
Advertise on podcast: The Painting Possibilities Podcast
Rating
5from
This podcast has
24 episodes
Language
EnglishPublisher
Ashley CassensExplicit
No
Date created
2026/01/02
Latest episode
2026/08/24
Average duration
24 min.
Release period
13 days
Description
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.
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Podcast episodes
Check latest episodes from The Painting Possibilities Podcast podcast
24: Which jobs are for the Portfolio and which are for the Paycheck?
2026/08/24
In this episode Ashley shares insights on creating for "the portfolio" versus for the paycheck.
Key takeaways:
Some jobs are for building your portfolio, others are for income, and knowing the difference is crucial.Showcase work in your portfolio that you want to do more of, not just what pays.Don't be afraid to turn down jobs that don't align with your style or goals.Unique circumstances in projects can be great portfolio pieces if you want to repeat them.
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Materials I use
My booking and CRM systems
My actual contract
Social:
Instagram
Facebook
www.ashleycassens.com
23: Behind the social media post (what it really takes to land the job and finish it!)
2026/08/17
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Materials I use
My booking and CRM systems
My actual contract
Social:
Instagram
Facebook
www.ashleycassens.com
22: Managing Clients - if you listen to only 1 episode, this is the one!!
2026/06/15
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 editingWhy 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 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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Materials I use
My booking and CRM systems
My actual contract
Social:
Instagram
Facebook
www.ashleycassens.com
21: Ladders, scaffolding and scissor lifts oh my!
2026/06/08
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-non-techy-artists-no-procreate-needed
Portrait painting course:
https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Materials I use
My booking and CRM systems
My actual contract
Social:
Instagram
Facebook
www.ashleycassens.com
20: What my first surfing lesson taught me
2026/06/01
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Materials I use
My booking and CRM systems
My actual contract
Social:
Instagram
Facebook
www.ashleycassens.com
19: Answer your questions!
2026/04/27
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Materials I use
My booking and CRM systems
My actual contract
Social:
Instagram
Facebook
www.ashleycassens.com
18: A Day in My Life
2026/04/20
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Honeybook
My actual contract
Social:
Instagram
Facebook
17: The outcome from "The Client that didn't pay" + more!
2026/04/13
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-simple-guide-for-non-techy-artists-no-procreate-needed
Portrait painting course:
https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Honeybook
My actual contract
Social:
Instagram
Facebook
16: 4 Things I'm automating to make more time for PAINTING
2026/04/06
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Honeybook
My actual contract
Social:
Instagram
Facebook
15: The WORST mistakes I've made!
2026/03/30
"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
Portrait painting course:
https://ashleycassens.podia.com/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Honeybook
My actual contract
Social:
Instagram
Facebook
13: What you need to know about Public Art Projects
2026/03/23
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Honeybook
My actual contract
Social:
Instagram
Facebook
14: What to do when a Client doesn't pay?
2026/03/23
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Honeybook
My actual contract
Social:
Instagram
Facebook
12: Boundaries in Biz
2026/03/16
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Honeybook
My actual contract
Social:
Instagram
Facebook
11: Quiet Habits to build Longevity
2026/03/09
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Honeybook
My actual contract
Social:
Instagram
Facebook
10: 5 Reasons you should raise your Prices (and some money mindset jazz)
2026/03/02
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:
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/view/courses/let-s-get-real-how-to-paint-realistic-portraits-with-oils-on-fabric
Resources I love for Artists:
Honeybook
Wave Accounting
My actual contract
Social:
Instagram
Facebook
Podcast reviews
Read The Painting Possibilities Podcast podcast reviews
mariner404 2026/02/06
Informal and informative
I am not an artist or running a business but I enjoy Ashley’s podcasts. She is sharing insight for life skills that can apply to every busy person. A...
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