Apr 28, 2015

How Laura Olin’s Emails Got Her Freelance Work and a Book Deal

Last September, when writer and digital strategist Laura Olin started a TinyLetter called Everything Changes, she had modest expectations.

“I thought my friends would subscribe and it might top out at 100 readers,” she says. “I would have been happy with that.”

But since then, the newsletter—the theme of which is that its theme is always changing—has found itself a much, much bigger audience. It caught the eye of a literary agent, and she’s now working on a book based on some of the newsletter’s issues. She was also approached by The Awl about sending Everything Changes from their mostly-dormant MailChimp account. In April, when her first Awl-backed issue ("Animal mascots rooting for their own demise") went out, it appeared in 13 times the number of inboxes she expected to reach last fall.

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Part of Everything Changes’ appeal is the element of surprise. From one week to another, Laura might deliver inspirational messages paired with corgi GIFs, a collection of reader responses to a question she posed the week before, or Joe Biden fanfiction. It’s an exercise in embracing email’s ephemeral nature, but even the silliest issues gesture towards certain existential depths. (If you’ve never felt spine-shivering fear while reading a short story inspired by the dancing bunny girls emoji, you’ve never read Everything Changes.)

Laura is no stranger to the internet: She ran President Obama’s social media strategy during his 2012 reelection campaign (“which is a fancy way of saying I tweeted as @barackobama, among other things,” she says), and now works at a small digital consulting firm. But even she has been surprised by the newsletter’s popularity.

“I thought it would be too weird for a big-ish audience,” Laura says. “So the fact that it’s gotten a bigger audience is a nice affirmation of one of those fundamental rules of the internet: that even if what you find interesting is kind of weird, you’ll probably still be able to find people who’ll find it interesting too.”

We don’t usually do Q&As here on the MailChimp blog, but in honor of the ever-shifting nature of Everything Changes, we thought we’d shake things up a bit to learn more about why she started the newsletter, how she puts it together week by week, and what the book might look like.

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Do you remember how you landed on the idea of doing Everything Changes? What appealed to you about having a new theme every week?

Seeing lots of writers doing interesting newsletters, I wanted to do something myself, but only if I could think of a concept that would contribute something new. I also knew that I wanted to do a newsletter that experimented with email as a form and the boundaries of what it can do. I come from the world of political campaigns, and I wanted to do something with TinyLetter that would let me try lots of stuff that we don’t really get to do in the political world (understandably, because the number one goal in political email programs is raising money). Then I figured that making it change each week by definition would help me check all those boxes.

Do you plan out themes in advance, or more on the fly?

It varies week to week. Some weeks I know what I’m going to do, and start planning for it, several days in advance. Others, I come up with an idea the morning I decide to send that week’s newsletter. Some of the ideas I’ve liked best have actually come up with no planning.

The time I spend on it also varies. The week I made a Thought Clock, it was several hours of putting all the replies in a spreadsheet and sorting everything properly. Other weeks, it can be just an hour. I try to spend more time on the newsletter during weeks when I have less going on in my day job and my life, and only spend less time on it when I really can’t afford to do more. I want to make sure it’s consistently good and also, I hope, raise the bar over time.

How did the Awl folks approach you about doing the newsletter for them, and what made you say yes?

John Herrman emailed me out of the blue and asked if doing Everything Changes under the Awl banner would be something I would remotely be interested in. We knew each other a bit because I’m a giant superfan of the Awl and had started a bot based on tags of Awl stories. Herrman asked me to come down to their office and meet with them, and they were pretty clear about wanting me to maintain creative control. I was excited to have a chance to work with them, so it seemed like a really easy decision to make.

I asked them if they wanted to see the first newsletter before it went out, or be surprised, and they said, “Surprise us!” So they’re part of the audience like everyone else. They just asked that I periodically mention that the Awl is a website that exists, and there are links to the site and social networks in the newsletter template, etc. We haven’t talked about when it’ll end. Hopefully with some operatic drama and explosions.

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How much do you pay attention to open/click rates, etc., and has that changed since the newsletter has moved from TinyLetter to MailChimp?

I’ve made note of subscribe and unsubscribe rates, but mostly in a "Huh, that’s interesting" kind of way rather than a "Here’s how I’ll change what I’m doing" sort of way. Some of my favorite content weeks were the ones that had the most unsubscribes. Maybe I’ll pay more attention to opens and clicks in MailChimp because they’re front and center for every mailing.

I’m really psyched about the chance to use segmenting and personalization. It opens up a world of new things I can do with the newsletter, so I’m excited to have access to that.

Do you have any idea what form the Everything Changes book will take?

It’s based on a week of the newsletter that consisted of form letters. Basically, it’s the Mad Libs fill-in-the-blank style applied to stuff you want to say to the people in your life but don’t have the words for—the guy inexplicably cutting his nails in the subway car, the person you’re now glad never loved you back, etc. The book will be something like 100 letters, formatted in a way that will encourage people to actually tear them out and fill them out and use them. I’m not sure how many people actually will, but it’ll make me super happy if they do.