Diane Whiddon

Diane Whiddon Results-driven Squarespace websites, digital marketing, and AI Photoshoots.

Website designer, writer, recluse, enthusiastic marketer, and recovering perfectionist.

Your site can load in two seconds, pass every SEO check, and still lose the client the moment they land on it.Speed was ...
08/05/2026

Your site can load in two seconds, pass every SEO check, and still lose the client the moment they land on it.

Speed was never what decided whether they trusted you. Perception was.

I built a free tool that checks that instead of pagespeed: 12 checks across the four things that decide whether the market reads you as an industry authority or just another consultant for hire. Positioning. Point of view. Proof. Platform. One honest score, no login, nothing gated.

Most audits tell you your site is fine. This one tells you whether it reads like you're worth what you charge.

swayrisecreative.com/audit

I was just on the Profitable Web Designer podcast with Shannon Mattern and we had the best conversation.We talked about ...
07/31/2026

I was just on the Profitable Web Designer podcast with Shannon Mattern and we had the best conversation.

We talked about how web designers can add AI headshots and brand photo shoots to their services - and why this is one of the most natural, profitable upsells in the business right now.

Because here's the thing... the problem isn't that clients don't want great photos. The problem is the whole process of getting them is a nightmare. The photographer hunt. The uncomfortable shoot day. The waiting. The hoping the images are actually horizontal.

AI changes all of that.

I shared how I price these services, the ethics framework I teach inside AI Designers Academy, and what I call "visual claims" - using AI imagery intentionally to build trust and handle objections before anyone reads a word on the page.

Go listen - link in bio (https://www.youtube.com/watch?v=1hyUOAUA1j4&views). Episode #202.

We tried to break Claude Design by feeding it the worst business idea we could think of: a combination taxidermy shop an...
07/30/2026

We tried to break Claude Design by feeding it the worst business idea we could think of: a combination taxidermy shop and smoothie bar.

It built a beautiful website.

And that's the problem.

AI can build you a pretty website in ten minutes, but it can't tell you the idea is horrendous. Crusty Pete's should not exist, and Claude had no idea.

So if it won't flag a strawberry matcha smoothie next to a taxidermied raccoon, it certainly won't tell you your offer is too vague, your USP is too general, or that you're selling the wrong thing to the wrong person. It just makes all of it look great, which costs you business.

Because looking great was n e v e r the hard part. The hard part is getting a person who has never heard of you to choose you over the ten other tabs in their browser. That takes judgment, experience, and discernment about positioning, strategy, and people. It's the reason you hire a designer instead of a prompt.

Meet Crusty Pete's. AI slop on purpose, and the project that made Barb Miller and I Top 15 finalists in the 2026 Women Build AI Build-a-thon. Full case study at the link in bio. 🦌🥤

The difference between being the obvious choice and just another person in your industry.
07/22/2026

The difference between being the obvious choice and just another person in your industry.

The difference between being the obvious choice, or any other person in your industry.

I knew a business coach making $100k/year who referred to her clients as "cash units."She also had a whole personal bran...
02/24/2026

I knew a business coach making $100k/year who referred to her clients as "cash units."

She also had a whole personal brand around being "real" and "heart-led."

This is the tension Christy Price and I are talking through live TODAY — what authenticity actually looks like when most marketing models quietly reward exaggeration and performance.

And how to sell in a way that actually lines up with who you are.

Come hang →

We’re constantly told that authenticity is the key to selling online. But in an internet full of exaggerated income claims, polished funnels, and “trust me” ...

Nothing says “healthy industry” like Super Bowl ads and public trash talk.My take on Anthropic's ads and Sam Altman's re...
02/11/2026

Nothing says “healthy industry” like Super Bowl ads and public trash talk.

My take on Anthropic's ads and Sam Altman's response.

A casual observation about ads, control, and trash talk

The bots created their own social network. Or did they?
02/02/2026

The bots created their own social network. Or did they?

They invented a religion, filed lawsuits against their humans, and things got weird fast, until we found out most of them were fake

12/08/2025

"The life you want is on the other side of what you're avoiding."

Yep.

This.

Address

Chicago, IL
60604

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