Challenging Painting Ideas for Every Skill Level

Whether you’re looking for design ideas, creative ideas, painting ideas, or color schemes, you’ve come to the right place. There are so many paint techniques out there that it can be confusing. That’s not a bad thing, really, but it can be hard to find that one thing that works for you.

You might like to start by figuring out the color combinations you intend to use, which will help you decide on the atmosphere you’re going for. To inspire yourself to come up with great art ideas, you’ve got to ask yourself the deeper questions, even if you don’t figure out the answers while you still have a blank canvas. Find out whether your atmosphere will be dark, or playful, or magical, and you’ll gravitate toward meaningful color ideas organically.

Some other tools that are at your disposal are texture variety, the size of your brushes(and therefore your brushstrokes), whether your finished piece will have a matte or gloss finish, and choosing an interesting backdrop. Decide early how you’ll be blending your subjects into the background, or using hard edges and brighter tones to disconnect your subject from its surroundings.

Getting Motivated with Art Challenge Communities

We’re not only going to talk about challenging painting ideas in this post, but we’re also going to talk about some great community art challenges you see happening around social media communities. I just couldn’t figure out how to get that all in the title. Personally, I always find out about these challenges after they’ve already started. Well, I’m sick of using that as an excuse, so in one section, you get to follow along as I compile a short list of cool art challenges that I think would be a great learning experience for artists of any skill level.

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Community art challenges are amazing for a few reasons. First, they get you practicing. Second, there are artists of all skill levels out there giving it their best. But the best part is, you’ll see plenty of people out there who don’t even have YOUR level of skills. It makes you see how far you’ve already progressed, and that’s when you realize the pros do the same thing over and over during their lives, and once upon a time they were at the level you’re at now. Yes, that looks like a long road when you’re just beginning, but every moment you spend in practice is like a step further down that road.

“Wow!” you might be thinking. And you would be right.

Have a Wild Brainstorming Session for Painting Ideas

But before we get into that list of painting ideas, we’re going to come up with some off-the-wall ideas that you might not have thought to try. And even if you don’t like these ideas, you’re an artist … your job is literally to use other people’s ideas like a trampoline (Painting Idea #1). Well, not literally … I don’t wanna be responsible for any of you out there who might try stomping on someone’s head. 

One thing that’s really fun to paint is a jumble of identical objects. My personal favorite subject to paint is stacks of solid gold bars(#3). But since those aren’t always readily available, I’ll list out some other objects to use instead. 

Cheap Buys to Get the Creative Juices Flowing

Candy is an easy choice, because it elicits an automatic nostalgia for the childhood delight you would have felt about seeing a big pile of candy when you were young. And because nostalgia is an emotion built around memories of the past, a painting that centers on the simple and classic lighting/setting will help push that emotion forward. And if you keep that emotional connection in your mind as you paint, the emotion will echo through your brushwork and color choices.


Another great thing about painting a bunch of simple shapes, is that once you do a few of them, you’ll be a pro at painting these identical candies, and you can experiment with how to best make them look delicious to the child in all your painting’s viewers. Leaving a few empty wrappers, or taking bites out of one of the candies, can support the idea that these painted candies are irresistible.

Take a page from your own life, and use something you’re familiar with. Or do it my favorite way, which is to look for volume merchandise at clearance prices. You can find an assortment of objects on clearance at the most random places, but if everything else fails, there will be something shiny and cheap at the dollar store that you can buy in bulk.

Paint Your Favorite Toys

Legos are another easy idea. You don’t really even need to build anything with them.. But I have always liked separating legos by their colors. What if you arrange those legos in color-coded piles and shapes, as if they’re arranging themselves. This idea could almost have a deeper meaning, as if you the artist were trying to show how your childhood creativity blends effortlessly into the way you use color as a painter. It’s a unifying technique, and you should certainly find more ways to make your subject here even more personalized, but I’ll leave that to you.

