100 Questions To Ask Everyone On Earth

Ideas for provoking conversation that really matters

The older I get, the less patience I have for dull questions. I want to get to know you as deeply and as quickly as possible. I want to see you think. And I want you to make me think in return.

The antithesis of this is smalltalk, and we’re all guilty of it. Smalltalk is a shallow exchange, low in curiosity, in which no substantive information changes hands despite both parties feigning satisfaction with nods and empty laughter.

Of course, smalltalk has its place. We could call it a tentative process of sizing-up, when we gauge initial impressions from the safety of our own isolation. Is this individual safe to be around, what’s their game, are they interesting, similar or strange, fun, friendly or creepy? How well do I want to know this person?

Photo by Simon Hurry on Unsplash

But real conversation only begins when we step beyond this fear-based, emotive reasoning, engage higher areas of our brain and allow ourselves to seek answers to more complex questions.

That’s the inspiration for this listicle. So the following 100 questions are in fact 100 ideas for progressing beyond smalltalk.

But first, a few words about fear, bravery and the realm of ideas.

The territory of the self

For the travel writer Colin Thubron, the greatest fear he admits to when travelling is that he will feel nothing. This is a man who has spent a lifetime navigating physical danger, moving alone through areas of the world scarred by division, upheaval and mistrust, encountering corrupt officials, thieves and worse (and a whole load of good people too). But as a writer, and as a curious lover of humanity, his greatest fear is that the experience of travel will yield no explanation, no revelation, no inkling of what may be beneath the surface.

In his 2006 book Shadow of the Silk Road, this fear is expressed in one of the imagined conversations which Thubron finds himself having with an ancient Sogdian trader:

He: What are you going for?

I [piously]: For understanding. To dispel fear. What did you go for?

He: To trade in indigo and salt from Khotan. Why should your understanding dispel fear, idiot?

I [worried]: It’s true, it may confirm it.

He: Are you, then, afraid?

I: I’m afraid of nothing happening, of experiencing nothing. That is what the modern traveller fears (forgive me). Emptiness. Then you hear only yourself.

It’s a conversation that reveals Thubron’s anxiety as an outsider, alert to the terror of discovering that, despite everything, he is alone. Of course, we happily forget that every one of us is in some ways an outsider, isolated within the confines of our own understanding. To explore is to come to terms with not only what we share in common, but also what differentiates us.¹

I bring this up because a similar trepidation lingers over the conversations we have with strangers. “If only I knew something interesting about this person,” we silently think to ourselves. “Something to pique my curiosity, a lifeline to grab hold of, to ask more about...” Often an inkling of interest might arise in our thoughts but we stumble over the tripwires of some form of etiquette, preventing our questioning from going too deep, causing offence or betraying a lack of self-control. A chain of questions isn’t a conversation – it’s an interrogation – so we tiptoe around them, not realising that it only takes a single thoughtful question to open a galaxy of conversation. And so, with the absence of insight, trapped in the doldrums of smalltalk, we learn nothing substantive and we feel nothing.

In the four books by Thubron that I have read, I don’t believe his fear of empty experience has ever materialised. His curiosity and openness always reveal some form of insight – either into the world he is travelling through, or into himself. Even an encounter with a barren land, like an apparently barren mind, can yield something revelatory. The nothingness we fear, that Thubron fears, retreats from the light of a sensitive question. Brave curiosity therefore, rather than cautious avoidance, can prevent what we fear from coming into being.

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Sidenote: I’m still feeling my way with this newsletter, unsure about exactly what I should be writing about, and for who, so I promise I’ll take any thoughtful feedback (positive or negative) constructively. I periodically rewrite my ‘About’ page as my motivations evolve, but you can read its latest incarnation here 👇

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Great questions explore ideas

Mundane talk fails to progress beyond highly specific questions. The answer is usually short and bounded – a person, a place or an event – rather than a story, an explanation or, better yet, an idea. The sooner a conversation moves towards the realm of ideas, the sooner it becomes interesting.²

Find someone who is as fired-up as you are about the potential for what might be, and you’ll have some of the best conversation of your life.

