How I Actually Decide What to Send My Email List (Even When I Have No Idea)

  Sam Vander Wielen: You sit down to write your newsletter by opening up a blank document and you’re totally blanking on what to say, or maybe you stare at last week’s email trying to figure out what you should say this week.

You want a newsletter that actually means something to your readers, one that feels current, builds trust, make sales, and moves your business forward at the same time.

But nobody taught you how to decide what to send. So you either freeze and ghost your list for a month, or you just pick a topic at random that feels fine, and hope it does something to send customers your way.

Okay, today I’m walking you through exactly how I decide what goes in my newsletter. Sam’s sidebar, every single week, including the week, I scrapped a finished email the morning it was supposed to go out and wrote something completely different instead, and it was a total hit.

So if you’re new here, welcome to On Your Terms®®. If you’ve been around for a bit, welcome back On Your Terms® is a podcast for online business owners who want to be as present in their lives as profitable in their businesses. And I’ve said it a million times and now I’ll say it 1,000,001 times that emails, email building an email list, and regularly leaning on email marketing is one of the absolute best ways that you can be more present in your life, but yet still profitable in your business because you can do so much when it comes to batching and automating and obviously reaching a lot of people all at one time with your emails.

Just the other day, my entire website went down actually, and my first thought was like, well that sucks, and we obviously we have to get that back up and running. But I also wasn’t really that fussed because I knew that in the background, my emails, my email funnels that all run through Kit that I’ve used for nine years now, , I knew that they were all up and running and we were still making sales even though my entire website was down for the day.

Obviously the same thing has happened many, many times in the last nine or 10 years in online business with social media, various platforms have come and gone. They’ve gone down for the day. World events have made it so that like nothing is working on social, but my email is the steady, steady horse that continues to let my business grow and make sales and run.

Now before I get into telling you the three ways that I decide exactly what to write to my email list, every week I have to tell you that I created a brand new question feature for you. So you can go down to the show notes below and you can send me a video, a voice note, or even send me a text message and let me know what’s something that you want me to explore here on the podcast or even in my weekly newsletter, Sam’s Sidebar.

It really helps me to hear from people like you so that I can create content that will actually help you grow your business. So just click that link down below, submit a question to me and maybe you’ll see it in a future episode.

All right, so let’s get into exactly how I decide what to send my list.

The very first thing that I do with almost anything in my business is zoom out. You gotta like zoom up and say what’s happening in the business. So this is the way I go about it. I look at what just happened first, right? So I look at the past. So are we coming off of a sale? Did I just email my list for like a month about some big promotion or about a webinar or something like that?

I then look at what’s happening right now. So like where are we at in time? This newsletter is going to go out on Monday, April 6th, so what’s happening at that time in my business, right? If I’m writing things ahead of time. And I also look at what’s coming up, what’s ahead? So is there something I need to start warming them up to? Right? If I’m leading to a sale or I have a webinar coming. Is this something that I want to start slowly laying the foundation for? Those are all things that I’m going to look at first off the bat to understand sort of what’s happening in the business. What do I need more of? What do I need less of?

Another way that you could look at this when you zoom out is look at what’s going on in your business and think, what do I want to focus on right now? Am I having a sales problem? So maybe we could do a month long in your newsletter of focusing on your offer, right? Like every week we are teaching a valuable lesson in your email.

But then we are the call to action in your email is actually your offer. Because right now you want to focus on making more sales. You are maybe coming off of a sale. You might say, I want to spend this month focusing on nurture and engagement. So I’m going to give my list maybe some resources, some links to things that I’ve already created without making them opt back into it. Or I’m just gonna give them super valuable content where like I really don’t hold back.

If something’s coming up and you’re leaning up to a sale, that might be where you decide to slowly but surely start dripping in mentions of like, something’s coming. I’ve got a free class. Oftentimes that’s where I will shift my focus. Like the topic of the email will start to shift to be about the thing that I have, um, coming.

