If your usual subjects are starting to feel too easy, these challenging drawing ideas are designed to make you slow down, observe more carefully, and solve harder visual problems.
I don’t think a difficult drawing needs to mean producing something hyper-realistic. Some of the best challenges come from overlapping forms, movement, unusual viewpoints, changing light, reflections, or simply taking away one of the habits I normally rely on.
My own approach is observational. I look for the largest relationships of light, shadow, shape, and movement before working into smaller information. The ideas below use that same approach but deliberately make the visual problem harder.
Challenging Drawing Ideas at a Glance
| Challenge | What it makes you practice |
|---|---|
| Cluttered desk | Overlaps and composition |
| Moving person | Gesture and speed |
| White pencil on black paper | Light instead of shadow |
| Hands | Proportion and foreshortening |
| Glass and reflections | Value and distortion |
| Complex street scene | Perspective and simplification |
| Memory drawing | Visual memory |
| Non-dominant hand | Observation without muscle memory |
1. Draw a Cluttered Desk
A single mug is fairly easy to isolate. A mug surrounded by notebooks, cables, pens, glasses, paper, and other objects becomes a much more complicated drawing problem.
I don’t try to solve every object separately. I squint at the scene and look first for the largest connected shadow shapes.
That helps turn visual chaos into a few manageable masses before I start separating individual objects.
2. Draw a Person Who Is Moving
Moving people don’t give me time to polish every proportion.
That makes them useful for practicing gesture, posture, weight, and the overall direction of the figure.
You can draw from life, pause a video at unpredictable moments, or sketch people from a scene where the poses don’t feel staged.
For more on capturing that energy, see my guide to drawing movement.
3. Draw With White Pencil on Black Paper
Black paper reverses the way I normally think.
Instead of adding darker marks to describe shadow, I have to identify where light strikes the subject and build outward from those illuminated areas.
Try a face, hand, shell, animal, folded fabric, or another subject with obvious directional light.
I cover the process separately in how to draw on black paper.
4. Draw Your Hand in an Awkward Position
Hands become significantly harder when fingers overlap or point toward the viewer.
Rather than choosing a flat open-hand pose, curl the fingers, grip an object, turn the palm away, or point several fingers toward yourself.
Look carefully at the negative spaces between the fingers and how much their apparent lengths change as they turn in space.
5. Draw Glass and Reflections
Transparent and reflective objects are difficult because the thing I’m drawing often isn’t the object itself.
I’m looking at distorted shapes, reflected surroundings, highlights, dark accents, and edges that appear and disappear.
Try a drinking glass, reflective metal cup, glass bottle, sunglasses, or jar near a window.
6. Draw a Complex Scene Without Outlining Everything
Choose a busy street, forest interior, café, room, or another scene with many overlapping forms.
Instead of outlining every object, start by finding the largest dark masses and major divisions of light.
This forces me to simplify before getting lost in windows, branches, chairs, signs, or other details.
7. Draw the Same Subject From Memory
Study and draw an object from observation first.
Then put it away and draw it again later without looking.
Comparing the two drawings quickly reveals which proportions and characteristics I actually noticed and which ones my memory replaced with assumptions.
8. Use Your Non-Dominant Hand
Drawing with my non-dominant hand removes a lot of automatic control.
Because I can’t rely on familiar muscle memory, I have to pay much closer attention to where the line is actually going.
The result will probably look rough. That’s part of the exercise.
See my guide to non-dominant hand drawing for more on this approach.
9. Draw a Pile of Fabric
Crumpled sheets, jackets, towels, or clothing create constantly changing folds and overlapping planes.
I look at the broad light and dark shapes first rather than trying to trace each wrinkle.
Once those larger folds feel convincing, I can add a few smaller creases where they help describe the form.
10. Draw a Foreshortened Figure
Choose a pose where an arm, leg, hand, or foot points toward the viewer.
Foreshortening becomes challenging because what I know about the body’s proportions conflicts with what I actually see.
I try to trust the observed shapes instead of automatically making every limb the length I expect it to be.
11. Draw a Room From a Corner
Interior spaces combine perspective, furniture, overlapping objects, verticals, horizontal relationships, and changing scale.
Choose an ordinary room rather than arranging a perfect composition.
