Windowsill Chats

In this replay episode, Margo is joined by tax expert Hannah Cole who specializes in working with creative businesses and mission-driven solopreneurs. A long-time working artist herself, she's helped tens of thousands of self-employed people skill up with accessible tax and money education, through her Money Bootcamp program, speaking engagements from Florida to Alaska, and on the Sunlight podcast. She is the founder of Sunlight Tax. As artists carve their paths through various industries, they encounter a myriad of challenges, yet financial literacy is rarely addressed, leading to feelings of failure and shame. Today's conversation with Hannah sheds light on this systemic failure and turns it into a journey of empowerment and self-compassion (something all creatives should have)!
Margo and Hannah discuss:
The responsibilities that come with being a small business owner in the US
Navigating self-employment taxes and optimizing deductions
Personal struggles that Hannah faced within her own creative career and financial literacy
What propelled her towards accounting education
How she acts as a translator between the creative and tax worlds
Simple advice artists can implement today when it comes to money management
Her Money Bootcamp program and podcast
How to save more money
And more!
Connect with Hannah:
www.instagram.com/sunlighttax
www.sunlighttax.com
www.sunlighttax.com/podcast
Connect with Margo:
www.windowsillchats.com
www.instagram.com/windowsillchats
www.patreon.com/inthewindowsill

Margo sits down with artist, writer, and creator Emily Gaines Demsky for a conversation centered on creativity, perspective, and the quiet power of noticing what's good. Emily makes vibrant floral paintings (symbols of hope and possibility), and is the founder of Tell Me 3 Good Things, a Substack community practice centered on noticing, naming, and sharing simple moments of goodness each day. Through her work, she invites others to shift their perspective in meaningful, life-giving ways.
Emily's approach blends art, writing, and daily ritual into a powerful reminder: even in difficult seasons, we have the ability to choose where we place our attention. From her father's lasting influence to the organic growth of her community, this conversation explores how small, intentional practices can create profound change.
Margo and Emily discuss:
How perspective is a daily choice—and how it shapes both creativity and resilience
The origin and impact of the "Tell Me 3 Good Things" practice
The role of grief, joy, and life transitions in shaping creative work
How authenticity fosters deep, meaningful community
The symbolism of flowers as hope, possibility, and light
Toxic positivity versus building resilience
How noticing and naming goodness can shift the way we experience our lives
Connect with Emily:
Website: www.emilygainesdemsky.com
Tell Me 3 Good Things on Substack: emilygainesdemsky.substack.com
Instagram: www.instagram.com/emilygainesdemsky
Connect with Margo:
Website: www.windowsillchats.com
Instagram: @windowsillchats
www.patreon.com/inthewindowsill
https://www.yourtantaustudio.com/thefoundry

Margo is joined by artist and illustrator Madison Phipps, the creative force behind Madison Phipps Studio. Known for her feminine, timeless botanical artwork rooted in nostalgia and storytelling, Madison shares how she's built a growing art business while balancing motherhood and a full-time job. From painting in the quiet margins of her day to landing dream collaborations and launching collections, this conversation is a refreshing and honest look at what it really takes to pursue creativity in the "messy middle."
Margo and Madison explore the mindset shifts, practical strategies, and courageous decisions that helped her turn a personal creative practice into a thriving business, without waiting until everything felt "ready."
Margo and Madison discuss:
Using the question "what's the best that could happen?" as a roadmap for growth and decision-making
How sharing her journey on TikTok helped her grow a community and gain visibility
Pitching yourself before you feel ready—and how cold outreach led to major opportunities
The inspiration behind her nostalgic, botanical artwork rooted in childhood memories
Launching and sustaining a snail mail print club as a recurring revenue stream
Lessons from collaborations, including her botanical collection with Paloma & Co
Balancing ambition, creativity, and family life without burning out
Connect with Madison
Madison Phipps Studio: https://www.madisonphippsstudio.com/
Instagram: https://www.instagram.com/madison.phipps.studio/
TikTok: https://www.tiktok.com/@madisonphippsstudio
Connect with Margo:
Website: www.windowsillchats.com
Instagram: @windowsillchats
www.patreon.com/inthewindowsill
https://www.yourtantaustudio.com/thefoundry

Margo is joined once again by Abby Campbell for a Creative Current Events catch-up episode, and this one is packed. After a short hiatus, the two dive right back into the ever-evolving world of art, design, and creative business—starting with Margo's firsthand experience exhibiting at the Birmingham Spring Fair's new Licensing Lab. She shares what stood out, from booth design trends to the shifting landscape of licensing and wholesale in a post-SurTex world, offering a behind-the-scenes look at where the industry is heading.
From there, Margo and Abby broaden the conversation into a curated mix of resources, trends, and cultural observations shaping creative work right now. They explore everything from artist-friendly AI tools and art competitions to trend forecasting, retail evolution, and immersive brand experiences.
Mentioned in this episode:
https://www.entrythingy.com/blog/best-art-calls-2026
https://business.pinterest.com/pinterest-predicts/
https://www.fastcompany.com/91504420/claude-can-turn-your-handwriting-into-a-font https://www.powderartfoundation.org/
http://southernliving.com/michaels-fresh-flowers-11920325
https://www.retaildive.com/news/aritzia-acquires-fred-segal/812686/

Margo is joined by artist, author, and teacher Sam Dion Baker for a conversation about creativity, sketchbook practice, and finding meaning in the everyday. Originally from Philadelphia and now based in Brooklyn, Sam spent over two decades as a graphic designer before returning to drawing in her forties—ultimately building a deeply personal and widely loved sketchbook diary practice. Through her books, teaching, and artwork, Sam encourages others to slow down, observe their lives, and express themselves in their own unique way.
Margo and Sam discuss:
How a lifelong exposure to art shaped her creative path (and why it didn't follow a straight line)
The transition from graphic design to a personal, sketchbook-based art practice
Why sketchbooks can act as a form of therapy, reflection, and emotional processing
Finding beauty and inspiration in everyday moments, not just big adventures
Letting go of perfection and embracing messiness as part of the creative process
Simple exercises to loosen up creatively (like continuous line drawing and using your non-dominant hand)
How to develop your own unique creative voice through observation and consistency
Sam's books and upcoming projects, including her new coloring book Color Your World
Connect with Sam:
Website: www.sdionbaker.com
Substack: www.samanthadionbaker.substack.com
Instagram: www.instagram.com/sdionbakerdesign


Connect with Margo:
Website: www.windowsillchats.com
Instagram: @windowsillchats
www.patreon.com/inthewindowsill
https://www.yourtantaustudio.com/thefoundry