How to Improve Your Sketching Skills in 30 Days: The Challenge

How to Improve Your Sketching Skills in 30 Days: The Challenge

Whether you sketch to brainstorm ideas for a bigger project, or as an artform in and of itself, I’m guessing you wouldn’t mind improving your sketching skills.

That’s why I’ve put together a guide with 30 fun ways to challenge yourself to get better at the art of sketching, and it also comes with a handy printable to keep you on track! Let’s get started.

Download it now!

A 30-day calendar to sketch like a pro.

Practice your way to better sketching with our 30-day challenge. Download and print this calendar to get started.

Draw on the Go

They say the best camera is the one you have with you. Same goes for sketchbooks: it doesn’t matter if you spent your hard-earned money on a limited-edition Moleskine, what matters is that you’re set with the tools to record your ideas when inspiration strikes. Create a habit of carrying even the smallest sketchbook, and don’t let another creative moment go to waste. Check out this sketchbook review to decide which of them is right for you

Brain Map

Think of this as a form of visual brainstorming. Instead of just scribbling your thought process, illustrate your thoughts in a creative, aesthetic way. Represent your ideas with symbols and add hand-lettering to emphasize key concepts.

Still Life

You know those classic paintings of lemon-filled bowls and cracked jugs? Still life doesn’t have to be so predictable! Place a few interesting objects in front of you, and really take the time to observe them and sketch them in detail. Study their texture, and how the light hits them, and challenge yourself to render them with just a pen or pencil, no fancy tools needed.


If you’re into drawing characters, what better practice than studying yourself in a mirror and sketching what you see in real-time? You can choose to try a realistic style, or a stylized version of yourself (think caricature, only less comic and exaggerated).

Flip It

One of the greatest challenges in sketching and drawing realistically is to train your hand to draw what yousee and not what you know, as you’ll hear often in many art classes. One of the most effective exercises I’ve found for this skill is to draw upside-down. Now, before you go looking for a trapeze by which to hang by your ankles, allow me to clarify: find a reference image of something you’d like to draw, and tape it upside-down to a page in your sketchbook. On the opposite page, try to copy the drawing. You may be surprised at how much this forces you to study each line you put to paper, and even more surprised at how awkward your drawn image looks when you finally look at it right-side-up. Try it, you’ll have a good giggle!

No Lines, Please

During a brief illustration course I studied years ago, our teacher taught us to learn to see things as shapes, not as lines, because if you think about it, there are no actual outlines for the real objects which surround us. This is another great method for slowing down your observation and focusing on rendering what is actually in front of you.

Be a Copycat

Well, not literally, because copying is a big no-no in the world of art (and any intellectual property, actually). But so long as it’s for your own personal learning, and stays within your sketchbook, you can totally go ahead and attempt sketching the Mona Lisa, or any other masterpiece that speaks to you. Doing so may stretch your abilities, and lead you to try techniques you may not have otherwise thought of, or inspire you to draw new subject matter.

Less is More

“Tools do not a craftsman make” — ever heard the saying? In the spirit of this challenge, try to clear your desk of all but two writing tools for one week (one if you’re really daring). This is a great way to let go of using fancy art supplies as a creative crutch, if you will.

Get a Grip

Of your pencil, that is. Experiment with grasping your pencil in different ways-holding it as you would a coin to scratch a lottery ticket, and gently sliding it over the paper, will give you an even, soft effect which is perfect for shading. Some pressure-sensitive stylus pens (like the Apple Pencil for iPad) will also respond to this technique.

Go Figure

Have you ever tried a figure-drawing class? One where a model poses for the students, sometimes clothed, and sometimes not-so-much? Whichever type of session you choose to attend, this is an excellent way to improve your understanding of the human anatomy. This isn’t to say that you’ll adopt a realistic drawing style, in fact, you’re free to draw the model in any style you like, but it’s great to know the “rules” (of anatomy) before you break them.

