Email Marketing Hasn't Changed. Your Audience Has.

After 10 hours of email marketing strategy calls, I discovered something surprising: a speech pathologist and a startup founder have the exact same email problem. So do divorce mediators, relationship coaches, therapists, and creative agency owners.

I recently spent time talking one-on-one with an interesting mix of solopreneurs about their email marketing. I offered these 30-minute strategy calls to give business owners a quick win, but also as research for relaunching email marketing retainers. It had been awhile since I managed someone's emails and I wanted to know if things had changed.

Spoiler: they haven't.

That's kind of the blessing and curse of email, isn't it? Social media means constantly jumping through new hoops and learning how to please the algorithms. Email is kind of always being email: reliable, (relatively) intimate, and a great way to make sales.

But just because it's simple doesn't mean it's easy.

Talking with business owners about what's really going on behind their email marketing — what's working, what's not, and what's quietly holding them back — showed me that many of the same roadblocks happen to all of us.

Here are three of the biggest fixes that made an immediate difference. They're all simple, strategic tweaks that helped a mix of business owners send better emails (and actually feel good about it again).

1. The Freebie Problem

The divorce mediator I spoke with had a beautifully designed 20-page ebook she'd been using for years to attract subscribers. She'd noticed that she was getting fewer and fewer opt-ins and wasn't really sure why.

The ebook wasn't awful. It was just outdated — built for a time when people still got excited about downloadable homework. In 2015, it probably made an incredible lead magnet. Back then, everyone got excited by the idea of a free book. That was also the era of courses that advertised 250 worksheets, 15 modules, 8 hours of video content, you get the idea.

But that was then and this is now. Every single person I talked to was struggling with their freebie, either because it no longer performs or it attracts the wrong people. In 2025, people don't want something that requires that much work; they no longer want the "ultimate guide to [very broad subject]." Between information overload and shrinking attention spans, your audience wants something they can take action on right away. They want a solution that shows you understand the very specific problem they need to solve and they want the quickest route to get there.

On our call, I asked her if she could really drill down and name a specific issue that's shared by a large percentage of her clients. She said they're often trying to determine if they're getting divorced. They aren't sure exactly how to make the decision—a decision made more difficult because of the emotional weight of deciding.

We decided she would swap the ebook for a one-page checklist for people in the "should I stay or go?" phase. Something like a "Divorce Decision Planning Tool" or "What to Expect: The Divorce Process Checklist." It will walk people compassionately through the things they need to consider before deciding whether or not to stay in their marriage. This is a freebie that calls in exactly the types of people a divorce mediator works with, and it also gives prospective clients a look at her approach without giving away everything she knows for free.

Takeaway: Today people want help and they want it now. Your freebie's job isn't to teach everything you know. It's to attract the right people — the ones ready to take the next step.

2. The Consistency Problem

Another one of my email strategy calls was with a successful creative agency owner. The agency's newsletter kept falling off her radar and not getting done. Part of this was a team issue — it wasn't super high priority so people took it on when they could. But it wasn't always clear who was responsible. That's easy enough to solve. But the bigger problem was that every time they sent something it was like starting from scratch. There wasn't an editorial calendar in place so they just sent out an email when they had a special offer or something to promote.

It won't surprise you that this "email only when we have something to sell" strategy is not it. Service providers, especially solopreneurs and small teams, should be emailing on a consistent basis to stay top of mind with their communities. (Note: If your team can only manage a monthly newsletter instead of weekly emails — great! Send a monthly newsletter! Just make sure it actually happens.)

When consistency is a problem, the solution is usually structure. So my strategy tweak was to suggest a simple four-email rotation:

• Connection (what's happening in your world — studio updates, behind-the-scenes, personal stories)

• Value (actionable tip, hack, tool, or quick win)

• Promo (the ask — your offer, service, or product)

• Greatest Hits (repurpose and update a top performer you've sent before)

One week they could send out what's happening in the studio, one week share a quick but valuable win, and one week could be dedicated to actually selling. For the fourth email in the rotation, I suggested going into the archives and repurposing their best performing emails and sending them again. I do this regularly and I find that no one ever remembers they already read something similar from me. Or if they do, it certainly doesn't bother them enough to unsubscribe!

With this simple rotation, her team can easily plan emails for the next 6 months or more and their email subscribers can start hearing from them again. There's a sustainable rhythm that doesn't depend on bursts of inspiration that show up when they show up.

Takeaway: You don't need to be original every week. You just need to show up every week. (Or month if that’s what’s sustainable for you.)

3. The Wrong Audience Problem

I also had a call with a mental health professional with a very niche specialty. She came to me convinced her emails weren't converting because her copy wasn't persuasive enough. The percentage of her subscribers who were actually buying her course was smaller than it should have been.

As we talked more about her social media presence, her funnels, and her freebies, it became clear that her audience was full of people who loved her free advice but were never going to buy.

This one is tricky. Because all of us want to grow our lists, right? Bigger audience means bigger sales. But if you attract the "wrong" audience, you can end up with a list of subscribers who are fans but not customers or clients. (I once took on a launch email project for a high-ticket coaching offer and got zero conversions. Let’s just say, it was a learning experience. )

So the first advice I gave her was to clean her list. It's hard to let subscribers go when we work so hard to get them. But when people aren't opening, aren't clicking, aren't interacting in any way, it actually hurts your deliverability.

Here's how we approached it:

Step 1: Identify the disengaged. We looked at anyone who hadn't opened or clicked in the last 90 days. These aren't bad people—they're just not her people anymore.

Step 2: Send a re-engagement campaign. Before removing anyone, she would send a short, honest email acknowledging the silence and asking if they still wanted to hear from her. Something like: "I've noticed you haven't opened my emails in a while. No hard feelings if you've moved on—but if you want to stay, click here to let me know."

Step 3: Let them go. Anyone who doesn't respond gets removed. Yes, the list shrinks. But deliverability improves, engagement rates go up, and the people who remain are actually interested. From there, use tagging to keep track of engagement and interests. I use Kit (affiliate link) for this—it makes it incredibly easy to tag subscribers based on what they click, which freebies they download, or which emails they engage with. This way, you're not just building a list; you're building an organized, segmented audience you can speak to more specifically.

Then we made a plan to focus on the smaller, more engaged segment—the people who valued her expertise and were ready to invest. By tightening her freebie to attract buyers (not browsers) and adjusting her messaging to speak directly to people ready to take action, she could build a list that actually converts.

Takeaway: If your list isn't buying, it might not be your writing — it might be your audience. When freebie funnels kind of took over online marketing in the late 2010s, people were seeing massive list growth. But not everyone was making sales or growing their communities. In some cases, smaller really is better.

The Bigger Picture

Most email "problems" aren't about the technical stuff or about sending at the perfect time of day or not being interesting enough. Often, it comes down to stepping back and making simple tweaks.

Test your fixes, check your analytics, and adjust as needed. Taking action is infinitely better than letting your email list gather dust. And here's the good news: email is still one of the most reliable, intimate, and effective ways to build your business. You just need to make sure you're speaking to the right people, showing up consistently, and giving them what they actually want right now—not what worked in 2015.

Note: This post contains an affiliate link to Kit, my preferred email service provider. I may earn a small commission if you sign up through my link, at no extra cost to you. I only recommend tools I actually use.