65 Of The Hardest Questions To Answer

When was the last time someone’s question left you speechless or fumbling for words?

Difficult questions have a way of throwing you off balance.

The best way to prepare for them is to consider some of the hardest questions and answer them for yourself.

To that end, welcome to our collection of 65 hard questions to answer. Start with one you’ve had trouble answering in the past.

The next time you hear it, you’ll have an answer ready.

65 of the Hardest Questions to Answer

To make the best use of these tough questions to answer, choose one each week (or each day, if you’re ambitious), and make it your goal to answer it thoughtfully and completely.

1. How do you define success, at least for yourself? Have you reached it?

2. Is there anything you know you should let go of, but you haven’t yet? Why?

3. If you knew this was your last day, would you do the same things you’re doing?

4. What kind of legacy do you want to leave behind? What steps have you taken to create it?

5. If the person who’s hurt you the most showed up at your door, what would you say to them?

6. If you don’t have what you want, what do you have to lose by going after it?

7. What does it mean to be good with money? Are you?

woman thinking while on a balcony hardest questions to answer

8. Is there anything your job gives you besides money? Is there anything missing?

9. What’s the biggest thing you want to accomplish in the next 12 months?

10. What responsibilities are you avoiding right now or which are you most tempted to avoid?

11. When it comes to your closest relationships, what do you struggle with the most?

12. What mistake do you keep making, and why do you keep making it? What has it cost you?

13. Name something you consider worse than dying. What makes it worse?

14. What’s something you wouldn’t want to die without doing? Why?

15. How would you define the word “American”? How do you define “unAmerican?”

16. If you had three wishes, what would you wish for, and why?

17. What fears are connected to your pursuit of success? How have you faced them?

18. What areas in your life are most in need of improvement?

19. How have your goals or priorities changed over the last decade?

20. What are your biggest regrets when you think over the past five years?

21. What realization has changed your life or your perspective over the past five years?

22. What is the biggest cause of stress for you right now? What worries you most?

23. Are you too hard on yourself or not hard enough?

24. What do you look forward to the most right now? Why?

25. What do you want to be remembered for when you die?

26. What dream (or dreams) have you given up on? Why?

27. What dream (or dreams) have you held onto the longest?

28. Is there anyone you’re jealous of? If so, why?

29. How are you contributing to the world? Or how do you want to contribute?

30. What is your default behavior when someone turns on you? What has it cost you?

31. When you look at the person you are right now, what are you proudest of?

32. What about yourself do you still need to work on every day? How do you work on it?

33. What have you learned that you might not have learned if you hadn’t suffered?

34. What five words would you use to describe yourself?


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35. What would you do if fear wasn’t an issue and you couldn’t fail?

36. What would you give to not feel the way you feel right now?

37. If you could go back and delete an email before sending it, would you?

38. If you could change one thing about your government, what would it be?

39. Have you ever regretted publishing something? If so, why?

40. Do you put political stickers on your car? Why or why not?

41. When was the last time you did something outside your comfort zone?

42. What are you risking right now by not stepping outside your comfort zone?

43. Are there any relationships you’d like to improve or repair? Are any beyond help?

44. Have you alienated people only to regret having done so?

45. Do you forgive easily when someone apologizes for hurting or offending you?

46. Have you forgiven someone who refused to apologize for hurting you?

woman holding her face with both her hands hardest questions to answer

47. Has someone in your life died before you could reconcile with them (or they with you)?

48. Have you felt the need to pretend you don’t need help? If so, why?

49. When have you felt as though you could finally let someone take care of you?

50. Why do you think so many people grow up feeling the need to be “low maintenance”?

51. Have you felt this way yourself? And when have you gotten a break from it?

52. What are the most amazing things you’ve achieved this past three years?

53. What goal continues to elude you? What action are you taking to reach it?

54. What characteristics have you struggled to develop in yourself? (confidence? tenacity? straightforwardness? courage? generosity?)

55. In what areas of your life and work do you feel most vulnerable? Why?

56. Do you make a point of expressing your gratitude and appreciation for others?

57. Do you easily become frustrated or irritated when things don’t go your way?

58. Would it serve you well to trust people more than you do,  or to be more careful of whom you trust?

59. Do you think people ask too much of you — or too little? Why do you think they do?

60. When was the last time you had a good laugh? What was it about?

61. What do you most often choose to ignore? Why do you ignore it?

62. If someone were to follow you around for a week, would your values and priorities be obvious to them? Would they match the ones you identify for yourself?

63. Have you ever abandoned a social media channel, not because of opposition to your views but because that opposition came from family?

64. Have you ever experienced the same unkind treatment you dished out to someone else in the past?

65. What is karma to you? Is it simply about justice, or do you see it as a deeply personal force that teaches us what we need to learn?

How will you use these difficult questions?

Now that you’ve looked through 65 of the hardest questions to answer, which one have you chosen for today?

Maybe you already have an idea of your answer, but take a few minutes (at least) to write down whatever comes to mind.

Don’t critique your answer before you’ve fully expressed it.

None of us has it all figured out. Asking these hard questions and being honest with your answers takes courage and a determination to grow.

Good thing you have both.

If you find difficult questions have a way of throwing you off balance, prepare yourself with these hard questions to answer so you can be ready.

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