Emily Ryan on The Small Mindset Shifts That Can Transform Your Email Marketing – And Make It More Fun

Emily Ryan, co-founder of Westfield Creative, says a few mindset tweaks can transform your email marketing—and make it fun. A former musical theater artist turned Mailchimp pro, Emily brings creativity and a focus on what matters to every campaign. 

Her tips? Enjoy the process, don’t sweat mistakes, start small for big results, embrace unsubscribes, and prune your email list to keep it thriving.

Want more of Emily’s fresh take? Check out the full interview below or watch the video version!

Here’s what Emily’s wisdom can teach us:

• Have fun with it. Email shouldn’t be a bore. When you’re yourself and enjoy the process, your audience can feel it too. And you’ll connect with them.
• Mistakes? They happen. It’s just an email, not a medical emergency. A typo or a flub isn’t the end of the world, and Emily’s here to remind us to simply learn from our mistakes.
• Little steps can make things happen. The tiniest tweak today – like a punchier subject line – can open you up to a whole new world. All you have to do is start.
• Subscribers leaving? It’s not a catastrophe. Emily’s got a refreshing take on why “unsubscribes” can actually be a good thing.
• Trim the excess. Just like a plant that thrives with a little pruning, your email list might need an occasional cleanup to stay healthy and engaged.

For the full experience, watch the video interview of Westfield Creative’s Emily Ryan on YouTube.

So Emily, in the context of email, introduce yourself to people out there. Who are you in this email world?

I think some people might say, “Okay, Emily Ryan is that MailChimp girl. You know her because she talks a lot about MailChimp.” And maybe they would have said that a few years ago, because that is true. 

I started out focusing on helping small businesses and brands that were using MailChimp as their email platform – everything from managing their weekly emails to designing templates to training. But over time, I started exploring the entire email marketing world. So, I’m very knowledgeable about more than just MailChimp. 

I have a small email agency. We’re going on our 10th year, based outside of Chicago. I work with my sister, and we have lots of clients. We literally just do emails all day long. We live on different email platforms, still a lot of MailChimp, and we do Klaviyo as well.

And it’s really fun. It’s creative and technical at the same time, and I love it. 

What is possible with email?

I still think it’s one of the most important communication channels of anything else we use. It’s so funny to me when I hear people say, “We’re only focusing on TikTok,” or, “We’re only focusing on social,” because you probably checked your email this morning. You probably did, or at least glanced at it. Email is still one of the top ways to reach somebody quickly and easily.

Related: Did you know that 93% of people check email at least once a day? 

So I think email is crucial. It’s crucial for every business out there. And that’s what is so cool about this business: everybody needs email marketing. I have not encountered a business that does not need email.

With that said, what do you see as some of the biggest missteps that people make with email?

There are so many. Email is a simple thing – it’s a communication tool – but it can get very complicated. You get into deliverability, how to land in the inbox, creating emails that convert. There’s so much that goes into making a great email. Having a clean list, accessibility – there are all these factors.

But the main mistake people make is overthinking it. I always tell my clients: keep things simple. Keep your email design as simple as humanly possible. Delete, delete, delete as much copy as you can, because we’re all busy. We don’t have time to read these long newsletters. The simpler you can make things for people, the more effective it’s going to be.

So overthinking your emails – that’s the number one mistake.

Something I see from people is that they look at how many people are opening their emails and think, “It’s not as much as I thought. I thought everybody was gonna love what I had to say.” And then you tell them, “Actually, you’re getting a great number of people reading these emails.”
How do you think somebody needs to look at open rates?

Oh, yeah, it’s tricky. I’m always telling people, email marketing is so important – it works. But the average open rate is around 21%. So you send to 100 people, and, “oh great, 21 people opened it” – that’s actually considered good. But then your clicks are much lower than that, your click rate can be around 3%.

But that could mean a lot of money for your business. One of our biggest clients has about a 40% to 50% open rate, but they still make so much money with email because we’re not looking for every single person to convert from the email list. 

I mean, in a dream world, yes, but that’s just not going to happen. So if 5% of the people you email convert, that could be a lot of money.

I tell people not to think about getting 100% conversions. And of course, it comes down to how clean your list is — that will give you better open rates and results.

I’m glad you mentioned email list cleaning. It’s another thing people need to rethink, especially if they’re new to email. Some people think, “Okay, so you’re telling me I’ve worked hard to get X number of subscribers, and you want me to run this through an email validation service that will take my subscribers away from me?”

How do you describe that or explain it to people?

There is nothing more important than having a healthy email list. Because if you’re not landing in the inbox, then what’s the whole point of this anyway? 

To keep getting into the inbox, you have to maintain a strong sender reputation. You need good open rates. That means every once in a while, you must look at the people who aren’t opening.

