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

deep questions to ask

Questions are powerful. They force answers.

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

As a coach, I use thoughtful questions to help 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 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.

Once during a particularly stressful and confusing time, my sister asked me the question, “What would happen if you let go and just allowed the universe to catch you?” In essence, she was asking what would happen if I stopped fretting and trying to control events and rather simply let life unfold?

It was a profound moment for me, as it forced me to realize two things. First, my stress and worry wouldn't change the way life happens. Also, I realized if I did let go of control, I wouldn't die. Nothing would happen that I couldn't cope with. The only control I have is over my own reactions.

You don't need a coach or family member 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.

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

I suggest you get a notebook or journal, and write the question on paper in longhand (not typing). Close your eyes, take a few deep, cleansing breaths, and repeat the question out loud or in your head. Then start writing what comes to your mind.

You might consider working on a 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 questions might involve creating new habits, breaking old patterns, or even overhauling an entire area of your life. As you have certain insights, 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.

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?

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?

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?

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?

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?

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?

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Read this list of 60 deep questions to ask of yourself and others. Asking these questions will help you get to know him or her.

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