50 Unordinary Questions to Kiss Writer's Block Good-Bye!

a quick note before you jump in...

These 50 questions are designed to shake up the way you think about an author's ideas. They're unordinary, unexpected, and a little playful - because thinking critically should be challenging and enjoyable. Whether you're analyzing an academic essay, an article, or a book, these questions will help you move beyond surface level observations and into the realm of deeper, more original insights.

Also, you can grab your FREE copy of 50 Unordinary Questions - along with a mini-workbook - to practice your critical and creative thinking skills at the bottom of this blog. You'll also find a link to my digital tutorial Quote Like A Grad: A Companion and Follow-Up to 50 Unordinary Questions teaching you how to effectively integrate and weave quotes into your writing - it's the perfect next step after pulling out your best ideas.

How to get the most out of these questions

• read through all the questions - then choose one or two from each section and record your answers in a notebook or journal

• go for thoughts. not answers - forget finding the "right" answer - there isn't one

  
  

• don't rush - choose a few questions that resonate with you, and take your time to reflect on them; these questions are meant to help you think in new ways, not "jump" to a quick answer

  
  

• mix it up - apply these questions to different types of texts - essay, opinion pieces, works of fiction, scholarly journals - anything you read!

  
  

• journal your thinking - write down your responses and then look for patterns in your thinking - also, you're more likely to tap into your creativity and open-up your mind to poking at new ideas in a personal notebook or reading journal, than you are on an "essay doc" that feels more formal

  
  

• make it personal - the best insights often come when you connect a text to your own personal experiences - so don't worry about keeping things formal or proper; remember, these questions are to inspire and spark curiosity - they don't have to end up in your essay

  
  

• include examples - let your creativity flow, but be sure to find and record a little piece of text to support each of your ideas; you want to be able to trace your creative thinking back to the text

  
  

• make language associations - when an image or idea is presented, think about language that's closely tied to it; for example, if you're asked to think about a photograph, think about words that come to mind when you think of photography (camera, snapshot, zoom in, resolution) and use that language to push your thinking in new directions

how the questions are organized

I've divided the questions into 5 categories: argument, style & tone, form & structure, evidence, and connection & revelation. I've focused on these specific sections to encourage you to see a text as complex and multi-layered, rather than just a bunch of words on a page to be understood. Each set of questions challenges you to think critically, creatively and personally. I wanted to make these questions not only help you dissect the text, but also connect it to your own experiences and unique perspective.

Questions 1-10: The Argument or Main Message

How strong, logical, or persuasive is the author's argument?

1. If this argument were a wooden bridge, what condition would it be in?  Would the wooden planks be strong and secure, worn and suspicious, or  missing and incomplete?

2. If you had to debate this author in a high-stakes argument, what’s the first  flaw you’d attack?

3. What’s the “heartbeat” of this argument—the one claim everything  depends on?

4. If this argument were a ceramic flower pot, would it be in one solid piece  or would it look like it had been dropped and glued back together with  noticeable cracks and chips? 

5. Does this argument sprint toward its point, take a scenic route, or wander aimlessly

6. Would this argument stand up in court? 

7. If this argument were presented as a photograph, would it be clear and  easy to see, a little blurry, or pretty hard to make out?

8. If you were going to put your name on this essay and have it published for  all your friends and family to see, what would need to change?

9. If this essay were a person at a party, would it be the guest who only likes to  listen to themselves and ignores what everyone else says, or the guest who  listens, participates in conversations, and is genuinely curious to learn about  new ideas?

10. If someone fully agreed with this argument, what other claims or ideas would they likely believe or consider valid?  

Questions 11-20: Style & Tone

How does the author's voice and word choice affect your understanding?

11. If this author were a painter, what two or three adjectives would best  describe their style? (e.g., bold? chaotic? minimalistic? realistic?  energetic?) How do these qualities affect the essay?

12. If this essay were a movie, what genre would it be? A drama? A thriller?  A documentary?

13. Imagine this argument being delivered as a speech. What kind of speaker  would the author be—passionate? dry? humorous? aggressive? personable?  arrogant? witty? pretentious?

14. Paints often have interesting names like Cloud White, Raindrops, A Little Bit  of Sugar. If you had to create a paint name for this essay, what would it be?

15. If you had to play a song in the background while this essay was read out  loud, what song would you choose?

16. If this author invited you to dinner, what would you expect the atmosphere  of the evening to be like? A lively debate? A formal lecture? Quiet and dull?  Silent and awkward?

17. If you walked into this author’s personal library, what kinds of books and  which authors would fill their shelves?

18. Is this writing like a tightrope walker (careful and balanced) or a  skateboarder (daring and unpredictable)?

19. If you were invited to meet this author for brunch, what topics and/or definitions would you want to brush up on to make sure you were able to  follow and engage in the conversation?

