All dispatches
September 07, 2026

I Used to Spend Sunday Nights Writing Emails. I Don't Anymore, and Here's What Changed

For a while I had a standing Sunday night ritual that I hated: sitting down to write the following week's emails, the welcome message for new subscribers, the follow-up for anyone who'd browsed but not bought, the occasional check-in for people who'd gone quiet. It wasn't hard work exactly, it was just repetitive in a way that ate an evening every single week for something that felt like it shouldn't take that long. I stopped doing it manually about a year ago, and the honest reason isn't that I found some magic tool. It's that the tools finally got good enough at the boring, repetitive parts that I stopped needing to.

What actually changed, specifically

The shift isn't that AI writes better marketing copy than a person, though it can produce a decent first draft. The real change is in the automation layer underneath the writing, the part that decides when an email goes out, to whom, and adjusts based on what that specific person actually does. A welcome sequence used to be something you built once and left alone. Now the better tools adjust the timing and even the content slightly based on whether someone opened the last email, clicked a link, or ignored it entirely, without you manually building ten different branches to handle every scenario.

The category people keep calling agentic workflows fits here too. Instead of a marketer manually researching a lead, drafting an outreach email, and scheduling a follow-up, the newer tools can chain those steps together on their own, research a prospect, draft something reasonably personalized, schedule it, and report back on what happened, largely without someone sitting there clicking through each step individually.

The tools people are actually settling on

A handful of names keep showing up consistently across anyone who's actually tested a range of these rather than just reading marketing pages. Mailchimp's AI features tend to get recommended for smaller teams who want clear guidance without a steep learning curve, it tells you plainly what's working and what isn't rather than burying insights in a dashboard you have to dig through. ActiveCampaign comes up specifically for anyone who needs real behavior-based automation, sequences that branch depending on what a specific person actually does, not just a generic drip. Brevo gets mentioned a lot for the price to feature ratio, handling things like abandoned cart emails and welcome sequences at a cost that doesn't feel steep for a small operation. MailerLite tends to be the answer for anyone who just wants something simple and doesn't want to pay for features they'll never touch.

What ties these together, and what actually made the difference for me personally, is that the good ones now handle a meaningful chunk of the actual writing and testing themselves. Instead of guessing at a subject line and hoping, several of these tools will generate a few variants, test them against a portion of the list automatically, and lean into whichever performs better before the rest of the list even receives it. That's the kind of small, tedious optimization that used to require either a lot of manual effort or just getting skipped entirely because nobody had time for it.

Where I'd actually be careful

None of this means turning the whole thing over and walking away, and the mistake I see people make most often is treating full automation as the goal rather than a means to an end. An AI-drafted email that goes out with zero human review reads exactly like what it is, generic, slightly hollow, technically correct but missing whatever made your actual voice worth subscribing to in the first place. The businesses getting real value out of this aren't removing themselves from the process, they're removing themselves from the repetitive parts, the scheduling, the branching logic, the first-draft writing, and keeping their attention for the parts that actually need a human judgment call, the tone, the occasional email that needs to say something a template genuinely can't anticipate.

There's also a cost worth being upfront about that isn't just money. Automating your emails doesn't automatically make them better, it just makes them faster to produce and easier to send consistently. If your actual offer or your actual writing wasn't landing before, automation just lets you send that same mediocre thing more efficiently and more often, which isn't really a win. Fix the message first. Automate the delivery of a message you already know is good.

What I'd actually recommend if you're starting from nothing

Pick one part of your email routine that's genuinely repetitive and low-stakes, a welcome sequence for new subscribers is usually the easiest starting point, and automate just that piece first rather than trying to rebuild your entire email strategy around AI in one go. Most of these tools let you start free or close to it, well under thirty dollars a month for something genuinely useful, so there's very little reason to overthink the choice before trying one.

What I've actually gained back isn't just the Sunday evenings, though that matters. It's that the emails going out now are more consistent than the ones I used to write manually and occasionally forget entirely when a week got busy. The automation didn't replace my judgment about what to say. It just replaced the part where I had to personally remember, and personally execute, sending it on time every single week without fail.

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