Windowsill Chats

What's the Best That Could Happen? Madison Phipps on Building an Art Business in the Margins

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

Creative Current Events: The Future of Licensing & the Reinvention of Retail

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/  

Draw Your World: Samantha Dion Baker on Sketchbook Diaries, Everyday Inspiration, and Letting Go of Perfection

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  

Following a Good Idea: Salli Swindell on Illustration, Creative Community, and Finding Joy Beyond Client Work

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. Margo and Salli discuss: The power of starting small and following curiosity instead of waiting for a master plan How Salli and her brother Nate built global platforms from the ground up Why partnerships with people who have different strengths can open unexpected doors Salli's shift from decades of client-driven illustration work to developing a personal creative practice The origin story of Snack + Sketch, a gathering that blends creativity, food, and meaningful connection Why community, creativity, and shared meals can be powerful pillars of wellness How simple gatherings around your kitchen table can spark inspiration and lasting creative friendships Connect with Salli: Instagram: https://www.instagram.com/sallistyle/ Website: https://freshfoodillustration.cargo.site Illustrators For Hire: https://illustratorsforhire.com The Illustrator's Circle: https://www.illustratorscircle.com They Draw: https://www.they-draw.com   Connect with Margo: Website: www.windowsillchats.com Instagram: @windowsillchats www.patreon.com/inthewindowsill https://www.yourtantaustudio.com/thefoundry

Get Paid to Draw: Mike Lowery on Building a Portfolio That Gets You Hired

Margo is joined once again by celebrated illustrator, author, and educator Mike Lowery for a lively conversation about the realities of building a creative career. Mike is the New York Times bestselling illustrator of more than 80 books for children and he's spent decades navigating the ups and downs of freelance illustration and publishing. In this episode, Margo and Mike pick up where their first conversation left off—diving into the lessons Mike has learned over twenty years as a working illustrator, what it actually takes to build a portfolio that attracts clients, and why being "good at drawing" isn't always the same as being hireable. They also talk about Mike's new course, Get Paid to Draw, designed to help illustrators create strategic portfolios, understand what art directors are really looking for, and turn their creative skills into real opportunities. Margo and Mike discuss: What Mike's younger self would think of his career today The behind-the-scenes work of running a creative business Why a strong portfolio matters more than raw talent when it comes to getting hired Portfolio tips to help art directors understand how your work fits their needs The difference between creating art for yourself versus creating work that attracts clients The power of community in a freelance creative career Mike's Get Paid to Draw course and how it helps artists build portfolios that actually lead to work The upcoming Portfolio Challenge starting March 11 and how creatives can participate Connect with Mike: Join the Illustration Portfolio Challenge: https://bit.ly/illoportfoliochallenge Website: https://www.mikelowery.com/ Course: https://www.gettingpaidtodraw.com/ Instagram: https://www.instagram.com/mikelowerystudio/ Connect with Margo: Website: www.windowsillchats.com Instagram: @windowsillchats www.patreon.com/inthewindowsill https://www.yourtantaustudio.com/thefoundry