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I Made It: How Ann Handley revived the “dead” newsletter

Discover how Ann Handley created her newsletter, Total ANNARCHY, plus her creative process for making her work stand out from the rest.

January 31, 2020 by Cyn Meyer

When you make it to the top of a mountain after a hard-earned climb, the view is typically epic.

Most people see it as the pinnacle goal and decide to rest easy after reaching nature’s plateau.

When it comes to chasing your career goals, it might be the same. 

Which makes sense because, after all, it takes an incredible amount of effort (and likely overcoming imposter syndrome and some coping with perfectionism) to become a successful entrepreneur.

But this isn’t the case for Ann Handley.

Nope. This marketing guru continues to take on new big challenges, even though she’s got the mecca of creative success already under her belt. 

She’s a renowned keynote speaker, partner and Chief Content Officer at MarketingProfs, and a two-time Wall Street Journal best-selling author. 

Not to mention, she’s the digital and content marketing expert.

And she still had it in her to take on the challenge of turning a so-called outdated format into a robust newsletter, Total ANNARCHY, which resonates with her growing readership.

We had the honor of sitting with Ann for the fifth episode of I Made It, a podcast for creators who get things done, where she shared with us the why, what, and how of creating her newsletter.

It doesn’t matter if you’re wondering how to start an online business from home, toying with side business ideas, or wanting to scale your profitable digital products -- there’s something of value to glean from Ann’s words of wisdom.

Let’s start by uncovering why Ann decided to produce a newsletter in the first place.

Ann’s purpose for her newsletter

Ann’s purpose for creating her newsletter is two-pronged. First, she simply wanted to make something she could claim as her own again.

After years of booming her business in a leadership role, she fell out of touch with physically crafting creative works. 

“I wasn't touching anything anymore. And when I went back, you know, 15 years, I was touching things all the time,” she fondly remembers. “I was producing the MarketingProps newsletter, I was editing content, I was reaching out to writers and getting their headshots.”

In an effort to get back into “touching” creative deliverables again, Ann was compelled to write her newsletter to satisfy her appetite for creating.

“Just that psychic satisfaction or feeling that . . . I'm actually making something that’s 100% mine.”

The second reason she committed to her fortnightly newsletter is she wanted to explore her interests, particularly her passion for writing. 

“I really wanted a place to explore my interests, which are around marketing, . . . content marketing, but also writing.” Ann claims, “I'm super passionate about writing, as you know. That's really my background and my first love.”

So, she rekindled her passion for writing -- in the form of her Total ANNARCHY newsletter.

As far as where her newsletter fits into the other preexisting arms of her successful business, it falls nicely in the center of all three parts -- MarketingProfs, her speaking business, and her books. 

“I think that it's sort of the nexus of those three things, which is really what the newsletter is about,” she states. “In all of those three things, it also touches the three components of my professional life.”

How’s that for a perfectly complementary creative work?

If you’re wondering why Ann decided to go with a newsletter format, she shares that, too.

Why Ann chose the newsletter format

A big reason why Ann was drawn to the newsletter format is because of the challenges it presented, one of which is being held accountable. 

“Because people can unsubscribe from a newsletter and you can never darken their doorstep again,” she reasons. “And I like that because it calls me to an accountability that I find really challenging.”

That’s not the only thing that presented a challenge. 

People were calling the newsletter “dead”. Ann read numerous articles calling email newsletters “old-school” and a trend that was “done” and “over”.

Naturally, she treated those claims like her own personal challenge for getting to the bottom of such hefty assumptions and turning them on their heads. 

“I love taking that and playing with it and experimenting with -- is it really? Is this not the case, or are we just doing it wrong?” she contends. “And so I think that is a place where I like to apply my creativity more broadly.”

As far as deciding on her newsletter’s distribution frequency, Ann went with every other week for two reasons. 

The first being the most practical -- she’s busy. 

Ann made a choice to produce something of value, knowing that it would require some thoughtfulness and dedicated time, so her schedule doesn’t allow for more frequency than that.

The other reason she went with sending a newsletter every other week is she wanted to experiment with her newsletter length, particularly long-form emails. 

“I also knew from the beginning that I wanted to play with length,” Ann muses. “I wanted to play with the idea that newsletters can't be long-form, that you'll lose readers, that people don't have the tolerance or patience for long-form, especially in an email.”

Which she reasoned, “it’s almost too much to ask people to read something long-form with more frequency.”

So, she decided to go with the fortnightly distribution of every other Sunday morning.

Why Sunday mornings? 

In a nutshell, “because it’s a very contemplative time,” Ann explains, “I think it's a good time to take a step back and put things in context a little bit, which is exactly what my newsletter tries to do.” 

