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The Painting Possibilities Podcast
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The Painting Possibilities Podcast

Author: Ashley Cassens

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An art-biz podcast that explores the honest version of how I quit my day job to paint full-time. Listen in for an open conversation of how I'm creating, while navigating motherhood and making money in the real world.
9 Episodes
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In this episode of the Painting Possibilities podcast, Ashley shares her journey of transitioning from a day job to painting full-time. She discusses the key insights she gained about growing her art business, including the importance of audience engagement, social media presence, and education. Ashley emphasizes three essential strategies that truly moved the needle in her career: effective pitching, having solid contracts, and continuous skill development. She encourages artists to focus on what truly matters for success rather than getting caught up in follower counts or formal credentials.TakeawaysThe size of your audience doesn't determine your success.Engagement and connection are more important than follower counts.Social media is not the only way to gain clients.Education can enhance credibility but isn't always necessary.Effective pitching can lead to significant opportunities.Contracts protect both the artist and the client.Skill development is crucial for long-term success.Networking with diverse groups can provide valuable insights.Tailoring pitches to specific businesses increases chances of success.Consistency in practice leads to improvement in skills.You can join my newsletter here:⁠⁠⁠⁠⁠www.ashleycassens.com/subscribe ⁠⁠⁠⁠⁠My FREE mural mock-up course:⁠⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠⁠⁠⁠⁠Portrait painting course:⁠⁠⁠⁠⁠https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric⁠⁠⁠⁠⁠Resources I love for Artists:⁠⁠⁠⁠⁠Honeybook⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Wave Accounting ⁠⁠⁠⁠⁠⁠⁠⁠⁠My actual contract⁠⁠⁠⁠Social:⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠Facebook⁠⁠
SummaryIn this episode of the Painting Possibilities podcast, Ashley shares her journey of transitioning from a day job to painting full-time while balancing motherhood. She discusses the challenges of vulnerability, the feelings of envy that arise when comparing oneself to other artists, and the importance of defining personal success beyond societal expectations. Ashley emphasizes the blessings of parenthood in teaching her the value of rest and recalibration, and she invites listeners to engage with her community.Chapters00:00 Introduction to the Journey02:03 Navigating Parenting and Creativity05:37 Dealing with Envy and Defining Success13:23 Making Choices: Opportunities and Parenting18:21 The Blessing of Parenthood in Creative WorkYou can find all my favorite art supplies ⁠⁠⁠⁠here⁠⁠⁠. You can join my newsletter here:⁠⁠⁠⁠⁠⁠www.ashleycassens.com/subscribe ⁠⁠⁠⁠⁠⁠My FREE mural mock-up course:⁠⁠⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠⁠⁠⁠⁠⁠Portrait painting course:⁠⁠⁠⁠⁠⁠https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric⁠⁠⁠⁠⁠⁠Resources I love for Artists:⁠⁠⁠⁠⁠⁠Honeybook⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Wave Accounting ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠My actual contract⁠⁠⁠⁠⁠Social:⁠⁠⁠⁠⁠⁠Instagram⁠⁠⁠⁠⁠⁠ ⁠⁠⁠⁠⁠⁠Facebook⁠⁠⁠
Summary The things I learned from window painting:It's okay to be a beginnerLet people in on the journeyRest can produce creativity and abundance in ways I wasn't expecting Chapters00:00 The Seasonal Artistry of Window Painting03:46 Pricing Strategies for Murals05:45 Personal Challenges and Running Events08:00 Injury and Its Impact on Work11:49 Social Media Engagement and Art13:17 The Snowball Effect of Window Painting15:37 Monetization Through Social Media17:51 Navigating New Artistic ChallengesYou can find all my favorite window supplies here. You can join my newsletter here:⁠⁠⁠⁠www.ashleycassens.com/subscribe ⁠⁠⁠⁠My FREE mural mock-up course:⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠⁠⁠⁠Portrait painting course:⁠⁠⁠⁠https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric⁠⁠⁠⁠Resources I love for Artists:⁠⁠⁠⁠Honeybook⁠⁠⁠⁠ ⁠⁠⁠⁠Wave Accounting ⁠⁠⁠⁠⁠⁠⁠My actual contract⁠⁠⁠Social:⁠⁠⁠⁠Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠Facebook⁠
In this episode, Ashley reflects on her personal growth journey, discussing her goals and intentions for the year. She shares insights on accountability, the significance of her 'word of the year', and the importance of creating space in her life and home. The conversation also touches on managing commitments, tracking health and fitness progress, and embracing new experiences.TakeawaysMy word of the year last year was Polish.I want to feel more spacious in my home.I took more time off last year than I ever did before.My word for this year is space.You can't do everything; balance is key.Chapters00:00 Setting the Stage: Personal Accountability and Goals03:12 Reflections on the Past Year: Word of the Year05:08 Intentional Living: Embracing Space and Time Off09:48 Balancing Life: Managing Overcommitment and Family Activities17:29 Health and Fitness: Tracking Progress and Accountability20:11 Navigating New Experiences: Learning and Growth22:32 Looking Ahead: Intentions for the FutureYou can join my newsletter here:⁠⁠⁠⁠www.ashleycassens.com/subscribe ⁠⁠⁠⁠My FREE mural mock-up course:⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠⁠⁠⁠Portrait painting course:⁠⁠⁠⁠https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric⁠⁠⁠⁠Resources I love for Artists:⁠⁠⁠⁠Honeybook⁠⁠⁠⁠ ⁠⁠⁠⁠Wave Accounting ⁠⁠⁠⁠⁠⁠⁠My actual contract⁠⁠⁠Social:⁠⁠⁠⁠Instagram⁠⁠⁠⁠ ⁠⁠⁠⁠Facebook⁠
5: Body Image + Murals