So like if I am teaching a free legal workshop, I’m gonna get really laser focused on talking about legal. Whereas on other weeks, I might be writing to you in Sam’s Sidebar about, you know, email marketing or funnels or mindset related to growing an online business. I’ll get hyper-focused on legal and I will slowly and like a little bit more each week start mentioning like, this live class is coming. This live class is coming. You’re gonna be able to sign up for this soon. And then as it gets closer, I get more and more specific. Maybe start mentioning dates, start, opening up, , a reminder, this kind of stuff.

So that’s the first thing is we have to understand where you’re at in the business, what your goals are right now.

Are you coming off of something where you kind of have to buy back some of their trust and the value, or are you leading into something where we would need to like nurture and warm them up to something?

After I’ve looked at exactly what’s going on in my business, the second thing I do is reverse engineer from my call to action. So the first thing I do, I think a lot of people, I bet you they think that the first thing you do is like, oh, I have this story, or I have this like tip, or I wanna teach this lesson, like I wanna teach about.

Why they’re like, why Brazil nuts having selenium is such an important thing. Like what does that do for your thyroid? So I’m gonna like start out with that thing. Okay, now what can I do from there? Like, how does that fit with my offer? Like, I think that’s how a lot of people go about it. What I would actually encourage you to do is think about the call to action first.

Then we’re gonna work backwards. So if your call to action, which is the thing we’re asking people to do, it’s the action we’re asking people to take from your email. If the call to action is to buy your course, right? Then we reverse engineer and think, what story do I have to tell that naturally lends itself to this course being the call to action or if you like, for example, really had your heart set on telling the story about why Brazil nuts having selenium is so important.

And you also know you want your call to action to be your course. You can think about telling the Brazil nuts and Selenium story in a way from an angle where your course actually makes sense, right ?Where that is the next logical step that your customer should take.

Your calls to action. Don’t always have to be offers though. That’s one type of calls. Call to action. Another type would first of all, just be engagement. The call to action can be hit reply on this email and let me know what you think, or hit reply on this email and tell me. Do you prefer coffee or tea?

Like it can just be engagement. That’s one thing. It can be clicking a link. It can be a, that link can go to your podcast episode. It could go to a blog post that you wrote, or a reel that you just did on Instagram. There are a number of different calls to action, right? You might have an affiliate link, like maybe you’re promoting a certain tool or a software that week.

So there are many, many different kinds of calls to action that you can have. The point is that I would start by picking, okay, what is the point? Where am I asking people to go from here? That’s really the call to action, that’s the point of the email. And if the point is that engagement that, um, you know, I just want people to reply.

I wanna hear from people, I wanna get to know them. Maybe I want a little voice of customer research here. You can then frame the way that you write the email in a way that you understand the whole time. It’s kinda like you’re charging ahead and the whole time you’re writing the email, you’re like, I know that the point of this email is going to be to get them to engage.

So you write it now through that lens. Do you see how that’s a totally different process than you writing something and then being like, oh, wait, so I want people to go buy my course, so like, how do I make this make sense? Like you’re, it’s like you’re connecting to things that without, like having thought of it the whole time.

Whereas if you think about it from the, from the start as like, I know where this is headed and what I’m asking them to do now I’m going to write this entire email with that in mind.

I wanted to give you a couple of examples. So if I’m coming off of a launch, , if I’ve just talked about my product for many, many weeks in a row, maybe talked about my free legal workshop many weeks in a row, I generally like to lean into my, my call to action being engagement or free content.

I do that because my focus at that time is to nurture people. Right? So I have no problem and I’m not, I’m not saying that there is a problem with you asking for sales, for talking about your product and offer for you making money that you’re a business. And as I always say, target is not apologizing for their billboards being on the highway.

They don’t feel bad. They don’t give a shit when you come in there and you spend so much money. Neither do I, right? Because if you need my product. I’m helping you and I deserve to get paid for it. And that’s okay for you too, right? So like that’s not why we’re not making up for this because we now owe it to people.

It’s more of a marketing thing, to be honest with you, that it’s like, I understand, I just put my list through like the sales adventure. That’s kind of how I think of it. And I have been talking about this product and maybe my free webinar. For a long time, in my case, right, the, the launches tend to have a long lead up time, and then the launch itself has a long process to it.

