To start the new year, I decided to try a series of personal challenges. For January, I wanted to answer a simple question: In just 30 days, could I master the self-portrait using only pencil and paper?

I documented my learning progress through a series of tweets and weekly emails that I compiled to create this post. I shared my starting point, my struggles, and what I learned along the way.

If you would like to stay up-to-date on any future challenges (and even get to vote on what I do next), be sure to sign up here:

My Starting Point

I began 2020 with the self-portrait challenge because I am not starting from zero with regard to artistic skill and ability. While I have never had any formal lessons or instruction, drawing has always come naturally to me. I spent a lot of time drawing as a kid but haven't invested any time developing the skill since highschool.

For this reason, success (while subjective) will be measured by whether or not I can master the self-portrait. The photo below demonstrates the level of quality I'm aiming for:

Example self-portrait
Example portrait from Vitruvian Fine Art Studio

The Rules

Before I go into the details of the challenge, let me explain the constraints I set for myself:


This challenge was strictly for January. I started drawing on January 1st and completed the challenge on the 30th. I allowed myself to use as much free time as possible to work on the challenge, although not all days were created equal. When it was all said and done, I spent a total of 31 hours on the challenge.


The challenge solely focused on pencil drawings, but I did use particular materials to assist in making the drawings as realistic as possible. Here is a list of all of the materials I used:


While there are many methods for drawing portraits, I referenced photographs displayed on my laptop to complete my drawings. I did not use any projections or real photographs that could be used for tracing. My goal was to see how much I could improve my perceptual and artistic skills by translating what I saw onto paper.

The Challenge

Week 1

I began the challenge by drawing my profile picture to gauge my starting point. Instead of spending any time upfront to learn professional portrait drawing techniques, I just started drawing so I could knock the rust off and begin building a daily drawing habit.

Self-portrait with pencil
Making progress on my self-portrait

I spent the next eight days trying to produce the most realistic self-portrait possible. In no time, I felt comfortable using the pencil again, almost as if I had never missed a beat from highschool.

After roughly 6.5 hours of total drawing time, I finished my first attempt.

My first self-portrait
First attempt at drawing a self-portrait

Overall, I thought it turned out quite well, but there are obvious areas in need of improvement. Some brief observations from my first attempt:

  • The importance of getting the proportions right before moving on (eyes too big and head not shaped properly).
  • I have no idea how to draw hair or lips correctly.
  • Knowing how to blend (shade) is half of drawing and can easily improve your work if you're used to line drawings.
  • It's fun to return to the hobbies that you enjoyed doing as a kid.

Even though my first attempt turned out well, it didn't meet my standard for what I would consider mastery. I can improve, but I lack the fundamentals to make the desired leap in such a short time. If I want to advance quickly, then I will need to seek professional help.

Week 2

I went searching for a way to quickly improve and soon discovered the Vitruvian Studios Portrait Drawing course. The course offered a comprehensive procedure for drawing realistic portraits by teaching a method of triangulation and "blocking-in". The course defines triangulation and the block-in method as follows:

“Triangulation” is a concept in trigonometry that says given any two points (A and B), we can find any third (C) if we know the angle of AC and BC. This concept is extremely useful in drawing where we seek to locate salient points of an object or composition.
The Block-in is the first stage of our drawing process where we try to get the broad proportions and structures of the head defined correctly... A Block-in is usually executed with broad, fluid, straight lines that reduce the subject to large geometric shapes.

I spent the remainder of the week working through the 10-hour course. At first, I just watched the videos to gain an understanding of the fundamentals but eventually restarted the course so I could draw along with the instructor.

I also purchased some new art supplies to aid in the drawing process. I bought a drawing board, white chalk pencils, 8B black pencil, and toned-gray drawing paper to add to the supplies I already owned. Learning how to use these new tools should help with producing more realistic work.

By the end of the week, I had the positioning and proportions of the model from the course down on paper.

Block-in method for drawing a portrait
Creating a portrait using triangulation and the block-in method

Week 3

I spent the entire week working through the portrait drawing course. My focus was to internalize the techniques taught in the course so I could apply them to my final self-portrait in the last week of the challenge.

I intended to finish the course by the end of the week, but I ended up completing just 80% of the course and starting to run short on days.

Pencil drawing progress
Week 3 progress

Week 4

I finished the course on the 25th, leaving me with six days to redraw my self-portrait. The last 20% of the course took much longer than expected due to the amount of detail covered in the final videos.

Even though I finished the course, the practice drawing I was working on was left incomplete. Due to time constraints, I decided to stop working on the drawing before finishing the details to her hair, neck, and shirt. I may revisit the drawing at a later date, but for now, I must move on to my final self-portrait.

Pencil drawing
Final progress of practice drawing

Final Results

I decided to redraw my profile picture so I could compare it to my first attempt. Doing so should make it easy to observe any progress I've made throughout the challenge.

However, I did make one big change between attempts. I decided to switch from using a cream paper to a toned gray paper to help with the transitioning of shadows. While this may seem like a minor detail, it could end up saving me a lot of time, which is of vital importance.

Reattempting the self-portrait
Using the techniques taught in the course to shape my face

Using the methods and techniques taught in the portrait drawing course, I set out to recreate my self-portrait. Having the proper fundamentals to rely on right from the start was a significant improvement from my original style of "winging it."

By this stage, I was comfortable enough with the techniques to hone in on my craft and make notable progress. After six days and roughly ten focused-hours later, I completed my challenge on January 30th with one day to spare.

Final self-portrait
My final self-portrait

What Did I Learn?

Thirty days ago, I set out to answer whether or not I could master the self-portrait. While I think there is still room for improvement, I am happy with how the final result turned out. I proved to myself that you could make significant progress towards a goal if you are dedicated to working at it every day, even if just for a month.

It was also an exciting time for rediscovering something I loved doing as a child. There is something deeply human about losing track of time while you fully immerse yourself in the creative process. The challenge further confirmed my belief in the importance of devoting some of your time towards a creative outlet.

More specifically, the challenge taught me a few important lessons:

  • Materials don't make the artist, but having the right materials will make a good artist an even better one.
  • Drawing, like any skill, can be improved no matter your current skill level. If your practice is deliberate and consistent, you will also improve quicker than expected.
  • Block off some time each week to create. It can be drawing, painting, writing music, or creating a new recipe — it doesn't matter. We are all meant to create, so find that thing you enjoy doing and give yourself time to do it.

And finally, a comparison shot of my self-portrait attempts 17 days apart from each other.

Before and after self-portrait comparison

Trying the Challenge for Yourself

If you would like to try a 30-day drawing challenge for yourself, here are some of my recommendations:

  • If you're new to drawing or have limited ability, don't start with the Vitruvian Studios Portrait Drawing course. Instead, I would suggest you check out the popular book, Drawing on the Right Side of the Brain.
  • If you already have some artistic ability, then start with the Vitruvian Studios Portrait Drawing course.
  • Learn how to prepare for a 30-day challenge so you can give yourself the greatest chance of success.

It's important to remember that everyone begins with different levels of skill and ability, so your final results may vary. Ultimately, the amount of progress you make will be tied to the amount of time you're willing to dedicate to practicing.

If you enjoyed reading about the challenge and would like to like to stay up-to-date on any future challenges (and even get to vote on what I do next), be sure to sign up here: