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Categories:
Getting to Know You
Creative Expression
Emotional Insight
Future Aspirations
Past Experiences
Fun and Humor
Team Building
Fantasy and Imagination
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1. Getting to Know You 🤨
1. What is your favorite hobby.
2. Draw your dream job.
3. Sketch a portrait of your family.
4. What's your favorite animal.
5. Where do you want to visit next?
6. Favorite food?
7. Draw your hometown.
8. Draw your self portrait
9. Favorite season?
10. Draw a favorite childhood memory.
11. What are you passionate about?
12. How are you feeling right now?
13. Share your favorite plant or flower.
14. What are you reading or watching?
15. Draw a formative experience in your life
16. What does your perfect day look like?
17. What are you grateful for?
18. What do you need most right now?
19. Favorite way or place to relax?
20. What is your superpower?
2. Creative Expression 🎨
21. Make a new invention you think the world needs.
22. Create a new mythical creature.
23. Sketch an alien
24. Draw a dream you had.
25. What does your ideal home looks like?
26. Make a mashup of two animals.
27. What fantasy world would you love to live in?
28. What does the future look like?
29. What superpower would you hate to have?
30. Draw something ugly
31. Recreate a piece of art you love.
32. What is going to save the world?
33. Create a new kind of plant or tree.
34. What does magic look like?
35. How will we get around in the future?
36. Draw an undiscovered dinosaur.
37. Illustrate a scene from your ideal vacation.
38. Draw a portal to another universe
39. What does happiness look like?
40. Create your personal flag.
3. Emotional Insight 😍
41. What makes you happy.
42. What makes you sad.
43. What excites you?
44. What does anxiety look like?
45. What does wellbeing look like?
46. Draw a situation where you felt proud.
47. Draw a time you felt scared.
48. What was the last thing that surprised you?
49. What does fear look like?
50. What do you want to let go of?
51. What is your biggest fear.
52. What does love looks like to you.
53. What gives you joy?
54. What are you proud of?
55. How do you feel about your life, overall?
56. Draw a personal achievement.
57. What were you scared to do at first?
58. Share a happy memory with family.
59. Where do you feel at home?
60. What does peace look like (without drawing a ☮)
4. Future Aspirations 🔮
61. Where do you see yourself in 5 years.
62. What do you want to let go of?.
63. Share a goal you have
64. What is your dream?
65. What world do you want to leave behind?
66. Draw an invention you’d like to create.
67. When you think about the future, what does it look like?
68. What are you most excited about?
69. What do you want to let go of?
70. What will we eat in 100 years?
71. Who are you becoming?
72. What does the future of ______ look like?
73. What is going to rock the world in the next 30 years?
74. What does your future house look like?
75. Illustrate a future adventure you’d like to have.
76. If you're successful in life, how will the world change?
77. Depict a change you want to make in the world.
78. Illustrate a future project you want to start.
79. What does nobody see coming in the future?
80. Sketch a future event you’re looking forward to.
5. Past Experiences 👶
81. Favorite trip you've been on
82. How was your childhood, overall.
83. Sketch a favorite toy from childhood.
84. What was your first memory?
85. Draw the best meal you ever had.
86. What was the best gift you've ever received.
87. Who was your best friend growing up?
88. Draw a significant event in your life.
89. What was your first job.
90. How do you feel about your childhood overall?
91. Draw a favorite childhood game.
92. Summarize your childhood in one image
93. What did you want to be as a kid?
94. Draw a significant achievement from your past.
95. Draw your family
96. What was a formative experience from your childhood?
97. You go back to 10 yrs old knowing what you know now, what do you do differently?
98. Who was your favorite teacher?
99. How did you feel during your first kiss?
100. When were you at your best?
6. Fun and Humor 😂
101. Draw the ugliest thing you can think of.
102. Draw someone around you without looking down
103. What's your favorite animal (wrong answers only)
104. Draw your favorite joke or pun.
105. Draw a caricature of yourself.
106. Weirdest food combination you've ever had
107. If you could be any cartoon character, who?
108. Draw a ridiculous invention.
109. What makes you LOL?
110. Draw the strangest dream you've ever had
111. If you had to eat a crayon, what color would you choose?
112. What is the craziest thing you've ever done?