So I think of it more as like, I’ve just asked them to do all this stuff. They’ve already said no. This is also like another thing that’s in my mind, right? So like most of these people have actually said no. Like I have an email list of 62,000 people at least of when I’m recording this. And most of them didn’t buy the Ultimate Bundle® when I just did the sale.

So now what am I gonna do with these people now that the sale is just done? Right? That’s the way I think about it is like, it’s my job now to give back to them, to nurture them. That maybe they’re not, um, quite sure about their buying decision yet. Like maybe it wasn’t the right time for them. I don’t give up on them ever, literally, ever.

I, I am like, okay, they’re still here. They stuck with me. Maybe it wasn’t the right product for them, period. That’s completely okay with me. If it’s never the right product, that’s completely okay with me. Maybe the product just wasn’t at the right time, or maybe they don’t see the value yet, so I’m gonna keep going.

So that’s more the mindset that I have when I switch out of launch mode and get back to nurturing my email list. But this is not to like make up for and apologize for the fact that I as a business have to sell from time to time.

I also wanna mention that when I come off of launches, literally the next day, so my launches always end on a Friday. Literally the very next day on Saturday, I turn immediately back to email list building mode. So I’m back on social media trying to get more people to my email list, new people to my email list.

So the other thing I’m keeping in mind during this period is like I might have a lot of new people here. I might also have a lot of new people who in my case, came to me for this live promotion, um, through an ad. And they don’t know me super well and they chose not to buy for whatever reason, but they’re still here.

And now it’s my job to get to know them better. So that’s just a little bit of the mindset of kind of what I’m thinking of, but for calls to action and how I’m treating my list, what I’m sending my list between launches.

Once I’m further away from a launch and I’m just kind of in this like weird no man’s land period in my business where like I am, I’m kind of a bit away from a launch and I also don’t have another launch coming up or a big sale coming up for a while, I might tend to do more of a call to action to either one of my smaller products, so maybe one of my individual legal templates or to my book for example.

And more than anything, to a call to action to go listen to my podcast episodes here on, On Your Terms®. So oftentimes during those periods, when I am short on a content idea, I’m thinking about my cornerstone piece of content for that week. So if that’s my podcast episode, for example, I think about what’s my podcast episode about?

I know that the call to action is going to be to go listen to my podcast episode. I don’t wanna just regurgitate what’s in my episode because then there’s really no point for them to read it. And personally, the way that I always think about emails that lead to something like a podcast or a YouTube episode is that the email newsletter itself should standalone, be valuable, like , the value should be in there because I don’t want people to join my email list just to go tell them to go somewhere else. Like that’s, that’s not really the point. I think of the call to action to my podcast episode or to a YouTube episode as like supplemental, like, if you wanna dive into this more, let’s go listen to this thing.

So that’s sort of what I do between launches in those dip periods.

Okay, now I know what you might be thinking and that’s why my third thing is, yeah, but how do you pick the topic, right? That comes up so often people are like, I just don’t know what exactly to write about. So now that you’ve looked at the time period at like, where are you at in the business? What’s going on?

What just happened? What’s coming up? You’ve figured out your call to action. Let’s pick the actual topic that you focus on in the email.

Now, there’s no right or wrong way to do this, as is true with most things in business, but I personally have a in real time preference. So, I don’t love batching my newsletter for like a month in advance or whatever. I do that when I have to go away or when I know that things are going to get very busy and I wanna make sure that my weekly newsletter, Sam’s Sidebar, stays consistent, right?

But in general, that’s not my preference. I really like my newsletters to feel current, both with whatever’s going on in online business, like maybe there’s some sort of breaking news or some trend. Maybe it’s that, that week I’ve been hearing from a lot of people, like, , a few weeks ago I was hearing from a lot of people saying like, what do we do during times like these when the world is feeling heavy and the news is really dark and like, I don’t feel like I should be talking about this or that on social media.

It would be a little weird in my opinion, if I just sent out an email about anything, right? It’s like I, I personally have chosen to stay a bit more current. That also means doing things a bit more in time, and that might not work for you. It might sound perfect for you. So you get to choose your journey.

