Behind-the-Scenes of my first email challenge & how to use challenges to grow your list

Behind-the-Scenes of my first email challenge & how to use challenges to grow your list

“People are not signing up for my email list. I’ve tried everything. How am I going to make this work? Should I just quit?”

We’ve all felt these things.

At some point in our entrepreneurial journey, we’ve come to the conclusion that we need to grow our email list, and we’ve all taken steps and strides to build them.

But it’s not as easy as people make it seem.

We gain one subscriber, and then we lose 10. Or worse than that, crickets. A month goes by, and no one subscribes. Three months go by, and we’re still in the same boat.

This was the case for me. My email list had plateaued, so I decided to do something about it.

Back in September of 2016, my best business friend, Kris, and I had a chat about a potential challenge that I could create to teach my readers and my clients about how to discover your Brand Personality. It ended up being a rough outline that landed itself right smack dab in the middle of my Bullet Journal. I wasn’t even sure what would come of it at the time.

In my head, it was just a happy dream. The doing part…scared me.

I wasn’t sure what the challenge would be because I’d never done it before. I’d heard a few bloggers mention email challenges, so I just decided to put my head down and start writing out my own challenge emails.

By the end of October, I had all seven emails written, and I started planning the photos to include in those emails.

In the middle of December, a massive brainstorm happened about how I could go about promoting the challenge. Kris had her Brand Voice challenge (a great compliment to my challenge) going at the same time, so we decided to make it a party for all of our followers

By the end of the challenge, I had created an email series that my readers enjoyed, and I had new subscribers on my list.

I consider that a huge success. No more plateau for me and my list!

Today I’m going to share with you what we did and why we did it, so if you’d ever like to do a challenge yourself, you have a guideline for how it could go down.

So here’s a behind-the-scenes look at how to create and use an email challenge to grow your list:

Step #1- Brainstorm!

I’ll admit that I spent a lot of time brainstorming how to create a challenge. It took me a long time to eventually get the challenge out because I stayed in this phase a little too long. I would share a picture of the brainstorm I did in my notebook…but it’s just too crazy.

The first step is to figure out what kind of challenge you’d like to do. Ask yourself what kind of result your readers are looking for: a new skill, result or a concrete finished thing they can celebrate at the end.

Then, you can explore how to execute the challenge itself. I decided that my challenge would be a 7-day email challenge that I’d make available to my readers through my website.

After 7 days, the challengers would have completed a Brand Personality vision board that they could hang in their creative space.

Step #2- Create the content needed to for the challenge.

The next step was to write out the emails for my Brand Personality Challenge, and I completed this during the month of October. Since the challenge would cover seven days, I knew I needed about seven emails.

I first made an outline of what each email would cover, then I wrote them all out in a Google Doc and sent them to Kris to be edited.

*Tip from Kris* “When you are editing your lesson or daily challenge e-mail, think about what you want your students or challengers to accomplish in that one lesson. What will they actually be able to do? Make sure you’ve described it clearly, and that it’s really specific, so that they can see the value of the day’s work.”

I decided to look at the challenge as a rough draft that I could someday come back to and make better. By looking at it that way, you can build the thing quickly (and without a ton of make-it-perfect-pressure) and get people on your list faster than by being a perfectionist and never actually getting it done.

Step #3- Create a landing page where people can opt-in to your challenge.

When I finished writing the challenge, I knew that I needed a place to collect the emails of challengers. I decided to make a landing page for the challenge so that I could just put the link to the challenge in all of my social media posts.

Remember that landing pages only have one call-to-action.

Uncluttered pages are best because they don’t have a bunch of different things that the reader can click, taking them away from the purpose of the page. They can make a quick decision if they want to join, or they can move along and find something else that works for them if they’d rather not.

At the time I had Ontraport as my email service, so I used their Ontrapages to create my landing page. I use Convert Kit now, so I would make the landing page directly on my WordPress site.

Step #4- Add a polite pop-up to your website that asks people to join the challenge.

Before the challenge, I had never tried out pop-ups. I had the concern that we all share: will it be annoying to my followers? I am always worried about bugging people (to a fault, according to Kris).

To combat this feeling, I decided to try an exit intent pop-up, which I created using Popup Ally. The exit intent pop-up ended up converting more than any of my other opt-in forms.

Step #5- Write 3-5 blog posts that are educational and related to the subject of the challenge – and add an opt-in form to them.

Now that my website was ready and I had a landing page set up, I needed a way to get the word out that I had a challenge to my audience and new readers.

I decided to write five blog posts along with some YouTube videos about the challenge. These posts would be one of the methods to get people on my email list interested in the challenge.

I also added an opt-in form right in my blog posts so that people could easily sign-up as they were reading.

Step #6- Implement a social media marketing strategy

Personally, I planned out my social media marketing strategy before I started the challenge. Kris and I also made some plans for how we could do something fun and surprise our friends on Instagram.

We decided to make a series of flat lay photos that would reveal a piece of a big puzzle each day, and that would also keep the excitement of our followers.

I tried hard to make sure that I was sharing, sharing, sharing but I’m still pretty sure that it wasn’t enough. Coming up with a plan, though, did make a difference to how much I probably would have shared and ultimately how many people signed up to my list in the end.

Step #7- End the challenge with a party or another fun event.

The high point of the entire challenge, for myself and my challengers, was the fun party that Kris and I threw at the end – party hats and all!

We hosted a live video call (PARTAY!) for our people and rewarded them with prizes for completing the challenge. This not only gave people more of an incentive to sign up but it also made our challengers feel good about doing the challenge and completing the daily tasks.

Step #8- Repeat!

Now, I can go back and run the challenge again and again. I know sort of what to expect, and next time, there will be even more subscribers added to my list.

The great thing about challenges is that you do all of the hard work the first time, and then each time it just gets easier and easier to run. Each time I run the challenge, I can add something to it to make it even better – like a Facebook group or some videos.

What I’d do differently next time:

The biggest issue with my challenge is that I didn’t have anything to offer at the end.

I did a lot of work to get people on my list and to give them awesome content, but it was all for free. Now, that’s not such a terrible thing because it’s great to build trust with your readers, but I am running a business. So it was a missed opportunity.

In the future, I plan to sell a workbook to accompany the challenge.

So maybe I didn’t solve ALL of my email list problems, but I definitely made some progress. Turns out, I hadn’t tried everything after all, and the success I had makes me excited about trying it again and testing some new ideas.

This post is a part of a series about growing your email list using opt-ins. If you haven’t read the other posts in the series, you can check them out below:

  1. Want to grow your list from your website? Your first step starts here.
  2. 8 Reasons why I chose ConvertKit
  3. How to strategically place your opt-in forms on your website & quickly grow your email list
  4. Behind-the-Scenes of my first email challenge & how to use challenges to grow your list


What kind of challenge might you try with your readers? Comment below!

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