Strelitzias by Damian Osborne_sketchbook_2020-drawing challenge
Strelitzia. The first drawing of my 21 day pen drawing challenge.


Pen Drawing Challenge

by Damian Osborne


Yup, it’s another pen drawing challenge! Drawing with pen is one of the best practices for artists to become more comfortable with sketching and drawing generally. You can’t rub out! Check out all the weird stuff I got to draw during this 21 day pen drawing challenge. 


Why should you start a drawing challenge?

Setting yourself a drawing challenge is one of the best ways to push yourself artistically.

By setting a goal to get a drawing done everyday, you’ll not only see great improvements in your drawing capabilities, but you will have also increased your artistic output.

This is a great practice if you would like to produce a coherent series of artworks as part of your portfolio.  

It’s also great fun! And a way to force yourself to focus and be more disciplined in your artistic output.

Especially if you’re constantly making excuses about not being in the mood to draw, or that you’ll do some art ‘later’.

We all know what that means. Later becomes never!

Many people, particularly illustrators, join the Inktober challenge, created by Jake Parker  in 2009. 

Since then, it has become a worldwide phenomenon, where thousands of artists use the prompts provided on the official Inktober website to do an ink drawing everyday during the month of October. 

Now, however, there is a new Inktober challenge, where you must draw a drawing every week for the whole year. 

Here are some of my Inktober drawings. You can see that I learnt quite a lot. Although, I think next time, I won’t bother to stick to the prompts. 

Another art challenge I think is a great idea, is the 100 Heads Challenge by Ahmed Aldoori.

There are many online drawing challenges you can join. And one of the best things about these online challenges is that they are social. So you can share your drawings on whatever platform hosts them, and in turn, be inspired by other artists’ works. 

Setting yourself a challenge to work on also gives you an opportunity to work on improving your weak spots.

For example, the 100 heads challenge is focused on drawing heads (as the name of the challenge obviously tells us). So you’re bound to improve your skills drawing heads during this challenge. 

For me, one of the best challenges I ever set myself was doing gesture drawings every day for a month. I filled an entire sketch book with 30-second ballpoint pen gesture drawings. And boy, did my gesture drawings improve by 1000%!

So the point is, you don’t have to join an official drawing challenge. You can also set your own personal challenge, and focus on any aspect that you feel needs more practice and attention in order to improve your drawing skills.


A pen drawing I did of my wife reading before bed during an Inktober drawing challenge. Sometimes I left my drawing to the last minute.


Why should you draw with pen?

Drawing with pen is really the best way to improve your general drawing confidence because it takes away the temptation to constantly second-guess yourself.

You can’t rub out!

Besides, pen drawings have a special beauty to them. And the mark-making is more bold and permanent than drawing with pencil.

It is also super convenient. You can take a pen with you anywhere. Even if you don’t have a pen, people often have one you can borrow. ‘Can I borrow your pen?’ There, a quick doodle or sketch done!

There are many styles of pen drawing which are not achievable with other media. Although hatching, for example, can also be done with pencil, it’s not quite the same effect.

And the values are usually a lot bolder with pen drawing, particularly with illustrators or comic artists that use powerful notans in their drawings. 

Notan is a Japanese term meaning a strong contrasting relationship between the darks and lights in a drawing. 

Pen drawing teaches you to be accurate from the start. That’s not to say you can’t draw light construction lines. Sometimes the light searching pen lines add a special authenticity to the artwork. They show the artist’s thinking process.   

Pen drawing has its own special challenges. For me, becoming comfortable drawing with pen, makes drawing with other mediums, such as pencil or charcoal, a cinch. 


Sketchbook drawing Janine Working on Laptop by Damian Osborne
Sketchbook drawing of Janine working on laptop.


Drawing random things around the house

My wife and I had just moved into our new home (no more renting) just before the 2020 lockdowns. Although I’m extremely grateful to have our own place, the previous owners dealt some bad vibes during the transfer period.

And they left the house in a despicable state. The house has suffered years of filth, neglect and really shoddy D.I.Y jobs.

So they left a lot to sort out — walls to paint and plaster, kitchen cupboards to build, a desolate ‘garden’, garage, paving, skirting boards, blah blah, the list continues…

And no studio to paint in!

So when our government ordered the first wave of lockdowns to cripple our economy and force people under house arrest, (the lockdowns keep getting extended), I decided to use the 21 days to do a drawing challenge and post the drawing videos on YouTube.

The curse of being an artist is that I’ll find any excuse to draw when I have other work I’m supposed to do but don’t feel like doing. 

Because everything was in upheaval, I decided to draw random things around me to take my mind off things. The challenge was to find something interesting on the property (since we were not allowed to go outside), and draw it from life. 

So no copying from photographs. And no preliminary pencil sketching. 

I used mainly scratchy micron pens and a soft cover notebook to draw in. But soon I wished it had a hardcover. Eventually I managed to get a clipboard to press on. 

Filming was also quite a challenge. I used natural light or the crappy lights the house came with, a broken tripod, an old Huawei phone and a DSLR camera, and very little space to work in.

So some of the drawings are a bit better than others. But this was a drawing challenge, so I just put it all out there. Too bad if some of them suck. That’s just the way it goes. 

Eventually my hatching started improving quite a lot, and I got used to the less than ideal drawing materials and conditions. 