Here’s an example of how I recently made this work. So on March 3rd, I had already prepped an email. , To my email list through Sam’s Sidebar, my weekly newsletter, and it was completely ready to go. Like I had already told the team, like, good, everything can be sent. , I had written it the week prior and I thought it was a fine email.

I was fine with it. But as the day got closer to send it, I had had a really hard week and it was a week where I was like really doubting myself and I was questioning a lot of different things of just being like, am I, am I doing this right? Like I’ve announced to everybody that I’m like taking this gap year, which I really spent that week and I’m still currently feeling like I wish I never would’ve ever told anybody about this because now I feel like all I have to do is explain it and like defend it all the time. And it’s been so like, misinterpreted by everybody and it’s really annoying and it’s really getting to me. And then I’m like the, the irony now is like me, having talked about my gap year is actually like causing me to have a worse gap year because I’m always having to explain it.

And so I was just feeling frustrated also that week I had a big uptick in comments and and emails that I had seen come through. That, and maybe I was just kinda looking for it at this point, but I saw a bunch of stuff come through of people like generally saying something to the effect of like, must be nice, right? Like, must be nice to take a gap year when I’m just over here trying to make my first dollar. And like, must be nice to do that and must be nice that you have all of these problems. And like, but you can walk away from your business. It was like, I didn’t walk away. What are you talking about? And like I and people were commenting on these things saying like, must be nice, you’re having a gap year. And I’m like, I’m working full time. I don’t understand like what people don’t get about this. You know, like it’s been so like misinterpreted. I’m trying to take a gap year of putting so much mental pressure on myself. That’s what I’m trying to take, not not working, right?

And so I sat there with this email and I saw that this email was about to go out and I was like, this just doesn’t feel right. I scrapped it and I decided to just sit down, you know? Well, first of all, let me tell you a, a hot tip about emails or anything you ever write. I’ve written emails before that then in the end, I’m just kinda like, eh, I don’t know. Always like copy and paste that copy and put it into a document. I have a document on Google Drive called Scrapped Newsletters and I have it all there and I’ll put little notes about like what date and generally what the topic is so that I can search for it.

It’s really helpful so that if in the future, I mean that that email wasn’t a bad email, it could go out on a different week. It just, I just didn’t feel good about it going out that week, right? So don’t like completely scrap it, but I scrapped it in that individual email and I just said, you know what?

I’m just gonna write down and like write from the heart and literally in like five minutes I wrote a complete email that I just quickly glanced through. It was like, it’s fine. I don’t care about it being so perfect. A couple people on my email list, uh, like to keep better track of it than I do, and so I was like, you know what?

This is, this is good because it came from the heart and I wrote about what was going on that week and you know what happened. The email went a little bananas. We started getting all these replies like, ding, ding, ding, ding. Like my inbox was lighting up all day. Right? You know why? Because it was real, and it makes you feel more human, that you see me being more human.

And sadly, I think that nowadays this is kind of something we actually need to prove to people. And it was really interesting how many of the replies in my inbox were like, oh, I really liked this because I thought that you, like, I’m paraphrasing greatly, greatly paraphrasing here, but like, I thought somebody at your like level or whatever, uh, as gross as that sounds, but they were like, as at your level would like never have these problems.

Like you would never doubt yourself, you wouldn’t face this thing, you know, whatever. And I’m like, what me? Like every day, what are you talking about? Also, I don’t see myself the way that apparently some people see me. And so I’m like, no, I’m like right there with you. I’m having all the same, all the same doubts, right? Like we’re all going through things. Um, I think like the same things in different ways.

All that to say that I think this is one of the benefits to not only keeping things a little bit more in time, but also to being real with your topics. I think that, you know, so many of us feel this pressure to like, act as experts and, and like project ourselves as experts to our audience.

And if you’re, whether you’re a health coach, a career coach, money coach, a dietician, uh, a copywriter, a photographer, you might feel like you have to be the most, the best photographer cook, you know, whatever person you all, you can never have a bad money day or a money doubt. Or if you’re a mindset coach, you can never have a bad mindset day.

