• The Ann Handley newsletter proves that what you focus on makes all the difference in growing an engaged email list
  • Don’t skip the must-do first step to create a newsletter that gets engagement
  • You need to consider more than open rates and click-through rates

Every other Sunday, I have coffee with Ann Handley.

Ann doesn’t know about this coffee time. Or me…

Nevertheless, the Ann Handley newsletter, Total ANNARCHY, is part of my Sunday morning routine.

And according to Ann, I’m one of more than 42,000 engaged readers.

So what makes Ann Handley’s newsletter so effective (and the talk of the marketing town)?

Let’s break it down:

6 insights from the Ann Handley newsletter you should apply to your own

1. Your newsletter needs a face. What do Family Feud, The Price is Right, and Jeopardy all have in common? A host. Ann Handley is the face (and sole creator) of Total ANNARCHY.

People like people. We want to see a person. If you don’t have a host for your newsletter, you need one.

2. Focus on newsLETTER. Many companies use their newsletter as an opportunity to spam subscribers with information about their company (news).

Ann Handley focuses on writing a letter.

By focusing on LETTER, Ann’s content starts and ends with what the reader will find relevant and valuable.

Ann says it best…

One person. One inbox. Massive opportunity to send a letter to that person.

3. Write to one person. If you want your newsletter to appeal to a larger audience, write it to just one person.

Ann’s writing feels personal, purposeful, and poignant because writing a letter means writing to a single person – not a crowd.

Check out the different ways Ann has greeted her reader in a 1:1 way, instead of opening her email newsletter with something like: “Hey, everybody!”

4. Tell stories that add value. Ann often hooks readers with an engaging, slice-of-life story.

Then throughout the newsletter, she connects the story to a broader takeaway that adds even more value for the reader.

As marketers and copywriters, it’s our job to weave engaging, unexpected, or relatable content with valuable information readers want.

Stories are an effective way to do that.

Here’s one example of an unexpected story Ann opened with:

Admit it. You want to hear more about this pizza-eating squirrel and see how Ann connects him to valuable information for her reader.

5. Use scroll-inducing sections. At the end of each newsletter, you’ll find an audience favorite: Ann’s “Department of Shenanigans,” a section where Ann usually shares a playful nugget for readers to enjoy.

Consider: What content could you place near the end of your newsletter that would get a reader to keep scrolling?

6. Obsess over onboarding. Onboarding a new subscriber is one of the most overlooked opportunities to build a long-term relationship with your reader (the open rates are pretty good too). 

Ann Handley uses her welcome email to set expectations, reinforce you’re in the right place and ask the reader for a bit of information about themselves (valuable insights for marketers).

If you have even one subscriber, you need to write this email now.

Ready to write a welcome email that’s as bada$$ as the Ann Handley newsletter email?

Here’s a tutorial to get ‘er done…

Other email newsletters we love (and the strategies they teach us)

The Daily Carnage – Carney
Lesson: Your newsletter needs a value proposition.
Before you start planning your newsletter, get clear on the reason for its existence.

Your first step is to determine how your newsletter will provide value to the audience and to your business. 

The Daily Carnage newsletter makes its value proposition clear in the homepage headline. 

Electric Speed – Jane Friedman 
Lesson: Keep a schedule.
You want readers to look forward to your newsletter in their inbox.

Get them anticipating by sharing how often and when they can expect it. 

The 3-2-1 Newsletter – James Clear 
Lesson: Set expectations.
Remind readers of the value you’re bringing to their inboxes.

James Clear named his newsletter in a way that expresses the value it offers: 3 ideas, 2 quotes, and 1 thought-provoking question. In every newsletter.

Your email newsletter (like the Ann Handley newsletter) needs a Sunday morning coffee test

We’re trained to look at open rates, click-through rates… and all the other email marketing KPIs.

But don’t overlook the harder-to-measure email newsletter success indicators: 

… A reader tells you her day feels off when she misses your Sunday morning newsletter with her coffee.

…Readers pause the cat videos they’re watching to read your newsletter.


…A reader says your newsletter always lifts their spirits.

Engagement like that goes far beyond high open and click-through rates.

Take a lesson from Ann Handley’s newsletter…

Write a value-focused newsLETTER.

“I want a reader’s relationship with me to be, ultimately, the trigger that would grow the list.”

– Ann Handley

Here are a few resources for your next (newsletter) steps:

Just remember…

Write to one person. Send to a list.