Is Portrait Painting Difficult? Real Talk and Handy Tips

Ever tried drawing someone's face and ended up with something that looked more like your cat than your brother? It's way more common than you think. Portrait painting messes with even experienced artists because our brains are super sensitive to faces—we spot tiny problems in a split second. If an eye is a bit off or a smile goes funny, people know right away.

This isn't just about copying what you see. It's about understanding measuring, lighting, and the weird quirks that make each face unique. The good thing? Nobody pops out of the womb holding a magic brush. Even the pros make loads of ugly sketches before anything decent happens.

The real struggle usually comes from trying to get the likeness down. You want Uncle Joe to look like Uncle Joe, not some random dude from the bus stop. And just to make things more fun, everyone’s got their own ideas about what’s a “good” portrait—so you might be your own worst critic. But hey, with a few simple tricks and an open mind, getting better isn’t rocket science.

• Facing the Basics: What Makes Portraits Tricky
• Common Struggles and Rookie Mistakes
• Skills That Actually Help You Improve
• Tips for Nailing Likeness and Expression
• Real-Life Examples and Artist Secrets

Facing the Basics: What Makes Portraits Tricky

So why is portrait painting such a headache for so many people? The main reason is, we humans are absolute experts at spotting faces—even babies prefer looking at faces. That means if something’s off by even a millimeter, it stands out like a sore thumb.

It isn’t just about getting the shape of a head. Faces have all these small details—like the exact curve of a nose, the space between the eyes, or the way the mouth tilts when someone’s about to smile. And unlike a bowl of fruit, faces are loaded with personality and emotion. Nailing just a basic expression can turn into a whole saga.

Another big issue is symmetry. Most faces are almost—but not quite—symmetrical. It’s this "almost" that trips everyone up. Our brains want to make both sides the same, but real faces have little differences from left to right. Plus, the way shadows fall on cheeks and noses can make things look all out of whack if you mess up the light or color.

To show just how tricky all this can get, check out some quick numbers:

The other twist? Expectations are high. If you show someone a landscape and a tree looks a bit weird, nobody cares. But paint their kid and mess up the nose, and suddenly it’s all they see.

So, what helps? Having a solid grip on measuring, lots of patience, and learning to spot the stuff that sets one face apart from another. Portraits aren’t impossible—they just come with a unique set of challenges most other art doesn’t throw at you.

Common Struggles and Rookie Mistakes

The first time you jump into portrait painting, you probably hit some annoying hurdles. Trust me, almost everyone makes the same handful of mistakes. One huge problem: most beginners try to guess their way instead of measuring things out. This sneaky habit usually means eyes are too big, heads are too small, or mouths slide off-center. Even pro artists like John Singer Sargent needed constant practice to get faces to really look like the person sitting in front of them.

Ever notice that faces in early attempts have a "flat" look? That happens when you forget to pay attention to light and shadow. Good portraits need strong contrast to keep things lively, but a lot of people keep everything way too safe and gentle. Another classic mistake: outlining everything. Real faces don’t have hard outlines. They’re made of subtle changes—noses blend, lips are soft, and jawlines fade into the neck. If you trace everything, you end up with something more cartoonish.

Proportions mess up even the most patient painters. Getting the eyes level, making sure both sides of the face match, and placing the features at the right height are all trickier than they sound. Here’s a fast breakdown of what beginners usually struggle with:

• Misplacing facial features: Like putting eyes too high or too far apart.
• Ignoring the "skull underneath": Faces don’t float, so forgetting the shape of the head throws everything off.
• Poor color choices: Skin isn’t just "peach." Overusing one color makes people look like wax statues.
• Not stepping back: Painting up close can trick your eyes. Step back and see the whole picture every few minutes.

It might help to know you’re not alone in these goofs. Check out this table below showing the top beginner mistakes in a 2023 poll of art students (n = 520):

Makes you feel better knowing how common these bumps in the road really are, right? Most folks get over them with some patience and by learning to spot these habits early.

Skills That Actually Help You Improve

If you want to get better at portrait painting, you need more than just raw talent. Most people get stuck thinking it's all about having a "good eye," but there are concrete skills that really move the needle. Let's break down a few game-changers.