You can never experience imposter syndrome. That is not the case. Right. And I think this, this email even goes to show as an example of what kind of topics you can think of is that you don’t always have to be in the expert driver’s seat, right? So not every single topic has to be the, like the way that I master my meal prep every single week, I would actually appreciate probably, I was just telling my friend Erin this the other day that like, I actually think it’s really great when people like her who are nutritionists and experts in, in all things like food and wellness.

If you write about a week that things went badly for you and why that happened, like what? Like, oh, this week I actually didn’t do any of my meal or like ingredient prep, it sent my whole week into a tizzy and here’s how I got back on track. I actually think that’s a much better story than here’s my perfectly prepped meals and all my perfectly glass, you know, things in my perfectly organized fridge that looks like it’s out of a fricking magazine.

I think that that’s better personally from a story perspective. So that helps when you’re a willing to be authentic and and vulnerable with your audience and not acting like an expert, but also when you’re willing to do it in real time.

What’s really, really important if you want to consistently write to your email list if you want these stories to connect with people, is that you have to broaden your mind and open up your mindset about what kind of stories you can tell.

Some of my most popular stories are about, as everyone knows, the bread guy at the farmer’s market at my local farmer’s market turned that into a business lesson. I write about Frasier, my favorite go to sleep show, all the like, and also just like one of my favorite shows. But I write about that all the time.

Like I, I write about completely random things. I’ve written about doing Hyrox competitions. I’ve written about brain surgery. I’ve written about personal stories, right? Like from my childhood or, uh, even from more recently, I’ve turned stories about grief right into business lessons. I just wrote an email this morning about that’s gonna go out next week about how my closet is like a, a shrine to all the things that I invested in that I thought I needed to have in order to be a successful business person. But then when push came to shove, I didn’t actually wanna learn how to use any of them because like what I realized is, for example, when I left the law. I wanted to be a famous food blogger, but I didn’t wanna do any of the things that actually helped me to become a famous food blogger.

Like I wanted the beautiful photos that the famous food bloggers had, but I didn’t wanna learn how to use the camera to take them. I just like wanted them to appear, right? And it taught me a lot about what I was, what I actually wanted, and what I was really willing to do for my goals. And so you have to look for topics everywhere.

Anything from media, like actual media, not just social media, like tv, podcasts, uh, whatever you listen to and consume, right? Movies, of course, but also from your own life and drawing from your own life experiences and everything doesn’t have to be so on the nose. If you’re a nutritionist, you don’t always have to write about food.

You know, if you’re a money coach, you don’t always have to write about money. Money has to do with a lot of other things, right? And there are a lot of different stories, and maybe the end point has something to do with money or the way we think about value. But not every story needs to be told of like, so I went to the bank the other day and here’s what happened, right?

So that not everything has to be so on the nose.

My best advice for this is to keep a running note wherever you choose to. I like an iPhone note because I just try to remove the complexity here of like that’s the easiest thing to reach for no matter what. And even if my phone is bricked, I can still get to my notes. And so I literally just keep a running note.

I write down a bunch of random things.

So I just wanna give this as a, an example of something that I jotted down in this running iPhone note that I have, , full of my content ideas to show how discombobulated and random it can be, but also show you an example of how I would turn this into a story.

So this one says skiing. Fear. Fear leads to mistakes because you’re hesitant and overthinking, telling everyone I was going and everyone was so negative watching the kids ski and they were so fearless. We are so resistant as we age. So that’s a, that’s a completely, like, I was just probably, I probably like wrote this like while we were skiing or like on the lift or something, but the point.

And like, it just is giving me enough to understand like if you’re gonna jot something down, like you jot down something you saw at the farmer’s market or something you noticed at the grocery store, just jot down a few words about like really what was the angle you were thinking of. Because that’s the, to me, that’s the thing you might forget is like not necessarily details of the story, but you might forget like, where was I going with this? Right? So I can tell that from this. I thought it was really interesting when I told everyone I was going skiing for the first time, that everybody’s reaction was just fear. It was like all just like, you’re gonna get hurt. And telling me like all the negative things that were gonna happen about skiing.