An empty chair is always a solid subject for a painting. Vincent Van Gogh is famous for having sent paintings of empty chairs to his brother by post. Vincent wrote letters too, of course, but the painting subject itself speaks volumes. If there are any empty chairs in your house, look at them as if the chair represents the absence of someone, temporarily or permanently. You can also stage a scene with that “absent presence” motif, by adding a few simple props near the chair, like a table, a lamp, a basket. Make the scene suggest someone specific by placing objects identifiable to them in the basket, on the table, perhaps a “favorite” blanket draped over the chair. Add hats, scarves, gloves, or just go wild and pile your shoes on and around the chair, as if the chair is attempting to embody the clutter of closet-space.

A Sea of Ideas 

I think there are a number of jumping off points in there, and though we could go at examples all day, hopefully you can conjure up an idea of how a bunch of identical things you have lying around can tell a story. If you can take care of this little creative bit of visual story-telling, your art will project an emotional experience regardless of how technically skilled you are. Because in the end, art needs to have soul, not robot precision.


I’ll leave it to you to find 50 traffic cones to arrange around the neighbor’s car, who like it or not, will seem like a notoriously bad driver in your painting. You might want to grab your dirty laundry basket, and lay piles of clothes around the yard, representing those taken in the rapture, or vanished in an unforecasted alien kidnapping raid. Make sure to include some funny lights in the sky either way. 

Rather than leaving your booty sweat out in the yard to attract raccoons as you try to paint the sensation of being left behind, just have a good look at the surreal scene you’ve laid out, snap a few reference photos, and see what happens. The important part is to draw attention to the surrealism of the clothing piles by painting the scene on a sunny day, or decorating the environment with party favors, to get the sense that something is not right here. Or wait for the raccoons, because that could make for a pretty wild atmosphere as well.

“If I could say it in words there would be no reason to paint.”

         -Edward Hopper


The point is, choose an object that when scattered in a certain place, pattern or direction, tells a story. Like a trail of rose petals leading around a corner or into a room. One trick to making one of these emotions into a key motif, is to do your part to express the emotion through your physical painting. If the gesture is angry, your brush strokes might be slashing and exaggerated, your color choices all blacks and blood reds. If the gesture is friendly and kind, or gentle, let your brushwork reflect a soft feather quality, where the forms almost blend together in harmony. 

I really hope some of these ideas and their explanations triggered a different kind of thought process for you when choosing your next painting subject. Hopefully some of you think the way I do, that narrative and storytelling might not make you better at painting, but it’s one way of making sure you sell some work along the way, as you’re practicing and improving.

So, let’s move on to the research stage. Roll the montage.

<<No montage in the budget, sorry.>> 

A List of Challenges to Jumpstart Your Painting Ideas

 Oh, wow, there are SO many … yeah, so I put together a list of the ones that I thought were cool, but there are way bigger lists of all the challenges. There seem to be two kinds of challenges: the kind you just take upon yourself for good practice, and maybe gain a following by producing regularly, and the kind that is actually hosted either by an artist, or an artists association. I’ve provided links to most of what I found, so if any of these sound fun to you, of course you’ll want to do more in-depth research on the rules and details.


 I just missed this one by again, not finding out about it until it had already started. It really does pay off knowing a month in advance you’re about to start a challenge. It sucks scrambling around for materials and spare time if you weren’t prepared for it. The name is pretty self-explanatory.


 Inktober sets a restriction on your artwork by taking away color and leaving you with a single value: black. I find painting with black to be kinda fun, but you can use any medium as long as you follow the general guidelines.


 Otherwise known as “Wrap Your Girlfriend’s Legs In A Different Blanket Every Day” -Month, if you live near the ocean, you’ve got a huge step up with this challenge. Just try to find out what the local mermaids’ favorite foods are, and maybe they’ll hold still long enough to let you paint their picnics.

Draw This In Your Style

 This challenge is usually being held by individual artists who sometimes offer prizes and notoriety by asking you to reproduce the artist’s work or characters in your own style. The artist gets to view all these creative alternatives to their characters, and the winners get to talk mad smack.

Strada Challenge

 The Strada Challenge is an RNG challenge, aimed at improving artists by forcing them to work from life, though the likelihood of getting picked for an easel is slim to nil. Still, it’s one of the more useful challenges out there if your true purpose is to push your own skill limit.


