Windowsill Chats

Longtime friend of Windowsill Chats and beloved artist, author, and creative entrepreneur Lisa Congdon is back for another heartfelt conversation. This time, Lisa is sharing a major shift in her creative career: the decision to step away from her thriving retail business and make more room for the thing that started it all—making art.
Margo and Lisa explore what it means to let go of something successful when it no longer aligns with the life you want to live. From the emotional weight of closing a chapter and saying goodbye to a team, to questioning the idea that bigger is always better, Lisa offers an real look at the courage it takes to redefine success on your own terms.
They also dive into the joy of returning to daily creative practice, finding inspiration in painting and collage, and embracing new possibilities. Plus, Lisa shares what's on the horizon, including Made to Matter, a new course with Emily McDowell for product-based creatives, and her upcoming book with Bridget Watson Payne, The Art of Finishing Things.
Margo and Lisa discuss:
The bittersweet process of stepping away from a successful creative business
Why growth doesn't always equal fulfillment
Giving yourself permission to pivot, even when things look great on paper
Reconnecting with the joy of making art through daily practice
Creating a business and life that support your well-being
What's next for Lisa, from new artwork and exhibitions to courses and books
Previous Episodes with Lisa:
Episode 100 – July 20, 2022

Episode 186 – What It Really Means to Have Creative Freedom

Episode 241 – January 29, 2025

Lisa's 2021 Gravel Racing Episode

Mentioned in this episode:
The Jaunt – Artist Residency

Egg Press

Cargo Emporium

Connect with Lisa:
Website: lisacongdon.com

Instagram: @lisacongdon

Shop: Lisa Congdon Shop

Made to Matter Course: Greater Goods Alliance

Margo is joined by Jennifer Smelker, the engineer-turned-artist, product designer, and founder of Tandem For Two. Since 2013, Jen has been creating colorful, travel-inspired artwork and gifts that celebrate the places we love and the moments that make life special. But her creative journey has been anything but linear.
From environmental engineering and graphic design to manufacturing, wholesale, and art licensing, Jen shares the twists, turns, and lessons that have shaped her evolving career. She and Margo explore what it means to embrace your identity as an artist, let go of perfectionism, and find the courage to try something new, even when you don't know exactly where it will lead.
They also dig into the realities of running a creative business, from scaling production and navigating industry changes to pitching artwork, building relationships, and discovering the power of community. Jen shares how a painting retreat in Portugal helped transform her creative practice, why she believes in sharing knowledge rather than gatekeeping it, and how curiosity continues to fuel her next chapter.
In this episode, we explore:
Finding your creative identity and overcoming perfectionism and imposter syndrome
The unexpected path from engineering to art and entrepreneurship
How community, mentorship, and creative challenges can spark meaningful growth
The behind-the-scenes realities of manufacturing, wholesale, and art licensing
Why persistence, thoughtful product presentations, and relationships matter when pitching your work
Embracing new technology, lifelong learning, and the freedom to reinvent yourself
Giving yourself permission to experiment, make imperfect art, and follow your curiosity
Mentioned in this episode:
Faire Wholesale Marketplace: faire.com
Adobe MAX (Miami, November): max.adobe.com
Atlanta Market: americasmart.com
The 100-day painting project: the100dayproject.org
Connect with Jennifer:
Website: https://tandemfortwo.com
Instagram: https://instagram.com/tandemfortwo
Facebook: https://facebook.com/tandemfortwo
Pinterest: https://pinterest.com/tandemfortwo
LinkedIn: https://linkedin.com/in/jensmelks

