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The Outstanding Artist Two Week Challenge

Make five pieces of art.
Learn how to make each one better.

Learn to draw in charcoal and graphite, then paint in oils and acrylics. You'll follow full project lessons from the Mastery Program and get personal feedback from an artist coach on the pieces you submit.

If you've been wanting to take your art further, this gives you five projects to begin with, instruction you can follow, and someone to help when you're unsure what to change.

Join the Challenge for $99

One payment. Lessons open immediately.

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Take a look at what you'll make ↓
The vibrant parrot oil painting taught in the Challenge
One of the five lesson projects. You'll create your own version with guidance along the way.

Let's start with what this is

A guided introduction to learning art with us.

The Challenge brings together five projects from the Mastery Program, our full art education program. You start with two drawings, then carry what you learn about proportion, light, and shadow into three paintings.

These are complete project lessons. You'll see the process develop, including the painting stages that take a piece from its first layer to its finishing touches. Then you'll try the techniques yourself and submit your art for feedback.

You can join as a beginner. You can also join if you used to make art and want to return to it, or if you already draw or paint and want guidance in a different medium. You don't need experience in all four materials before you begin.

You'll need a willingness to practice and time to do it. Some of these paintings take several sessions. The suggested two-week schedule gives you a plan, and your 30-day access gives you more room to work through the lessons.

The five projects, explained

Here's what you'll make and what each piece teaches you.

The artwork below comes from the lessons. Your version will be your own. The purpose is to practice the techniques and understand your next step, so submit your pieces even if they don't look the way you hoped.

Finished charcoal portrait shown in the Challenge lesson
Project 1: charcoal portrait

Suggested days 1 to 2 · Charcoal

Understand the face before chasing every detail.

You'll study portrait proportions and the planes of the face: the surfaces that turn toward or away from the light. Using charcoal, you'll build a portrait with shapes, angles, light, and shadow.

The lesson helps you look for the structure underneath individual features. That gives you something to check when a face feels off, instead of repeatedly redrawing an eye or a mouth.

There's also an introduction to charcoal so you can experiment with the material before tackling the portrait.

Graphite horse drawing from the Challenge lesson
Project 2: graphite horse

Suggested days 3 to 4 · Graphite

Give yourself a way to check your drawing.

With a horse as your reference, you'll learn the 3-D Drawing Method: determine your middle, define an angle, and drop a line.

You'll use angles and vertical and horizontal guides to compare where features belong. It's a practical way to check proportions while you draw, and a method you can use with other subjects afterward.

The assignment asks you to apply the method to an animal drawing.

Vibrant parrot oil painting from the Challenge lesson
Project 3: vibrant parrot in oils

Suggested days 5 to 8 · Oil paint

Build a colorful painting from a dark first layer.

This project develops over three lessons. First, you'll lay down a thin, dark layer and lift paint away to reveal lighter shapes. This is the subtractive method.

Next, you'll add transparent color through glazing. Finally, you'll use more opaque paint to develop feathers, highlights, and the surrounding shapes.

You'll see why those stages happen in that order, and how the early light-and-dark structure supports the color you add later.

Expressive oil portrait from the Challenge lesson
Project 4: oil portrait

Suggested days 8 to 11 · Oil paint

Paint a portrait from broad shapes to expressive details.

The course calls this the Monster Portrait project. You'll begin with a loose, transparent block-in, then build the face with larger brushes and areas of color before refining the features.

Across three lessons, you'll practice facial structure, skin tones, eyes, the mouth, and hair. You'll also see how visible brushstrokes can give the finished portrait character.

This is one of the longer projects. Plan for several painting sessions, with drying time between stages.

Colorful acrylic bear from the Challenge lesson
Project 5: optical color mixing in acrylics

Suggested days 12 to 14 · Acrylic paint

Discover what happens when your eye mixes the colors.

You'll paint a bear over a black surface, placing separate strokes of color beside one another. From a distance, your eye brings those colors together. That's optical color mixing.

After a warm-up exercise, you'll work through three painting stages, using the direction of your brushstrokes to describe the bear's fur and form.

It's a chance to be more adventurous with color while making deliberate choices about where each mark goes.

