The Art Biz ep. 145: Gaining Marketing Skills Quickly by Leading a Creativity Challenge with Kristen O’Neill

In art school, teachers and professors give provocative assignments to help students explore materials, methodology, and subject matter. To push them.

After school, and without this instruction, we’re left to our own to experiment. To find inspiration. To source ideas and material worthy of our attention.

We must recognize on our own when we’re in a rut and need fresh insights.

We have to, in a sense, create our own assignments to keep us engaged with our work.

Kristen O'Neill painting
©Kristen O'Neill, Cushendall Coastal Path, Northern Ireland. Acrylic on Panel, 12 x 12 in.

In this episode of The Art Biz, I talk with Kristen O’Neill, who has been a team member of mine for 5 years. In the Art Biz Connection community, Kristen serves as an artist mentor to help answer questions and share her experience.

Kristen is an accomplished artist and, like me, a former museum educator. In January of this year, she created a 30-day challenge for her online followers to help kickstart the New Year.

As you’ll hear, the challenge consisted of daily art lessons for those who took her up on it. But I’m not sure if it was more of a challenge for them or for her.

Kristen and I discuss:

  • What she hoped to get  from this challenge (and if she got it).
  • How she organized the many moving parts.
  • How much of it was planned ahead.
  • What her workflow was like—including all of the platforms she used to share the content.
  • What she would do differently if she were to do it again.


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  • Details of Kristen’s 30-Day Art Challenge and what she hoped to get out of it. (1:29)
  • How Kristen shared the challenge while honoring her email list expectations. (6:10)
  • Creating and organizing a workflow that worked all month long. (10:42)
  • The time commitment and unexpected challenges behind the challenge. (16:35)
  • Lessons learned from the challenges of this challenge. (22:25)
  • Staying motivated and accountable throughout a challenge. (27:52)
  • Tracking the participation, success, and results of the challenge. (30:15)
  • The value of Pinterest for artists. (38:30)
  • What Kristen would do differently next time. (41:07)
Kristen's 30 Day Painting Challenge spreadsheet.

Kristen O'Neill Quotes

  • “I’m always looking for different opportunities and ways to reach out to more students and interact with more painters.” 
  • “It’s really important to honor what you say you’re going to do with your list.” 
  • “I picked up lessons more quickly than had I done the same amount of work spread over a longer period of time.”
  • “If you haven’t figured out your system ahead of time, it’s going to be harder than it needs to be.” 
  • “Often we spend so much time guessing what is the right way to do something, and we could put that energy into just doing it.” 

About My Guest

Kristen O’Neill paints the essence of landscapes based on real locations, including those from recent collaborations with long-distance hikers. Her Oregon Coast Trail series was also featured in a solo exhibition at the Grants Pass Museum of Art.

Kristen graduated from the School of the Art Institute of Chicago, and now lives in Southern Oregon where she has become passionate about teaching art. She teaches both online and in-person, leads a field trip program that has taught art history to thousands of 5th graders, and is an Artist Mentor for Alyson Stanfield’s community.

Follow her on Instagram @kristenoneillart

Kristen O'Neill

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