2021 Spring Acrylic Portrait Painting Challenge is Coming!

It was last year around this time that I got news of my state doing a lockdown because of the new coronavirus that was spreading like wildfire.

I thought, What would happen to my art business? I won’t be able to do art shows or teach classes anymore. If the economy tumbles, will I be able to pay the mortgage?

You probably had similar thoughts brewing in your mind too. You still remember what it felt like after the initial news of this unknown pandemic.

Many businesses were hunkering down, trying to stay afloat while the sea of uncertainty and fear poured in around them.

I didn’t know what to do either.

But one of my business mentors, Graham Cochrane, said “this is not a time to hold back. This is a time to be generous.”

I thought, “I could do a portrait challenge. Many artists are stuck at home, sheltering in place. It would not only give us all something productive to do, but would help conquer the fear that can come from just letting our thoughts run wild.”

Additionally, I could teach a whole class on how to paint this portrait, for free, showing all the steps from start to finish.

But then the other side of my mind protested, “If you do that, if you give it all away for free, who will ever buy your courses again?”

“No!” the right side of my brain said.“I’m going to trust God. I’ll be generous like Jesus is to me and just trust God will take care of me and my family!”

So I listened to that part of my brain (and God) and launched the Spring Portrait Acrylic Painting Challenge. We painted this portrait of “Lockdown Larry” the man with the hat, supplied by

Matt Philleo painting an acrylic portrait from a photo for the Spring Portrait Painting Challenge, ©2020 by Matt Philleo

Over 700 artists took the challenge. Many never painted a portrait before, but through their hard work and perseverance, at the end of the challenge produced a portrait they could be proud of!

Some even said they were struggling with severe depression, and the challenge helped lift them out of it!

When the challenge was over, some of these artists went on to do commissioned portraits and are now thriving! Others are painting portraits of their grandchildren, loving every moment of creating a special gift they can give and capture memories.

What a joy to hear these stories and be a part of it!

And the teaching side of my art business has increased incredibly since the challenge last year. God has blessed me and my family. The best part is, I am part of a wonderful community of artists in the All-Access Membership. We have such a great time learning and encouraging each other to do our very best portrait work.

Well, it’s almost spring here in Wisconsin and we are doing the challenge again. I will soon be putting out a call for images that we can vote on as a group to paint from.

I am excited and look forward to teaching you and helping you paint a portrait you can be proud of!

—Matt