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Beginner's Luck and a Breakthrough

6/16/2026

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​Do you believe in beginners luck? I do. Beginners luck is what happens when you try something new and don’t have grand expectations. You don’t know what you’re doing, so you suspend judgement and give it a try. Maybe you break a few rules because you don’t know what they are. And sometimes the result is surprisingly good. That’s what I call beginner’s luck.
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From an early session of Drawing Is Free, which I did in pencil.
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I’m not sure everything we might want to learn is subject to beginners luck. But in drawing and painting, I’ve seen it work. It happened to me recently when I started doing weekly sessions with Drawing Is Free, drawing portraits to music with 2 to 5 minutes for each one. The many artists who are involved take turns posing for the others to draw in a great big zoom session. The first couple of times I did it, I didn’t expect to finish most of the drawings, and for sure didn’t think they’d look like the sitters. But most were actually decent.
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I’m making progress, trying out different pens.
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I also loved to look on Instagram at other people’s versions of the portraits I drew. I was amazed that I could recognize the same sitters that I’d drawn. And I was even more amazed at what some artists could accomplish in such a short time, especially adding color. And guess what? My next few sessions didn’t go so well. I’d raised the bar. Beginner’s luck was over.

But I kept at it, hoping to get faster, in order to add color. And then I had a breakthrough. I’d been struggling, drawing the shape of the face first, then fitting in the eyes, nose, and mouth. What If I drew those first, and then put the face around it? That worked much better! Now I’m usually finished drawing in 2 or 3 minutes.
Picture
In one session, I was a sitter. I didn’t realize how hard it is to hold a pose for 5 minutes, but it’s a lot of fun to see the results. Above is my favorite of me, created by @homebakedart, from Instagram. Many thanks to them!
Above are some of my latest, where I worked quickly in light pencil and followed that with pen. (The blue color is an artifact.) The times available are on the bottom right, but I didn’t always need the total. I think some color may be coming soon. I'd also like to try this with boats. They swing on their moorings, so it will be a bit different.

If you want to try this, and I highly recommend it, here are two options:

www.drawingisfree.org Mondays at noon EDT, thanks to Chloe Briggs

Pencils4Tea Thursdays at 1PM EDT, thanks to Kirsty Lockhart

You can find them both on Instagram as well, and #drawingisfree and #pencils4tea on Instagram will show you lots of examples.

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    Bobbi - Painter. Sketcher. Teacher. Boat and Dog Lover.

    2009-2019 blogposts are located HERE

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  • Home
  • Shop
    • Clayton's House Show
    • Available Paintings
    • French Favorites
    • Selected Favorites
    • How to Buy a Painting
    • Your Own Custom Painting
  • Blog
  • Events
  • Classes
    • Classes Login
    • Values Download
    • Classes and Workshops
    • What's It Like to Study With Bobbi
    • Materials Lists
  • Resources
    • Beginning Painting Tips
    • Managing Multiple Projects
    • Framing
    • Your First Plein Air
    • Notes - Confident Drawing
    • Videos
  • About Bobbi
  • Contact
    • Newsletter