You know that feeling when you hit “send” on an email campaign and your stomach does a little flip? Maybe you wonder if anyone will open it. Maybe you’re hoping someone, anyone, will reply. Or maybe you’re just hoping you didn’t get their name wrong. I’ve been there. For years, my approach to email marketing was simple: do it myself, keep it safe, and try not to mess up. But when I handed over the reins to AI, everything changed—sometimes in ways I expected, and sometimes in ways that surprised me.

Letting Go: The Vulnerability of Trusting AI

Let’s get real for a minute. Small business owners and side hustlers like us are used to wearing every hat. We write, we sell, we troubleshoot at 2 a.m. We know our audience because, in a lot of ways, we are our audience. So, when someone suggested I let AI handle my email marketing, my first reaction was…well, let’s just say it wasn’t excitement.

It was fear. Not the kind of fear that keeps you up at night, but the kind that makes you hesitate. Would AI get my voice right? Would it treat my subscribers like people, not just data points? Would it see the little details—the ones that make someone feel noticed, not just numbered? Vulnerability isn’t just about sharing your story; it’s about letting go of control, even when it feels risky.

But here’s the thing: I was tired. Tired of feeling behind, tired of second-guessing every subject line, tired of wondering if my emails were connecting or just adding to the noise. So, I decided to try something new.

The Experiment: AI Takes the Wheel

I started small. I set up my MailerLite account to integrate with an AI-powered tool. My goal wasn’t to automate everything—it was to see if AI could help me connect with my audience in a way that felt more personal, not less.

The first step was letting AI analyze my existing emails. It looked at open rates, click rates, even the times people were most likely to engage. Then, it started drafting emails for me. At first, I hovered over every line, tweaking words and adding personal touches. But as the weeks passed, something unexpected happened: the AI started to learn my style. My “Hey there, friend” greeting. My habit of asking real questions. My tendency to share a story before making an offer.

It wasn’t perfect. There were moments when the AI got a little too formal or slipped into jargon. But it was learning—and so was I. I learned that personalization isn’t just about using someone’s name. It’s about making your audience feel seen, heard, and valued. AI, when trained well, can help with that. It can notice patterns I’d never spot on my own. It can test subject lines and segment audiences in ways that would take me hours. It can remind me to follow up, to check in, to say thank you.

Here’s what surprised me most: my open rates went up. Not by a little—by a lot. People replied to my emails, telling me they felt like I was writing just to them. One subscriber wrote, “This is the first newsletter I’ve actually looked forward to all month.” I sat with that for a while. Because, honestly, that’s the dream, right? To make someone feel like they matter.

The Messy Middle: Lessons Learned (and Mistakes Made)

Let’s not sugarcoat it—there were bumps along the way. The first time I let AI send an email without reviewing it, I felt like I’d left the house with the stove on. What if it said something off-brand? What if it made a mistake? And yes, there were mistakes. Once, the AI sent an email with the wrong product link. Another time, it used a joke that landed flat. I cringed, apologized, and—here’s the key—asked for feedback.

What I learned is that people are forgiving when you’re honest. When I sent a follow-up email admitting the mistake, I got more replies than I’d ever gotten before. Not complaints—encouragement. “We all mess up. Thanks for being real.” That’s the power of vulnerability. It’s not about being perfect; it’s about being human, even when technology is involved.

I also learned that AI is only as good as the input it gets. If I wanted my emails to feel personal, I had to feed the AI with stories, values, and a clear sense of who my audience is. I started sharing more about my journey—what it’s like to run a business with a tiny budget, what I’ve learned from failure, why I care about creating income opportunities for others. The more I shared, the better the AI got at mirroring my voice.

And the results? My unsubscribe rate went down. My click-through rate went up. But more than that, my audience started to feel like a community. They wrote back. They shared their own stories. They told me what they needed, and I listened.

What I’d Tell Anyone Thinking About AI and Email Marketing

If you’re on the fence about letting AI handle your email marketing, here’s my advice—straight from the heart:

• Start small. Let AI draft, but you approve. See what feels right, and don’t be afraid to make changes.
• Teach it your voice. Feed it stories, values, and real examples. The more you give, the more you’ll get back.
• Don’t expect perfection. There will be mistakes. Own them. Your audience will appreciate your honesty.
• Focus on connection, not just automation. AI can help you scale, but it can’t replace your humanity. Use it to free up your time so you can show up more fully.
• Ask for feedback. Invite your audience to tell you what’s working (and what’s not). Make them part of the process.

Here’s what I know for sure: Personalization isn’t about technology. It’s about empathy. AI is a tool—a powerful one—but it’s your willingness to be real that makes the difference. When you show up with honesty and heart, your audience feels it. And that’s what keeps them coming back.

So, if you’re tired, if you’re stretched thin, if you’re wondering if it’s okay to get a little help—the answer is yes. You don’t have to do it all yourself. You don’t have to be perfect. You just have to be you. And sometimes, letting AI handle the busywork is the bravest thing you can do.

Let’s keep going, together.

To your success,

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