These are the 16 painful lessons I learned writing 10,211 headlines in 100 days

“Yeah, I love you too,” I said. My boyfriend and I were boating on the lake I grew up on. In Texas. In the blistering summer heat.

“But it’s SO HOT. Why did you stop the boat? Can we please go?”

Then I realized why he was saying so many sweet things to me – he was proposing. To marry me. And I got excited. Not about the usual stuff: a gorgeous white dress, table full of presents, wedding cake, the 200+ peeps who I wanted to celebrate that day with me, the honeymoon and, y’know, my future husband.

But also about something else. Something only a marketing geek would think about in that moment.

Emails. It was an exciting challenge I was totally game for.

More specifically, I started to wonder how I would use email to get my 213 ideal guests to:

• RSVP on time,
• Understand the logistical details and
• Not ask me a million questions at inopportune times, like in the 2 or 3 manic days leading up to the wedding.

It was a challenge I was totally game for. You get it. You’re reading this, so you get it – the interest in optimizing emails of any kind, even and especially for a wedding. Fast-forward through the tough negotiations with my parents and in-laws – I loaded up my guest list into MailChimp. I was going to write one helluva show-up sequence for my wedding. I was going to email the sh*t out of my wedding. I was going to make Joanna Wiebe proud.

…Turns out only a little proud since I failed at automation.

BUT! I did get:

• An average 77% open rate,
• Only one unsubscriber and
• Just ONE truly epic failure that cost us a fair amount of money in the end.

Here are the marketing lessons I learned from treating my wedding invitations as an email marketing case study.

If my wedding email copy was going to convert, I needed to focus on one specific segment.

You sit down to write. And seconds, minutes, hours later, you’re still staring at that blinking cursor. You’re not struggling because you’re a bad writer. You’re struggling because you don’t know whom you’re writing to. This was exactly the problem I had with our wedding email list.

My wedding invitation list was made up of people with almost nothing in common: single people, coupled people, heavy drinkers, non-drinkers, conservative friends, #imwithher friends… and people we honestly didn’t know. (You had them at your wedding too. They gift well, so it’s cool.) There was no way I was going to please everyone. Plus, trying to would dilute the quality of the content.

The bigger reason was I wanted to make sure they saw my emails. Lyris Annual Email Optimizer Report found that 39% of marketers who segmented their email lists experienced higher open rates. I decided to focus on the people who I really wanted at the wedding but who were still on the fence about whether or not they were coming. The obligatory invites were gonna show up no matter what; I needed to convert the on-the-fence people.

In sales funnel parlance, I was gunning for the qualified leads. The people who had expressed interest but weren’t committed. My challenge was how to turn these qualified leads into buyers (aka attendees at my wedding).

How do you convince people with a half-dozen wedding invitations each summer to choose to go to YOURS?

Our wedding was going to be the 31st wedding we’d attended in five years. No, not a typo. Everyone we knew was being invited to a bajillion weddings every year. My job was to identify the message my on-the-fence would-be guests needed to read to choose us.

I needed market research. Luckily, my fiance and I – with 30+ invitations received in the last years – were fully immersed in the market. We were the market. And we knew this: Emailing out professional photos of us lovingly gazing at each other wasn’t going to cut it. In fact, it would have the opposite intended effect. If you’re on the wedding circuit, getting yet another invitation doesn’t get you excited for the wedding. Instead, you think twice about the several thousand dollars you have to commit to flushing down the toilet spending on people you love.

Not to mention, our emails had to stand out in our guests’ inboxes. In 2016, an average of 33 emails was sent per day. Plus, our invitation had to stand out from all the OTHER wedding invitations they were getting. We needed to emphasize the reason on-the-fence people go to weddings: FOMO. So, we had to make it seem like we were a blast and that the event was going to be awesome. So awesome that you’d want to tell everyone you know about it. So awesome you wouldn’t dare miss it.