don't need a coach to trigger these insightful moments. If you know the right questions to ask, you can ask them of yourself to encourage the same insights and self-awareness.

However, some people have difficulty asking themselves the kind of questions that lead to self-awareness and change. Understanding the reasons why it's challenging and how to move past your fears can help you learn to coach yourself to new mindsets and positive change.

Why It's Difficult to Ask Yourself Deep Questions

If you find yourself resisting the inner work it requires to explore self-questioning, it could be for one of the following reasons:

  • It's uncomfortable to face certain truthful questions about yourself.
  • You fear the necessary changes the questions will provoke.
  • You don't want to experience the possible pain of self-reflection.
  • You feel confused about what your next steps should be.
  • You worry your new awareness might negatively impact a relationship.

All of these are valid reasons to feel hesitant about exploring your inner world through questioning — but don't let them sidetrack you from this valuable work.

man reflecting thinking Deep Questions To Ask Yourself

The only way to grow and evolve to a new level of happiness, self-confidence, and inner peace is by exploring what is holding you back and then taking action to move forward.

There are ways you can make the process less daunting and even something you look forward to.

I suggest you get a notebook or journal and write the deep question on paper in longhand (not typing).

Close your eyes, take a few deep, cleansing breaths, and repeatedly ask yourself the question out loud or in your head. Then start writing what comes to your mind.

You might consider asking yourself a deep question a week, writing your initial thoughts, and then coming back to the question over the subsequent days to create action steps or ideas about how to implement any changes the question invites.

Some questions might compel you to meet with someone, to seek advice or counsel, or make physical changes in your environment.

Other deep questions to ask yourself might be around:

  • Creating new habits
  • Breaking old patterns
  • Overhauling an entire area of your life

As you have certain insights around these deep life questions, you might experience grief, remorse, or regret — but you also might experience elation, freedom, and surprise.

Allow yourself to feel these feelings, knowing they will pass in time. As you make positive changes based on your responses to these questions, your initial reactions will ultimately transform into contentment and inner peace.

Here are 60 deep questions to ask yourself to create “aha” moments:

1. How am I living outside of my integrity and out-of-alignment with my values?

2. What am I leaving unresolved or unfinished that needs my attention?

woman outside in snow alone deep questions to ask yourself

3. What legacy am I leaving the world after I'm gone?

4. What am I struggling against that I can simply release?

5. What deep needs do I have that aren't getting met?


This may interest you:

Would you like to question your way to lasting love and intimacy?

If so, then check out my bestselling book called “201 Relationship Questions: The Couple's Guide to Building Trust and Emotional Intimacy“.

Mutual questioning is a powerful technique to draw out deeper emotions and desires and address potential areas of conflict before they disrupt your closeness.

The right questions inspire understanding, compassion, and action for positive change.


