Behind My Website Redesign: What I Learned; What I Broke

Behind My Website Redesign: What I Learned; What I Broke

A version of this story appeared in Total Annarchy, my fortnightly newsletter that helps you be a better writer, storyteller, marketer. Get it in your inbox; you’ll love it.

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Well, well… lookee here! New vibe, new branding, new me.

Late last week, I quietly relaunched a brand-new website at AnnHandley.com—my first redesign in… maybe 8 years?

Not sure how long it’s been. All I really know is that the jacket I’m wearing on the old home page is from the DVF 2016 collection. (And the prescription on those glasses is so outdated it would now not help me read the words on this page.)

Screenshot from Ann's old website homepage

Old branding, old site: circa 2017

Launching a site is HARD. It’s not just technical; it’s existential. It forces you to answer: Who am I? Who am I becoming?

Woof. It’s like a therapy session that you then publish on the internet.

Here’s what I learned from the relaunch—and what you might find useful, too.

1. HIRE A WRITER

I’m a writer. Why would I hire another one?

Because writing about yourself is like trying to describe a house while you’re standing inside it.

I can tell you about the books on the shelves… the garden view… how the spaniel curled on the carpet looks exactly like a croissant.

But what’s the house look like? No idea. Not a clue.

When you’re inside, you can’t see the shape of the thing.

I called the phenomenal Rachael Kraft.

2. ANSWER TWO BIG QUESTIONS!

Rachael helped me focus every page around two questions:

  • What do you want people to feel in the first 3 seconds? (Feel. Not buy.)
  • How can you balance personality with clarity?

I learned that clarity isn’t a solo sport.

3. DESIGN IS A CONVERSATION

I worked with my longtime friend and collaborator and therapist, the incredible Michelle Martello. We wanted the site to feel modern, but also… unmistakably me. (What do you want people to feel, you know?)

Michelle built something that nods to my enduring belief in the power of analog—clean grids, thoughtful typography, generous white space—but still looks like it belongs in 2025, not 1999.

I love hearing artists explain their work. Here’s what Michelle said:

“I overlaid a half-tone texture on top of a custom-made color-shifting gradient. The dotted pattern is a subtle nod to old-school newspaper print”—a nod to that analog belief again.

“A slightly askew quote bar adds visual interest,” she says. Another subtle nod to print.

Every element—from headline hierarchy to margin spacing—became another sentence in a visual story.

GOR-JUS, that intention behind the work. Seemingly random choices are not random at all.

Design isn’t just about making something look good. It’s about listening—and then translating the words for your eyes.

4. LIMIT YOUR CHOICES

The challenge with AI is that it gives you infinite choice… all the fonts! More words! More options!

“Would you like me give you 10,000 equally valid alternatives?” ChatGPT asks. “Would you like me to smooth the flow? Would you like me to shape this? Would you like me to microwave you a waffle?”

The bugger! NO, I would not. Go away, AI.

AI can undermine you in subtle ways. Not by arguing… but by offering too much.

Good creative work isn’t about infinite—it’s about intentional.

It’s choosing this, not that. Centering on one core idea, not a thousand possibilities.

5. GOOGLE ‘ASKEW’

I forgot to mention this earlier… you know that slightly askew quote bar that Michelle mentioned? She also said: Google the word “askew.

Go ahead. I’ll wait.

Fun, right?

6. AVOID THE ALGO ZOMBIE GLAZE

You know the look… that vacant, frictionless sameness shuffling across the internet… it’s the Algorithmic Zombie Glaze.

RUN THE OTHER WAY.

Your work needs fingerprints. Bite marks. Hoofbeats. Heartbeats.

Leaving in a bit of oddball is a quiet rebellion against the Algo Zombie Glaze. Warmth and imperfection signal trust in a way automation and uniformity never can.

In an age of sameness, humanity is the new differentiator.

👉 One way to avoid Zombie Glaze is to make things a bit weird. I’m not going to point out where my weird shows up specifically—they’re meant to be small surprises you’ll discover on your own.

7. DON’T TAKE YOURSELF TOO SERIOUSLY

This was me, on the daily, messaging Michelle: Can you change this? Swap that? What if we used a photo here?

I started to feel like a nightmare client.

Michelle introduced the Dog Tax: every change request had to come with a photo of my dog, Augie.

It kept things light—and reminded me to stop being a pain in the peach. 🍑

8. SAVING THE HARDEST FOR THIS LAST POINT: THOSE BIG EXISTENTIAL QUESTIONS

This redesign made me think hard about myself and my brand. I don’t mean brand as veneer—I mean the idea that thrums through your veins, your heart, that crackles in your central nervous system.

Who am I? What am I actually about?

“Ridiculously good content and writing”? Yeah.

But underneath than that… it’s about paying attention. Choosing what matters. Moving through the world with clarity, courage, and a sense of joy that comes from being fully alive in your own work.

The hardest copy to write on the new site was the line in the middle of the home page under the header: Get to know Ann Handley.

That copy might change. Or it might not. I can decide later. The relaunch is a snapshot, not a finish line.

Websites—like people—are never really done.

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