Optimizing for Relationships is the Annswer: Inside the Total Annarchy Newsletter
Ann Handley shares the content strategy behind her hugely successful newsletter for writers and marketers.
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Ann Handley might be the best person I know at relationships.
Not only is she a great writer, a great marketer, and a brilliant speaker, but she’s also just a SUPER nice, funny person that is a treat to talk with. Every time Ann and I have chatted over the years, I come away inspired, I feel ‘in sync’ with our content thinking… and I always feel like she is a person I would love to spend more time with.
This is the magic of Ann Handley, not just for me, but for over FORTY THOUSAND email subscribers to her massively popular Total Annarchy newsletter. They all want to spend more time with Ann. It’s not an accident.
If “location, location, location!” is the rallying cry of the real estate agent, Ann’s might well be “relationships, relationships, relationships!”
Here’s how she does it…
The High Bar for Earning Attention
To build a large newsletter audience, you really have to earn it. People have to opt in. It’s an exceptionally high bar. People have to VOLUNTARILY invite you into their inboxes. Not just once, but over and over and over again.
They sign up for my email newsletter because the value that I provide is something that they want.
They want to hear from me, they want information from me. For me, that's the Holy Grail of Earning Attention from anybody.
I love that that bar is so high, and I love the fact that the minute that I disappoint them or that I don't deliver on their expectation, they can unsubscribe and I can never darken their doorstep again.
And I love that kind of pressure as a marketer and as a person.
This is the mindset of someone who puts the audience first: acknowledging and embracing the height of the bar.
Optimize for the Relationship
If you are thinking to yourself, “I put the audience first!”… prepare to come down to Earth a bit. Ann is next level. I wanted to know why Total Annarchy earns so much attention. She earns attention because she pays attention. She pays attention to EVERY aspect of the newsletter.
I've optimized for it. Every choice that I make is always in service of providing a better product to the people on my list.
The email newsletter is free, right? I don't charge for it. I don't have a subscription model behind it, BUT I think of it as something that people will be willing to pay for.
Every choice that I make, every decision that I make, starting from the subject line to the things that I talk about in the newsletter, to my onboarding experience is all in service to the subscriber, the reader.
And I want them to feel that, like I want them to know that to me, I've optimized for the relationship with me instead of the fact that I have this email newsletter.
I think of individual readers first and I think about the product second.
I think the reason why it's been successful is the way that I run it and the way that I onboard readers to it - I think it feels different than any other newsletter.
I’m not going to lie. I’m currently second-guessing whether I’ve thought deeply enough about my own newsletter (the one you are reading right now…)
The Handleysphere - Building a Strategic Content Ecosystem
The Total Annarchy origin story is a classic “scratch your own itch” start-up story.
I started the newsletter four years ago-ish. I couldn't find anything that talked about the craft of writing, especially through a marketing lens and through an inherently personal lens. That's really what I wanted, I couldn't find it, so I decided to make it.
Here’s the interesting thing - Ann did a LOT before starting her newsletter. She published books, she keynoted conferences all the time, she led Marketing Profs, she consulted, she was a journalist, and much more. But the newsletter quickly became the hub of her entire ecosystem.
It’s all driven by the newsletter because the newsletter is where I do my best thinking. Writing is thinking, right? And so, the newsletter is the place where I show up most consistently and where I share my best thoughts.
They're not always fully baked thoughts, and they may evolve into a speech, they may evolve into a book, or sometimes even a LinkedIn post. But the thinking all starts there.
So that's the core of the ecosystem.
It's the foundation of my relationships with anybody who could potentially hire me. It keeps me relevant to an audience that will hire me to speak, that will buy my books, will recommend my work and will recommend me for other opportunities. Most of my opportunities come from the newsletter. So that's kind of the business reason why I do it.
OWBR: Think Differently About Measuring Content
James Clear, the author of Atomic Habits, suggests regularly asking the question “What am I optimizing for?” The reason is that you might be spending time on activities that are optimizing for the wrong thing - for example, you might be optimizing for money when you actually want more time.
Once you know what you’re optimizing for, you should then ask “How do I measure it?”
Content operates in a similar way - creators should regularly ask themselves, “What am I optimizing for?” Am I optimizing for money? For brand awareness? For impact? Each one of these answers would lead to different focuses for measuring whether you’re successful.
Ann is crystal clear about what she’s optimizing for: relationships. And so, again very smartly, she has created her own metrics (!) to measure the effectiveness of her relationship-building.
My issue with a lot of marketing metrics, particularly email metrics, is that they tend to measure things that don't necessarily relate to the relationship between the brand and the customer, or the prospect.
We can look at click-through rates sometimes for a landing page for example. You can see how many of those resulted in sales. And while that measures an action, it doesn't measure a metric that is a little bit softer, but ultimately is more powerful: the relationship between you as a brand (or me as a person), and your reader, your customer or prospect.
And so I've evolved to using metrics that I've made up to measure the impact of my work. One of the metrics that I look at is what I call the O.W.B.R., which is my Open to Write Back Rate, also known as OWBR.
This means how many people will open an email newsletter that I send and are inspired to write back to me. So they open it, they read it, and they write back to me. I literally optimize for that particular metric.
