I started drawing by hand in a group challenge back in May 2022. Outside of mandatory art classes in school, I had no other experience.
Now with the rise of AI, and more and more images being machine-generated. I tried it. Even used it for a few experimental projects.
But ultimately, I felt locked out of my own creative process. The AI images didn't feel right.
That's why I started to draw by hand. To carve out my own artistic style, just like I've done with writing.
After several starts and stops, I recommitted to this drawing challenge in April 2025.
I'm using Proko's excellent "Drawing Basics" course to learn. I also have a few Japanese art books I picked up when I was living in Okinawa.
If you've always wanted to draw, Proko's course is an awesome starting point. Use the button below to browse their courses!
I became an affiliate for Proko because I believe in their courses. So if you buy through this button, I might get some compensation.
Day 49 - "Critique - Organizing Line Weight - 32% complete"

Day 48 - "Demo - Depth and Form Line Weight - 100% COMPLETE!"

Keith’s Clips — Sketch

Day 47 - "Demo - Depth and Form Line Weight - 76% complete"

Day 46 - "Demo - Depth and Form Line Weight - 21% complete"

Day 46 - "Demo - Different Ways to Use Line Weight - 100% COMPLETE!"

Day 45 - "Demo - Light and Shadow Line Weight - 100% COMPLETE!"

Day 44 - "Demo - Light and Shadow Line Weight - 73% complete"

Day 43 - "Demo - Light and Shadow Line Weight"

Day 42 - "Demo - Hierarchy of Importance Line Weight"

Day 41 - "Project - Organizing Line Weight"


Day 40 - "Project - Organizing Line Weight"

First Drawing Video (Short)
First Drawing Video (Full Video)
Day 39 - Begin - "Project - Organizing Line Weight"

Day 39 - "How To Draw With Line Weight" - 100% COMPLETE!
Day 39 - "6 Habits For Good Line Quality" - 100% COMPLETE!
Day 38 - "Warmups to Improve Line Quality" - 100% COMPLETE!




Day 37 - "Critique - Learning to Sketch From Imagination" - 100% COMPLETE!

Day 36 - "Critique - Learning to Sketch From Imagination" - 82% COMPLETE

Day 36 - "Critique - Learning to Sketch From Observation" - 100% COMPLETE!


Day 35 - "Critique - Learning to Sketch From Observation" - 79% COMPLETE

Day 34 - "Critique - Learning to Sketch From Observation" - 42% COMPLETE

Day 33 - "Critique - Learning to Sketch From Observation" - 16% COMPLETE

Day 32 - "Demo - Learning to Sketch From Imagination" - 100% COMPLETE!


Day 31 - "Demo - Learning to Sketch From Imagination" - 68% COMPLETE


Day 31 - "Demo - Learning to Sketch From Observation" - 100% COMPLETE

Day 30 - "Demo - Learning to Sketch From Observation" - 71% COMPLETE

Day 29 - "Demo - Learning to Sketch From Observation"


Day 28 - "Demo - Learning to Sketch From Observation"

Day 27 - "2 Week Drawing Challenge: Day 12 - Project - Learning to Sketch From Imagination"

Day 26 - "2 Week Drawing Challenge: Day 11 - Project - Learning to Sketch From Imagination"


Day 25 - "2 Week Drawing Challenge: Day 10 - Project - Learning to Sketch From Observation"


Day 25 - "2 Week Drawing Challenge" - : Day 10 - Project - Learning to Sketch From Observation"



Day 24 - "2 Week Drawing Challenge: Day 9 - Project - Learning to Sketch From Observation"





Day 24 - "Critique - Simplify to C-S-I" 100% COMPLETE!
Day 24 - "How to Draw Confident Lines - The Tapered Stroke" 100% COMPLETE!
Day 24 - "Searching Lines" 100% COMPLETE!
Day 23 - "2 Week Drawing Challenge: Day 8 - Screen Background C-S-I"


Day 22 - "2 Week Drawing Challenge: Day 7 - Boots Simplification"

Day 22 - "2 Week Drawing Challenge: Day 7 - Camel Simplification"

Day 22 - "2 Week Drawing Challenge: Day 7 - Skull Captain Simplification"

Day 21 - "2 Week Drawing Challenge: Day 6 - Snail Simplification"

Day 21 - "2 Week Drawing Challenge: Day 6 - Boots Simplification"

Day 20 - "2 Week Drawing Challenge: Day 5"

Day 19 - "2 Week Drawing Challenge: Day 4"

Day 19 - First sketchbook review video
Day 18 - "2 Week Drawing Challenge: Day 3"



Day 17 - "2 Week Drawing Challenge: Day 2"

Day 16 - "2 Week Drawing Challenge: Day 1"


Day 15 - "Project - Simplify to CSI": 100% COMPLETE!




Day 14 - "Warmup Mushrooms": 100% COMPLETE!

"Intro to Lines": COMPLETE!
"Project - Simplify to CSI" (Boots): 13% COMPLETE

Day 13 - "Critique" - Simplify Portrait From Observation": 100% COMPLETE!
Day 12 - "Critique" - Simplify Portrait From Observation": 65% COMPLETE
Day 11 - "Critique" - Simplify Portrait From Observation": 34% COMPLETE
Day 10 - "Critique - Simplify Pear From Observation": 100% COMPLETE!
Day 10 - "Critique" - Simplify Portrait From Observation": 17% COMPLETE
Day 9 - "Critique - Simplify Pear From Observation": 42% COMPLETE
Day 8 - "Critique - Simplify Pear From Observation": 24% COMPLETE
Day 7 "Demo Portrait" - 100% COMPLETE!

Day 7 "Demo Portrait" - 82% - COMPLETE

Day 7 "Demo Portrait" - 73% COMPLETE

Day 6 "Demo Portrait" - 61% COMPLETE

Day 6 "Demo Portrait" - 51% COMPLETE

Day 5 "Demo Pear" - 100% COMPLETE!

"Demo - Simplify Portrait" - 33% COMPLETE

Day 4 - "Demo Pear" - 40% COMPLETE

Day 3 - "Demo Pear" - 36% COMPLETE
Redrawing the pear while following along with the video

Day 2 - "Pear"

Day 1 - "Chase Well"

Day #48: Charcoal study focusing on proportion & minimal tone.
Behind the sketch: Did half of this one with my right (dominant) hand and the other half with my left.
The line lay‑in was rough and wasn't looking very promising, but careful charcoal edges pulled the form together in the end.
First try with a charcoal pencil while exploring new grip styles.