Not only does her newsletter attempt to do that, but it achieves it with flying colors. Ann regularly receives feedback from her readers that they save her newsletter for a Monday morning read and a fresh start to the week. 

A fresh read is exactly what Total ANNARCHY delivers, even when you compare it to Ann’s other published goodies.

How Ann’s newsletter is different from her previous written works

Unlike her best-selling books, Everybody Writes and Content Rules, composing her newsletter takes a different spin from her previous creative processes. 

For one, she writes with a more intimate mindset and composes her newsletters with one person in mind, rather than her whole audience. 

While it may be a typical tactic to address a specific avatar, there’s something more personal about writing her newsletters. 

“There was something about that newsletter,” Ann shares. “The fact that I'm writing it to a single person who is  looking at their phone or they're opening up their email, and they're by themselves.”

This mindset shift of addressing an individual in their personal environment as they read her material impacts the way Ann communicates through her newsletters. 

“I think once I realized that, the shift was super powerful for me as a communicator,” she divulges. “I think it gives my writing a sort of intimacy and a sort of shorthand . . . because I think I'm talking to one person.”

Which is why she refers to her readers with single salutations like, “hello, friend” and “hey, you,” giving them a sense that she knows them individually. 

On top of that, Ann also manages to address individuals within an audience that’s made up of a varied demographic, ranging from sole proprietors to consultants to her sister.

How? She calls them out in her subject lines -- something she learned to do overtime. 

If you take a look at her first newsletter, the subject line, “TA #1: New Year, New Newsletter,” is more generic and addresses her audience holistically.

It’s a stark difference from her more recent newsletter with the subject line, “TA #51: What Matters More Than a New Year's Goal; New Storytelling Template; Things to Stop/Things to Adopt in 2020,” which captures the attention of several types of people among her readers.

Not only does Ann focus on addressing individual recipients, but she also reveals more about her authentic self and writes with a vulnerability that aims to feel like a one-to-one ratio.

“It's really important for the creator to realize the same -- that there’s one person on the other end and they've got to be useful to them,” she explains. 

Which is a concept that applies to all forms of creative works.

“It's not about the creator, it's not about the writer, it's not about the podcast -- it's about the value you're delivering . . . that equation is balanced when you think of it only as one person to one person,” Ann coaches. 

Not only is Ann’s newsletter different from her previous written work, but it’s also unique from other newsletters.

What sets Ann’s newsletter apart from the rest

What makes Ann’s Total ANNARCHY so unique from other newsletters is the focus on the “letter” part, rather than the “news” part of “newsletter”.

In other words, unlike most companies, she treats her newsletter more like a traditional letter than a news announcement about products and services. 

“One of the epiphanies that I had was that this really is truly a letter,” Ann shares. “A lot of brands, a lot of companies, a lot of people, when they think about an email newsletter, they focus on the ‘news’ part of the word.” 

By changing her focus from “news” to “letter,” her entire communication style and thought process moved, too.

“It’s a shift in how you think about things,” she explains. “I think, ultimately, that shift eventually changes the way you communicate, changes the way you market. I think it changes the way you think about the people you're marketing to.”

To focus on the “letter” part of her newsletter, Ann adopted a daily journaling habit. 

“I write down things that happened that made me laugh or just like stuff that I see that I think is ridiculous or that I may be able to use it at some point somewhere,” she shares. “That's really where a lot of these letters come from.”

It doesn’t get more personal than writing authentic letters -- inspired by personal daily journaling -- to individual readers.

Ann’s personal sharing doesn’t stop there, either. In fact, it’s the topic of her parting advice for creators.

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Ann’s advice for fellow creators

When it comes to making a unique and memorable business, Ann’s advice is to go beyond building trust and to also build affinity by sharing your authentic self.

Put another way, your audience needs to both trust and like you.

“There are a million ways to do it, but I think that the intersection of two things -- of the trust and the affinity -- is ultimately what really will set your company apart,” Ann explains. “And it's something that no one else can copy. No one else can be you.” 

Most businesses head straight for the trust factor and stop there. 

“So many other people can maybe act with that same impulse toward trust,” Ann warns. “But I think showing who you are as a person, as a company, and as a brand, is also a massive differentiator.”

Ready to inject more of your personality into your brand? 

Great. We’re here to support you as you ship your ‘uniquely you’ products into the world. (In fact, a full support team is readily available on the other side of this 2-week free trial from Podia.) 

Otherwise, for more great advice from successful leaders like Ann, sign up for our exclusive email list and receive each I Made It episode straight to your inbox.

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