75 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 75 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.

What Is The Hardest Question Ever?

Maybe that question itself is the hardest because there are so many difficult questions to answer.

Many people think the question, “What is truth?” is the hardest because the truth is often difficult to quantify. Science claims that truth is based on facts and reality, but many philosophers disagree and think the truth is subjective.

We think one of the toughest is, “Why do I exist?” You may have your own ideas or reasons, but finding a universal answer to this question is daunting.

What's The Hardest Question to Ask?

The most challenging question to ask is the one that may cause you or another person pain, disappointment, fear, or some other unpleasant emotion.

Think about these questions:

  • Is this disease going to kill me?
  • Is there really a Santa Claus?
  • Do you love me?
  • Where were you last night?

The truth may set you free, but it can be pretty painful when you first hear it.

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?

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?

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?

10 of the Hardest Questions About Life

Have you ever been asked a question that made you stop and think? Questions that make you ponder about your life, relationships, and values? 

Here are ten questions that will make you reflect and re-evaluate your life choices. 

66. What would you do if you only had one week or one month to live?

Knowing your time is limited can be a frightening thought, but it can also be a powerful motivator to make the most of each day. This question encourages you to reflect on what matters to you in life and how you want to spend your time before it runs out.

67. How can you make a lasting difference in the world?

Everyone wants to make a difference, but it can be hard to know how. Thinking about what matters most to you and how you can impact society, those around you, and even the world at large can help you identify ways to make a lasting difference.

68. How far are you willing to go to achieve your goals?  

Have you ever considered what sacrifices you may have to make to achieve your goals? Answering this question will help you contemplate the price of success and reflect on what you’re willing (and not willing) to do to reach your dreams.

69. What has been the biggest lesson that life has taught you so far? And how have you applied it in your situation?

Life is full of lessons, from recognizing the power of love and friendship to appreciating the small moments. Learning how to apply these lessons to our own lives can help us become better individuals.

70. How will you know when it's time to let go of something that isn't working for you?

Whether it's a relationship, a job, or a friendship, it can be hard to know when it's time to cut the cord. Learning to recognize the signs of a situation that has become unhealthy or unproductive is key to knowing when it’s time to move on and make a change.

71. What is your biggest fear regarding your loved ones?

This question can help you identify and acknowledge your fears for the people dear to you so that you can better be prepared to face those fears in times of crisis. 

Whether it's fear of death, illness, or even the loss of a relationship, it's essential to acknowledge and accept those fears so that you can be in a better place emotionally.

72. How would you handle conflict between two opposing views?

Conflict is inevitable, and arguments are a part of life. However, how we navigate them can make all the difference. Being able to come to a compromise that suits both parties and respects different points of view is an invaluable skill we should all have.

73. Are there any problems too big for you to tackle? If so, which problems are these, and why do you think they are too big for you?

No problem is too big to tackle, but some may require more resources than we have. Acknowledging our own limitations and enlisting help is often the best way to approach a difficult challenge.

74. What would you do if money wasn't an issue? 

We all have financial constraints, but what if money wasn't an issue? This question can help you think more broadly and explore possibilities that would otherwise be unreachable.

It encourages you to dream bigger and consider different ways to achieve fulfillment.

75. What do you struggle with the most when seeking happiness?

Finding true and lasting happiness can be challenging, especially when our lives are filled with stress, sudden unwanted changes, and uncertainty.

Understanding what blocks us from being truly happy can help us develop strategies to better manage our emotions, thoughts, and behaviors.

How to Use These Difficult Questions to Answer

While it's essential to take the time to think through these difficult questions, it's also important to know how and when to use them. Below are two tips to help you get the most out of your answers.

  • Use them as a life guide: While being honest with yourself in answering these difficult questions is important, don't forget to use them as a guide for making decisions and setting goals. Consider how the answers might help inform important choices or the plans you make throughout your life in the future.
  • Use them as a conversation starting point: These questions can be great conversation starters for those close to you. Ask your friends, family, or partner the same questions and compare notes on the answers. It's often enlightening to discuss complex topics with others and gain a different perspective that we may not have considered on our own.
  • Use them as journaling prompts: If writing helps you better process your thoughts, use these questions as journal prompts. Choose questions that relate to a challenge or goal in your life, or follow the questions sequentially and answer one a day.

How will you use these difficult questions?

Now that you’ve looked through 75 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.