Time Yourself

Pick a subject to draw, and set a timer for five, ten, and fifteen minutes, drawing the same subject in each of the three time slots. Notice how your style changes when you limit yourself to five minutes, versus when you can take your time to focus on the smaller details. Which style do you prefer? I find that my natural way of drawing is quick and “sketchy”, but when I force myself to lengthen the time I spend on a drawing, I stretch myself out of my comfort zone and the results are often surprisingly wonderful.

Left vs. Right

Try using your non-dominant hand for your next sketch, so all you lefties- use your right, and vice versa. I love this exercise, because it often yields a playful and wonderfully awkward aesthetic, one that I’m not always able to achieve when I’m overly conscious of it. You’ll most likely see your lines be quite wobbly, and things won’t come out quite as your brain wants them to, but you just might come up with something that you’ll wish to re-create with your dominant hand.

Abstract It

This one’s easy. Just fill a page with abstract shapes. Perhaps you can find an interesting way to connect them and make them cohesive. Don’t make it more complicated than it is: this is a glorified version of when you doodle while talking on the phone. This is a great exercise to warm up your hand, to free your mind from over-thinking, and to possibly come up with interesting shapes to use in future illustrations. Here’s a fun twist on this exercise: Use watercolors to place some abstracts blobs on the page, and let dry. Stare at your blob (squint if you must), and just like imagining seen objects within the clouds, use your imagination to think of what these blobs could be. Then, using a pencil or fineliner, add a few details to create the final illustration. It’s super fun, give it a try!

Trace It

Grab a photograph of an image which strikes your fancy and trace it. You can do this by placing a light source under a glass coffee table, or putting your photograph up to a window, with a blank page on top. You can of course also use a lightbox, designed especially for tracing. An even easier way is to use tracing paper or vellum paper. Or, you can opt to do this digitally by placing your photograph as a layer in Photoshop, and drawing on a layer above.

Tracing can help train your eye and hand to study the shapes of things, like the curve of an eyelid, or the many lines on a flower petal. Consider picking your photo based on the subject you normally sketch on your own, and perhaps you’ll be surprised at some details you’d been overlooking this whole time.

Vary Your Angles

Who said you need to sketch things with a front-view? For your next sketch challenge, I’ll ask you to draw something from a bird’s eye view, or with a fish-eye effect (imagine looking at your object through a door’s peephole). Once again, this challenges us to look at our world with fresh eyes.

New Media

One of my latest discoveries is that I love to draw with my four-year-old son’s markers. On the cheapest printer paper. No offense to my beautiful Copics, but there’s just something about the limited color palette, and the squeaky nibs, that makes the experience very playful and fun!

If markers aren’t your jam, try any other tool (a perfect excuse to treat yourself at the art supply shop!). Fineliner lovers may discover they love messy gouache, and classically-trained oil artists may love to draw with a Wacom! This month we’re all about trying new sketch techniques, and this one is a really exciting one! I’d love to know if you tried and loved this!

If markers aren’t your jam, try any other tool (a perfect excuse to treat yourself at the art supply shop!). Fineliner lovers may discover they love messy gouache, and classically-trained oil artists may love to draw with a Wacom! This month we’re all about trying new sketch techniques, and this one is a really exciting one! I’d love to know if you tried and loved this!

Draw Every Day

This one is easier said than done, but if even just for this month, you can try to draw something (anything!) every day, I truly believe you’ll see a difference in your sketching abilities. Artistic skills can and do get rusty, and putting them to use daily can do wonders for them.

Play with Space

Experiment with different ways of filling up your page’s blank space. Do you like a stark background with your object being the one and only focus of the illustration? Do you love a busy page filled with details and patterns? Study the illustrations that you love, and analyze how they fill the space.

Do It Your Way

Limit the amount of time you spend searching for inspiration online, and spend the time more wisely by discovering your own visual style. As a Pinterest-holic myself, I’ve found that I have to place a literal, timed limit on my search for mood-board images. It’s tricky to shut out all the visual noise online, but a Better Sketch challenge wouldn’t be complete without my encouraging you to find your own artistic voice.