Why do I do that? If I am in the relationship business - and I believe all of marketing is a relationship business - then I want people to have a relationship with me.
And so I want them to write back to me.
OWBR-driven Content
Ann does not stop at identifying and measuring OWBR. She designs and writes for an OWBR outcome. Knowing that she is optimizing for relationships and that OWBR is her chosen metric, she has built features and queries into the newsletter itself to drive OWBR success.
I put little triggers in an email newsletter. Sometimes overtly like, ‘Tell me what you think about this.’ And sometimes less overtly, like in the footer of every email newsletter, there are five ways that you can support this newsletter or that you can support my work. And one of them is ‘Hit reply and say hi.’
I track that metric. If it's low in one particular week after one particular send, I wonder about it. Why didn't this resonate quite as much as I thought it would?
Another metric I track starts right at the beginning of the relationship. When you sign up for my email newsletter, you'll get an autoresponder that says immediately, ‘Thank you for signing up. Here's what to expect.’ It sets expectations immediately for what they get, when they get it, and then I ask them two questions:
How did you find me? (Who was recommending my work is what I want to know in that situation. What brand, what person, did they see it on? LinkedIn? Twitter? Was it forwarded from a friend?)
What do you hope to learn here? (Which is very valuable to me, just to know how are people perceiving me? What do they think I'm all about?)
Close to 90% of new subscribers open that first email, the introductory email that sets expectations. And about half of them write back to me. That's amazing. And then I will write them and say, ‘Thank you, nice to meet you.’
And the question I get a lot is, isn't that, doesn't that take you an enormous amount of time? Maybe it takes me an hour a week, but I put that in the marketing bucket. That is an effort that ultimately benefits me long term.
That is some impressive relationship-building strategy!
Forget Best Practices
The internet is FILLED with advice and best practices about how to grow an email newsletter. And you can see the sameness in many email newsletters that follow the conventional best practices.
However, when you know what you’re optimizing for and it’s not the same as everyone else, you can feel much more confident in chucking best practices out the window and doing the right thing for your goals and your audience.
Ann designs for relationships and that means doing things differently.
I have never listened to the best practices around email newsletters. If you read them, it's “Keep it short because people want to get in and get out!”
Mine is very often 1500 words. It’s giving yourself permission to push back against best practices and not take them at face value. If my newsletter wasn't growing and if the feedback I got from people all the time was that they couldn't make it through, then I would reconsider that long-form email newsletter.
But that's not what I get. What I get is “This is 1500 words that didn't feel like 1500 words.”
Formatting & Pacing FTW!
Making 1500 words not feel like 1500 words is not a happy accident either. It is a deliberate, thoughtful strategy focusing on formatting and pacing.
Formatting is one piece, like having subheads and like having predictable pieces of it. For example, the Department of Shenanigans. I know for a fact that that is the most clicked thing on the website. Events is always a section. Very often I have a Content Tools section.
But the pacing is vital. Paragraphs are typically no more than one or two sentences, sometimes three. Lots of white space. One paragraph leads to the next. I obsess over the pacing of it and like making sure that it pulls you through.
So it starts with a story very often. I want to pull the reader through and I want to lead them along. I don't want it to feel like, “Ugh, I'm gonna skip this paragraph because that looks like a chunk of great text right there.”
I understand because I am that person, too. I am incredibly impatient.
I LOVE how incredibly generous and thoughtful Ann is about Total Annarchy. Clearly, she is not kidding when she says she’s examined every element and optimized for relationships. She even publishes on an unusual cadence - every two weeks, or fortnightly as Ann puts it.
I am a huge fan of “fewer things better” and leaving people wanting more. I always look forward to Ann’s next newsletter because each one is so good and I have to wait two weeks for the next one.
Takeaways
What are you optimizing for with your content?
Is every element of your content designed for that optimization outcome?
Is your measurement aligned with what you’re optimizing for?
Have you considered optimizing for relationships?
How could you encourage stronger relationships with your content?
Which best practices are you following that are not aligned with what you're optimizing for?
There’s more to come from Ann about how to think about brand voice in the next edition! In the meantime, sign up to Total Annarchy and for loads more ideas about creating ridiculously good content, check out Ann’s best-selling book, Everybody Writes (Second Edition).
What’s Earned My Attention Recently
The Year of the Slim Volume
Esquire has a piece about why short books are hot in 2023. I’ve just read new short non-fiction books by Seth Godin and Michael Bungay Stanier and they explicitly call out that these are short books designed for compressing valuable information into efficient reads.
This Format Outperforms
The answer: what is “Game Shows”? It’s fascinating to watch the passing of the baton to the next generation of game show hosts. Ryan Seacrest is the latest, signing on to become the new host of Wheel of Fortune when Pat Sajak retires. Wheel, along with Jeopardy, The Price Is Right, Family Feud, and many others are incredibly valuable formats and franchises.
Measuring Content from Brands
Signal Hill Insights continues to share smart insights about measuring the effectiveness of content, particularly from brands. Brands make content for different reasons than media companies, and so they need to think differently about what to measure (much like Ann!). This article nails the unconventional metrics that matter.
If you’re seeking to create a differentiation strategy for your business and your marketing, please reach out to The Creativity Business.