Skip to main content

Ann Handley started her first newsletter when she was eight and now she’s pioneering cryptocurrency adoption for the creator class. Eclectic and prolific don’t even come close. She also knows how to organise a bookshelf properly… by colour. Let’s do this.

Tell me about Ann. Where are you? Where did you grow up?

Where are you. This question. Right off the bat. What a doozy.

I just thought about it for a very long time. Here goes.

Where am I. Right now, Google Earth will tell you I’m outside Boston, Massachusetts. I’m in my Tiny House Studio.



View this post on Instagram


A post shared by Ann Handley (@annhandley)

And outside (in winter)…


View this post on Instagram


A post shared by Ann Handley (@annhandley)

Where am I: In the year. It’s a Friday in mid-October. A glorious, golden day after an insanely busy week. Soft air. Warm sun.

Not really atypical for this time of year in Boston. But still it feels a little precious and rare. We won’t have many more days like this. Winter is coming, as George RR Martin had Lord Stark say.

Where am I: In my life. I’m loved and needed and feel a sense of belonging. I’m generally happy and upbeat.

Where am I: Existentially. I search for purpose and meaning like the rest of us. Writing gives me that. Our days slip by fast. Writing helps me pause. It helps me not just document but actually notice.

. . .

I sense that was more than you wanted. I over-thought this answer, didn’t I LOL.

Let’s add “chronic over-thinker” in there somewhere.

Oh, and I grew up one town over from where I live now.

I am the youngest in a family of 6, and we lived together in a minuscule ranch house with 3 bedrooms, 1 bathroom. You can imagine the arguments each morning.

I grew up riding my bike to this town’s library. And it made me want to live here. Eventually I did.

How did Total Annarchy come about? (What a name, btw!!)

A few reasons:

1) I missed making things.

The further you get along in your career, the less you touch things. You manage people who touch things. You strategize the things. But you tend to not be the person pushing the buttons. I wanted to push the buttons again.

2) I speak and write about how businesses can be stronger digital marketers. I wanted to be able to understand what it takes to grow a list and community from the inside-out.

If I’m telling others how to do it, I should do it, right? Right.

3) I wanted to. The psychic and creative satisfaction I get from writing and publishing every two weeks is enormous. The fact that I’ve never broken the chain after 3 ½ years makes me feel accomplished in a small but measurable way. (That matters to no one but me. And that’s ok.)

(And thanks!) < for loving the name

Annarchy as is punk/chaos? or anarchy as in burn down government? Am I reading too much into it?

LOL maybe you’re reading too much into it. But I’m the last person to judge anyone for over-thinking. We’ve established that. (See Q1.)

One definition of “anarchy” is a Utopian society without a government. I suppose in some ways I am speaking to the “Utopia” within us all.

Through my work, I want to encourage the best versions of ourselves.

As marketers. As writers. As people.

I’m guessing this isn’t your first newsletter, how is inbox publishing evolving?

My first newsletter was What’s Up?!, a neighborhood newsletter I launched when I was 8 years old. There was no internet. This was print.

I shared neighborhood news and updates. I wrote about the Hoyle’s new car (used). I narced on the Spencers, who ignored the leash laws and let their slobbery hound roam the streets and molest everyone’s trash.

My dad Xeroxed it at his office and I distributed it on my bike. 100% open rate. But the click-thru was terrible. 🙂

Decades later, the internet happened.

I built my first company (ClickZ) and now MarketingProfs around the inbox. Certainly the tech has evolved. But at the same time, the ability to write a letter to one person at one time isn’t just fundamental to the inbox… it’s critical to marketing in 2021, 2022, and beyond.

Your email newsletter is less about the news, and more about the letter. The smartest people recognize that the newsletter is not a distribution strategy; it’s a unique opportunity to write directly to those who matter most to you.

In Everybody Writes in 2014, I wrote that publishing is a privilege. I will believe that to be true.

The more you live that, the more success you’ll have.

What else are you working on?

Right now: The As to your Qs. (Is anyone still reading?)

Later today: The 2nd edition of Everybody Writes.

