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

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 work and family life, the practical realities of maternity leave, and her biggest lessons on team structure and workflow. If you’re weighing freelance vs. agency life or planning to step back for family or health, Kelsey’s open-book approach is both reassuring and eye-opening. They also take a few minutes to celebrate simple wins, like the joy of a good pastry!

Kelsey’s top tech stack:

• Slack [https://slack.com/]
• Pipedrive [https://www.pipedrive.com/]
• EOS/90.io [https://www.90.io/] (Entrepreneurial Operating System organizing tool)

Find Kelsey at https://www.weekofthewebsite.com/ or https://www.bykelseygk.com/

Sponsor: SquareKicker

What if you could have unlimited creativity on Squarespace? ⁠⁠⁠⁠⁠The SquareKicker Pro Extension⁠⁠⁠⁠⁠ gives you powerful design control, with an intuitive, visual UI right inside your Squarespace editor.Created by designers, for designers, over 100 no-code tools empower you to customize Squarespace far beyond its native capabilities. Visit squarekicker.com for a free trial—no credit card required. Use SOMEWHAT15 to get 15% off all SquareKicker products today.

⁠⁠⁠⁠⁠Learn More

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 and wellbeing. You’ll walk away with practical changes you can make to your Squarespace site, and a few reminders that taking care of yourself is just as important as impressing your clients. Oh, and we share a lot of love for pets, so if that’s your thing, stick around!

Sponsor: SquareKicker

What if you could have unlimited creativity on Squarespace? ⁠⁠⁠⁠The SquareKicker Pro Extension⁠⁠⁠⁠ gives you powerful design control, with an intuitive, visual UI right inside your Squarespace editor.Created by designers, for designers, over 100 no-code tools empower you to customize Squarespace far beyond its native capabilities. Visit squarekicker.com for a free trial—no credit card required. Use SOMEWHAT15 to get 15% off all SquareKicker products today.

⁠⁠⁠⁠Learn More

Donald Miller book: https://storybrand.com/building-a-storybrand-book-new/

See the site Christy made about Beyla

Will’s Squarespace Designer Toolkit Chrome Extension

Workflow.Design

Christy’s Workflow.Design walkthrough

Where to find Kristine:

https://kristineneil.com/

https://www.linkedin.com/in/kristineneil/

https://www.youtube.com/@kristineneil