The most important part of the newsletter is the letter, not the news.

I've been obsessed with email newsletters since January 28, 2018, when I relaunched my newsletter Total Annarchy (annhandley.com/newsletter) to 2,111 subscribers. Now, close to 50,000 people receive a letter from me every other Sunday morning.

Those 2,111 people were subscribed to blog post triggers at AnnHandley.com. I can't even really call them “subscribers”—because an email alert and a newsletter are not the same thing.

The former is auto-generated. Soulless. Bloodless. More like a ping that it's time to change the batteries in your smoke detector.

Let's do the math: 2,000 to 50,000 is a 2,400% increase. Yet I've grown the list with a focus on engagement, not size.

Size is a byproduct, not a goal.

Here is my approach to creating and writing a newsletter as well as growing an engaged audience—because the two go hand-in-hand.

Let's talk about what worked, what didn't—all with a focus on ideas you can steal.

I have a lot to say on this topic. Empty your bladder. Grab a drink. Settle in. Here we go.

1. Create what you wish existed. For years I searched for a marketing newsletter that focused on writing and storytelling. That walked the walk—meaning, the writing was fun and engaging. Writing I wanted to read.

   Why doesn't it exist? I used to muse, stroking my metaphorical ascot. More musing: How can Marketing see the power in writing?

   Like … duh. Do it then, I told myself. Be your own best fan.

2. Feed yourself first. I get as much joy out of writing a newsletter as I hope subscribers get reading it.

   No good writing is created with dread in your heart and a pit in your stomach. If writing the newsletter felt to me like I was getting a root canal … you'd feel that.

   Weird metric I use: I try to make myself laugh in every issue.

3. Say no. What don't you write about? is as important a question to answer as what you do write about.

   Marketing is big, broad, complex. I leave Rev Ops to the people who are passionate about that kind of thing.

4. Have a clear niche. Specific bests sweeping.

   In the age of content abundance, your niche is already covered. No problem. Add your point of view.

   Your voice is the only thing no one else can copy.

5. Set a schedule you can manage. “I'll write only when I have something to say” doesn't work. It'll instead just give you an excuse NOT to publish.

   Set a schedule. Stick to it. Every week, twice a week, once a fortnight … doesn't matter. Just show up when you say you will.

   Let your audience learn to anticipate you. Do not break the chain. You've got this.

6. Purpose defines goals. My purpose with my newsletter is to build relationships and have fun. That keeps me focused on what matters. I glance at the open rate and click-through rate (CTR).

   But I invented my own metrics to track:

   • OSR (Open to Save Rate): Do your customers save your emails?
   • OWBR (Open to Write Back Rate): What percentage of people start a dialog with you? Especially on that critical Welcome email.
   • RR (Resub Rate): When people change jobs, do they resubscribe with their new email?
   • TUPER (Trust U with my Personal Email Rate): How many subscribers find you so valuable that they invite you into that protected personal inbox? (We all have one.)

     Did I make these metrics up? Yes I did.

     How do I “track” these? Anecdotally.

     How do I do that? I proactively ask in my Welcome email. I watch what people say on social. People write to tell me.

7. Do unscalable things. Because over time … unscalable scales.

   A better header might be “Think Small and Grow Big.” But that feels like a book you'd see in an airport Hudson News.

   The point is: Slow down. Invest where it matters.

   • Spend a lot of time on craft. Writing my newsletter takes me eight hours, on average. Crazy? To some maybe. Worth it for me? Yes.
   • Obsess about voice. Your email is reaching one person at one time. Use your honest voice. Your personality. Your point of view. That's what I mean by “letter” versus “news.”

   You are showing who you are and how you think—not just what you think.

   Sharing what you think might attract an audience, but sharing who you are and how you think will build a lasting relationship between reader and writer, between you and me.

   By the way, your voice can take a while to emerge. Your first issue will probably be awkward and self-conscious and not good. That's okay.

   Think about the first seasons of your long-running favorite shows: At first the characters can seem wooden and weird; it takes a while for the actors to spread out and fully relax into their roles. The same is true of newsletter writers.

   • Spend time on building subscriber relationships. Connecting with subscribers individually matters. More on this in a second.
   • Spend time on building influencer relationships. I hate using the word “influencer” here because it feels transactional. But it's good shorthand for other newsletters, companies, marketers, writers.

   Call out the good work of others. Share the love. Don't expect and ask for reciprocity—that's not friendship, that's coercion.

   (“Actually it's quid pro quo,” some pedant shouted from the back. Whatever, Pedant. No one likes it.)

8. Ditch the forced opt-in, lead magnets, popovers. Yes, they work. No, they aren't for everyone.

   If you use them, make sure you're clear on your goals versus you just read a Best Practices article on how to grow your newsletter list. (I guarantee *THAT* was behind a popover.)

   For a hot minute I once implemented an email signup popover on my site. I took it down a hot minute later. It wasn't me. I'm more interested in the quality of the list than the size of the list.

   I want a reader's relationship with me to be, ultimately, the trigger than would grow the list.

