‘Tis the season when my inbox threatens to hit triple digits of unread emails, and I bet that between Amazon orders, holiday sales and well, the entire capitalist structure raining ads down upon you, you’re doing what I’m doing.

Starting a newsletter!

Kidding! No, you’re hitting Unsubscribe to every unnecessary thing!

But, I’m doing both. At the same time.

I’m starting a newsletter AND I’m unsubscribing from every unnecessary thing. So let’s just talk about that cognitive dissonance for a second.

I’ve been opposed to doing a newsletter for a long time. I figure nobody, but NOBODY, needs another damn thing in their inbox.

Including me.

But then there were some newsletters that survived my semi-annual culling of unnecessaries. And these newsletters made me wonder: Could I write a newsletter that lifted, lightened and brightened your day?

Because that’s what the newsletters I keep have in common.

For those of you who have newsletters or who are considering starting a newsletter, come join me in nerdy analysis land as we figure out…

What is the real difference between the few newsletters I read and the hundreds I’ve asked, very nicely, to please never contact me again?

My theory on how to make a newsletter people (not just your mother) want to read

Make it personal

This flies in the face of what marketers tell you to do. Most marketers will say that you have to pack SO MUCH VALUE! into every communication that you train people to open and read your emails. Joanna Wiebe (one of the best copywriters in North America) and Tad Hargrave (you should totally follow him) do this incredibly well. But, confession: Even though each of their emails is jam-packed with immediately useful, sometimes profound information, I don’t tend to read them very carefully. I haven’t hit unsubscribe either, to be fair.

But I’ll tell you what would make me open every email: If Joanna shared who cuts her hair and where she shops (because hot damn, that woman has so much style), and if Tad gave regular updates on his gardening and extracurricular projects.

It’s not that I don’t care about their expertise - I do. But I also like to know the real people. Not just what they know that can potentially benefit me.

The newsletters I love most are the ones that are personal missives (Katherine North) and love letters (Susannah Conway). Bonus points if they include pretty pictures or animal photos. And yes, sometimes these emails include a launch or an invitation, but mostly, they’re just fun to read.

Empathy comes first

The other thing I’ve noticed about the emails I read is that they start with empathy. Like “Here’s where I’m at, maybe you’re here too, and the world is going sideways, but here’s the way I’m finding to muddle through.” That is the basic structure.

Funny enough: That is also the structure of how I begin sales pages, and sometimes about pages. You start by empathizing with how your prospects feel. Here, we flip it, and start with how we’re feeling, with the hope that we are not alone.

Because we’re never alone. Not really.

Today, it’s November 30th and I’m already overwhelmed by December (it’s COMING. TOMORROW. I’M NOT READY).

You feelin’ what I’m feelin’? Probably. Or you are far more on top of it than I. (And I would like to shake your hand.)

And just that little bit of connection, that empathy, starts to build a bridge between us, so neither one of us feel quite as alone as we did.

That’s what a newsletter should do too, I think.

But a newsletter isn’t just a personal letter between friends.

There’s a pressure to make it more than that.

Because I do run a business (and so do you), and we’re not just here to chat (well, sometimes we are), we’re here to help.

And that is the last piece of what makes a good newsletter tick.

Help your readers be better, do better, feel better

Once we’ve started with empathy, once we’ve made it personal, then you’ve got to deliver something of use. Something that helps the person you’re writing to do something better or feel better, maybe even have an ‘aha’ moment.

This is where most newsletters begin and end. They are purely useful, and thus impersonal and rather boring. I’ve read one newsletter that manages to be warm, human AND helpful (Caroline Leon - highly recommend her newsletter for authentic business insights). But most don’t manage it.

I used to feel like only other copywriters would care to read copywriting tips. I couldn’t imagine a business owner would be interested. But, with all of the Tea Dates and free draft sessions this year, we have had the BEST TIME nerding out and talking shop on those calls! And it’s been fun. So I’ve been proven wrong. Many of you do enjoy learning about how to write better, more authentic, more honest and connective copy for your businesses.

So if you’re crazy enough to start a newsletter, here’s how to do it

How to Make it personal: Be yourself. Be your weird, quirky, funny self and don’t hold back. I spoke with a client whose social media moniker was “Marigold Mopp” — a name she’d picked out as a child — and she was wondering if she had to use her real name on social media for her business. I said “nope. I love the name Marigold Mopp. It’s charming and quirky. You just need to explain it, and maybe give her an About page.” Lean into your weird is what I’m saying.

How to Empathize: Start your letters with how you’re feeling, what you’re doing, how you’re coping, what you’ve been struggling with. This can be really hard for those of us who feel like we need to Have All The Answers. We, and I use “we” intentionally here because I do this too, we have trouble showing vulnerability. Notice that instead of telling you how fucking terrified I am of starting a newsletter, I’m instead telling you how to do it. Yeppers, I have a ways to go.

How to say something helpful or useful: I like it when the ‘lesson’ goes with the story. So the personal thing you share, that empathetic moment — what have you learned from that? How can your experience give someone else a useful insight? That’s how to make it interesting, because we are naturally more interested in human experience than in cold, textbookish lessons.

And finally, include:

• Pretty, funny or animal-centric photos

• Recipes

• Books you’re reading

• Teas you’re sipping

• The hand-lotion you love

• And if you’ve finally found the perfect pair of undies that don’t give you a wedgie

People want to know.

And maybe that’s the biggest lesson here, at least for me.

People want to know.

(Really? You’re really interested in what I have to say? That’s SO WEIRD!")

Because most of us struggle to believe that.

We can’t believe that people want to take the time to read or hear what we have to say.

I think that, more than anything, is what stands between conscious business owners and writing really great newsletters.

You can sign up for my newsletter here. And if you unsubscribe, I completely understand.