Why re-release a consistently strong-selling book? I decided to add more about newsletters and email and update some dated references. And also take the opportunity to fix some things that bug me about the first edition. It’ll be out sometimes next year.

How many subscribers do you have, right now? What have you done to grow the audience? What worked? what didn’t?

The newsletter started 3 years ago with just over 2K subscribers. Today it’s 42K addressable (+2,000%).

I’ve grown it organically. No forced opt-in or lead magnets or coercion or popovers.

That might sound judgmental about popovers… it’s not. Popovers work, but they’re not right for my newsletter. I wanted a reader’s relationship with me, ultimately, to be the trigger than would grow the list.

I’m more interested in quality of the list than size. So I can make decisions based on that vs. reaching as many people as quickly as possible.

How I’ve grown it, specifically:

Direct referrals from current subscribers who pass it along to friends
Social referrals from current subscribers who share it on social channels
Soft sell in speeches, podcasts, etc (“If you’ve liked what I’ve had to say… please subscribe.”)
Referrals from those whose work I celebrate in each issue

BUT! The biggest trigger to growth:

Make something no one else does.

My newsletter is useful, fun, readable, personable, and—for many—a Sunday morning must-read.

What’s your big goal for Total Annarchy? How does it fit in with your other projects?

My first and biggest goal is personal: To continue to have fun and to love doing it. To experiment. Try new things. Evolve my writing style and voice and relationship with readers.

My second goal is to use the newsletter as a way to differentiate myself. You can’t read my newsletter and think, “Oh, this sounds like Seth Godin.” Or: “This sounds like Tina Fey.” (LOL) It’s how I carve out and publicly own my own POV. (I bolded that because it’s important.)

My third business goal is to promote my speaking, my books, my company, partnerships, and any other current projects. But that’s secondary (third-erary?) because for this to work at all the first two goals MUST be checked.

I’m obsessed with other peoples’ process – how does your newsletter come together? What’s your workflow? What tools do you use? Who else is involved?

I want to draw this flowchart for you. But instead here’s the narrative version…

THINK Sometimes I’ve had an idea in my head for days and days… and some weeks it’s harder.

WRITE Every two weeks I start to freak out because – even though I publish only every two weeks and I SWEAR that this week will be different! I’ll work on it a little bit throughout the 14 days versus doing all the work while crying and stressed (LOL)

REWRITE It takes me about 7-8 hours over 2 days to write usually 4 drafts.

EDIT I send draft #4 to my longtime editor. He edits. I tweak.

LOAD into Aweber.

TWEAK again within the platform.

SCHEDULE. Tee it up.

TWEAK (OMG ENOUGH ALREADY) a final time literally moments before it mails at 6 AM ET-ish Sunday.

I’m an endless tweaker. Which is why that not-breaking-the-chain deadline is so critical to me. Otherwise I’d never ship.

Love that you created your own $WORD token (and bought a little). What’s your vision? Is this the beginning of a new economy for creators?

Thank you!

Right now I’m using it as a way to call out and celebrate good work through the newsletter itself. Eventually I’d like to implement a way that enables others to use $WORD to do the same.

Coins like $WORD helps any one of us give unique value to fans and communities… and vice-versa.

What’s your business model for Total Annarchy?

I think I explained this in my Goals answer, above.

The model is to integrate with other things I’m doing. Not “monetize” it on its own. I’m not interested in paid subs or advertising, for example.

It’s right for many. Not for me.

What big idea would you love to work on if you had unlimited time and money?

I haven’t written a novel or book of short stories. I’d love to do that. But is that because of a lack of time? A lack of money? Let’s end this interview where we started… by over-thinking questions.

It’s a copout to say that I haven’t done it because of time or money.

It’s an excuse to say I don’t have time.

The real reason is… I don’t know. Fear, maybe? Some laziness?

Here’s the thing: Writers who we think of as successful aren’t the most talented. They’re successful because they have developed habits of mind and habits of muscle.

Disciple and doing. That’s all.

Subscribe to Total Annarchy

Subscribe ↗