The Silliest Drawing

Small drew his very first tree the other day, actually it was the first thing he’s ever drawn that was recognisably a thing. I got my reaction to it totally wrong. I was just so unbearably proud! I was so excited, I took photos of it to send to grandparents, I hung it up on my bedroom wall, I couldn’t stop going on about it and I couldn’t wait to see what the next recognisable picture was. Only there were no more pictures of anything. I had some how managed to totally wreck drawing and I really needed to get the fun back. So we had a Silliest Drawing session. 

What you’ll need

  • Paper
  • Pens, pencils, chalks, paints, pastels


  1. Explain that you’re going to try together to do the silliest, funniest drawing ever in the world
  2. Grab your tools and go wild
  3. Don’t praise or compliment anybody’s work, just laugh, a lot!
  4. Be open to silly advice from your Small


The Silliest Drawing was really very difficult for me. I can’t do a drawing without trying to make it into a pattern or shape. Small noticed that and realised that he could help me with it. We did laugh a lot. Small remembered that he loves to draw and that it’s really fun. He discovered some coaching skills to.

I don’t think there’s anything wrong with praise and everyone likes to feel appreciated. I just don’t want to create a situation where we’re worrying about doing things the right way… or the praise worthy way. I want Small to know that I love him with or without tree pictures. I’m someone who values self improvement but trying to be perfect on somebody else’s terms is ultimately very limiting. So there’s a balance I need to find and I’m still working on it.

I read a lovely quote from artist Nicholas Wilton “…art, among all the other tidy categories, most closely resembles what it is like to be human. To be alive. It is our nature to be imperfect. To have uncategorised feelings and emotions. To make or do thing’s that don’t necessarily make sense. Art is all just perfectly imperfect.”

I suppose I’m hoping that Small discovers his artistic license. Or at least that we both stop taking things so seriously!


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