Learn from my major email marketing mistake:

Automation gone bad and why being human is the best way to promote what you do

Oof. This Type-A, recovering perfectionist really hates making mistakes.


It used to be that if my partner Ben caught a typo in one of my emails, I could barely restrain myself from following up with a message just to explain that “I actually do know how to spell, thank you very much, don’t judge me.”

These are mistakes I’ve learned to let go of and move on from quickly. Little oops moments that no one really cares about and don’t affect the bottom line in my business.

Progress over perfection, right, bosses?

Sometimes, though, a mistake is more than a small slip-up. It’s a full-on affront to the thoughtful and kind digital marketing that I stand for. And I made one of those massive mistakes last month.  🤦🏻‍♀️

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You may remember that I co-hosted the “I’m The Boss Giveaway” with a large number of awesome #girlbosses, giving away some of our signature workshops, memberships and resources for free to one lucky winner.

The giveaway was geared toward entrepreneurs looking for expert advice on how to build their businesses – aka my favorite people. Ready to learn, open to new ideas, hungry for info and trusting that no one can do it alone.

Well, we had about 400 awesome people sign up for this giveaway.

These folks knew they were trading their emails for the chance to win. And I knew that some of them were going to be thrilled to be a part of our growing community at AJM, while others were going to unsubscribe straight away.

How do you balance those disparate interests? Well, friend, I had a plan.

Before I even knew there would be a single giveaway entry, I had crafted a series of welcome messages just for those new subscribers.

The subject line would be compelling and provide context.

The body of the first email would be warm and inviting and personal.

There would be a big, fat UNSUBSCRIBE button to give them the option to opt-out immediately if they weren’t feeling my vibe.

Subsequent emails would welcome them into our tribe of marketing mavens, providing easy access to our best, free resources, and assigning some marketing homework (since putting tips to action is my style).

I turned off my other automated emails triggered to new subscribers, so they wouldn’t receive any welcome emails that didn’t pertain to them.

But when I uploaded my 400 new email subscribers into my Mailchimp list, my everyday welcome series triggered anyway!!!!!

🚨Red alert!! Red alert!! 🚨

I just spammed 400 people with something they had no idea they were about to receive, containing ZERO context for why they received it!

My stomach turned over itself in somersaults. I started pacing around my standing desk, tugging on my braid.

What should I do?!

I figured I had two options:

  1. Act like nothing was wrong. Follow up the next day with a second email offering more context and some of those free resources I was planning to share, OR
  2. Admit I f*cked up and apologize. Follow up immediately with a second email explaining what went down and giving them that option to unsubscribe if they needed. 

Admitting you screwed up can be mortifying.

Especially when you’re claiming to know #allthethings about email marketing, and yet, here you are, making major email marketing mistakes.

I’ve always admired my friends, colleagues or contractors who own their mistakes. And the older I get, the more I realize that having the courage and integrity to admit when you’re wrong is a truly standout quality.

As I was debating the merits of owning up vs. moving on, I received my first-ever “hate” email from a new subscriber. (OK, hate is a strong word. But it was the first negative email I ever received from someone on my list.)

They knew their marketing. They asked where I got their email address and scolded me for emailing without context or consent.

Instead of crawling under the covers (which, believe me, I wanted to do), I wrote them back. I told them about my mistake. I explained why they were a new part of my email list and asked what they would prefer I do: own up or move on?

They picked own up, and I agreed.

Fixing my mistake

To fix my mistake, I wrote an email to my 400 new sign-ups with the subject line: “Proof even the experts make mistakes.”

In it, I explained what I did wrong. I told them that I had received their email from the “I’m The Boss Giveaway.” I described how I had meant to introduce myself in a targeted welcome email, but instead had accidentally spammed them with an automated email. I included a GIF of Jennifer Lawrence making a cringe face. I promised to answer all of their replies and questions, with kindness and thoughtfulness, and without taking myself too seriously. I apologized.

Here are the results.



grateful, human responses

Several people replied to my email, thanking me for my apology and telling me they’ve made email errors like this one, too. Isn’t that nice?


reasonable unsubscribes

The mistake email had a really high open rate of 75%. It also had 33 unsubscribes, many of which marked their reason as “I did not sign up for this list.” My apology email open rate was 55% – more respectable than I expected after essentially spamming these people. Only 25 unsubscribed, and that time, the majority of them said they “were no longer interested.”

None of them considered me to be spamming them anymore! And if they’re not interested, I don’t want them on my list either! I don’t want to waste their time or interrupt their lives. (This is the healthy way to think about unsubscribes. Please take note – I want you to feel the same way about them.)

Only time will tell…

But I have a feeling the ones who forgave my mistake and chose to stick around will have a greater respect for my teaching style, a deeper trust in my brand in the long run.

Even my first “hate” email has turned into a new LinkedIn friend. 🙂

I often remind my clients there are humans at the end of their digital marketing. I do not often think about the fact that they might forget we’re human on our end, too. We should show them when we have the chance. We’ll all be the better for it.

For when your subscribes are intentional…

Our free welcome email template will help you introduce yourself and your services to your new email subscribers, so everyone knows what they signed up for. And it offers yet another touchpoint where you can delight your potential new clients and customers.

    I strategize, consult and manage digital marketing and communications for small businesses and creative entrepreneurs. I’m based in Brooklyn, because I have a thing for exposed brick, cozy, local coffee shops and the can’t stop, won’t stop energy of New York.

    Because I work with small companies, I get the chance to really know my clients – what makes them tick and how and why they should stand out in a crowded marketplace. A lot of my clients have a smaller staff, a limited budget and are already stretched thin for time. This leads us to tailor marketing strategies and solutions to each company’s unique needs and actual capacity.

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