Somewhat Useful

AI bot traffic is projected to surpass human traffic by the end of 2027. In this episode, we discuss how web design is changing and what we can expect for the future. We talk about whether the extra SEO effort is worth it, adding AI clauses to design contracts, and why we still believe we should build for humans first. Mentioned in the episode: Internet traffic composition: https://blog.will-myers...

In this episode, Will sits down with Becca Harpain from Inside the Square and Dave Hawkins from Made by Dave to discuss all things AI: vibe coding, what they will and won’t use AI for, how their workflows have shifted now that AI tools are widely available, and the main skills Squarespace designers should be focused on right now.  Thank you to our sponsor, Breely! Breely is modern scheduling softw...

In this episode, we discuss the concept of "killing your darlings" — letting go of products, processes, or tools in your business that no longer serve you to make room for what's next. Will shares how he’s rethinking his plugin strategy and Christy reflects on services she’s no longer offering. We also discuss the shifting landscape of the web design and development industry and deba...

Today we're joined by Kelsey Gilbert-Kreiling (of Week of the Website and Eventually) to chat about launching the new event ticketing platform she built with her husband Zach. We learn about the origin story, how they use Claude in their build process, and discuss how AI is shaping the future of in-person gatherings. Will explains why he moved Code Curious off of Squarespace, and Christy share...

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...

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 an...

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 des...

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...

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 notif...

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&...

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,...

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 d...

In this episode, Will and Christy touch base about wrangling code updates, keeping up with Squarespace’s ongoing changes, and the debate between live and pre-recorded marketing. Then they bring in Kelsey Gilbert Kryling, founder of Week of the Website, to talk honestly about what it’s like running an agency and the day-to-day realities of digital business. Kelsey shares what it takes to balance wo...

In this episode, Will and Christy talk about everything from big Squarespace updates (especially around e-commerce), to taking real sick days (or not), and why it’s actually okay if your website isn’t the prettiest thing on the internet. We get into what dogs can teach us about web design, using loyalty and clear directions as guiding lights, and even where to find that “sunny spot” for your work...

In this episode Christy and Will debrief the Kit conference and weigh the pros and cons of doing live and pre-recorded content. Then they bring on Hoyd Breton, principal product designer at Squarespace. They discuss the power of minimalism, story driven design, and the tools to support it. Hoyd shares his sources of inspiration as well as Squarespace’s most underrated feature. They also talk about...

In this episode, Will and Christy review the tips from their last Circle Day talk, “ 7 Ways to Save Time as a Web Designer ” and discuss which are still relevant. Then they talk with Liz Ellery about helping clients find their voice, bringing a sense of spirituality into her business, and what to look forward to in her next Summit. Liz emphasizes the importance of being intentional in your busines...

Will and Christy kick off this week’s episode talking about the fun industry events they recently attended. They share their top three feature requests for Squarespace as well as a couple Squarespace updates. Then they talk with Dreyah Bohlen-Harrington about how becoming a mom changed the way she runs her business, specifically around schedules, setting boundaries and delegating tasks. Dreyah exp...

In this episode Christy and Will talk about their favorite chrome extensions and share the latest Squarespace update. They are joined by Jen Maher who discusses her ADHD diagnosis and how it impacts the way she runs her business. She gives her take on the common advice of charging your worth and encourages us to self evaluate and chart our own path as entrepreneurs. Chrome extensions: Squarespace...

In this episode of Somewhat Useful, Will and Christy talk about how they are using AI in their workflows and share a couple platform updates from Squarespace. Then they chat with CSS expert Chris Schwartz-Edmisten about his journey from coding to photoshop mockups to helping clients customize their Squarespace websites. Chris shares insights on content marketing strategies, diversifying income str...

In this episode, Will and Christy chat about the pros and cons of social media for their business and discuss how they manage their social media usage. They are then joined by Lex Roman, who talks about their journey from TV to web design, to growth and monetization, and now community building and virtual networking events. Lex discusses their “ Legends ” membership as well as their  " Journa...

In this episode, Christy and Will debrief Squarespace’s State of the Web Design Industry report, and share their thoughts on setting deadlines and shipping products. Then they talk with LaShonda Brown of Bootstrap Biz Advice about her YouTube channel growth strategies. She explains that fun is essential in creating an engaging learning environment. LaShonda shares the Pomodoro technique that helps...

In this episode, Christy and Will chat about email marketing and how it fits into their business. Then they talk with Jeremy Schwartz, General Manager of Channel Partnerships at Squarespace. You’ll hear about the evolution of Squarespace over his 12 years there, including ongoing efforts to support us creative professionals. He takes us behind the scenes of Squarespace Circle and explains the reas...

In this episode, Christy and Will talk about whether or not you need a website copyright and share their Somewhat Useful tips for your business. Then they talk with Kate Scott about her journey from WordPress book blogger to successful Squarespace educator and template creator. Kate discusses the advantages of Squarespace over WordPress and how she transitioned from client work to selling template...

In this episode, Will and Christy discuss getting past perfectionism and give their Somewhat Useful tips. Then they talk with Weglot CMO Eugène Ernoult about the company’s innovative translation solution. You’ll hear about Eugène’s journey into marketing and his transition from being a founder to working at a startup. He shares Weglot’s business practices around employee wellbeing and the environm...

In this episode, Will and Christy talk about the intersection of Google and AI. They share the big projects they’re currently working on and give some tips for your business. Then they talk with Becca Harpain of Inside the Square. Becca shares the challenges she faced with Google’s new algorithm and how it forced her to adapt and innovate in her business. You’ll hear about the launch of her exciti...