Ironically, deeper questions also tend to be less intrusive. If you’ve ever seen a podcast guest suddenly open up about something personal which they haven’t described before, it’s usually because the host is prompting with questions that explore the ideas or motivations behind a sensitive event, rather than the event itself. We’re more willing to open up to someone who shows genuine interest in the inner fabric of who we are.

You can can make sure you’re pursuing genuine insight by tweaking the specificity of a question. It’s dialled correctly if a good answer is unique to that individual, but doesn’t reveal concrete or sensitive information about them. “Where do you live?” is a smalltalk starter because no unique information is revealed (many different people could live in the same area) and we learn nothing about why the person lives there. By contrast, “What do you like most about where you live?” would (mark you out as being quite weird but) invite a much more unique, interesting response.

Similarly, “Do you trust yourself?” is potentially too vague to achieve a revealing answer. I might trust myself to brush my teeth before bed, but not to resist the urge to buy too much stock when my favourite investment is suddenly making moves. By dialling up the specificity, we can arrive at a more thought-provoking question: “Under what circumstances do you trust yourself the most/least?”

Notice also that Thubron’s Sogdian trader, quoted above, prods him about his purpose, motivation and fears, rather than the concrete facts of his journey. (This dimension characterises much of Thubron’s travel writing – I’m a fan.)

Thoughts and dreams, committed to wood, huddle on a footbridge near a floating market in Bangkok. (The water beneath is thick with lugubrious carp.) Despite feeling unitary, we are each a composite of selves – how else could we ask questions of ourselves and not already know the answers?

So here’s my list. I won’t pretend I have the guts to drop these questions into every casual conversation. They’re just too weird, and I’m too cowardly. But I aspire to be someone who would. Anyway, perhaps these types of questions are better directed inwardly first of all. Like Thubron, we can learn to understand ourselves better when we perceive ourselves through the eyes of another.