The awkward relationships are what make the exercise useful.
12. Draw a Bird Before It Changes Position
Birds rarely hold a pose for long.
Instead of trying to record every feather, I concentrate on the angle of the body, head direction, weight, silhouette, and a few important dark shapes.
My broader bird drawing guide goes further into observational bird sketching.
13. Draw a Self-Portrait With Strong Side Lighting
A mirror and one directional light can turn a familiar face into a difficult value study.
Instead of concentrating immediately on eyes, nose, and mouth, look for how the large shadow shape crosses the entire head.
Try building the face around that division first.
14. Draw a Bicycle
Bicycles are complicated because several mechanical shapes need to relate correctly at once.
There are ellipses, narrow tubes, repeated angles, overlapping parts, and perspective changes throughout the structure.
I would start with the overall relationship between the two wheels and the largest frame shapes before chasing cables and gears.
15. Draw a Tree With Many Overlapping Branches
A mature tree can become overwhelming if I try to follow every branch individually.
Instead, I look at the major directional movements and the negative shapes of sky between clusters of branches.
The challenge is simplifying something complex without making it feel generic.
16. Draw Water and Reflections
Water changes constantly and breaks reflections into shapes that may not immediately make visual sense.
Rather than drawing “water,” look at horizontal value changes, distorted reflected forms, highlights, and the edges where objects meet the surface.
17. Draw One Object From Five Different Angles
Choose something moderately complicated, such as a shoe, skull, camera, shell, plant, or small appliance.
Turn it after each drawing.
Repeatedly drawing the same object reveals how poorly one view alone can teach me its actual structure.
18. Fill a Page With Failed Attempts
Choose something you find difficult and make ten or twenty small versions instead of one precious drawing.
Don’t erase each attempt when it goes wrong. Start another beside it.
Repetition makes the subject less intimidating and turns mistakes into useful comparisons.
This fits closely with the ideas in my guide to messy drawings.
19. Draw a White Object on a White Background
A white cup, egg, shell, folded cloth, or other pale object against a similarly light background forces me to look for very subtle value differences.
The challenge is describing the form without relying on a dark contour around it.
20. Draw an Entire Scene in 10 Minutes
A strict time limit can make a complicated scene harder in a useful way.
I can’t record everything, so I have to decide what matters most.
Look for the largest value masses, strongest directional lines, major overlaps, and one or two focal details.
What Makes Something Difficult to Draw?
The hardest subjects aren’t always the ones with the most detail.
A drawing becomes challenging when it asks me to solve several visual relationships at once.
- Overlapping forms: clutter, crowds, foliage and interiors
- Movement: people, birds, animals and changing water
- Foreshortening: forms pointing toward or away from the viewer
- Perspective: architecture and interior spaces
- Reflections: glass, mirrors, metal and water
- Subtle values: light objects and low-contrast scenes
- Time pressure: subjects that move or disappear
How I Approach Complicated Things to Draw
When a subject looks overwhelmingly complicated, I try to avoid solving every part independently.
I squint at it and ask what the largest visual relationships are.
- Where is the largest dark shape?
- Where is the strongest light?
- What is the dominant direction or gesture?
- Which forms overlap?
- What can I leave out?
Once those large relationships begin to work, the smaller pieces have somewhere to belong.
That is much easier for me than beginning with a tiny detail and trying to expand outward through a complicated scene.
Make the Same Drawing Even Harder
If one of these subjects starts feeling comfortable, change the constraint rather than immediately finding a new subject.
- Use ballpoint pen so you can’t erase.
- Use your non-dominant hand.
- Cut the drawing time in half.
- Change the viewpoint.
- Draw only the shadows.
- Draw it once from observation and again from memory.
- Switch from white paper to black paper.
Don’t Confuse Difficult With Detailed
I don’t think the goal is simply to cram more detail into a drawing.
A drawing with thousands of tiny marks isn’t automatically more challenging in a useful way.
The challenges I find most valuable make me observe differently: unusual angles, shifting poses, difficult light, overlapping forms, subtle value changes, or a constraint that removes one of my familiar habits.
Those problems can make even an ordinary subject difficult enough to become interesting again.
For a wider range of subjects at every difficulty level, continue to my main drawing ideas guide.