Portrait Drawing Challenge Takeaways

Amy Beach, one of the first well-known female composers from the U.S.

My January portrait challenge taught me a number of things. The most important?

I don’t ever want a job drawing just composers. Especially ones with wigs. Take a hike, Mozart.

(Here are round 1 and round 2 of my month-long challenge.)

More insightful revelations also surfaced.

For one, our brains lie to us all.the.time. They tell us that the eye line for faces is higher than reality. That eyes are ovals, that ears are squished up tight to the face for profile drawings.

For instance, these tabletops are the same size. My left brain still doesn’t believe me. Measure them if you don’t believe me!

My skill development plateaued around week 2-3. I wish it simply coincided with being siiick of drawing old dead guys, but I think it was because I was just doing drawings vs deliberate practice and exercises to improve my beginner skills.

I’m slowly working on overcoming left brain bias via Drawing on the Right Side of the Brain, but I simply didn’t dedicate enough time to the exercises. There are still so many basics I need to focus on to continue improving:

  1. Perceiving negative space
  2. Positioning of facial features
  3. Sighting (aka measuring relative sizes of things and transferring it to a drawing)
  4. Light logic (aka shading, but I sound cooler using art expressions)

Deliberate Practice Works Better

My friend Jono sent me a blog post on a portrait drawing challenge from the author of Ultralearning. That dude spent a month drawing FIVE HOURS (!!) a day, much of it deliberate practice.

Moving forward, I’m planning do follow his example and do the following:

  1. Study drawing techniques and practice them.
  2. Do multiple quick sketches to improve placement of facial features.
  3. Overlay drawings on the original image to compare them.
  4. Not draw only composers. Maybe I’ll do a mountain biker series?

To be fair, I drew Taylor Swift and a self-portrait. The latter will be a good reference point for future development, even if it annoys me that my eyes are too narrow, my jaw too square, and so on. Baby steps…

All in all, this was a useful, enjoyable challenge that yielded solid improvement with only 30-45 minutes a night of effort. A benefit is that I’d listen to each artist’s work while I drew, so I exposed myself to new work.

But for now, it’s back to T. Rex fail drawings for awhile. Onward!

By the way, dig these kinds of posts? Sign up for the free Traipsing About newsletter to level up your life around outdoor adventures, creativity, and travel.

This final round of portraits included: 

  1. Fabrizio Paterlini – modern Italian composer.
  2. John Lennon – maybe you’re heard of him?
  3. Taylor Swift – Chelsea rocked her music all last week, so why not draw Taylor?
  4. Phillip Glass – modern minimalist composer
  5. One of my favorite musicians: self-portrait of me!
  6. Upside-down drawing of Stravinksy – an exercise to decouple the left and right brain
  7. Joseph Kosma – composer of the jazz standard Autumn Leaves
  8. Dirk Maassen – modern German composer. I’m listening to this excellent album by him right now.
  9. Mozart – yup.
  10. Amy Beach – one of the first famous female composers from the United States.
  11. BEETHOVEN, BABY! He’s looking rather serious, but his long lashes soften the stern aspect.

And as a reminder, here’s where I started earlier this month…

Ludovico Einaudi portrait
Portrait #1: Ludovico Einaudi…eyes wayyyy too high and so on!

Let’s make this easy: here’s the 2nd batch, followed by the first! Satisfying to look back and see progress.

Second round:

First round:

Beethoven portrait sketch

Ditching a Self-Bullying Mindset

monteverdi composer sketch portrait
As part of learning to draw and reading about music history, I’m doing a quick daily portrait of a composer. Here’s opera pioneer Monteverdi and his badass beard.

I’m one of those Type-A people who enjoys filling a 30-day calendar challenge with X’s. Solidly motivating for me, or at least a simple reminder to practice my Italian!

Recently I saw a challenge with a different take: a repeating loop of “do activity, get less awful.” (Paraphrased.)

I found it funny…until Chelsea pointed out how that mindset is essentially bullying myself. Which hadn’t registered at all for me. 

In fact, I often beat myself up for falling short of self-prescribed expectations. I want to be GOOD at things. But what does that even mean? 

If we think we’re not “good” at something, is there a finish line? There’s always someone more skilled at a hobby, richer, fitter than us.

How freeing would it be to drop all (or at least most) comparisons and be happy with our efforts and current abilities simply for the joy of the activity? Enjoy the journey, not the results. Draw composers because the process entertains me, not for the finished sketch.

Would you trade it all?

Reminding myself how much effort and sacrifice goes into proficiency – much less mastery – of anything helps me gain perspective. As Ryan Holiday writes, would you permanently swap your entire life with someone – negative and positive aspects – to have their talent?

I sure wouldn’t trade all my hours of travel and outdoor adventures for portrait drawing ability or the wizardry to play Beethoven piano sonatas. (Welllll…how many hours are we talking here?)

This felt like a powerful reminder that approaching life’s activities with a negative mindset – “I’m not good enough, so I need to improve myself” is a recipe for life-long disappointment. “I’m bad at piano, so I need to practice” pales for long-term motivation next to “this process is satisfying and I’m excited about learning it no matter the progress.” I want to practice the latter.

What if we talked to ourselves the way we talk to a best friend? Supportive. Inquisitive. Loving us for who we are and celebrating us as a human being, not a human doing. If we can do that for our closest friends, surely we can do so for ourselves.

I’m still aiming to put the X on the calendar to keep my streaks alive. And also to feel fine if I miss a day or struggle with a piece of music.

Practice–>Enjoyment–>Practice–>Enjoyment. That’s a loop I want to be in!


P.S. Check out this podcast with Jim Loehr from minutes 25-30 for more insight on our inner voice. From the chat: “Would you broadcast what your inner voice is saying on a Jumbotron?”

Beethoven portrait sketch
Beethoven! Looking a bit stern and with six fingers because hands are impossible to draw. Just ignore the bike flying over his head.