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