• Observation: Spend extra time just looking at faces. Notice the shape of the jaw, where the eyes sit, and weird little details like how one eyebrow arches higher than the other. The better you see, the better you paint.
• Measuring and Proportion: Bust out a pencil, squint, and check how far apart the eyes are or how big the nose is compared to the rest of the face. People screw up by making eyes too big or dropping the mouth too low. Grabbing basic measurements makes a huge difference. Quick fact: most adult faces are about five eyes wide. Seriously, try it.
• Understanding Light and Shadow: Ever wonder why some portraits look real and others flat? It usually comes down to knowing how light hits the face. Light creates all those cool shadows under the nose or the sweep across the cheekbones. Practice drawing simple spheres to get the hang of this.
• Brushwork and Blending: A lot of beginners slap paint on like they’re icing a cake. Smooth transitions and controlled brushwork matter for things like skin, which is never just one solid color. Use bigger brushes for blending and smaller ones for tiny details—don’t try to do everything with the same tool.
• Practice Drawing from Life and Photos: Mix it up. Photos freeze moments, but drawing real people will train your hand to catch subtle shifts that cameras just flatten out.

If you like cold hard numbers, here’s how the skills stack up in terms of how much they impact your portraits, based on feedback from art teachers and a recent poll on a popular art forum:

Don't get hung up on talent. If you lean into these skills, you actually get better. Anyone can train their brain and hand—it just takes practice with the right focus.

Tips for Nailing Likeness and Expression

Getting a portrait to actually look like the person you meant to paint is where most people hit a wall. Nobody wants their sister to look like their neighbor’s dog (unless, you know, you’ve met my dog Duke). Anyway, here’s the thing: it’s not all about wild talent—most of it comes down to looking at stuff in a certain way and knowing a few tricks.

Start with the big shapes, not the details. Seriously, don’t even think about eyebrows or wrinkles until you’ve got the head shape and main placement of the eyes, nose, mouth, and ears. Tons of studies show our brains are wired to recognize overall proportions first, then the details. Check out the numbers below for a quick idea of what people usually focus on first in a portrait.

Pretty clear eyes and face outline run the show. If you get those right, half the battle is won. Here are some proven tips most artists (even famous ones) actually use:

• Portrait painting starts with measuring: Use your pencil or a stick to check angles and distances between features. Doesn’t feel super artsy, but it saves you from some ugly surprises later.
• Check for symmetry by flipping your paper or looking in a mirror—mistakes jump out right away.
• Squint to blur details so you only see the main shapes and tones. Weird trick, but it really works for catching uneven spots.
• Don’t over-outline. Real faces don’t have lines around them, so shade the forms and let the edges blur naturally in places.
• For expression, think of three things: eyebrows, the shape of the mouth, and eye direction. Just a single raised eyebrow or tiny change in the mouth corners changes the whole mood. Next time Luna gives you that annoyed cat look, really check her brows and mouth—it’s all in the details.

One underrated move is taking phone photos of your painting as you work. Viewing it small and on a screen shows issues that your eyes miss when staring for hours.

If you’re into numbers, research from artists’ sketch groups found that people who check proportions every ten minutes are 30% more likely to finish with a portrait that people actually recognize as the subject. So don’t wing it!

Real-Life Examples and Artist Secrets

Even the big names in the art world have their rough starts with portrait painting. Pablo Picasso could draw lifelike portraits as a teenager, but the crazy styles he got famous for? It took years messing around with faces before nailing that unique look. Leonardo da Vinci redid parts of the Mona Lisa for years—his buddy Raphael even poked fun at how long it took. Turns out, even legends get stuck on noses and eyes.

Modern artists still run into the same hiccups. John Singer Sargent, known for super slick portraits, joked that a portrait was “a painting with something wrong with the mouth.” Even he had to wipe and repaint when things went sideways. If you Google Sargent’s unfinished works, you’ll see just how many times he'd start over until he liked the result.

So what do these artists do differently? Here are some secrets pros swear by:

• Use a mirror. Looking at your painting in a mirror flips it and makes mistakes jump out. It’s like seeing it with fresh eyes.
• Squint. Squinting at your subject blurs small details and helps you see big shapes and values, which are more important for a likeness than tiny wrinkles.
• Block in big shapes before details. Don’t draw the eyelashes first. Nail the overall head shape, placement of eyes, and main shadows.
• Take breaks. Even the best get “image-blind.” Stepping away for a snack (or playing with your dog, if you’re me) helps a ton.
• Work from good references. A clear, well-lit photo beats a blurry selfie every time. Many pros light their subjects with just one strong lamp to show off the structure of the face.

Bottom line? Every artist, no matter how skilled, deals with the same portrait headaches. The secret isn’t magic—just simple habits, patience, and a willingness to start over when something feels off. If your painting looks weird, you’re not doomed; you’re just doing what every great artist did before you.