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100 Day Portrait Challenge: 10 Tips for Success

Updated: Mar 6

The 100 Day Portrait Challenge is a free Instagram art challenge hosted by artist A.J. Alper. He generously shares his tips, advice, and video demos on how to paint portraits. I first started the challenge in August 2019 and completed it in December 2019. I learned a lot about not only how to make portraits, but more importantly, I also learned more about what kind of artist I want to be and what habits I need to practice so I continue to grow and improve as an artist.


In this post, I share the top 10 things I learned from doing the challenge. This list is a reminder for me to keep up the art-making habits I developed from the 100 Day Portrait Challenge and I hope it helps other artists participate and complete the challenge.


How to Prepare Yourself For the 100 Day Portrait Challenge


Motivation and Mindset


1. Decide what kind of artist you want to be by the end of the challenge. Having an intrinsic motivation for why you are participating in the challenge will help you stay focused each day. It also will help you make decisions about how you work and what you work on during the challenge. For example, I wanted to accurately recreate how a person’s face looks so throughout the challenge, I looked for techniques to help me learn how to do that and then I practiced using those techniques in each portrait.


2. Give yourself time to be creative. One of my big issues when I started the challenge was finding time to work on my art. I always seemed to have something else that was more important than my work. Looking back, I realize now that my procrastination came from my fear of putting myself out there. I had to learn how to give myself permission to be creative. Artist and Psychotherapist Nancy Hillis talks about learning to trust yourself and step into your creativity in her book The Artist’s Journey: Bold Strokes to Spark Creativity:

Trust yourself to explore the things that scare you. These are the unexpressed, unexplored parts of yourself where your un-lived dreams reside. This is the realm of play, improvisation, and pure creativity. This is where the magic is.

- Nancy Hillis, The Artist’s Journey


I committed to spending one hour every morning, right after I sent my kids to school. Instead of loading the dishwasher or running the laundry, I went to my desk. I initially set up a timer, but I soon realized that once I just started working, the one hour would eventually turn to 2-3 hours as I got more involved in what I was doing. The important thing was to just start.

Your Environment and Materials


3. Make it easy to get started each day. In his book, Atomic Habits, author James Clear talks about how much your environment influences your habits. He talks about designing your environment so you have multiple cues to remind you to do your new habit. For me, this meant I had to set up my art materials right next to my easel so I could just walk right up to it and get to work.


4. Have your photo references ready. I spent way too much time trying to pick out photo references to draw. Pick them out ahead of time and print them out or else you’ll waste valuable art-making time scrolling through the Internet. Make sure to credit your photo references because it helps you connect to other photographers who have similar interests in the kinds of people you want to draw or paint.


5. Pick photo references that are support your learning goals. I wanted to learn how to accurately capture a person’s likeness so I realized that I had to pick photos that made it easier for me to see shadow shapes on the face. When the shadows under the eyebrows, the nose, and the lips are dark and have relatively hard edges, I found it easier to draw the shadows and make the face look more realistic. You might want to focus on drawing specific facial features, like noses, or types of people.

Examples of portraits I did based on photo with good shadow shapes.

How to Make Significant Progress During The Challenge


Mind Tricks to Push Yourself


6. Focus on exploration, not completion. Since the main reason I joined the challenge was to spend learn how to make better portraits, I experimented with many different mediums and tools. Some of these supplies I had been hoarding for years. This was the perfect opportunity to try something new and see what happened. I specifically told myself to think about learning and not trying something to sell or add to my portfolio or hang in a show. Removing the pressure to make beautiful work right away made it easier to just have fun. And when I found something I liked, I looked for ways to make it easier to do over and over again.


7. Work in a series. The idea of creating 100 portraits can be overwhelming. Around Day 50 of the 100 Day Portrait Challenge, I started to focus on exploring a specific theme for the week. One week I spent on pencil drawings and the next week, I worked on charcoal drawings. Another example is when I also participated in #Inktober; I used Alphonso Dunn’s book Pen and Ink Drawing as a guide and practiced one of his techniques each week. Breaking up the time into smaller chunks made the challenge feel less like a grind because I could review my work and appreciate how much I learned just hat week.


8. Work on multiple pieces at one time. During Days 70-80, I got stuck in another rut so for Days 78-80, I started and worked on three portraits all at the same time for three days. This process gave me permission to move from one portrait to another when I started to feel stuck or frustrated. When I came back to the portrait, I found new things I could work on and I could apply something I learned from doing the other portraits.

Days 78, 79, and 80 from the 100 Day Portrait Challenge by Filipina Pate.

Find Resources and Support


9. Learn about the anatomy of the head. I had a big epiphany on Day 46 when I learned about facial anatomy. When I first started, I used to look a series of different landmarks that you need to measure and connect to form the face. This approach works, but when you learn where the facial muscles and skull bones are located it makes it easier to add values to your portrait.


10. Reflect on your work. One of the important, and maybe the most underrated, benefit from doing the challenge is that you have a chance to reflect on what you learned that day. My daily post helped me remember what I was trying to teach myself with each portrait. What did I do well in yesterday’s portrait that I want to do in today’s portrait? What should I avoid? Writing a daily post made me feel more responsible for how I was spending my time on this challenge. I believe it played a large part in helping me gradually improve.


Final Thoughts


The biggest thing I learned from doing the 100 Day Portrait Challenge is: A little progress every day adds up. Doing a daily challenge is a big time commitment and a test of your patience and perseverance.


If you’re in the middle of the challenge, keep going. If I can do it, you can too. It will feel slow sometimes, so try to mix it up with media or techniques or subjects. Maintaining a growth mindset helped me remove the pressure to finish a perfectly rendered, photorealistic portrait and focus instead on how to improve each day.


If you’re thinking about doing the challenge, decide how much completing the challenge matters to you. How do you want this challenge to help you become the kind of artist that you want to be? If you have a clear answer to this question, you’re more likely to make the most of this challenge. If you don’t have a clear answer, I recommend you try a smaller, shorter version of the challenge and review if you want to keep going.


I hope this post has been helpful. Let me know in the comments if you have other questions about the challenge and good luck with your art!


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