If we had to start over today, with no audience, no email list, and no reputation, what would we actually do?

In this episode, we break down what still works for building a web design business, what we'd skip completely, and where we'd focus if we had to rebuild from scratch in 2026. We also talk about SEO, YouTube, AI search, email lists, Instagram, digital products, client work, and the slow reality of growing something that lasts.

Plus, Christy shares the story of winning $5,000 at Sponsor Games, and Will talks about how he's in his Claude era.

Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.

Mentioned in the episode:

Sponsor Magnet by Justin Moore

Atomic Habits by James Clear

Kit Conference

Web Designer's Playbook

Will's Toolkit

Will's email list

Christy's email list

In this episode, Christy and Will discuss recent and upcoming conferences, Squarespace updates, and Will’s evolving opinion on OpenClaw. Then they chat with Gavin Zuchlinski, founder of some of the best scheduling tools on the market, including this season’s sponsor, Breely! You'll hear about how he created Acuity as a side hustle, the Squarespace acquisition, and why he wanted to build yet another scheduling platform.

Mentioned in the episode:

Will’s article about OpenClaw

Final Surge app

Die with Zero book

Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.

AI tools are moving fast, client work gets messy, and some days, business feels heavier than it should. In this episode, we talk honestly about what makes entrepreneurship feel miserable, how AI is adding new anxiety (hello, OpenClaw), and the boundaries that actually help.

You'll also hear a few timely Squarespace updates (and bugs), plus what the next year might look like for Squarespace designers and developers as AI keeps changing the workflow.

Mentioned in the Episode:

Squarespace Circle

The Web Designer Summit (March 5)

Thanks to our sponsor Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.

We start this episode by reviewing what’s new with Squarespace, including the retirement of the Amazon block and our thoughts on search functionality. We also discuss Squarespace’s recent Super Bowl ad. Then we’re joined by author and writing coach Jacq Fisch to talk about:

• Writing in 2026 and how to stand out in a sea of noise and AI-written content
• Ways to use AI without selling your soul

Find Jacq at:

https://theintuitivewritingschool.com/

https://jacquelinefisch.com/

https://jacquelinefisch.substack.com/

https://www.instagram.com/theintuitivewritingschool/

Mentioned in the episode:

Monacle search

Voxer

Otter

Thank you to our sponsor, Breely! Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.

In this episode we chat about what 2026 looks like for web designers and developers. We'll share what we're leaning into this year and what we're leaving behind.

Mentioned in the episode:

Kit conference

Sponsor Games

Christy's YouTube Growth Lab

Sponsor:

Breely is modern scheduling software with every feature unlocked for free, including signatures, payments, and Email or SMS notifications. Start for free at breely.com/useful and streamline your entire client booking workflow.

Follow:

⁠⁠Follow Christy on Instagram⁠⁠

⁠⁠Follow Will on Instagram⁠⁠

⁠⁠Sign up for Will's Newsletter⁠⁠

⁠⁠Sign up for Christy's Newsletter⁠

Want to know how web designers feel about AI? In this bonus episode, Christy and Will dive into the new 2026 State of the Web Design Industry Report with Sam Zelitch and Sarah Greisdorf from the Squarespace Circle team.

Read the report: https://pros.squarespace.com/web-design-industry-report

Follow Christy on Instagram

Follow Will on Instagram

Sign up for Will's Newsletter

Sign up for Christy's Newsletter

We break down the biggest updates from Squarespace Circle Day, why this year felt different, and what matters for your client work. We cover Finish Layer in ProTools (animations, layers, grouping with Stacks, hide on mobile, copy and paste styles), the new custom fonts workflow, Circle dashboard upgrades that reduce Impact headaches, connected commerce and extensibility for stronger integrations, and Beacon AI, including SEO help for LLMs.

Follow:

⁠⁠Follow Christy on Instagram⁠⁠

⁠⁠Follow Will on Instagram⁠⁠

⁠⁠Sign up for Will's Newsletter⁠⁠

⁠⁠Sign up for Christy's Newsletter⁠

AI is transforming everything, from how we work to how we build businesses. But what does that actually mean for entrepreneurs and creatives like us? Are we on the brink of losing our jobs… or stepping into a new era of possibilities?

In this episode of Somewhat Useful, Christy and Will have an honest, slightly nerdy, and surprisingly hopeful conversation about:

✅ How AI is already shifting our day-to-day workflows

✅ The tools we’re experimenting with (and the ones we avoid)

✅ Why we’re not panicking about job loss, and what we’re focusing on instead

✅ The mindset shifts that help us stay adaptable in a rapidly changing world

Whether you’re excited about AI, skeptical, or just trying to keep up, this episode will give you perspective (and maybe even a little peace of mind).

If you’re a web designer, freelancer, or someone exploring online business, you’ll get practical insights, career tips, and a sense of what’s ahead. Stick around for their stories, shoutouts from the live chat, and lightening round questions at the end.

Thank you to our sponsor SquareKicker. Get 15% off all SquareKicker products with code SOMEWHAT15 today: ⁠https://squarekicker.com/⁠

Circle Day

SEOSpace

Christy’s tutorial on SEOSpace

Podia

AI Tools Discussed:

ChatGPT

Midjourney

Manus

RightBlogger

OpusClip

Cursor

Claude