And not to say that they’re not legitimate concerns. ’cause people be, I don’t know if you guys know this, but people get injured at an alarming rate just skiing. But anyway, I just thought it was really interesting how that that was everyone’s response. And the immediate flip around in my head and the way that I would approach this with a newsletter is like, that’s the same thing that people do with business.

So I would probably tell the skiing story and then I would say like, have you ever noticed how, when you tell people you’re starting a business, that everybody’s first thought is to tell you all the ways that it could go wrong? Most businesses don’t survive past year one. Did you know that X number of restaurants don’t even make it to six months and blah, blah, blah, blah, blah.

Or people put all their, they project all their stuff onto you about how scary it is to be out on your own or like, aren’t you worried about not having health insurance or whatever? So. I would’ve turned that into a story about how that same fear is going to get put onto us and how that, those are legitimate fears, however we are choosing to do it anyway.

Right? And so like, that’s just an example of where I would’ve jotted that down, turned it into a newsletter and written about it.

Sometimes I also reverse engineer this the other way around, so I might generate a topic from the call to action itself. So for example, like I was saying earlier, if you’re choosing the call to action, first and my call to action I already know is going to be my five legal steps, , free webinar. My legal class.

I might think of a recent example of something that happened, like a DM that I got from someone saying, um, that some bad legal thing had happened to ’em because they didn’t know what they didn’t know. And then I would write about this story and then be like, that’s why you should take my free legal class, right?

So I might reverse engineer it that way.

Or like the example I gave about the, my closet being a shrine to all the tech tools that I’ve purchased over the years that I’ve never even bothered to learn how to use. That was like, I knew what I wanted my call to action to be, which was the podcast episode I did on learning how to build an audience, um, and how, what we need to focus on first if you want to build an audience.

And I then reverse engineered that to be like, what’s a story? Of a time in my life that I focused on the wrong thing. That’s how I thought of it. And the the time that it came to mind immediately was, oh, when I wanted to become a famous food blogger, I focused on buying all this stuff because I thought buying all this stuff was what would make me a famous food blogger. But what I realized is that I wasn’t actually willing to do the work. And so that’s just how I work in reverse sometimes.

This is actually something that I go into a lot more detail about in my book called When I Start My Business, I’ll be happy if you haven’t read it yet, you definitely wanna check out my book because my book is actually not about legal stuff at all. I don’t think I even hardly mention it other than explaining maybe what I do. In my book, I’m actually teaching you not only how to decide what to send your email list every single week, but I teach you how to build your email list in the first place. ’cause you know, it doesn’t really help to learn what to write people if there’s nobody there.

So I’ll teach you how to build that email list both with and without freebies using my easy email list strategy and several other things that are working for me really, really well to consistently build my email list. And then I teach you in my book about how to take those people on your email list, nurture them properly, and turn them into future buyers and fans.

You can click the link down in the show notes to buy my book anywhere books are sold, but my book is called When I Start My Business, I’ll Be Happy and you’re definitely going to wanna read it, if you’ve ever thought, Hey, I wish Sam would be like offering some sort of business coaching or business advice, or do you ever sell something?I don’t sell anything. It’s all in my book. So I’ll leave a link down below in the show notes to grab a copy of my book. It’s almost been one year since she came out on April 15th. I can’t believe it.

But go grab a copy of When I Start My Business, I’ll Be Happy, now. If you also wanna see how I do what we talked about today in real time, make sure you sign up for Sam’s Sidebar. That’s my free weekly newsletter. . You can just click the link below in the show notes to sign up for Sam’s Sidebar now. With that, thank you so much for listening and I can’t wait to chat with you next week.

Thanks so much for listening to the On Your Terms® podcast. Make sure to follow on Apple Podcasts, Spotify, or wherever you like to listen to podcasts. You can also check out all of our podcast episodes, show notes, links, and more at samvanderwielen.com/podcast. You can learn more about legally protecting your business and take my free legal workshop, Five Steps To Legally Protect and Grow Your Online Business at Samvanderwielen.com and to stay connected and follow along, follow me on Instagram at samvanderwielen and send me a DM to say hi.