113. What is your favorite word?
114. Create a comic strip.
115. If you could only use one emoji for the rest of your life, what would it be?
116. Create your own version of a famous artwork.
117. What fashion statement should definitely not catch on?
118. Draw an angry banana
119. Draw your favorite food eating YOU.
120. What do you do for fun?
7. Team Building 👏
121. Design a new logo for your team.
122. Create a team mascot.
123. What does your ideal workspace look like?
124. What does success look like?
125. How do you feel showing up to work?
126. What is your team’s biggest achievement.
127. What are we working towards?
128. What do you need most right now?
129. What is your superpower?
130. What is our teams superpower?
131. Depict your role in the team.
132. What do you want to celebrate right now?
133. What should we start, stop, and do differently as a team?
134. How do you feel about the last week, month, quarter, year?
135. What gets you going in the morning?
136. If our company was a mode of transportation, what would it be?
137. What are you passionate about outside of work?
138. What tradition or ritual should we start?
139. What is your team’s vision for the future.
140. What does collaboration on our team look like?
8. Fantasy and Imagination 🐲
141. Draw a dragon.
142. What is your dream house?
143. What do faeries look like?
144. Draw a pyramid and what it's used for.
145. What is your wildest dream?
146. Invent a magical creature.
147. Sketch a fantasy landscape.
148. What's really going on in space?
149. Draw your favorite alien.
150. Draw a mystical artifact.
151. Draw your least favorite alien.
152. What is waiting to be discovered?
153. Draw a spaceship.
154. Sketch an underwater kingdom.
155. Depict a fantasy battle.
156. Draw a hidden treasure.
157. What does a ghost look like?
158. Draw God.
159. What does your consciousness look like?
160. What does death look like?
161. Draw a talking animal.
162. Depict an enchanted garden with plants never seen before
163. What does the city of the future look like?
164. Draw a mystical mountain.
165. Sketch a wizard’s beard that's home to animals.
166. Draw a mermaid in her unnatural environment
167. Draw a magical storm.
168. Draw yourself drawing yourself.
169. Make random dots, then connect them into something
170. Illustrate a scene from a mythical realm.
171. What cat-sized animal would you love as a pet?
172. What were you doing before you were born?
173. Depict a legendary creature.
174. What do you believe in that you've never seen?
175. Draw something that has never been drawn before.
176. Depict a mythical beast.
177. Sketch a magical forest elf.
178. Where are you on your hero's journey?
179. Invent a fantasy weapon and share what it does.
180. What do you hope for?
181. Draw a portal to another dimension.
182. What epic adventure is waiting for you?
183. Draw a map to the treasure you seek.
184. What superpower would you hate to have
185. Invent a silly disease and draw someone with it.
186. Illustrate a magical transformation.
187. Turn yourself into a mythical hero.
188. What element would you most want to control?
189. Draw a sunset on another planet
190. Draw another planet you'd want to visit.
191. What still needs to be invented?
192. What would change the world?
193. Sketch a magical creature’s lair.
194. Draw your favorite dwarf.
195. Illustrate a scene from a story
196. What is hiding inside the Earth?
197. Sketch a tremendous tree.
198. Depict a legendary treasure.
199. Illustrate a scene from a fantasy epic.
200. What quest are you on?
201. Give an ordinary object magical powers
202. What does dark matter look like?
203. How will we travel faster than light?
204. What is inside a black hole?
205. Where should humans move to next?
206. What does the world need most right now?
207. You're president of the universe, what do you do?
208. Draw the universe
209. What do you like playing with in your imagination?
210. Create a shape that has never been seen.
211. Name a new color
212. What epic quest are you on?
213. Where does your magic come from?
214. How do you feel about your feelings?
215. Invent something that would only benefit you
216. Draw the path to heaven or hell.
217. What shape is water?
218. If you weren't human shaped, what shape would you want to be
219. Create your own personal flag
220. What color is your aura?
221. What is a defining moment from your future?
222. I AM ______ (draw all that applies)
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These questions are designed to inspire creativity and connection. The drawings are a jumping off point for a deeper, richer and funner conversation. Enjoy!
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