What 300 Episodes Has Taught Me About Creativity, Confidence, and Staying the Course
Release Date: 01/28/2026
The Magic of Letting Go: Motherhood, Illustration, and Redefining the “Successful Artist” with Natalie Lundeen
Windowsill Chats
Margo is joined by illustrator and children’s book artist Natalie Lundeen for a candid conversation about creativity, motherhood, burnout, and redefining what it means to be a “successful” artist. Based in Clearwater, Florida, Natalie specializes in children’s books, greeting cards, and licensed artwork, with illustrations spanning indie publishing, Etsy products, and now traditional publishing through Flamingo Books, an imprint of Penguin Random House. Her newest books, Dear Mom and Dear Dad, were released this spring. Natalie shares the winding path that led her from fine art and...
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Embracing the Messy Middle: The Twisty, Turny Path to a Creative Life with Nicki Traikos
Windowsill Chats
Margo is joined by artist, author, and educator Nicki Traikos for a conversation on creativity, perfectionism, and building a life rooted in art. Known for her approachable watercolor teaching style and the global community she’s built through life i design, Nicki shares the winding journey that took her from a corporate career and makeup artistry into the world of watercolor, online education, and publishing. Margo and Nicki explore the realities of creative growth—the messy middle, the pivots, the comparison traps, and the courage it takes to keep showing up for your art. Nicki opens up...
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Rhinestones, Reinvention & the Art of Embracing Your Multi-Passionate Mind with Kim Bloomberg of Studio Art Beat (Replay)
Windowsill Chats
In this replay episode, Margo is joined by multi-passionate creative Kim Bloomberg, the joyful force behind Studio Art Beat. A fine artist, educator, and self-proclaimed art supply nerd, Kim brings a refreshing perspective to the creative journey—one that’s less about staying in your lane and more about following curiosity wherever it leads. With a background in both fine art and education, over two decades of teaching experience, and years running her own jewelry business, Kim shares how she ultimately found fulfillment by embracing her ADHD-fueled love for switching mediums and diving...
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More Play, Less Perfection: Embracing Experimentation and Finding Your Creative Rhythm with Lisa Solomon
Windowsill Chats
Margo is joined by artist, author, and educator Lisa Solomon to discuss her newest book, Art, Craft, Color—a thoughtfully curated collection of essays, reflections, and creative projects designed to inspire a more playful, hands-on approach to making. Lisa’s work explores the intersection of art, craft, and personal history, often blending unexpected materials and techniques to challenge traditional boundaries. Alongside her studio practice, she teaches at the college level and has authored several books on color and creativity. In this conversation, Lisa offers a behind-the-scenes look at...
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Paint Brushes to Balance Sheets: Financial Literacy, Tax Knowledge and How to Break the Starving Artist Stereotype With Hannah Cole (Replay)
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...
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Three Good Things: A Practice in Perspective, Hope, and Everyday Joy with Emily Gaines Demsky
Windowsill Chats
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...
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What’s the Best That Could Happen? Madison Phipps on Building an Art Business in the Margins
Windowsill Chats
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...
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Creative Current Events: The Future of Licensing & the Reinvention of Retail
Windowsill Chats
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...
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Draw Your World: Samantha Dion Baker on Sketchbook Diaries, Everyday Inspiration, and Letting Go of Perfection
Windowsill Chats
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...
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Following a Good Idea: Salli Swindell on Illustration, Creative Community, and Finding Joy Beyond Client Work
Windowsill Chats
Margo is joined by illustrator, creative community builder, and industry champion Salli Swindell, who has spent nearly five decades in the illustration world. Salli began her career at American Greetings before co-founding several beloved platforms with her brother Nate Padavick—including They Draw, The Illustrator’s Circle, and Illustrators For Hire—all dedicated to celebrating and promoting illustrators around the globe. Margo and Salli explore Salli’s creative evolution, from decades of client-driven illustration work to embracing a more personal, self-directed creative practice....
info_outlineIn this 300th episode of Windowsill Chats, Margo sits down for a special solo conversation—answering thoughtful listener questions that span creativity, confidence, career longevity, leadership, and the magic that keeps artists going.
With over two decades of experience in the creative industry, Margo reflects on how her relationship with art has evolved, what she’s learned from running The Foundry, and the advice she returns to again and again when mentoring artists.
Margo shares:
- How she makes space for her own creativity—and what her personal art practice looks like now
- Ways to quiet imposter syndrome and trust decades of lived creative experience
- The artistic work she’d most love to take to marketplace and why
- Her favorite and most challenging parts of creative work and leadership
- How the rise of AI has shifted client interest in traditionally created artwork
- The advice she gives artists most often—and what truly matters day to day
- Lessons from trade shows, licensing, and running The Foundry
- What keeps her going, where she finds creative magic, and why it’s never too late to begin
Mentioned in this episode:
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