20. If you were in a book-buying Secret Santa and chose this author, what book  would you choose for your gift?

Questions 21-30: Form & Structure

How is the essay organized, and does it help or hurt the argument?

21. If this essay were a set of driving directions, would you arrive at your destination on time and in good spirits? Or would you arrive much past your  ETA (estimated time of arrival) and feel frustrated?

22. If the paragraphs were pieces of furniture in a room, do they feel well placed? Do they need to be rearranged to improve flow? Does one feel mismatched or crammed in?

23. Does the introduction “hook” you like a great first line in a novel, or does it  feel mechanical? How did this affect how you read the remainder of the  essay?

24. If each argument were a bedroom, who lives in each bedroom? messy  teenagers? clean-freak parents? squabbling siblings?

25. Is the conclusion satisfying, or does it feel like the author slammed on the brakes and moved on to his next chore?

26. If this essay were a blanket, would it be tightly woven and seamless, loosely  stitched with gaps, or heavy and difficult to fold?

27. If this essay were a car, would it be a nice, smooth ride or a stilted and  sputtery one?

28. If you were a director and the essay was the script you were handed to turn  into a movie, would you make any changes to the organization of the  material, or keep the sequencing of the material as is?

29. If this text were a jacket, would it be something you’d expect to find at a  high-end store, a basic retail store, a second-hand store, or a garage sale?

30. If you had to cut one paragraph without hurting the argument, which one  would it be?

Questions 31-39: Evidence

How does the author present and support their claims?

31. Does the language used by the author in each piece of evidence and  explanation have more in common with sand (hard to hold /not easy to  grasp), glass (easy to shatter), or steel (solid / firm)?

32. Imagine there are 4 buckets on a desk. The first one is filled with fact blocks,  the second with emotion blocks, and the third one with expert opinion blocks, and the last one with personal anecdote blocks. Does the author dip into each bucket  equally? If not, what is the impact of this unbalanced selection? If so, was this a smart decision?

33. If this evidence were food, is it fresh and nourishing, or does it feel processed  and artificial?

34. Imagine the essay as a Jenga tower that’s teetering and tottering. Which one  piece of evidence, if removed, would cause the Jenga tower to collapse?

35. If this essay were published in a newspaper, would it appear in a credible one or a trashy tabloid?

36. You’re a publisher and this author has been accused of providing misleading or unreliable evidence. Make a case to dismiss or accept their paper.

37. Does the evidence resemble more of a quilt—pieces of information tied  seamlessly together—or more like a patch that’s been ironed onto a backpack  that sits on the surface and hasn’t been woven into the analysis?

38. If each piece of evidence was a photograph, which one piece would you say  is the “most blurry” and in need of being photoshopped or retouched.

39. There’s always that one wobbly table in a coffee shop. Which piece of  evidence would most likely be given the “wobbly table” designation?

Questions 40-50: Personal Connection & Powerful Revelation

How do you connect with this essay?

40. If you only read the opening paragraph of the essay, would you do a Google  search to find and read the rest?

41. Create an Instagram username for the author based solely on their essay.

42. You’ve been accused of being narrow-minded. Use this essay to show how  that statement is completely ridiculous.

43. Imagine you’re presenting this essay at a university seminar and you want to  attract the right people. What details do you mention in the description to  make sure you get the right attendees?

44. You have to create a piece of art for your room using one quote from the  text. Which one do you choose?

45. You’re at Starbucks grabbing a drink and you run into the author. What do you say to strike up a conversation?

46. Does this essay reflect the author’s time, or could it have been written in  another era?

47. If this essay were a wine, is it likely to age well over time or rot and turn bad?

48. If this text were displayed in a museum or gallery, where would it be placed,  and what pieces of art would be in close proximity? What does this say about  the text’s themes, style, or cultural significance?

49. You’ve been tasked with using a piece of this essay in your graduation  speech. Which section do you choose?

50. You’re the editor of a magazine, and you need to choose a photo from your phone’s camera roll to feature alongside this essay. Which one do you pick?

I hope you found a handful of these questions helpful. Remember, the goal isn't to answer all of them. It's to find a few that push you to think about a text in a new way.

Want your own FREE copy of 50 Unordinary Questions to Kiss Writer's Block Good-Bye! Click on the link below.

Also, don't forget to pick up your 20 minute intensive tutorial, Quote Like A Grad: A Companion & Follow-Up to 50 Unordinary Questions.

This is the tutorial that gives you easy-to-apply strategies and helpful tips to weave an author's words into your writing seamlessly - the skill you'll need to perfect if you want your writing to sound tight and polished.