 This is not so much a challenge, as an instagram artist’s way of introducing their own face at the center of 8 of their own pieces. Imagine watching the Brady Bunch except it’s just Alice alone in the house with all her oil paintings.


 Some people love this challenge, because it has a real emotional appeal. The idea is to pull out one of your terrible drawings from any number of years back, and redraw it using all of the skills you’ve acquired since. It’s cool looking back at something, especially if it was terrible, and letting your childhood self pass the torch to you, the more practiced and mature you.


 This one is mainly for cartoonists, because you take a single character, and illustrate it in a style reminiscent of 8 other artists whose work you’re influenced by. This is a pretty big step for most artists, because even though I’m influenced by Eugene Delacroix, you won’t find me creating a painting anywhere near reminiscent of his style or mastery.


My point being, if you’re at the point where you can name 8 influences in your area of focus, then adapt your own creation for their visual worlds, you’re probably neck-deep-familiar with your own polished style of illustration, and this is not so much a challenge, as a way for you to show off. Get out of my experimental amateur learning space, you professionals! 

Just kidding, please stay. Tell us ALL your secrets … 

The Hundred Heads Challenge

 A hundred heads in 10 days, using whatever medium you like. 10 a day sounds tough. I imagine by head #100, you’ve got a lot better grasp of the portrait than when you started. A tasty challenge indeed!


 Here’s a link describing Smaugust, but if you know anything about dragons, you’re probably already on your way to their page. Dragons are cool, but I didn’t really become interested in dragons until I began seeing them depicted as noble and intelligent pets, or companions. I guess it was easier to imagine a small dragon because there were cats and dogs whose behaviors remain recognizable even if another creature, like a dragon, is performing them.

Magical March

 Something to do with Sailor Moon? Or maybe just do magical scenes for a month. It’s worth looking into.

Monster March/Kaijune

I grouped these two because they’re both about creating monsters for a month. I guess a month of monsters wasn’t sufficient. 

Whatever Monsters want … Monsters get …


I can vaguely remember watching The Last Unicorn animated movie as a child, and being kind of terrified by the real danger the characters found themselves in. So yeah, terrified of unicorns.


 Dogs. Meh.


 Why didn’t I keep those James Gurney books I had when I was a kid?

The Hundred Day Project

The 100 Day Project is open to the artist’s preferences, so basically, sign up to do whatever you want for 100 days, and reap that notoriety of success or failure. I mean, why start a challenge if there’s any intention of not following it through to the end?

Daily Paintworks

Daily Paintworks has a huge list of people participating in the community’s monthly challenges, and let’s you create your own profile to post your work in their community. The winners get a lot of notoriety, and of course, winning these challenges is a first step in testing yourself for greater achievement.

The Brooklyn Art Library

 This is a really cool project to participate in. Basically, you sign up, they send you a 28-pg sketchbook, and you send it back to their library of artists. Filled with artwork, hopefully. Sounds awesome right? 

Tinkerlab Art Challenge

 This challenge keeps things pretty open, with 365 word prompts spread out over a whole year. If you can manage this challenge, you’ll have grown so much as an artist, that day 365 won’t even look like the same clumsy artist that started on day 1. Good luck if you try to take on something finished every day for a year, it’s a huge investment of time, struggle, and materials.

So there you have it, a ton of painting ideas, and if you still haven’t found the right subject, it never hurts to bench yourself to the studio, and brush up on your skills with one of these fun challenges. Sometimes a great idea can’t come to you unless you’re at the level you want to be on to accomplish it. I’ve got some amazing goldfish paintings in mind for future me to do. But until then, I’ll just write these blog posts where I trail off randomly at the end. Like, trust me, I’d love to be painting right now, but fine art has so much overhead. Why am I still writing? No one is going to read til the end, they’re going to click on one of those amazing links and whoosh, vanish like they were never here. Life in the fast lane …


Is anyone out there like, a blog-post OCD completionist? I mean, if I just kept writing, are you now obligated to go to the end? This is probably really annoying you right now I’ll bet. BWAH-Ha-hahahahaaaaa