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


Lockdown Pen Drawing Challenge


Yup, it’s another pen drawing challenge. At the time of writing, it’s May 2020, and if you’re reading this in the distant future, perhaps the new world order has prevailed and zapped your brain. Perhaps you have forgotten that basically the whole world has been under lockdown because of a hyped-up viral pandemic. And yet we still have Influenza. If you still believe your government has your health and best interests in mind, then I really don’t know what to tell you.

Anyway, let’s put frustrating politics and so-called conspiracy theories aside and talk about this drawing challenge. 


Why the hell did I start a drawing challenge?

O.K., so besides having plenty to do while the world was going into shut down, I decided I needed an extra project to burden myself with: a 21 day drawing challenge.

My wife and I had just moved into our new home (no more renting) in February. 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 I have a lot to sort out. And I don’t even have a studio to work from at the moment. I have walls to paint and plaster, kitchen cupboards to build, a garden to grow, garage, paving, skirting boards, blah blah, the list continues for years.

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. 

I haven’t done any oil painting since we moved in here. All my art materials are packed in boxes. And with the house being really difficult to move in, with boxes and furniture dumped in piles up to the ceiling, the lounge being a building site with drop sheets, tools and cement bags, I just couldn’t face painting pictures. 


Drawing random things around the house

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. 


Day 1 – Bird of Paradise Flower Drawing

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 – Drawing 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

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


Day 8 – Tree Drawing in 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 lessons you can learn. I explain some of the art tips I’ve learnt here, including longitudinal shading and cross hatching.


Day 14 – Drawing 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 Bird 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 a Rose 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 – Drawing 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 simple 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

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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