Head Drawing Challenge

Do you want to improve your head drawings and portraits but are struggling to stay motivated to draw? Do you need structure and accountability to make your practice time more organized and productive?

If you want a fun and challenging way to improve your head drawing and join a worldwide community of like minded artists, join the official 2020 Head Drawing Challenge.

What is the Head Drawing Challenge?


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This challenge is a fun way to add structure to your drawing time and give you the motivation to draw EVERYDAY. To keep themselves accountable and record their progress, artists share their daily drawings everyday on social media.

Take the Head Drawing Challenge

To make this an opportunity to focus and improve head and portrait drawings, I’ve created three unique challenges:

#1 Timed Poses Challenge

#2 Anatomy Challenge

#3 Masters Challenge

As a bonus, I’m also offering prizes to selected winners who complete the challenge.

Scroll down for complete information and details of the the guidelines, challenges and prizes…


Free Lessons & Resources


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To help you make the most of the Head Drawing Challenge, I’ve created a free Head Drawing Quick Start Mini-Course. This course has 7 unique lessons that include videos, text and handouts. Each lesson will help you with a different topic in head drawing and help you to complete the 2020 Head Drawing Challenge.

Here’s the lessons you’ll receive:

  1. How to Start a Head Drawing

  2. How to Get a Likeness

  3. How to Draw with Planes and Rhythms

  4. How to Draw the Features

  5. The Eyes and Facial Anatomy

  6. Shading Techniques in Pen and Marker

  7. How to Learn from a Master

Each lessons will be sent directly to you by email. You will receive a new lesson everyday for 7 days.

This special Head Drawing Challenge Mini Course is available for free. To get started, enter your email below and click ‘Get Access’ to join today.

To learn more about the official official challenges and how to qualify for prizes and giveaways, scroll down for complete information and details…


Official Guidelines

This challenge is a fun way to get motivated and focused to draw everyday for the month of October 2020. Here are the official guidelines for the 2020 Head Drawing Challenge.

#1. Complete at least one drawing everyday from one of the selected head drawing challenges (see below).

#2. Make a daily post of your completed daily drawing to the official Facebook group.

That’s all that’s needed to participate in the challenge and also qualify for the prizes.


Official Head Drawing Challenges

For those who want to make Inktober a month to focus on and improve their head and portrait drawing I’ve created the following structured challenges. These challenges are the same assignments I give to my students to help them improve rapidly.

For some incentive to complete the month long challenge, I’m offering prizes as a reward for selected winners. See ‘Prizes and Giveaways’ below for more information on how to win a prize for completing the challenge.

Challenge #1 – Timed Poses


5 min poses from life, ballpoint pen and marker on toned paper.

5 min poses from life, ballpoint pen and marker on toned paper.

Description: Improve your drawing and observation skills by drawing from a timed life drawing pose or use a timer.

Dates and Topic:

October 1 – 7 = 5 minute poses

Oct 8-14 = 10 minute poses

Oct 15-21 = 20 minute poses

Oct 22 – 28 = 30 minute poses

Oct 29 – 31 = 1 hour drawing*

*Note: For the longer, drawings, 30 minutes to 1 hour, the same drawing can be worked on over multiple days or drawing sessions. For example, if a drawing takes 3 (or more hours) to complete but at least 1 hour a day is spent on the same drawing , then this meets the requirements for this challenge.

Challenge #2 – Anatomy Challenge


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Description: Improve your portrait drawing realism and accuracy by studying the anatomy of the head and human body everyday. For those who want to invent or draw faces from imagination with accuracy and consistency, knowledge of anatomy is a must for your toolkit.