6. How could I be more engaged in life?

7. How am I living or behaving inauthentically?

8. What (or who) am I tolerating that I really don't want in my life?

9. How am I making choices based on “I should” rather than “I desire”?

10. How am I not accepting someone I love for who they really are?

11. How am I behaving as a reactor rather than an initiator?

12. How am I censoring what I really think or feel because I'm afraid?

13. In what ways do I diminish other people to make myself feel better?

14. Where am I holding back forgiveness?

Simple Self-Confidence

15. How do the people who surround me reflect who I am?

16. Where do I have a “lack” mentality?

17. What negative thought patterns do I have consistently?

18. How do I allow other people to cross my boundaries?

19. What vulnerabilities am I afraid to share with others who love me?

20. How am I getting too caught up in other people's problems?

21. How am I fully present with the people I love when I'm with them?

22. How am I manipulating someone in order to get my needs met?

23. Where am I making my life more complicated or difficult than it has to be?

24. Are my beliefs about life, religion, my kids, my family, my spouse, or politics the absolute truth?

25. How am I using tasks, television, work, or the computer to avoid facing something?

26. How does my living space reflect my inner world?

Related: How To Write a Personal Mission Statement

27.  How am I mistreating my body or compromising my health?

28. What do I feel passionate about, and how can I spend more time on my passion?

29.  What relationships require more of my time and nurturing?

30.  How have I created a miscommunication or misunderstanding?

31.  How much time do I spend dwelling on the past or worrying about the future?

32. What events from my past are hindering my ability to live in the present?

33. How do I feel I'm not deserving or worthy?

34. In what parts of my life do I need to create actionable goals?

35. How am I waiting for someone else to solve my problems?

36. In what ways am I allowing fear of change to hold me back from growth?

37. How am I spending too much time on things that aren't my priorities?

38. Where do I need more learning or skills in order to make the next leap?

39. What would my friends and family say are my strengths?

40. What would my friends and family say are my weaknesses?

41. How am I violating someone else's boundaries when I know I shouldn't?

42. How am I denying my own role in a relationship problem?

43. How does my work reflect my passions, skills, and interests?

44. Where am I prioritizing money and material things over relationships and my values?

45. What do I allow to distract me from really living?


This may interest you:

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Whether you’re a beginner or an experienced meditator, the Mindful Meditator Cards will enhance and reinforce your practice so that you can enjoy the proven benefits of meditation, including better health, improved focus, more creativity, and increased joy.

Each of the 58 cards has a different meditation prompt topic.




46. What is my vision for the next five years?

47. How am I helping others become their best selves?

48. If I died tomorrow, what would I regret not doing?

49. How am I living a life someone else has defined for me?

50. What makes me consistently happy?

51. What has my intuition been telling me that I might be ignoring?

52. What really pushes my buttons that doesn't need to?

53. What drains my energy and how can I change it?

54. How am I being irresponsible or unwise financially?

55. What parts of my home don't reflect who I am?

56. How am I afraid to show or express love?

57. What expectations do I have for my kids that are more for me than them?

58. What do I need to do to take the next big leap in my personal growth?

59. In what ways is longing for an outcome preventing me from enjoying the journey?

60. How am I holding back love for myself?

Did you find any value from these deep questions about yourself?

I hope you enjoyed these questions and found that some of them triggered a new level of awareness for you.

You may find in the weeks to come that answers to these questions will continue to arise in your psyche. One simple question about yourself can unlock so many insights if you pay attention.

Would you like to help others?

Would you be willing to send out some love to your friends and family? Please share these deep questions on your preferred social media platform.

Click Here to Leave a Comment Below 9 comments
  • Sandra Pawula

    This is one of my favorites: ” If I died tomorrow, what would I regret not doing?” I would add this questions: “Am I cultivating spiritual qualities like love, compassion, forgiveness, tolerance, and patience each and everyday?”

    Reply
  • Anne-Marie

    Wow! These are great – and on point with a lot going on in my own universe right now. Definitely going to go through this exercise and hopefully end up with some healthy re-alignments that bring balance and peace in the coming year… thanks, Barrie!

    Reply
  • holly

    These are great questions which require deeper processing. One jumped out at me, #48. Many years ago when I had a thriving psychology practice I took a leave of absence to go work on a 4 masted sailing ship in the Caribbean. Some people thought I was crazy but I knew I’d feel much more regret for not taking the leap to have that adventure. Seriously, I couldn’t picture myself as an old woman rocking on my porch saying, “yup, I’m sure glad I never went sailing and just did the safe thing.” So I went to the Caribbean and had the adventure of a lifetime.

    Reply
  • Rose Costas

    Thanks for another great post. So many of them applies to me I might have to copy them all here but I will most definitely be asking myself many of these questions.
    I am expecting a great life in 2015 better than any I have had before and these questions will truly help me to get where I want to go.

    This is such a great list. Thank you very much.

    Reply
  • Brian

    Powerful questions. I’m buying my note book tomorrow and looking forward to improving my life in 2015.

    Reply
  • lynne

    Hi, awesome thoughts, I’m positive that your readers like me, can relate to these questions, it opened my mind and gave me some thinking to do. Thanks for sharing. Great Read.

    Reply
  • Queenesther

    This Is The Most Challenging Question “what Legacy Will I Leave In The World, When Am No More.. This Will Really Help me Actualise My Goals. Thanks

    Reply
  • +-Life.

    Thank you for this article!

    I think this serves as a reminder that we should always be asking ourselves questions so that we never remain stagnant.

    Questions provide answers.

    Answers provide opportunities for solutions and growth!

    Reply
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