Explore every episode of the podcast The Painting Possibilities Podcast
| Title | Pub. Date | Duration | |
|---|---|---|---|
| 24: Which jobs are for the Portfolio and which are for the Paycheck? | 24 Aug 2026 | 00:44:50 | |
In this episode Ashley shares insights on creating for "the portfolio" versus for the paycheck. Key takeaways:
Chapters 00:00 Introduction and podcast overview 01:56 Rosie O'Donnell's story of bravery and luck 03:49 The importance of bravery in taking opportunities 04:45 Getting back into meditation and mindfulness 07:03 Choosing projects for your portfolio versus paycheck 08:54 Examples of portfolio work: large murals, unique projects 12:49 What to include in your portfolio and what to avoid 16:07 Jobs for the paycheck: styles and projects to avoid in portfolio 19:50 Handling projects you don't love but pay well 23:09 The value of style and subject matter in portfolio building 24:56 Final thoughts and encouragement to take brave steps You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My booking and CRM systems My actual contract Social: Instagram | |||
| 23: Behind the social media post (what it really takes to land the job and finish it!) | 17 Aug 2026 | 00:35:51 | |
In this episode I dive into the real work behind the shiny finished photo. If you ever wondered, "How did she get that job?". It's not the highlight reel, it's the REAL real. 01:54 Initial contact and project scope 05:14 Managing delays and scheduling challenges 09:50 Working with big organizations and client collaboration 15:06 Preparing for outdoor painting in Florida's climate 19:56 Using boom lifts and safety considerations 24:47 Overcoming technical challenges with equipment 30:09 Community reactions and project impact 34:49 Reflections and lessons learned 40:10 Final thoughts and resources You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My booking and CRM systems My actual contract Social: Instagram Facebook | |||
| 22: Managing Clients - if you listen to only 1 episode, this is the one!! | 15 Jun 2026 | 00:25:42 | |
If you listen to only 1 episode this year, let it be this one! I'm getting real about how I vet clients. Specifics on:
01:47 Defining Personal Boundaries in Art Business 03:02 The Importance of Vetting Clients 13:23 Color Theory and Hex Code Matching 18:16 Establishing Communication Boundaries 22:26 Managing Client Expectations and Revisions You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My booking and CRM systems My actual contract Social: Instagram Facebook | |||
| 21: Ladders, scaffolding and scissor lifts oh my! | 08 Jun 2026 | 00:31:56 | |
This week I'm sharing all about the equipment (ladders, scaffolding, and lifts!) Plus a little snaffu I ran into on a scissor lift recently. Did I mentioned I'm scared of heights? You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My booking and CRM systems My actual contract Social: Instagram | |||
| 20: What my first surfing lesson taught me | 01 Jun 2026 | 00:27:00 | |
03:12 Balancing Creativity and Motherhood 06:04 Navigating Business Decisions and Pricing Flexibility 08:55 The Importance of Community and Connection 09:53 Learning to Surf: A New Adventure 21:06 Lessons from Surfing: Embracing the Beginner's Mindset 26:53 The Value of Asking for Help You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My booking and CRM systems My actual contract Social: Instagram | |||
| 19: Answer your questions! | 27 Apr 2026 | 00:17:37 | |
I'm answering your questions! Dive in with me as I share how I get customers, how introverts can win in biz, and window painting (is it worth it?). Takeaways This podcast has personally helped me grow. Approaching businesses can be done through email. Introverts can thrive in the art world. Starting with personal projects can lead to opportunities. Window painting is a low-cost entry point for artists. Networking in local communities is essential. Embrace imperfection in your creative journey. Consistency and practice lead to improvement. Be afraid to put yourself out there, but do it anyway! Chapters 00:00 Introduction to Painting Possibilities Podcast 01:03 Engaging with the Audience: Questions and Feedback 01:45 Approaching Businesses for Art Services 10:55 Navigating Introversion in the Art World 12:15 Starting a Window Painting Business 16:50 Embracing Imperfection and Progress You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My booking and CRM systems My actual contract Social: Instagram | |||
| 18: A Day in My Life | 20 Apr 2026 | 00:18:20 | |
A little throwback to Cribs, but artist edition! There will be early 2000s references! Stay for it. You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My actual contract Social: | |||
| 17: The outcome from "The Client that didn't pay" + more! | 13 Apr 2026 | 00:15:51 | |
This is my most asked questions so far - What happened with the client whose payment was late? An update up top, plus why all those small things you're doing consistently is working in your favor. Perfect sucks. ;) You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My actual contract Social: | |||
