
Weekly Portrait Drawing Challenge
We all know that practice makes us better, so let me drag you into my little journey of discovery. I’ve been drawing weekly portrait drawings for a year now, which is about 52 portraits in total! To make sure I didn’t spend too much time on each one, I limited myself to 30 minutes. This helped me work faster and not over think.
What did I learn? I figured out how to simplify shapes, draw quicker, improve proportions, create better flow, and it gave me more confidence. In this blog, I’lll share what I’ve learned, how my approach has evolved, and tips for improving your portrait sketchbook.


How Weekly Portrait Practice Improved Traditional Portraits
I don’t know about you but if I am drawing I tend to obsess and start trying to create “masterpieces” but the purpose of this little challenge was to get faster and more confident. Looking back, it’s wild to see how much I’ve progressed. In the beginning, my eyes were way too big, and the face shapes were all wonky but hey that’s why we practice right!? Now (not always, but mostly) my proportions are a lot better and the challenge is definitely working! If you want to get better at something try to challenge yourself, make it a routine, make yourself accountable by posting your progress or sharing with a friend.
Quick Tip: Learn to Draw Faster
- Practice weekly or daily doing one type of style
- Limit your drawings to 30 minutes
- Stay consistent
- Don’t get discouraged, power through
Improve Your Portrait Drawings with a Timer
My goal was to draw traditional portraits faster and, of course better. I originally started drawing them every Monday, but eventually swapped it for Tuesday. Mondays were chaotic so Tuesday just made more sense for me. Pick a day and make it part of your routine, I preferred waking up early to do them so I don’t let the day activities weigh me down.
To keep myself on track, I bought a cute little frog timer so I could visibly see the countdown and feel the rush to finish on time. At first, the timer gave me anxiety. I was constantly feeling like I didn’t have enough time, 30 minutes felt like 10 minutes. But don’t give up! Sometimes, putting yourself in an uncomfortable position is what helps you grow.
I’m not sure exactly when I stopped using the timer but it was probably after four or five months? But eventually, I just didn’t need it. My drawings were naturally finishing within the 30 minute window and I no longer felt rushed. So, no more loud beeps in my ear! In case you decide to challenge yourself, make sure your timer sounds pleasant. Some of these timers may be cute but they all tend to have that generic beep sound. MAYBE, just maybe it will actually encourage you to get faster so you can avoid the beep of doom, whatever works for your brain.
Improving Proportions in Traditional Portraits
You ever wonder why your portraits look strange or even cartoony? It’s probably because your proportions are off. Starting off this challenge I had multiple portrait sketches that just looked silly–more like a cartoon than a realistic portrait. I couldn’t quite pinpoint what was wrong, but now after doing this challenge and realizing how incorrect my proportions were, it was definitely a nice relief. I’ve created a little analysis of a drawing from the beginning of my challenge vs one from a year later.
For some reason my eyes and mouth were so big in my drawings and my nose was small and way to low on the fast. I had to write nose to distract people because it looked way worse. If you see the shape of the eyes my right eye had a weird wonky oval shape. My shading was continuous from the side of the face to the underside of the chin. There is no way to differentiate where it stops.

I started focusing on sizing and how shapes in the face relate to one another. When you break it down to shapes and spacing it makes it easier to get your proportions correct. Imagine your drawing eyes and a nose and then you finish and you’re like why is everything so big or small?? When you start drawing parts of the face try to see it more as shape and draw your next shape next to it but paying close attention to how much space is between the two shapes then your proportion start making more sense. I know that was a little hard to follow, I said shape like a 1000 times and I hope that makes sense. I created a little diagram below for all my visual learner cuties like me.
Growing Confident Drawing Portraits
I became happier with my sketches, proud to show my partner and even started experimenting–with color and mixing sketchy and detailed styles in the same drawing. I even started looking for portraits on Pinterest that had more elements like animals that I could draw. If you want to nice little collection of portraits to practice with, I’ve created a pinterest board you can follow. I try to avoid any AI images, because its more fun to draw real people.

Join the Weekly Portrait Drawing Challenge!
If you ever want to get better at drawing traditional portraits, I challenge you to try a weekly drawing session with a time limit. Learn how to draw faster, more confidently and with better proportions. I’ve learned so much from this process, and I don’t think I am stopping anytime soon!
I might even push myself further – maybe keep my 30 minute Tuesday challenge and add a Thursday one-hour challenge or something similar. Even if portraits aren’t your thing, I encourage you to challenge yourself in something you are passionate about. Try it, stick with it and see how much you grow. If you want to see some of my progress videos I created a little album on YouTube, find the collection here.
More Blogs
- All Posts
- Art
- Back
- Illustrations
- How To's
- Art Challenges

Weekly Portrait Drawing Challenge We all know that practice makes us better, so let me drag you into my little...

Digital Painting Process Step-by-Step Welcome to my little digital painting process blog! I’ll walk you through how I created my...

2024 Inktober Alternative With Cats Inktober is around the corner and I love themes, I have always looked at the...

How to Make Digital Artwork Okay! So what does digital artwork even mean? If you search on google there’s so...

How to Digitize Your Drawings As artists, many of us like to draw on paper. There is just something beautiful...

A Guide to Drawing Maps Drawing maps is easy! With a little creativity and a strategy, this will take you...
Newsletter
Sign up for news, blogs, challenges, prints and more!