After eight years away, I sent this email to my dormant list. No tricks. No pretending I’d been posting regularly. Just honest about the gap and where I’m heading next with AI. Sometimes transparency is the best re-engagement strategy.

Waking up an 8-year-old email list

Right. First job of the rebuild. I’ve got an old MailChimp account I haven’t properly touched in eight years. Eight. And somehow there are still 110 people on the list who never unsubscribed.

I’m not going to drag those 110 contacts into my new email setup and tank my deliverability on day one. So before I move anything anywhere, I’m running a re-engagement campaign on the old system first. Only the people who actively click through come across to the new one. Everyone else stays where they are, quietly haunting MailChimp.

This is the bit most people get wrong when they switch email platforms. You import a list that hasn’t heard from you in years, your open rates fall off a cliff and your sender reputation goes with it. Do the cull on the old system. Bring only the warm ones across. Future you will thank present you.

The email itself

I kept it short and honest. Subject line: It’s been a while, but I’m back documenting something new.

The body basically says: it’s been eight years, you probably don’t remember subscribing, I don’t blame you if you want out. Back then I was all about WordPress and design. A lot has changed. I’m rebooting the site around AI for web, AI for business, AI for design and working out whether any of it is going to take my job.

If you want to stick around, click the button. If not, no hard feelings.

That’s it. No clever copy, no big pitch. Just a straight ask.

The holding page problem

The button needed somewhere to go. My current site is properly old school (the last post was about selling my WordPress theme business, the comments don’t even work anymore) so I didn’t want to point people at that. I just needed a simple confirmation page while I rebuild the rest of the site properly.

So I jumped into a Claude co-work session and gave it a quick brief. Simple landing page, here’s the title, here’s the copy, here’s a screenshot of my current site so you know what to match. Sonnet handled it fine, no need to reach for Opus on something this simple.

First pass was actually pretty good. I asked it to centre the logo and add an Instagram link with the icon, then uploaded the static file to my server. Done.

And here’s the thing. In an ideal world I’d have spent another hour fiddling with it. Different layout, better type hierarchy, maybe a subtle animation. But that is exactly the trap I’m trying to avoid with this whole series. The point is to build stuff and ship it. Done is better than perfect while I get going.

Refresh, cache cleared, button works, page loads. Move on.

What happens next

The campaign goes out at 7am tomorrow. I’ll watch the click stats roll in over a few days, then move only the people who clicked the button into my new email system. Everyone who ignored it stays in MailChimp where they can keep ignoring me in peace.

Step one done. Step two is sorting out the blog properly. That’s the next post.

If you want to follow along as I rebuild this thing in public, chriswharton.me is where it’s all happening. Or find me on Instagram and TikTok at @cdwharton, where I’m posting the shorter cuts of all this.