100 questions, ideas, or conversations to explore

1. What is the weakest argument in favour of your least popular opinion?

2. What is the strongest argument against your most mainstream opinion?

3. What conviction have you never questioned?

4. What have you achieved that wasn’t worth the sacrifice?

5. How does your life now compare with what you thought it would be like?

6. What’s holding you back?

7. What makes you cry unexpectedly? Do you know why?

8. What does home mean to you?

9. What’s the biggest threat to your community?

10. What could the world learn from your community?

11. What could I learn from you?

12. How readily do you reach out for help?

13. What do you need more than money, and what’s stopping you from having it?

14. How readily do you discount your addictions?

15. What kinds of crisis are you most/least prepared for?

16. Are you working towards peace, or victory?

17. What law would you change, and how?

18. Would you rather be more privileged than you are?

19. What would you destroy, if you could get away with it?

20. What do you look forward to?

21. What does wealth mean to you?

22. What does freedom mean to you?

23. What does solace mean to you?

24. Are you soothed by silence, or unsettled?

25. Where do you feel like an insider?

26. What would your ideal week look like?

27. What are you reading, and why?

28. What are you not getting around to reading, and why?

29. Would you prefer to be good at impulse control, or free from difficult impulses?

30. Would you like more people to be more like you?

31. What qualities do you admire most in other people?

32. Are you as playful as the people you admire?

33. How strategic are you?

34. Do you have an over-arching purpose to your life?

35. Would you live forever if you could?

36. If you could recreate the institution of marriage, what would it look like?

37. What one thing would you like your great-grandchildren to know about you?

38. In what ways do you think you’re different from the norm?

39. What is your most innate aptitude?

40. To what extent have you capitalised on it?

41. Do you look forward to retirement?

42. Are you more concerned with causing joy or alleviating suffering?

43. Have you ever ended a friendship? How?

44. When was the last time you lost your temper?

45. How do you define your identity?

46. Could I tell, from looking at your living space, whether your preoccupations lie mainly in the future or the past?

47. In what ways do you tend to be similar/different from your friends?

48. Are you an introvert or an extrovert?

49. Do you prefer the company of introverts or extroverts?

50. What kind of trouble are you most likely to cause?

51. Would you rather have fame or power?

52. Freedom or security?

53. Would you rather be safe or strong?

54. What do you fear most?

55. Do you have a dream? (When did you stop dreaming?)

56. Do you plan to achieve your dream?

57. Do you think you will die in the way you would like to die?

58. Does anyone have a better idea of your strengths/weaknesses than you do yourself?

59. What would you never sacrifice for anything?

60. How has your outlook changed over the last decade?

61. How would you spend your first million? And your second?

62. Do you believe you’ll ever be wealthy?

63. In which areas of life are you most/least tolerant of risk?

64. What’s the most stupid thing you don’t regret doing?

65. Would you prefer more space, or less stuff?

66. What are you most likely to be petty about?

67. Under what circumstances do you trust yourself the most/least?

68. How much authority would you trust yourself to have?

69. How much authority would you trust your closest friend to have?

70. Do you have enough friends?

71. Do you have close-enough friends?

72. What’s the best/worst thing about you?

73. What annoys you most about me?

74. Do you find yourself solving big-picture problems or small ones?

75. When you witness poverty/wealth, what do you feel?

76. How would power change you?

77. Would you rather be powerful or admired?

78. What are you learning at the moment?

79. Do you need anyone’s validation more than your own?

80. What is the most enduring thing you have created?

81. What’s the most beautiful thing you’ve seen?

82. What captivates you more easily: natural beauty, artistic beauty or abstract beauty?

83. How often do you feel the intimation of something transcendent?

84. Do you seek beauty? Do you make sacrifices to bring beauty into your life?

85. How realistic is your to-do list for today?

86. How much influence do you have over the types of problems that preoccupy you the most?

87. Would losing your map spoil your holiday?

88. How varied are the conversations that interest you?

89. How varied are the conversations you have?

90. Do you feel your age?

91. What do you think is the ideal age to be?

92. How much energy do you have left?

93. Are you having enough fun?

94. Do you have enough peace?

95. Do you see more potential in the child you were, or the adult you’ve become?

96. Do you prefer answering questions or asking them?

97. On a scale of 1 to 10, how honest are you being with me?

98. What would you like to be asked?

99. What do you want to ask me?

100. Are you ok?

101. (Whoops.) Can we help each other?

Final thoughts

Please use, abuse, share, modify – but don’t just copy verbatim, because more important than any one question is the spirit of questioning. Like a meaningful answer, a meaningful question derives from a train of thought, a line of curiosity, and opens onto a two-way window of understanding. Both questions and answers are revelatory; your 100 questions would reveal something about you, just as these questions have revealed something about me.

I’m learning to practice asking, to practice stripping away the layers of selfhood and social norms that stand in the way of constructive, direct, compassionate discovery. It’s bloody hard, but I believe it’s a path towards more meaningful relationships.

If you can master this, you’re better at it than I am.

PS. No, I don’t have 100 good answers.

1. Thubron expressed a similar idea in this BBC interview, back in 1989 (skip to 5:50).

2. An exception to this rule is talk between enthusiasts of a particular topic. If you’re mad about spoons, you could have a deeply rewarding conversation with a spoon expert for hours without needing to consider any of this wishy-washy stuff about ‘ideas’. And maybe… maybe that’s an evolutionary benefit of the (predominantly male) propensity to develop long-term fanaticisms for highly-specific topics of questionable utility; it’s a vehicle for bonding and team building, regardless of a person’s ability to reveal meaningful self-insight through conversation. Maybe its origins are older than our ability to do so.