Ashley Cassens

The Painting Possibilities Podcast

Arts EN ↓ 22 episodes

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.

Author

Ashley Cassens

Category

Arts

Podcast website

www.ashleycassens.com

Latest episode

Jun 15, 2026

Where to listen?

Podcasts in the app Replaio Radio Coming soon

Podcasts are coming to the app soon. Install now and be the first to see a whole new take on podcasts

Get it on Google Play Install for free Android 5M+ downloads · 4.8 rating iOS soon

Episodes

22: Managing Clients - if you listen to only 1 episode, this is the one!! 15.06.2026

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: What boundaries I set before I ever start painting. How I deal the endless requests for editing Why someone else's business in the same industry can look different and that's a okay! Your business - your rules 01:47 Defining Personal Boundaries in Art Business 03:02 Th...

21: Ladders, scaffolding and scissor lifts oh my! 08.06.2026

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: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-n...

20: What my first surfing lesson taught me 01.06.2026

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 c...

19: Answer your questions! 27.04.2026

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...

18: A Day in My Life 20.04.2026

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: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠⁠⁠⁠⁠⁠⁠⁠⁠ Portrait painting course: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ashleycasse...

17: The outcome from "The Client that didn't pay" + more! 13.04.2026

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: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-...

16: 4 Things I'm automating to make more time for PAINTING 06.04.2026

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: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠ Portrait painting course: ⁠⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ashleycassens.podia.com/v...

15: The WORST mistakes I've made! 30.03.2026

"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: ⁠⁠⁠⁠⁠⁠⁠⁠⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a-simple-guide-for-non-techy-artists-no-procreate-needed...

13: What you need to know about Public Art Projects 23.03.2026

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 competitiv...

14: What to do when a Client doesn't pay? 23.03.2026

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...

12: Boundaries in Biz 16.03.2026

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...

11: Quiet Habits to build Longevity 09.03.2026

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...

10: 5 Reasons you should raise your Prices (and some money mindset jazz) 02.03.2026

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 t...

9: Things I thought would move the needle and DIDN'T (and what actually did!) 23.02.2026

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 pitch...

8: Balancing Motherhood and Ambition 16.02.2026

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...

7: Window Painting (and why I should never say never) 09.02.2026

Summary The things I learned from window painting: It's okay to be a beginner Let people in on the journey Rest can produce creativity and abundance in ways I wasn't expecting 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...

6: My word of the year - SPACE 02.02.2026

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 M...

5: Body Image + Murals 26.01.2026

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 t...

4: Pricing - My most asked questions! 19.01.2026

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, emphasizi...

3: The big 3's 12.01.2026

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 e...

2: The Reality of Quitting 05.01.2026

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: ⁠https://ashleycassens.podia.com/mural-mock-ups-made-easy-a...

1: The Experiment 02.01.2026

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 avenu...

Listen to the The Painting Possibilities Podcast podcast in Replaio

Radio and podcasts in one app - free, with no sign-up. Install today and do not miss the launch

Get it on Google Play

Replaio is not a podcast publisher; show names, artwork and audio belong to their authors and are distributed through public RSS feeds.