The One-Line Method

I wish I could take the credit for inventing this fun exercise, but it’s been around forever. It’s so simple, and yet the results it produces are often quite beautiful. For your next sketch, do not lift your pencil off the page. Not even once. You may find your illustration becomes a beautiful, intricate web created by your one line, or you may find a clean, simple way to render your subject. Check out this perfect example by artist CJ Hendry, an artist who is more commonly known for her incredibly realistic renderings.

Learn to Hatch

Hatching is a shading technique by which tiny little lines are drawn to give dimension to an illustration. The more lines are drawn, and the more closely drawn to each other, the darker the hatch effect. Cross hatching is a similar technique, in which the lines overlap. And let’s not forget stippling, not for the impatient type among you, a technique which renders shading using tiny dots placed either densely together or sparsely.


Want to improve your sketching skills? One great way is to focus on an often-overlooked element, which is the texture of your subject. There are many great tutorials online for tips and tricks to drawing metallic surfaces, shaggy fur, or jagged rock.

Embrace Mistakes

While sketching is a low-stakes activity to begin with, working with a pencil and eraser is one of the easiest ways to allow yourself to take creative risks. Knowing your lines aren’t permanent takes the pressure off of ruining a blank page. Just remember to use a light hand when laying down your initial sketch to make for easy erasing.

Block It Out

If you’re unsure how to tackle rendering the subject in front of you, try envisioning it as being made up of a few simple shapes– this is also a great way to help you plan out the proportions. Remember to use soft, light pencil strokes, as you’ll be erasing these later. Next, start layering on the details, and when you’re happy with how it looks, you can go back and erase the basic shapes you started with.

Blend It

Do you own a blending stump? They’re inexpensive tools which help you create smooth transitions in your pencil work. You can also use your fingers to blend, but I find that a blending stump makes the transitions more seamless, plus it has a pointed tip, which is great for getting into the tiny details. If you don’t already own one, give it a try- it’s a great tool to have on hand.

Notice the Light

Next time you’re sketching, whether from life or from your imagination, try to incorporate some interesting lighting elements- where is the light coming from? Does it create shiny, sparkly lines on the water’s surface? Does the setting sun (even if it’s not included in your illustration) cast a long shadow on your character as he’s walking home? Does it create a soft glow in between the trees? Taking the extra time to notice these details can add so much depth to your work.

Drawing Prompts

If you’ve never tried drawing prompts, you should. These are basically lists of things to draw daily- they may be themed or totally random. and there are so many to be found on social media (often with hashtags so that people taking part in the challenge can find one another). It’s a great solution for when you’re stumped on what to draw.

It’s all in the Proportion

If realistic rendering is your thing, it’s very helpful to learn a technique to keep proportions accurate. I’ll link to a full tutorial, but the idea is to extend your arm all the way while holding your pencil out in front of you. You then squint your eye and look past your arm and onto the subject you’re drawing. You then use your thumb as a guide to measure between two certain points of your subject. The pencil is a constant, and serves as a reference for proportions of your subject. It’s easier to understand with a visual, and you can learn more here.

Get to Know Your Pencils

A pencil is a pencil, right? Wrong. Pencils can be found in a range of hardness, and each can give you a different effect. Hard pencils leave a light mark, though they will scratch your paper if you use a heavy hand. Soft pencils give a darker, more variable line (if you alternate pressure while drawing). Learn to see what types of pencils you love to use, and which are right for the type of sketching you plan to do.

Have Fun!

Remember: sketching is meant to be fun! So grab your favorite drawing tools and a cup of coffee, and enjoy yourself!

I’d love to know what best practices you use to improve your sketching skills. Let me know in the comments below!


Download it now!

A 30-day calendar to sketch like a pro.

Practice your way to better sketching with our 30-day challenge. Download and print this calendar to get started.

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