How To Write An Email

How to Write an Email (really) - Popovers - Pyragraph

Last time I talked about how not to write an email. This time, something more useful. Something more practical. This, here, is how we make our cinnamon toast. It’s an often overlooked, yet delicate art.

I only have two rules for you. Here’s the first.

Be yourself. 

This is something that Derek Sivers talks extensively about in his fabulous ebook that I apparently haven’t gotten tired of linking to yet (herehere, and here, for example).

When I was in college I worked at the theater on campus as a combination techie-stage-manager-assistant-to-theater-manager-sometimes-booking-person person. Once I put together a comedy show, and I got in touch with Demetri Martin, who sent me back probably the best email ever.



thanks for contacting me.

my booking agent is {blah blah}. he works at {blah de blah blah}.

you can reach him at {blah blah blah de blah}.

i’m just starting to book spring shows.

hope life is good.


If you know Demetri Martin’s comedy, then you can just tell that he is totally the one who wrote this email. When I read this, I feel like, OMG, Demetri Martin actually emailed me, whoa! My favorite part is the salutation. I mean, who else does that? This—this—is how to write an email.

So, chances are, your version of being yourself will not match Demetri Martin’s, who is very good at being himself.

Here’s the second rule.

Think about the other person over there, being him or herself.

What is this person’s job? How will your request affect them? Are they probably busy? (Yes.) Are they probably stressed out, at least some of the time? (Yes.) Like I’ve said, people who book shows probably have a lot more on their plates than just booking shows. So your job is to make it as easy as possible for them to book you.

This also means you must think carefully about your subject lines. If I wanted someone I don’t really know to add me to the bill for an upcoming show, I might say something like “Add me to the bill for your upcoming show, please!” This is far more effective than “Hello from Sage,” because the person receiving this email doesn’t really know who I am. This might result, on the email-receiver’s end, in a few moments of staring at the computer screen, perplexed, trying to figure out I am, how I got their contact info, and what on earth I would want from them. In the long run this isn’t such a big deal, because, whatever, I mean, they read the email and eventually figure it out, but it’s nice to save them the trouble.

I’ve certainly made many a lame subject line. Here’s one that I wrote not long ago when I contacted an artist about making art for my duo’s CD-in-progress. I wrote, “Sage and Jared’s Happy Gland Band CD art,” which was stupid, because I should have written something like, “Please make art for me! I’ll pay you!” and then gone into our band name in the body of the email. I mean, I’ve e-met this person, but before a few days ago she had no idea who the hell we were, and it’s highly unlikely she’d ever heard our band before that. The art thing and the commission thing were the most important details to her.

On the other hand, just yesterday I composed a subject line that I think I will forever be proud of. I recently read the articles of Pyragraph’s own Danielle Vincent and started getting very excited about the merchandising possibilities for my band. So, the subject line of my email to her read, “Will you make soap for my Happy Gland?”

How to Write an Email (really) - Toast Muffins - Pyragraph

So this is how to write an email.

Be nice. Be friendly. Be sincere. Basically, just tell the truth. Basically, be yourself.

“Hey, I’m a person who has feelings, and I bet you are too, and I want you to 1) book me at your venue, 2) give me advice, 3) read the first draft of my screenplay, and/or 4) give me a million dollars for recording my newest and most fabulous CD. Will you, please? It’s okay if you don’t want to, but I’ll totally 1) bake you cookies, 2) give you my old mandolin, and/or 3) buy you a beer, if you do.”

So, here you have it: how to make cinnamon toast. Use plenty of butter, delicious rustic bread if you’re feeling fancy, your grandma’s old baking soda jar filled with cinnamon sugar, and a toaster oven.

Good luck.

Photos by Sage Harrington, taken from early editions of Betty Crocker’s Picture Cook Book, and some from Pillsbury Best of the Bake-Off Collection.

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