5: Body Image + Murals

2026-01-2620:09

SummaryIn this episode, Ashley reflects on her experiences as a woman in a male-dominated field, discussing the insecurities and challenges she faced while painting murals. She shares her journey of self-acceptance, the impact of gender on professional presentation, and the importance of embracing authenticity in the workplace. Through personal anecdotes, Ashley encourages listeners to overcome their fears and take up space, reminding them that they are not alone in their struggles.You can join my newsletter here:⁠⁠www.ashleycassens.com/subscribe ⁠⁠My FREE mural mock-up course:⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠⁠Portrait painting course:⁠⁠https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric⁠⁠Resources I love for Artists:⁠⁠Honeybook⁠⁠ ⁠⁠Wave Accounting ⁠⁠⁠My actual contract⁠Social:⁠⁠Instagram⁠⁠ ⁠⁠FacebookTakeawaysAshley shares her experience of recording a podcast every day for January.She discusses the insecurities she felt as a woman in a male-dominated field.The importance of self-acceptance and authenticity in professional settings is emphasized.Ashley reflects on the pressure to conform to gender norms in her work attire.She acknowledges the psychological impact of body image on her confidence.The conversation highlights the need for women to support each other in their professional journeys.Ashley encourages listeners to embrace their uniqueness and take up space.She shares insights on the dynamics of engaging with others in public spaces as a woman.The episode serves as a reminder that everyone has insecurities, regardless of experience.Ashley concludes with a message of empowerment and creativity.Chapters00:00 Introduction to the 31-Day Challenge01:50 Navigating Insecurities in a Male-Dominated Field04:30 The Impact of Gender on Professional Presentation14:50 Body Image and Self-Perception in the Workplace21:56 Embracing Authenticity and Taking Up Space
SummaryIn this conversation, Ashley discusses her journey from being a self-proclaimed terrible math student to embracing math as a vital part of her art career. She highlights how math has become a source of freedom and creativity, allowing her to express herself artistically while also managing her career effectively. The discussion explores the intersection of creativity and numbers, emphasizing that math can enhance artistic expression and personal growth.You can join my newsletter here:⁠⁠⁠⁠www.ashleycassens.com/subscribe ⁠⁠⁠⁠My FREE mural mock-up course:⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠⁠⁠⁠Portrait painting course:⁠⁠⁠⁠https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric⁠⁠⁠⁠Resources I love for Artists:⁠⁠⁠⁠Honeybook⁠⁠⁠⁠ Thumbtack⁠⁠⁠⁠Wave Accounting ⁠⁠⁠⁠⁠⁠⁠My actual contractTakeawaysYou can be a terrible math student and still succeed.Math is used daily in various careers, including art.Embracing math can lead to personal freedom.Creativity and math are interconnected.Learning math can be enjoyable and liberating.Math enhances artistic expression.Past struggles with math can be overcome.Art and math can coexist harmoniously.Understanding math can lead to personal growth.Math is essential for managing a successful career.
3: The big 3's