Without further ado, here are the results of my 21 day pen drawing challenge:


Day 1 

How to Draw a Bird of Paradise Flower

To begin, lightly draw the main sheath-like ‘beak’ or spathe of the flower and indicate the direction of the petals and sepals. Include the stalks and leaves.

Once you’ve completed the light general layout of the drawing, start building up the shadow areas of the dark leaves and add bolder lines.

Add longitudinal and contour hatching to show the roundness of the spathe, the stalks, and the curved surfaces of the large leaves. 

I started my drawing challenge with one of the only flowers in the garden at the time. I have much gardening work to do. 


Day 2

Pen Drawing of a Bowl of Fruit

My fruity side. Drawing the symmetry of the bowl is the most difficult part. Totally botched that!


Day 3

Pen Drawing of Seashells

Seashells are great to sketch because of all the abstract shapes and the tiny details.


Day 4

Drawing Insects in Pen

This is probably my worst pen drawing ever! Really bugs me!


Day 5

Drawing Lemons with Pen

Something to zest up my sketchbook. 


Day 6

Feet Pen Drawing

My wife kindly allowed me to draw her feet while watching her favourite T.V. show.


Day 7

Drawing a Vegetable with Pen

A quick pen sketch of a vegetable still life. Ever looked in your fridge and wondered what to draw?


Day 8

Drawing a Tree with Pen

I love drawing trees because of their beautiful shapes rhythms and textures.


Day 9

How to Draw a Cat with Pen

How to draw your cat. I wait for him to keep still! Then I grab my sketchbook and a pen and start drawing.


Day 10

Pineapple Drawing with Pen

Sketching a pineapple with pen is a great drawing exercise! They are made up of hexagons.


Day 11

Drawing a Pile of Books

Drawing an old pile of books helps to practice 2-point perspective and to draw simple structures.


Day 12

How to Draw a Teddy Bear 

Drawing a teddy bear is a great subject for learning how to do contour hatching. Doctor William W. Williams is a professional model and mentor who joins me on the show.


Day 13

How to Draw Onions

Drawing onions is one of the best drawing exercises you can learn. I explain some of the art tips I’ve learnt here, including longitudinal shading and cross hatching.


Day 14

How to Draw Mushrooms

In this quick mushroom drawing tutorial, I decided to use linear and contour shading techniques. Drawing mushrooms with pen is a good practice for learning to shade around the form.


Day 15

Drawing Rocks with Pen

Drawing rocks with pen is a good way to practice cross hatching and other shading techniques. You can depict smooth or rough textures when drawing stones by the spacing, direction and length of your lines.


Day 16

How to Draw a Pigeon with Pen

I was busy sketching pigeons from life, until our cat Silas caught one. Thus the dead bird become a drawing study.

In this video, I show how I draw a bird with pen. This pigeon pen drawing was a good exercise in learning bird anatomy and practicing the textures of feathers.


Day 17

How to Draw Roses with Pen

Drawing roses with pen is quite relaxing and makes a lovely pattern or design. I tried to keep the pen hatching to a minimum to create a more illustrative style of pen drawing.


Day 18

How to Draw an Apple with Pen

In this draw an apple tutorial, I draw an apple that is back-lit, and an apple that is side-lit. I show how lighting in drawing changes.

Apples are deceptively difficult to draw with pen. They are good exercises for learning shading and hatching around a spherical form. So use them to practice light and shade in drawing.


Day 19

How to Draw Shoes with Pen

Drawing sneakers is a fun way to practice pen sketching. With this sneakers pen drawing, I kept the hatching quite minimal with a thin nib, and used a thicker nib pen to accentuate the shadows and solidify some of the lines.

These Converse sneakers were actually my wedding shoes.


Day 20

Drawing Drapery with Pen 

Drawing drapery is a great exercise for practicing your cross hatching with pen. In this example, I had pipe folds, zig-zag folds and drop folds in the fabric to draw from.


Day 21

Drawing a Self Portrait with Pen

My final drawing challenge day. I ended up looking a bit stiff and serious. Drawing a self portrait from life is really challenging. Especially since your head is prone to move around. I share a little tip when it comes to how to draw a self portrait with pen.



Doing a drawing challenge is pretty fun, and I certainly didn’t take myself too seriously with this project. Many of these drawings are not my best. But it doesn’t matter. I learnt quite a bit, and became more confident knocking off pen drawings and making short videos. 


If you have any comments about any of the videos or this post, please feel free to leave them below or on YouTube. Thanks for watching! 


 To view more of my drawings, go to Figure Drawing.


3 thoughts on “Pen Drawing Challenge”

  1. Hi Damian,
    A worthwhile challenge, and it’s whats We artist should be doing every day, but life gets in the way.

    I particularly liked your portrait 👍

    Well done

  2. Hi Damian
    I feel your frustration at not being able to paint while everything around you is a mess and your creativity is dying to escape being locked down, but you’ve done well in counteracting it with this lovely series of drawings.
    I love the feets drawing and the self-portrait but they’re all very good and certainly creative. I can’t say I’d find the same inspiration right now to draw a vegetable.
    I admire your efforts at maintaining sanity and good luck with the renovations.

  3. Damian, I love this series… very inspirational. The garden has absorbed all my creative power. Every beautiful day draws me out into the garden and to breathe, and while I’m digging, I’m wondering…what is Damian going to sketch next!
    The autumn air and subtle color changes in the light is food for my soul. This strange period in Time has been for me, a period to feed the soul.

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