Episode Details

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