3: The big 3's

2026-01-1219:56

SummaryIn this episode of the Painting Possibilities podcast, Ashley shares her journey of transitioning from a day job to painting full-time. She discusses the challenges and triumphs she faced in the first 90 days, emphasizing the importance of community, mentorship, and learning from experiences. Ashley reflects on her early mistakes and successes, providing insights for aspiring artists and entrepreneurs.You can join my newsletter here:⁠⁠⁠www.ashleycassens.com/subscribe ⁠⁠⁠My FREE mural mock-up course:⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠⁠⁠Portrait painting course:⁠⁠⁠https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric⁠⁠⁠Resources I love for Artists:⁠⁠⁠Honeybook⁠⁠⁠ ⁠⁠⁠Wave Accounting ⁠⁠⁠⁠⁠My actual contract
SummaryIn this conversation, Ashley discusses her journey of facing fears and embracing change in her career. She reflects on the misconceptions surrounding job security and the importance of preparation in making significant life decisions.You can join my newsletter here:⁠www.ashleycassens.com/subscribe ⁠My FREE mural mock-up course:⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠Portrait painting course:⁠https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric⁠Resources I love for Artists:⁠Honeybook⁠ ⁠Wave Accounting ⁠My actual contractSocial:⁠Instagram⁠ ⁠FacebookTakeawaysI didn't quit because I didn't have fears around quitting.I felt ready enough for the next steps in my career.The fallacy of a salaried job is that it feels secure.I could have been let go from a salaried job at any time.Preparation is key to facing career transitions.Understanding the reality of job security is crucial.Embracing change requires confronting personal fears.The next three months felt manageable, even without a clear plan.Job security is often an illusion we create for ourselves.Being ready for change is more about mindset than circumstances.Embracing Change: A Journey of Self-DiscoveryThe Reality of Job Security: Myths and Truths"I didn't quit because I didn't have fears.""I felt ready enough.""It felt like it was security."Sound BitesChapters00:00 Introduction to the Journey02:27 The Reality of Quitting a Day Job05:00 Planning for Transition07:23 Building a Portfolio and Gaining Confidence09:44 First Mural Experience12:32 The Snowball Effect of Success14:55 Balancing Family and Career17:17 The Emotional Toll of Leaving Teaching19:45 Resources for Transitioning Artists22:34 Mindset and Mantras for Success24:58 Conclusion and Future Insights
1: The Experiment

1: The Experiment

2026-01-0222:47

In this conversation, Ashley Cassens shares her journey as an artist, detailing her transition from a teaching career to becoming a full-time painter. She discusses the challenges of balancing motherhood and creativity, the impact of her 31 Day Challenge, and the lessons learned from navigating the art world. Ashley emphasizes the importance of finding one's creative path and the various avenues available for artists today.You can join my newsletter here:www.ashleycassens.com/subscribe My FREE mural mock-up course:https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-neededPortrait painting course:https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabricSocial:Instagram FacebookAshley Cassens is a full-time painter who transitioned from teaching.She completed a 31 Day Challenge to improve her artistic skills.Balancing motherhood and art is a significant theme in her journey.Ashley emphasizes the importance of community and support among artists.She learned valuable business skills through podcasts and coaching.The idea of success for Ashley includes being present with her family.She created a series called the Eye Trap series during her artistic journey.Ashley believes in the importance of scheduling creative time.She was not taught essential business skills in art school.Her journey highlights the diverse paths available for artists today.From Teacher to Full-Time Artist: Ashley's JourneyThe 31 Day Challenge: A Path to Artistic Growth"I wanted to stay with my husband.""I had a three-year plan to leave teaching.""I guess I have a lot to share."Sound BitesChapters00:00 The Artistic Journey Begins07:25 Navigating Art Education and Career Paths09:56 The Reality of Balancing Art and Life12:49 Finding Success as a Creative Parent15:25 The Importance of Community and Learning18:29 Creating Time for Art21:05 Transitioning from Teaching to Full-Time Artist
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