Email Marketing Failures and Lessons Learned

Could this be the worst marketing mistake I ever made?

The Day I Wanted to Resign – from Everything Online

Well, you had the best intentions.

When you make a mistake, you’re supposed to look back at why it happened. Right?

For example, when I got a ticket because I was singing and thinking about how happy I was. There were no other cars. I did not come to a full stop. Nope, I rolled right through. And, I got a ticket for that ride.

By the way, that happened twice back in Glen Ellyn. Lesson: be more attentive when singing.

On day 50 of COVID-19 home confinement, I decided to reach out and connect with people.

I wanted to invite them to a weekly show, something I’d seen others do. The AMA or ask me anything format is popular on Reddit. And, many folks in the know invite you to ask questions about whatever you want. All you have to do is text. So, I added a text option.

I decided to come up with a variation on the AMA theme: AHA or ask her anything. The AMA is American Medical Association, American Marketing Association, and who knows what else. It would be fun, creative, and inviting – or so I thought.

I spent a couple of hours creating the ad/feature photo. After browsing through images, I settled on one of my cat Rocco hanging out on the back of my chair. The copy was short and had one button call to action – “I’ll be there.”

The trickiest part was buying the domain name and then redirecting it to the zoom registration page. But, that set off an error message. Who wants to visit an unsafe site? As a workaround, I set up blog posts on both and And then I redirected the new URL,, to the blog post on

I was all set to send an email invitation.

As I clicked through the options of lists stored in my CRM, I started with subscribers and then I clicked a few more without checking [hint: stop and check your list].

This is kind of like sending out invitations to people you’ve met somewhere along the way, but they don’t remember you. You don’t remember them, either.

In my case, the list was an import from LinkedIn – dated 2012. These folks had never, ever gotten an email from me. Who knows how close we were? Because I joined LinkedIn in May 2005, it’s possible that 15 years had passed since we’d exchanged messages.

Without double checking the send list, or considering the consequences of sending, I hit schedule. I felt good. I was inviting people to get answers, get together and make new connections. This was going to be great!!!

And, then I checked the dashboard. Unsubscribes started rolling in. Eight people clicked the complaint button, which is like turning you into the email police.

Fearing the worst, I checked my email. “Aha. Go away,” one person typed on their iPhone. This person is a CEO – I got their attention and not in a good way. I sent them an email and deleted their record. Another person called the email bad form. A third pointed out the date in the subject line was wrong.

“I’m resigning from marketing,” I told my husband.

Being super supportive he said, “You’re so smart and funny, though. I’m sure no one wants to cause you harm or see you go away.”

“At least ten people do,” I said. I spent all day Saturday in the worst funk. Maybe it was good to be upset about something that really was trivial. All I wanted to do was be helpful.

And then the good emails started coming in . . . “ this is cute” “I love this idea!” “you’re doing such important work” “thanks -can’t make this one – keep me posted”


19% Open rate

.5% click throughs

1.6% opt-outs

25% bounces

3 Registrations

One last email came in from my email provider. I have a week to send in answer as to why this happened. Rather than go through email court, I’m going to change providers – and delete every other list except for subscribers before I move into the new place.

Email Marketing Failure Lessons Learned

  1. Cherish all relations, even the 15-year-old ones.
  2. There’s no expiration date on friendships.
  3. Really think about who you want to attend your event or euchre party – and invite them personally.
  4. Cat people are cool.
  5. Welcome new people in.
  6. Forgive yourself – especially if your intent was to be helpful.
  7. Realize some people don’t want or need help.
  8. Find your tribe and hang out with them.
  9. Explore other ways to get the word out like PR, ads and social media.
  10. Don’t give up! Learn from your mistakes.

How about you? What’s your biggest email marketing challenge?

Need ideas? Set up a virtual coffee talk.


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