You can ask about your own art

Get feedback on the piece in front of you.

When you're unsure why something looks wrong, submit your drawing or painting to the Challenge community feed and ask your question.

Your artist coach reviews the assignments you submit and helps you understand what to keep practicing and what to try next. The coaches have completed the Mastery Program themselves.

You don't need to make a piece perfect before sharing it. Helping you improve is the reason feedback is included.

Here's how to use the lessons and coaching together.

  1. Watch the full lesson first. Seeing the process through helps you understand where each stage is going.
  2. Watch again while you make your piece. Pause, replay a section, and take the time you need to practice.
  3. Photograph your art and submit it. Post your assignment in the Challenge community feed. Tell your coach what you're finding difficult.
  4. Use the feedback in your next session. Return to the piece or carry the advice into your next project.

Coaching begins with your Saturday cohort. You can submit your Challenge art for feedback for 30 days from that date.

What about live calls?

Live group calls are included alongside the recorded lessons and community feedback. Your cohort's call details are shared in the community when it opens. These are group calls; the personal feedback on your submitted art happens through the Challenge community.

Who's teaching, and who's helping me?

The project lessons are taught by Milan Art Institute co-owners Elli Milan and Dimitra Milan. Your artist coach helps you apply the lessons to your own art. The team can also help with practical questions about your account and getting started.

The time commitment

Two weeks is the suggested pace. Here's what that actually involves.

You'll be doing more than watching videos. There are two drawings and three paintings to make, and the oil paintings develop in layers that need drying time.

The oil portrait alone has about 1 hour and 48 minutes of instruction across three videos. Its assignment guides suggest roughly 4 to 10 hours of painting in total, depending on your pace, plus drying time. That estimate doesn't cover the other four projects.

The charcoal portrait assignment suggests about 1½ to 2 hours of drawing. The acrylic bear's three painting stages suggest about 5 to 10 hours altogether, in addition to the instruction and warm-up. Your own pace may be different.

Before joining, think about where those sessions will fit into your week. If you have only a few minutes a day, you'll likely want to spread the projects across more of your access period.

The course's suggested project schedule
DaysWhat to focus on
1 to 2Portrait proportions and the charcoal portrait
3 to 4The 3-D Drawing Method and graphite drawing
5 to 8The oil parrot, from its first layer to the finish
8 to 11The oil portrait across three stages
12 to 14The acrylic bear and optical color mixing

Day 8 appears in both oil projects in the course schedule. Treat this as a suggested rhythm, and allow for drying time between painting stages.

What if I don't finish in 14 days?

You have lesson access and feedback for 30 days from your Saturday cohort start. You can use that additional time to continue the projects and revisit instruction. This isn't lifetime course access, so plan your sessions within that window.

Before you buy supplies

You'll work with charcoal, graphite, oils, and acrylics.

Art materials are purchased separately from the $99 Challenge. A supply guide and project instructions are included with your lessons. Here's an overview so you can look at what you already own before deciding to join.

For the two drawing projects

  • Drawing paper and the project reference images.
  • Vine or willow charcoal and a kneaded eraser for the portrait.
  • Graphite pencils, an eraser, and a sharpener for the animal drawing. The lesson lists HB, 2B, 4B, and 6B pencils.

For the oil paintings

  • Oil paints, painting brushes, and canvases.
  • Linseed oil, the solvent specified in the supply guide, and a suitable container.
  • A cotton rag and tools for lifting paint, such as cotton swabs or sponges.
  • The project reference images.

For the acrylic bear

  • Acrylic paints and brushes.
  • A black canvas, or paper painted black as described in the lesson.
  • White charcoal or a small brush with opaque paint for the initial drawing, plus water and paper towels.

Do canvas sizes matter?

The parrot lesson uses an 18 × 24-inch canvas. The oil portrait instructions call for 16 × 20 inches or larger and specifically advise against going smaller. Check the project guide before buying your surfaces.

How much will supplies cost?

That depends on what you already have and what you choose to buy. Supplies aren't covered by the enrollment price. If you're starting from scratch or want to substitute materials, email info@milanart.com before enrolling so you can check what you'll need.

Want to check the full list now? Open the Challenge art supply list (PDF). You can review it before you enroll.

