Staying Creative in the Age of AI with Andy J. Pizza on Circle Live
Squarespace Circle’s 2026 web design industry report revealed how optimistic Circle partners feel about AI and web design, and how they’re using AI tools for client projects. As AI becomes more prevalent, more designers are automating repetitive tasks, leaving more space for human creativity.
During the March 2026 episode of Circle Live, guest Andy J. Pizza revealed his thoughts on how creativity can go hand in hand with AI tools.
In this conversation with Squarespace’s Sam Zelitch, Senior Community Events Manager, and Sarah Greisdorf, Team Lead, Channel Partner Program, the New York Times-bestselling author and illustrator goes deep on human creativity’s role to designers in the modern service world, offering unique insights inspired by his artist background:
“It’s really difficult to make a mistake when you’re drawing digitally that looks good, that looks like a happy accident. It almost always looks wrong, whereas when you’re painting, the opposite is true. And so, for me, getting out of my own way looks like, ‘oh, I’ve kind of become too knowledgeable about this to where I’m too in control, and I need to change something so that I can be less in control.’”
Watch this episode to learn:
How to let AI handle the business of creativity so you can spend more time making
How to hone your services for an industry you’re interested in to maximize income and fulfillment
How to establish yourself as someone clients can trust to encourage sales
The value of embracing human error, both in the things you enjoy and as a way to unlock unexpected work opportunities
Related resources:
Circle Day 2025: In Conversation with Anthony Casalena and David Lee, Squarespace
Squarespace Circle: State of the Web Design Industry 2026 report
Expressing Style, Personality, and Technique with the Creative Process Trend
Listen to the podcast version of the episode.
Subscribe to the Squarespace Circle YouTube channel for videos on product features, interviews with Circle partners and Squarespace product managers, and more.
Want more?
Check out Squarespace Circle, Squarespace’s program for professional designers and web design agencies. Along with exclusive content, discounts, and other perks, Circle brings professionals together from across the globe to exchange advice while connecting with new clients and collaborators.