   That line above was a revelation to me. And it made me realize …

9. Your From line matters more than your Subject line.

   There are a ton of tools that help you optimize your Subject line.

   There's no shortcut to optimizing a From line. That's all on you and the value you provide.

10. A relatable “emcee” for your newsletter. It should come from a real person. Not “Marketing@ThisDomain” or “Newsletter@ThatDomain” and absolutely not from “DoNotReply@TheOtherThingDomain” (I hate that guy).

    I see you there, B2B tech company, countering: “But we're a B2B solution.”

    All the more reason for you to anoint an emcee, because it'll make your company more human-scale and accessible.

    That's why the New York Times sends its morning newsletter from senior writer David Leonhardt. That's why CB Insights sends its daily email newsletter from CEO Anand Sanwal. And that's why technology company Toast sends its email newsletter On the Line from Tyler Cumella—a real person who is really a member of the Toast demand-gen team.

11. Snuff out anything with a whiff of “Dear Valued Customers.” Replace it with “Dear You.” You're writing to one person in one inbox—not a roomful of people. We talked about this in Part I. It's critical here.
12. Lots of yous. Count the number of yous in an email newsletter. (From Part I: If you run out of fingers, you're doing great.)
13. Context for curation: “Here's why I'm sharing this useful thing with you; here's why I believe it's important.”
14. Mostly insights; some promotion. Never flip that script.

    You need numbers? Fine: 90/10.

    No: 95/5. (You should flip that script for straight-up direct response email, as in Chapter 73. But we're talking newsletters here.)

15. Obsess over onboarding. You'll never get a second chance to make a first impression, as our Greek god Pinterest tells us—and sells as a frameable poster in his Etsy store.

    Pay attention to that first touch. What does a subscriber get when they sign up for your list? What's the vibe you're giving off? The tone you set?

    • High-five! They should get an immediate, friendly, human Welcome high-five message from a real person.

      Write it in your voice and tone. Do not use your email provider's default. “That's a wasted opportunity,” Greek god Pinterest warns.

    • Set expectations. When will you mail? What will you promise to deliver?

      I learned this by realizing what didn't work (again): One woman unsubscribed via hate-mail when she received her first issue of my newsletter early on a Sunday morning. “I don't want to think about work on the weekend!!!!!” she wrote.

      Yes! With five! Exclamation! Points!

      A little aggressive with the punctuation. But fair enough.

      Now I make sure new subscribers know exactly what they'll get. And when.

      Pro tip for Marketing (and Life): Setting expectations neuters rage.

    • Create an easy ask. Invite subscribers to write back and tell you a bit about themselves. When they do, you get great information about who is on your list—and also help ensure future deliverability.

      I aim for 50% response rate to this specific Welcome email—in other words, I want half the people who get it to answer me. About 30% tend to hit reply and answer. Working on that.

16. Prompt subscribers to share. In each issue, subtly invite your current subscribers to share your newsletter easily with others. I say subtly because if you sell too hard, you'll come off like you care more about your next subscriber than the one right in front of you. Nuance is your comrade here.
17. Create reading momentum. Don't make 1,500 words FEEL like 1,500 words. (Don't make salad feel like salad!) Build momentum.
    • Short sentences
    • Short paragraphs
    • Pattern breaks
    • White space
    • Same template and format every week to set familiarity and continuity
    • Strong, relatable writing voice
    • A “scroll magnet” at the bottom that invites your audience to wonder what's at the end of this email? (even if the rest of the email that week doesn't capture their attention). A scroll magnet might be a joke, a pun, a bit of insider-y info you regularly include that trains your audience to scroll down.
18. Create momentum outside each issue, too. Your newsletter is not a tower; it's a bridge to your other marketing. Your social media, especially.

    Do you have a LinkedIn or Facebook group? Highlight questions or discussions in the newsletter.

    Have an Instagram? Share its images in the newsletter.

    This goes both ways, of course: Let social show your newsletter some love, too.

19. Promote on social, but … Important: Share the value, not the event. Another mistake I've made. (I talk about this later in this section, in Writing for Social Media.)
20. Use other list growth tactics. There are lots of trickling feeder tributaries that together flow into a steady stream. Like:
    • 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 people whose work I celebrate
    • The most unlikely places. My favorite example came a from then-new subscriber Avi, who wrote me in an email: “I actually first heard about you from, of all people, my chiropractor, who, when I hinted at the possibility of writing for him told me he does all his own copywriting and no way was he gonna spend money or time on someone to write for him! His source of writing knowledge? Everybody Writes by Ann Handley!”

    But! The biggest trigger to growth: happiness, joy all around.

21. Make something no one else does. And then deliver more value than an audience would reasonably expect.

    If you do this, you will get more out of your newsletter than you give.

    You will become a better writer. You'll know your audience more deeply. You'll understand the value you provide at almost a cellular level. And you will become more attractive with 12-pack abs and a tighter bottom.

    That last one is aspirational maybe.

    But why not?

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