| 16: 4 Things I'm automating to make more time for PAINTING | 06 Apr 2026 | 00:19:13 | |
4 Things I'm really cool with automating (let it be EASY!) in my art studio. You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My actual contract Social: | |||
| 15: The WORST mistakes I've made! | 30 Mar 2026 | 00:24:42 | |
"Artists, they're just like us!" I'm laying out some truly embarassing mistake I've made in my art business. I hope you leave with a chuckle. You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My actual contract Social: | |||
| 13: What you need to know about Public Art Projects | 23 Mar 2026 | 00:15:31 | |
Takeaways Ashley discusses her transition from a day job to full-time painting. Public art calls are often organized by government entities or nonprofits. Creative Pinellas is highlighted as a supportive organization for artists. Visibility in the community is a significant benefit of public art. Applying for multiple public art jobs increases credibility. The application process can be competitive with low acceptance rates. Community connections can lead to new opportunities in public art. Experiences with public art can vary greatly depending on organization. Personal stories from the mural projects add depth to the discussion. Chapters 00:00 Introduction to Painting Possibilities Podcast 00:18 Exploring Public Art Calls 05:38 Finding and Applying for Public Art Opportunities 10:54 Creative Pinellas and Successful Projects 15:12 The Orlando Project Experience 19:11 Reflections on Public Art Experiences Chapters 00:00 Introduction to Boundaries in Life and Art 01:17 The Importance of Setting Boundaries 05:19 Personal Experiences with Boundaries 11:53 Scripts for Saying No 16:36 Conclusion and Encouragement You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My actual contract Social: | |||
| 14: What to do when a Client doesn't pay? | 23 Mar 2026 | 00:16:26 | |
Takeaways Set up systems to encourage timely payments. Clear contracts can prevent payment issues. Use invoicing tools to streamline payment processes. Communicate openly with clients about payment expectations. Establish late fees to encourage prompt payment.
Chapters 00:00 Introduction to the Podcast and Personal Journey 01:23 Facing the Fear of Late Payments 04:25 Setting Up Payment Systems and Contracts 10:03 The Importance of Late Fees 14:37 Mindset Around Payments and Valuing Your Work You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My actual contract Social: | |||
| 12: Boundaries in Biz | 16 Mar 2026 | 00:16:56 | |
Takeaways Boundaries are essential for personal and professional growth. Saying no is a powerful tool for maintaining mental wellness. It's important to set boundaries with clients early on. Knowing your artistic interests helps in making better choices. Scripts for saying no can help maintain relationships. Being selective with projects leads to better work quality. Personal time is valuable and should be protected. Setting boundaries can lead to increased creativity. Chapters 00:00 Introduction to Boundaries in Life and Art 01:17 The Importance of Setting Boundaries 05:19 Personal Experiences with Boundaries 11:53 Scripts for Saying No 16:36 Conclusion and Encouragement You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: My actual contract Social: | |||
| 11: Quiet Habits to build Longevity | 09 Mar 2026 | 00:18:59 | |
Takeaways Sustainable habits are crucial for long-term success. How I created a "painting" work week allows for better work-life balance. Physical well-being is essential for artists - be strong! Mindfulness practices can enhance creativity. Habit stacking can improve productivity. How to set up focus modes on your phone to help minimize distractions. Planning my outfits in advance saves time and energy. Chapters 00:00 Introduction to Painting Possibilities Podcast 00:35 Sustainable Habits for Creative Success 05:53 Balancing Work and Personal Life 10:29 Effective Time Management Strategies 14:46 Mindfulness and Meditation Practices 16:59 Habit Stacking for Productivity You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: Social: | |||
| 10: 5 Reasons you should raise your Prices (and some money mindset jazz) | 02 Mar 2026 | 00:23:16 | |
