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8 Challenges For Intermediate Oil Painters

You’ve figured out the basics of painting in your style of choice. The paintings you’re creating look great and you’re proud of your work. If you want to switch things up a little or push your skills to the next level try these 8 challenges for intermediate painters!

Photo by Yannis Papanastasopoulos on Unsplash

Every challenge will push your limits a further and help you grow as an artist. You will not only get better at the technical aspect and develop your manual skill but also on the artistic and observational aspect of painting.

Challenge #1: One Brush Only

There is reason we have five to ten different kinds of brushes in our toolkit. Fan brushes, filbert brushes, liner brushes or background blender brushes – they all serve a purpose and let you create different effects.

It’s time to drop all but one of them and paint a picture using only a single type of brush. For starters we recommend something like a one inch blender brush.

The Challenge

Paint a picture using only a single type of brush – everything from background to details. No knife allowed.

What You Will Learn

With this challenge you will really get to know your brushes. You’ll learn how they behave when you load them differently with paint and what effects they are especially good for. Maybe you’ll discover a secret technique on how to paint mountains with a liner brush – if you do you have to promise to tell us!

To put it in the words of one of the biggest martial artists of all time:

I fear not the man who has practiced 10,000 kicks once, but I fear the man who has practiced one kick 10,000 times.

Bruce Lee
Photo by Yaopey Yong on Unsplash

Challenge #2: Knife Only

Let’s take it one step further. This time we are leaving all of our brushes out of the game. Knowing how to handle your painting knife is an invaluable skill every painter should master.

The Challenge

Paint a picture using only your painting knife. Using a brush for the sky and/or water is allowed.
Hard Mode: No brush allowed at all

What You Will Learn

Similar to Challenge #1 you’ll really get to know your painting knife and what it can do. But this one will not only challenge your technique and manual skill.

Painting with only a knife will also challenge how you think about details and shapes: How do you paint a round bush with a square knife? This one is for you to find out.

Photo by Steve Johnson on Unsplash

Challenge #3: Paint In Black And White

This one takes us back to the Fifties, back before color TV was invented and everyone could only see (and paint) in black and white. Did you know that it was a real challenge to decide Mona Lisa’s hair color in 1957 when they finally added color to that painting?

Jokes aside, painting with only two colors is a fantastic challenge for every oil painter.

The Challenge

Paint a picture using only different black, white and grey.
Hard mode: No different types of grey (like warm grey or cold grey) allowed.

What You Will Learn

Eliminating all colors from your palette forces you to focus on the value of the objects you paint. You’ll learn a lot about aerial perspective and how to create depth by varying the contrast of different parts of your paintings.

Challenge #4: One Color Only

I think we’re done removing things from your toolbox and colors from your palette. Don’t you agree?

Let’s take the palette from Challenge #3 and add a single color of your choice to it. Painting in black and white is one thing, but how about a painting using only different types of green, blue or yellow?

Did you know that Swedish painter Anders Zorn only used four colors at all? While it is one more color than you will be using for this challenge Zorn managed to create stunning works with this limited palette consisting of Ivory Black, Titanium White, Yellow Ochre and Vermilion Red.

Anders Zorn

The Challenge

Paint a picture using only black, white and a third color of your choice.

What You Will Learn

Just like with Challenge #3 this tasks puts a special emphasis on value. You’ll also become real good friends with the color of your choice. You’ll learn how it reacts to the addition of black and white and exactly what kind of hues you can mix and use.

Challenge #5: A New Subject

As an intermediate painter you’re probably pretty good at painting one kind of subject already. For me this is landscape art, classic Bob Ross style. Mountains, Hills, Rivers, Trees – winter or summer, those are my bread and butter.

But there is one thing we all know: Great things happen outside of our comfort zone.

So take those brushes and paints – all of them if you want, you’ve earned them after Challenges #1 to #4 – and paint something you’ve never painted before.

This could be a little mix up (like painting a seascape for me) or something entirely different (like a portrait or something abstract).

To get something you’ve never had you have to do something you’ve never done before.

The Challenge

Paint a subject you’ve never painted before.

What You Will Learn

Pushing the limits of what you can paint is a fantastic thing. You’ll learn to generalize shapes and the interactions between light, angles and different objects.

I’m not going to say that a nose is just a mountain in someone’s face, but you know what I mean.

In addition to the learnings you’ll take from this challenge it’s just fun to switch things up from time to time.

Challenge #6: Use A New Medium

Painting is so much more than just applying colors to a canvas. It’s time to take everything you’ve learnt about composition, perspective and color theory and put it to use in another medium.

Whether you switch to acrylics, watercolors or pen and ink – let’s see what you can do!

Photo by Bench Accounting on Unsplash

The Challenge

Paint a picture in a medium you haven’t used before.

What You Will Learn

This challenge will really hammer home those transferable skills mentioned above. Be it acrylics or oils, composition matters in both cases. Ink or watercolor, you need to get your perspective right.

In addition you will learn to appreciate all the things your medium of choice does for you: painting reflections or leaves on trees is easier done in oil than in ink.

Challenge #7: Reproduce Someone Else’s Work

Who is the painter whose unique style you admire most? It’s time to try and recreate it!

Just like Pablo Picasso Steve Jobs said: “Good artists copy, great artists steal”.

The Challenge

Copy a painting of another artist as closely as possible.

What You Will Learn

Copying another painter’s work will give you great insights on how they create effects you adore and how they use composition and color to invoke feelings of awe.

Besides discovering new techniques it will also train your eye to paint what you see instead of what you think you see.

Challenge #8: Paint Faster

A tip we always give to beginners is “paint slow and take your time”. Once you have the basics down it’s time to speed things up!

If a painting in your style of choice takes you an hour try to do it in 30 minutes. If it takes a day try to do it in an afternoon.

Photo by Veri Ivanova on Unsplash

The Challenge

Paint a picture in half the time it usually takes you.

What You Will Learn

Working faster forces you to think faster and paint more loosely. You won’t have time to get hung up on mistakes or to plan out every aspect of your painting before putting it on the canvas.

This allowes you to learn to forgive yourself if you make mistakes, You’ll also learn which parts of your paintings can be abstracted (or dropped altogether) without reducing the quality of your work.

What do you think about our challenges? What did you learn from them?

Join over 1000 painters on and share your paintings and knowledge with us. We’re looking forward to seeing you there!

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