60 Deep Questions You Should Ask Yourself When Approaching Your 30s


1. Have I learned the value of confidence? 

2. Have I shown up for myself?

3. Have I acted in a way my children would be proud of? 

4. Do I know my worth? 

5. Have I accepted myself for all of my flaws 

6. Am I using negative language when referring to myself?

7. Have I expressed gratitude towards myself for all that I can do?

8. Do I challenge myself and my abilities?

9. Do I try my best to be a good friend and partner? 

10. Where do I still have room to grow? 

11. Do I trust myself and those closest to me? 

12. Do I continuously try to make improvements in my life? 

13. Am I educating myself often on current issues going on in the world?

14. How often do I tell those closest to me that I appreciate them?

15. Do I wake up with excitement and enthusiasm or with weary and dread?

16. When was the last time I verbalized how I feel out loud? 

17. Are my days spent doing things that elicit joy and spark my passion? 

18. Where do I feel the most comfortable and safe?

19. Am I doing everything I can to take care of myself physically, mentally, and spiritually? 

20. Do I take pride in my personal achievements the same way I do my professional ones? 

21. Do I treat myself with the kindness and respect I know I deserve?

22. Have I only invited positivity into my life and distanced myself from bad energy? 

23. Have I discovered what truly makes me happy? 

24. Do I act like my true, authentic self? 

25. When was the last time I had a good cry? 

26. What qualities am I most attracted to in a person? 

27. What do I want and need from a committed partner? 

28. Do I have someone to call that will listen to my problems just like they would my triumphs?

29. Where is my favorite place in the world and when was the last time I visited there? 

30. Who am I? 

31. Have I developed the skills needed to succeed in my field? 

32. Do I frequently step away from my work to come back with a fresh perspective?

33. What do I need to incorporate more or less into my life? 

34. Do I try to understand my feelings or ignore them in hopes they go away? 

35. Am I pleased with the path that I’ve chosen? 

36. Do I admit to myself when I’m lonely or feeling down? 

37. Do I have people in my life I’d feel comfortable reaching out to if I was in pain? 

38. Do I have any regrets in my previous relationships and am I willing to make adjustments in my love life going forward?  

39. How do I react to unpleasant situations? 

40. Do I practice what I preach to others? 

41. Am I comfortable in my own skin? 

42. Do I perform to the best of my ability? 

43. Do I prioritize myself and my relationships just like I do my responsibilities at work?

44. Do I take the time to move my body regularly? 

45. Do I practice focusing my attention on the present moment or do I dwell on the past?

46. Am I bothered by society’s imperfections? 

47. Am I working towards achieving my dreams?

48. What are my expectations for myself during my 30s? 

49. Am I too hard on myself, often tracking my “failures”?

50. Am I uncomfortable with attention and public recognition?  

51. What are my goals for the next decade? 

52. Can I accept the changes that may alter my original path? 

53. What kind of person do I want to become? 

54. Am I my biggest cheerleader and supporter?

55. Do I love myself? 

56. Am I approaching my 30s excited for what’s to come? 

57. Do I allow other people to influence my decisions?

58. Do I feel a connection with myself as well as with others?

59. What’s something I used to wish for that I currently have? 

60. What’s one thing I can do today to make my 30s the time period when my dreams will come true?