The newsletter donut hole

I have two email newsletters (technically, there's also the LinkedIn one).

If people know about either of them, it's probably Mail Fails.

Mail Fails is easy to talk about. It's a bite-size daily newsletter about email flubs, the kind that make you laugh and then make you think about what went wrong.

When someone posts a wild inbox mistake on LinkedIn, I drop a comment and mention it. When someone asks if I have an email list, Mail Fails usually comes up first. The description takes one breath and people immediately get it.

My other newsletter is Inbox Welcome.

This is the one that's tied to my actual business. The one that should be generating leads, positioning me as a thought leader, doing all the things the advice says a professional newsletter is supposed to do.

You can't just call it a weekly update—people don't want your newsletter, they want the results. But how are you supposed to name the transformation before you've written enough to know what the transformation is?

Mail Fails had none of that weight. It was an unhinged side project.

I had a clear idea for it, built the sending engine myself, designed it my way, and gave it full permission to just be what it was. The identity showed up on day one because nothing was in the way.

Inbox Welcome newsletter came first. It had a real launch—a podcast appearance that brought in subscribers. It had a built-in business case. Every strategic advantage. And for over a year, I struggled to describe it with the same ease. Every time I tried, I had to stop and think. That half-second of hesitation was always enough to make me reach for Mail Fails instead.

For a long time I thought that meant something was wrong with me: not disciplined enough, not clear enough on my positioning.

Then I started noticing the same pattern in other people.

A newsletter owner in a Power Up Hour session had been running ads to grow their list. The subscriber count looked healthy, but engagement dropped the moment people joined.

A mental health nonprofit in a pro bono session was paying for Facebook ads while sitting on a dozen community partners who already had engaged audiences and already sent their own newsletters.

They'd never once asked any of those partners to mention them.

In both cases, they knew organic sharing was an option. They just hadn't done it.

I don't believe the problem was shyness. I think it was the same thing I'd been experiencing: they couldn't describe the newsletter clearly enough to feel confident asking someone else to promote it.

Most newsletters grow in three phases.

At the start, your subscribers are people who already know you: friends, colleagues, people you met "in real life". Engagement is strong because they already have context for who you are.

Then that pool runs out.

The newsletter isn't large enough to generate clear feedback: replies are rare, open rates bounce around, and you're still figuring out what the newsletter is actually about. Publishing every week can feel like sending into a void, so many just...stop.

This is the newsletter donut hole.

Nearly every variable is wobbling independently: your topic is evolving, your audience is shifting, your cadence might be inconsistent.

The feedback loops that normally help writers sharpen their thinking are too faint to read. And from the inside, all of that instability feels like a personal failing rather than a structural stage that nearly every newsletter passes through.

When you're in the donut hole, impersonal growth channels become very attractive.

Ads promise subscribers on demand. Recommendation networks promise access to other audiences through a checkbox the subscriber barely noticed.

These channels feel safe because you don't have to describe the newsletter to anyone. You don't have to ask someone to put their credibility behind something you're still figuring out.

You can just pay, automate, and grow the number.

But the way subscribers arrive shapes how they behave once they're on your list.

When someone subscribes because a friend forwarded your newsletter and said "you need to read this," they arrive with context. They open the next email expecting something useful.

When someone subscribes through an ad or a recommendation they barely registered, they arrive with almost no context. Your next email lands and they think, who is this? They ignore it. They unsubscribe. Sometimes they mark it as spam.

Those reactions aren't just lost subscribers. Gmail, Yahoo, and Microsoft are watching how people respond to your emails—the opens, the ignoring, the complaints—and using that data to decide whether your messages belong in the inbox or somewhere else.

Low-context subscribers who arrive in large numbers can dilute those signals and quietly erode your deliverability. The list gets bigger but the signals stay noisy. Scale increases but clarity doesn't.

The growth channel that felt safest can actually make the donut hole worse.

Direct referrals work differently, and not just because they're free.

When you ask someone to share your newsletter, they're going to ask a very natural question: what should I tell people it's about?

In the donut hole, that question is uncomfortable. But it might be the most useful question anyone can ask you. Because answering it forces clarity. Not the theoretical clarity of "what should my positioning be," but the practical clarity of "what do I say to a real person in one sentence." And every time you try a description and watch whether it lands, the newsletter's identity gets a little sharper.

The subscribers who arrive through sharing behave differently too. They show up already knowing what to expect. They open, they read, they sometimes reply. Those engagement signals are exactly what inbox providers use to decide your emails are wanted.

Referrals don't just grow your list. They increase signal density in a system that's been too noisy to read.

The audience quality improves. The engagement data gets clearer. The writer gets better feedback. The system stabilizes.

That's what happened with Inbox Welcome newsletter. Slowly, through the writing and through conversations with readers and clients, the description got sharper. I stopped trying to name the transformation and started paying attention to what I was actually exploring: the triangle between what senders do, what subscribers do, and what mailbox providers do in response.

The psychology and mechanics of getting emails seen.

It took over a year. But now I have the sentence.

If your newsletter is in the donut hole, here are a few things that help.

Give people the words. Don't ask someone to share "your newsletter." Give them a sentence they can use. If you don't have that sentence yet, try describing it to five different people this week and pay attention to which version makes them lean in.

Give them something specific to share. Point people to a post about the newsletter or ask them to forward one issue you're proud of—something that made a subscriber reply or taught someone something they didn't expect. People share things that make them look helpful to the person they're sending it to.

Make the link easy to say out loud. Buy a short domain that reflects what the newsletter is about and redirect it to your signup page. Inbox Welcome's tagline is "From Sent to Seen", so I bought FromSentToSeen.com.

The answer to "where do I subscribe?" becomes a phrase instead of a string of random characters from a form builder.

Ask once, honestly. At the bottom of your next email, try something like: If this was useful, I'd be grateful if you forwarded it to one person who'd get something out of it. This newsletter is still young, and every share makes a real difference. You don't need to be clever. You need to be direct.

Let go of subscribers who aren't there. If you grew through ads or referral engines and those subscribers aren't engaging, consider letting them go.

That's not throwing away money. It's clearing noise so you can read the signal (and maybe even reducing your costs).

A 200-person list of readers who chose to be there will outperform a 2,000-person list of people who barely remember subscribing on all metrics: in engagement, in deliverability, and in how it feels to hit send.

The donut hole is where most newsletters quietly die. Not because the author wasn't committed or the writing was bad, but because the signals were too weak for the writer to know whether they were on the right track.

The ones that survive aren't the ones with the best growth tactics. They're the ones that kept writing long enough to find the sentence, and then started asking people to share it.

I'm still in it. But I can finally see the way out.