Margo is joined by artist, watercolorist, and educator Catherine Jennifer for a conversation about the power of play, the freedom of imperfection, and making space for creativity in everyday life. Originally from South Africa and now based in the UK, Catherine has built a creative life around painting, teaching, and helping others rediscover the joy of making art.

Margo and Catherine explore the barriers that keep us from creating, how personal loss can reshape our perspective, and why even 20 minutes of creative time can make a difference. Catherine also shares the magic of her in-person Art Club, her playful approach to teaching, and the inspiration behind her new Watercolor Joy app. It's a refreshing reminder that creativity doesn't have to be perfect or productive to be worthwhile. Sometimes, the joy is simply in showing up and seeing what happens.

In This Episode, You'll Hear About:

• Making Time for Creativity: How Catherine balances painting, teaching, and raising four boys, and why even 20 minutes a day matters.
• Embracing Play & Imperfection: Why letting go of expectations and welcoming the wild, wonky, and unexpected can lead to more joyful art-making.
• Finding Joy Through Life's Challenges: How profound personal loss changed Catherine's perspective on creativity, time, and living intentionally.
• Overcoming Creative Resistance: How to quiet the inner critic, release limiting beliefs, and rediscover the freedom to create.
• The Magic of Creative Community: How Catherine's in-person Art Club brings people together through experimentation, friendship, and shared creativity.
• Teaching with Playfulness: Catherine's unconventional approach to teaching on Skillshare and helping students build creative confidence.
• Making Watercolor More Accessible: The inspiration behind her new Watercolor Joy app and its personalized approach to learning.
• Letting the Process Lead: How shifting from what to paint to how to paint has transformed Catherine's own artistic practice.

Connect with Catherine Jennifer

• Website & Original Artwork
• Watercolor Joy App
• Skillshare Classes
• Instagram
• YouTube
• Facebook

Mentioned in This Episode

• Carolyn Gavin — Website | Windowsill Chats Episode (March 2021)
• Gabriella Buckingham — Website | Courses | Windowsill Chats January 2023 Archive
• Manchester Art Fair — Website
• Janet Pulcho — Website
• Lilla Rogers / Make Art That Sells — Website
• Helen Dardik — Website

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