People sign up for lists all the time – for a giveaway or something – and then they fall off or lose interest in your brand. I would rather have a thousand people on my list who are opening, clicking, and engaging than 10,000 people who signed up for a giveaway and aren’t actually interested. That’s just a waste of my money to market to those people.

Email is all about reaching the right people at the right time with the right message. You want the right people on your list. You should always be growing and always be cleaning. It’s okay to lose people because you’re constantly gaining new ones – that’s the dream. 

You’ll have unsubscribes with every email, but you’re also bringing in fresh subscribers.

Time to verify your list?

What you have with your email newsletter is a tremendous amount of authenticity. People feel like, “I know Emily Ryan. If I saw her in line at the grocery store, I could talk to her. I know her so well.”

What has having your own email newsletter taught you? 

It’s been amazing, honestly. I started it just for fun years ago. I really didn’t have a goal in mind. I just thought, “Okay, I guess I should send out my own email.” And I love lists. I love lists, and I love links. So I just wanted to make it really easy. (Editor’s note: Emily’s “9 Things” emails are usually listicles of things she finds interesting and useful. You can subscribe here.)

But over the years, I realized how much it helped my business and even built a bit of a personal brand. And the more I was just totally myself, the better my business did. The more I got to do things like this.

Because it helps build your personal brand. So when I’m creating these emails, I always ask myself, “Do I really love this content? Did I actually read all these articles I’m listing?” And sometimes I’ll throw in a graphic at the top that’s so weird, and I think, “God, people are gonna think I’m weird,” but I love it.

If I love it, other people will hopefully enjoy it. So that’s what I’ve stuck to the last couple of years – just putting out something fun and as much me as possible in the email. And it really works. It’s crazy.

Well, on the note of being your authentic self, which you’ve done so well, suppose you were playing in the World Series. And you’re a very well-known ballplayer – so much so that when they hear the first few notes of your song, the crowd just goes crazy.  What is the song that plays when Emily Ryan walks toward the plate?

Oh my gosh! Is there a song about being a tired mom? Because that might be my song. I’m tired.

But I could probably list 20 songs! I automatically think of something really generic, like Bob Marley’s Three Little Birds — “Don’t worry about a thing, ’cause every little thing is gonna be all right.”

I studied musical theater, which some people don’t know. I did lots of musicals growing up, so I would probably go with something like Judy Garland’s Get Happy — “Forget your troubles, come on, get happy!” Because my whole thing is to stop worrying so much. Stop worrying, have fun.

That would be one option. I’d also probably pick Run the World (Girls) by Beyoncé. Maybe a mix of the two. But yeah, it would have to be something really old — I love old jazz.

Never in a million years did I think we were gonna get a Harold Arlen song.

You know Harold Arlen! I used to sing Harold Arlen a lot. I had a whole book of his music. Wasn’t he One for My Baby (and One More for the Road) ? Yeah, I used to sing that.

Yeah, he wrote that one. He wrote Get Happy. He wrote Over the Rainbow. It’s Only a Paper Moon. What else do you want?

Yes! I love Harold Arlen. That’s awesome that you know that.

Emily, what do you think the best emails have in common? Whether they come from a list, like a newsletter, or they’re personal.

I’m gonna say three things – and I’m making them up as I go:

• First, they’re very easy to read and digest. I can look at it and know exactly what the message is right away — like 25% off, okay, I see that. Or maybe it’s an educational email. I know without trying to read the tiny 12-point font what it is. So, easy to read.
• Second, nice big CTA buttons. Some of the most beautiful emails I love have large things to click on. People like to click! I always tell people: design your buttons so they’re really clickable.
• And third: humor. You can make people laugh, even if you’re a serious business. We’re all human. We all want to laugh when we look in our inbox. Humor is great.
• Oh, and fun design, fun images. Photography is so important. I think people don’t always understand how important that is, especially for a lot of the brands I work with. Photography is huge.

That’s four things!

Is there somebody that sends out a newsletter or emails that every time you see them in the inbox, you think, wow, these guys always come with it? Who is that company?

Yeah, so many people I enjoy. 

Even Starbucks – every time I see an email from them, I think, whoever is designing their emails is really good, because they’re always perfect.

But I love Josh Spector. He’s not necessarily in the email world, but in marketing. He sends out these very simple emails, literally one sentence and a link. And for some reason, I open them and click on them every day because it’s so easy for me to just read one sentence and move on to the next email.

I also really like a company called Big Spaceship. I think they’re an agency, but they send out a daily email of links, and they’re all funny – funny TikToks and random internet things. I always click on it.

Do you have an example of something a company did with their newsletter that you just thought, oh my goodness, how bad, how bad? 