Summary In this episode of the Painting Possibilities podcast, Ashley discusses the challenges of balancing creativity with motherhood and the realities of making a living as an artist. She shares insights on mindset, money management, and the importance of understanding one's money archetypes. The conversation delves into pricing strategies for artists, the impact of raising prices, and how to identify and deal with difficult clients. Ashley also emphasizes the value of art and shares empowering mantras for success, encouraging listeners to embrace growth and change in their creative journeys. Takeaways Balancing creativity and motherhood is a real challenge. Mindset is crucial when managing finances as an artist. Understanding your money archetype can help with financial decisions. Pricing strategies should reflect the value of your work. Raising prices can lead to better clients and more freedom. Empowering mantras can shift your mindset towards success. Growth in your career can come with challenges, but it's part of the journey. You are not behind; you are exactly where you need to be. Chapters 00:00 Introduction to the Painting Possibilities Podcast 05:19 Exploring Money Archetypes 12:42 Signs It's Time to Raise Your Prices 18:38 Empowering Mantras for Creatives You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: Wave Accounting My actual contract Social: | |||
| 9: Things I thought would move the needle and DIDN'T (and what actually did!) | 23 Feb 2026 | 00:21:04 | |
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. Takeaways The 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: Portrait painting course: Resources I love for Artists: Social: | |||
| 8: Balancing Motherhood and Ambition | 16 Feb 2026 | 00:22:17 | |
Summary In 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. Chapters 00:00 Introduction to the Journey 02:03 Navigating Parenting and Creativity 05:37 Dealing with Envy and Defining Success 13:23 Making Choices: Opportunities and Parenting 18:21 The Blessing of Parenthood in Creative Work You can find all my favorite art supplies here. You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: Social: | |||
| 7: Window Painting (and why I should never say never) | 09 Feb 2026 | 00:18:33 | |
Summary The things I learned from window painting:
Chapters 00:00 The Seasonal Artistry of Window Painting 03:46 Pricing Strategies for Murals 05:45 Personal Challenges and Running Events 08:00 Injury and Its Impact on Work 11:49 Social Media Engagement and Art 13:17 The Snowball Effect of Window Painting 15:37 Monetization Through Social Media 17:51 Navigating New Artistic Challenges You can find all my favorite window supplies here. You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: Social: | |||
| 6: My word of the year - SPACE | 02 Feb 2026 | 00:21:45 | |
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. Takeaways My 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. Chapters 00:00 Setting the Stage: Personal Accountability and Goals 03:12 Reflections on the Past Year: Word of the Year 05:08 Intentional Living: Embracing Space and Time Off 09:48 Balancing Life: Managing Overcommitment and Family Activities 17:29 Health and Fitness: Tracking Progress and Accountability 20:11 Navigating New Experiences: Learning and Growth 22:32 Looking Ahead: Intentions for the Future You can join my newsletter here: www.ashleycassens.com/subscribe My FREE mural mock-up course: Portrait painting course: Resources I love for Artists: Social: | |||
| 5: Body Image + Murals | 26 Jan 2026 | 00:20:09 | |
Summary In 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: Portrait painting course: Resources I love for Artists: Social: Takeaways Ashley 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. Chapters 00:00 Introduction to the 31-Day Challenge 01:50 Navigating Insecurities in a Male-Dominated Field 04:30 The Impact of Gender on Professional Presentation 14:50 Body Image and Self-Perception in the Workplace 21:56 Embracing Authenticity and Taking Up Space | |||
| 4: Pricing - My most asked questions! | 19 Jan 2026 | 00:21:57 | |
Summary In 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: Portrait painting course: Resources I love for Artists: Takeaways You 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 | 12 Jan 2026 | 00:19:56 | |
Summary 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 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: Portrait painting course: Resources I love for Artists: | |||
| 2: The Reality of Quitting | 05 Jan 2026 | 00:30:49 | |
Summary In 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: Portrait painting course: Resources I love for Artists: Social: Takeaways
Sound Bites Chapters 00:00 Introduction to the Journey 02:27 The Reality of Quitting a Day Job 05:00 Planning for Transition 07:23 Building a Portfolio and Gaining Confidence 09:44 First Mural Experience 12:32 The Snowball Effect of Success 14:55 Balancing Family and Career 17:17 The Emotional Toll of Leaving Teaching 19:45 Resources for Transitioning Artists 22:34 Mindset and Mantras for Success 24:58 Conclusion and Future Insights | |||
| 1: The Experiment | 02 Jan 2026 | 00:22:47 | |
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: Portrait painting course: Social:
Sound Bites Chapters 00:00 The Artistic Journey Begins 07:25 Navigating Art Education and Career Paths 09:56 The Reality of Balancing Art and Life 12:49 Finding Success as a Creative Parent 15:25 The Importance of Community and Learning 18:29 Creating Time for Art 21:05 Transitioning from Teaching to Full-Time Artist | |||