After you join

You can open the lessons before your cohort starts.

1. Get into your account.

Your lessons are in the Milan Art App. Use the same email address you used at checkout. If you're new, look for the welcome email from milanart@mn.co and follow the Get Started link to set up your account.

2. Get ready to make art.

Open the TOA Two Week Challenge, watch the getting-started lesson, and review the workbook and supply guide. Your confirmation information gives you your cohort date.

3. Meet your Saturday cohort.

Your Challenge community, coaching, and live group calls begin with that cohort. Your 30-day lesson and feedback period runs from its Saturday start date.

Already have a Milan Art account?

Sign in using the email you used to purchase. If the Challenge doesn't appear or you purchased with a different email, contact the team for help connecting your access.

Can't find your welcome email?

Check your spam and promotions folders, then email info@milanart.com. You can access the community in a web browser at app.milanart.com or use the Milan Art App.

From a Challenge participant

“I can't believe what I've learnt and how well I can paint since I have taken the 2-week challenge”

Tracey Power, Google Play review, July 15, 2026
Read the review on Google Play

You can also read reviews of Milan Art Institute on Trustpilot. Those reviews cover the institute's programs, beyond this Challenge.

Your Challenge enrollment

Five projects, complete lessons, and personal feedback.

$99 one time

There's no subscription. Art supplies are purchased separately.

If you decide to continue into the Mastery Program, your $99 Challenge payment can be applied toward it. Joining the Challenge doesn't enroll you in the Mastery Program automatically.

Join the Challenge for $99

Lessons open immediately. Coaching begins with your Saturday cohort. Lesson access and feedback last 30 days from that start date.

Here's what you get.

  • Full instruction for two drawing projects and three painting projects, including the multiple stages of the oil and acrylic paintings.
  • The Challenge workbook, project assignment briefs, reference material, and supply guide.
  • Personal artist-coach feedback on the Challenge assignments you submit during your access period.
  • The Challenge community and live group calls with your cohort.
  • A suggested two-week project schedule, with 30 days of lesson access and feedback from your Saturday start.
  • A “How to Sell Your First Painting” bonus for finishing your five projects.

A few more things you might be wondering

Let's answer those, too.

What if I don't think I'm talented enough?

You can begin without already knowing how to draw a face or paint in oils. The lessons teach the process, and your coach can respond to the art you make. Expect to learn through practice, questions, and corrections. Your first attempt doesn't need to match the lesson artwork.

Do I need to attend the lessons at a particular time?

The project lessons are recorded. Watch and pause them when you have time, within your access period. Live group calls have their own schedule, which is shared with your cohort in the community. If attending calls is essential to your decision, contact the team to check the schedule before you enroll.

Can I work on only the projects that interest me?

You can choose how to use your lesson time. The full Challenge is designed around completing and submitting all five assignments, and the completion bonus is tied to finishing those five projects.

Does my art have to meet a certain standard to count?

Challenge completion is based on submitting all five assignments. It's about participation and practice, rather than making every piece perfect.

Is this digital art, or will I use real art materials?

The instruction and community are online. You'll make the drawings and paintings on your own paper and canvases using charcoal, graphite, oil paint, and acrylics. You'll need internet access to watch the lessons and a way to photograph and upload your art for feedback.

Is the entire Mastery Program included?

The Challenge includes these selected projects from the Mastery Program. The full program is a separate enrollment. You can use the Challenge to experience the instruction and coaching before deciding whether you'd like to continue.

What happens after the Challenge?

You can take the techniques you've practiced into your next drawing or painting. If you want a fuller course of study, the team can explain the Mastery Program and how to apply your $99 Challenge credit. Continuing is your choice.

What if I need to check something before buying?

Email info@milanart.com. In particular, check with the team before enrolling if you need a different cohort date, have questions about refunds, or need to confirm whether the call schedule or supplies will work for you.

Give yourself five projects to learn from, and a coach to help you improve.

Start with the lessons. Make your first piece. Bring your questions to your coach, then use what you learn in the next one.

Join the Challenge for $99

One payment. Supplies separate. 30-day lesson and feedback access from your Saturday cohort start.