Dates and Topic:

October 1 – 7 = Skull studies in multiple views and positions

  • Day 1 = Front

  • Day 2 = Side

  • Day 3 = 3/4

  • Day 4 = Looking up

  • Day 5 = Looking down

  • Day 6 = Extreme up view (head looking up)

  • Day 7 = Extreme down view (head looking down)

Oct 8 -14 = Facial muscles in multiple views and positions

  • Day 8 = Front view

  • Day 9 = side view

  • Day 10 = 3/4 view

  • Day 11 = looking left 

  • Day 12 = looking right

  • Day 13 = looking up

  • Day 14 = looking down

*Note: for anatomy studies, copies of medical diagrams or other anatomy illustrations are acceptable and recommended. 

  • Oct 15 – 21 = Facial features

  • Day 15 = eyes, front & side view

  • Day 16 = nose, front and side view

  • Day 17 = mouth, front and side view

  • Day 18  = eyes in various positions

  • Day 19 = nose in various positions

  • Day 20 = mouth in various positions

  • Day 21 = Ears in front, side, top and bottom view

Oct 22 – 31 = Anatomy of the neck and upper torso

  • Day 22 = neck muscles, front view

  • Day 23 = neck muscles, side view

  • Day 24 = neck muscles, 3/4 view

  • Day 25  = neck muscles, head looking left/right

  • Day 26 = neck muscles, head looking  up/down

  • Day 27 = bones of the upper skeleton, front view 

  • Day 28 = bones of the upper skeleton, side view

  • Day 29 = bones of upper skeleton, back view

  • Day 30 = Upper torso muscles front view

  • Day 31 =upper torso muscles back view

Challenge #3 – Masters Challenge


Master copy after Ilya Repin, ballpoint pen on toned paper.

Master copy after Ilya Repin, ballpoint pen on toned paper.

For those who want to improve their shading, finishing and composition and overall understanding and mastery of portrait drawing, studying and copying the work of great master artists from history is an excellent practice. If you want to make the most of this Inktober this year, study the work of these great masters from history:

Oct 1 – 7 = John Sargent and Anders Zorn (paintings, drawings or etchings)

Oct 8 – 14 = Diego Velazquez

Oct 15 – 21 = Rembrandt (paintings or etchings)

Oct 21 – 28 = Ilya Repin and Nicolai Fechin drawings

Oct 29 – 31 = Dean Cornwell (paintings or drawings)


Official Facebook Group

To help you stay motivated to draw everyday and communicate with fellow artists from all over the world, I’ve created the official facebook group for this challenge.


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—>Click here to join the official Facebook group….

Facebook is the best way to get your work seen and archived. Making daily posts will allow you to see and track your progress. You can also be a part of a worldwide community so you can stay motivated by supporting other fellow artists who are on the same journey.

For those who want to qualify for the prizes, I will use Facebook to review your work at the end of October. Winners will be selected from those who draw and post everyday for the entire 31 days.

When you make a post make sure to include the day and the hashtag #dwcchallenge. For example:

“Day 15 #dwcchallenge”

For Instagram users

You may also participate in the head drawing challenge by sharing your work on instagram. To qualify, simply make a daily post and use the same format as facebook. For example…

“Day 15 #dwcchallenge”

Make sure to also tag @chrislegaspi_art in your post description.

The most important thing is to draw everyday and make sure your all of your can be easily reviewed at the end of the month.


Prizes & Giveaways

To provide some motivation to complete the challenge and draw everyday, I’m offering the following prizes:

#1 First prize

Full Scholarship to Master Head & Portrait Drawing Online Class ($597 value)

Scholarship Winner will receive full access to one semester of Mastering Head Drawing Online Class. This includes the live lectures, weekly critiques, private Facebook group and student resource Dropbox.


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#2 Second prize 

Signed original pen and ink portrait drawing  ($500 value)

#3 Third Prize

Signed original, timed pose head study ($150 value)

To be eligible for a prize, winners must:

  1. Meet the official guidelines (see above)

  2. Complete their selected challenge, and

  3. Make a daily post in the Facebook group

Winners will be selected randomly in the first week of September 2020. Winners will be notified by email. If you are not already. make sure to subscribe for email updates and notifications.

Subscribers will also get access to the free Head Drawing Quick Start Course and other free resources in the members area.