Abby is back on the Windowsill for another round of Creative Current Events! This week, she and Margo are diving into the latest headlines making waves in art, design, branding, and retail—and, as always, there's plenty to unpack.
From collectible handbags blurring the line between fashion and art to luxury brands rolling out the red carpet for our four-legged friends, the creative world is full of surprises. They explore Polaroid's cheeky campaign encouraging us to put down our screens, the return of Bed Bath & Beyond in an unexpected form, and why Hermès is doubling down on hand-drawn illustration in an increasingly AI-driven world.
Margo and Abby discuss:
The intersection of art, fashion, and collectible handbags
Polaroid's clever push for analog experiences in a digitally saturated world
Why luxury brands are increasingly catering to dogs (and their devoted humans!)
Kirkland's transformation into Bed Bath & Beyond Seasonal Living and what it says about retail reinvention
Hermès' embrace of hand-drawn illustration and the growing value of human creativity in the age of AI
The bigger cultural shifts shaping what we buy, how we create, and what we value
Articles:
Polaroid's Analog Summer Campaign Pushes Against Digital Overload — PetaPixel
Dogs Became Luxury's Fastest Growing Customer — Art of the Brand
Kirkland's Stores to Become Bed Bath & Beyond Seasonal Living — NBC Chicago
Hermès Goes All-In on Illustration in the Age of AI — Highsnobiety

This week on Windowsill Chats, Margo is joined by novelist Jane Ward, author of four books, including her latest, Should Have Told You Sooner. With a lifelong love of storytelling, cooking, baking, and art, Jane has built a creative life rooted in curiosity, observation, and finding inspiration in unexpected places.
Jane began writing her first novel, Hunger, nearly thirty years ago while living in Iceland with her Navy husband, finding space for storytelling during the long, dark winters. Since then, she's continued exploring the complexities of human relationships through fiction, often weaving together themes of family secrets, forgiveness, regret, and the things we leave unsaid. Her latest novel was inspired by something as simple as a lawn sign spotted during an early morning dog walk.
Margo and Jane discuss:
The meaning behind the question on Jane's website, "What's done is done. Or is it?" and why the past has a way of resurfacing

Writing about family secrets, forgiveness, and the complicated relationships that make us human

How Jane develops fictional characters who begin to feel like real people

Finding inspiration in unexpected places, including the lawn sign that sparked her latest novel

The creative freedom found in bread baking, photography, travel, and other everyday pursuits

Her upcoming sequel and its exploration of motherhood in all its complicated forms

The importance of making space for creativity outside of your primary artistic practice

Jane's plans for a Gothic novel set in Switzerland, inspired by her childhood love of Daphne du Maurier

Connect with Jane Ward:
Website: janeaward.com

Instagram: @authorjaneward

Threads: @authorjaneward

Facebook: @janealessandriniward

What does it look like to build a creative career that keeps evolving, without losing the curiosity that got you started?
This week, Margo is joined by illustrator, designer, cartographer, educator, and all-around creative powerhouse Tania Willis. With a career spanning editorial illustration, advertising, pictorial maps, heritage interpretation, products, licensing, and education, Tania has spent decades finding new ways to make a living from her creativity. She's also the co-founder of The Good Ship Illustration, where she helps illustrators navigate the business side of a creative career.
Tania and Margo talk about the power of creative community, adapting as the industry changes, and why even established artists sometimes need to reinvent their work. They also explore the value of diversifying your income, following your genuine interests instead of trends, and creating supportive spaces where artists can learn without fear or shame.
Margo and Tania discuss:
Why collaboration and community can accelerate creative growth
Adapting your business as social media and the illustration industry change
Teaching, mentoring, and sharing what you've learned along the way
Reinventing your style when your work starts to feel too predictable
Following curiosity instead of what you think you "should" be making
Building a resilient career through freelance work, teaching, products, and licensing
Why relationships and unexpected opportunities often shape a creative career
The enduring value of handmade, imperfect, distinctly human work
Creating safe, encouraging spaces for artists to experiment and learn
Why sometimes you just have to fly your freak flag
Connect with Tania:
www.taniawillis.com
Instagram: www.instagram.com/tania.willis
The Good Ship Illustration: www.thegoodshipillustration.com
Instagram: www.instagram.com/thegoodshipillustration