Oh, man. The thing is, we all make mistakes. I’m going on my 10th year, and I make mistakes all the time with clients’ emails – and I shouldn’t say that, but it’s so easy to have a typo or a bad link.

There was one email that went viral from an HBO employee. Remember? It was like, “This is a test” or something. It went viral because it was a mistake. It was just to prove that we all can make that kind of mistake. That’s why triple-checking everything is so important.

You get so busy that you think, okay, the email’s good, I’m tired of looking at it, but you really need a second set of eyes a lot of times. I’ll work on an email for so long, then send it to someone for a preview, and they’ll be like, oh, this is misspelled. And, I never saw it!

So really, really triple-check, especially those merge tags. Merge tags can get you. You put in the first name, and then it doesn’t populate the first name for someone. So making sure those are always checked is crucial.

Your answer is so kind and forgiving and also informative. It’s like, hey, let me help you out so that this doesn’t happen. My example that I always go to is so cynical. There is a popular television personality, and he sends out a newsletter, and for the longest time, I’m talking like a year, when you clicked unsubscribe—

Oh gosh.

—and I screenshot this one time, it said,

Opt-out is not available or is no longer available. And I’m talking about a huge list, and this went on and on.

That’s crazy. Yeah, I saw an email the other day that the unsubscribes said, “You do not need to unsubscribe.” Because you have to have that unsubscribe in the bottom, but they added the words, “You do not need to unsubscribe.” And I was like, “wow, that is wild.”

There’s somebody out there with an idea to go into business for themselves. And they’re thinking, “Golly, do I really have the chutzpah?” or “Is it in me to do this?” 

What would you say to that individual?

I love talking to people about starting their own business because I truly believe that if you want to work for yourself, work from home, you can do that and make great money.

The main thing is having something that drives you. For me, I always knew I had to make a certain amount of money each month, so that drives me. I have lots of bills to pay. When you have no choice but to figure it out, you absolutely will. 

But you need a reason. I’ve talked to young girls in college who don’t really need to make a ton of money, and it’s not going to happen for them. You have to wake up when you’re super tired and get online and work with clients. You have to be motivated; everything else can be taught and figured out. ?

I’m still learning. With every client we take on, I’m still learning something. I do still have that drive because I gotta pay the bills.

If you could go back in time and sit down and have coffee with the young Emily, what would you say to her?

That’s an amazing question that I will think about probably all day. I think I would just say to enjoy it more, enjoy the ride more. 

In my 20s, I was living in New York City, and it was very hard because I had decided not to go the musical theater route. That was all I had known my whole life. I spent my high school, and my whole entire childhood performing, so I didn’t really know anything else.

 I was working these jobs in offices, and they were horrible. I felt so stuck, like I couldn’t do this forever. I can’t get up and go into an office and work a job that I don’t care about. 

I would love to tell my younger self: you’re gonna be fine. This is part of the journey. Every little step, every job you take, is all part of that journey. Even right now, whatever I’m doing now is part of where I’m going. So just know that it’s gonna be all good.?

It amazes me how many people would remind themselves not to worry and how we can apply that every single day.

Yeah, I bet everyone says that, right? I would tell myself to stop worrying so much. So I need to tell my kids that, you know? You’re gonna be all right.

Yeah, there are different versions of it, but it almost always comes down to that, and it is true. Usually in the end, it’ll be fine.

So sad, right? Yeah, and that’s why I would say: “come on, get happy.” Just don’t worry.

How can anyone make today better? This very day, how can they make it better?

Man, I love that. Well, I would say you just have to start… First of all, put on a good playlist. Number one, you can make today better just by turning on some music. I literally have music playing in my house at all times, and it just lifts my mood. 

But I would say just start. If you think, “Okay, I want to make a certain amount of money,” or “I want to do this thing that I’ve always dreamed of doing,” just do one thing today towards that. 

It can be super small. It could be literally just writing it down on a sheet of paper: “I want to quit my job in one year.” Just write it down and tape it on your wall. 

But just start.

Well, anything in closing that you’d like to say to everybody out there? I know that it’s Westfield-Creative.com and EmilyRyanLikes on Instagram. Anything else?

Definitely come find me on Instagram. It’s kind of like my creative outlet. So I post on stories like all the time there and do a lot of email tips as well. 

If I could tell you anything, it would be to have a little more fun with your emails, a little more fun with your marketing. Don’t take it so seriously. After all, it’s just an email. We get hundreds of emails every day. 

And I know it feels like, “Okay, what if my newsletter isn’t perfect,” but people are sifting through so many emails that they honestly glance at them for a few seconds probably and move on. 

So don’t worry – and have fun!