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Reviving the "dead" newsletter with Ann Handley

Episode 5January 31, 2020

About the episode

If you focus on earning your audience’s trust and building affinity, your creative work will soar. Learn how Ann Handley turns an old-school newsletter format into a thriving long-form letter that intimately speaks to her individual readers.

For more great stories from successful creatives like Ann, sign up for our free, exclusive email list, where we’ll deliver a link to every episode straight to your inbox.

You can join the conversation by tweeting JayPodia, or Ann, and sharing your thoughts about the episode. 

Podia is an all-in-one platform where creators who sell online courses, digital downloads, and memberships, publish their creative works to the world. 

Episode transcript

Jay: Eight, eight times. That's how many reschedules, cancellations and outright ghostings I experienced to bring you this episode. When I look at our editorial calendar for the show, and by the way, we release every other Friday, just FYI. When I look at that calendar and I see where this episode fit into our production schedule, I shiver, I shutter, I start drinking. And look, we have a pretty rad lineup of guests if I do say so myself and I just did. Chase Jarvis, Joanna Wiebe, Joy Cho, YouTube celebrity Gibi, four times over "New York Times" bestselling author and a million times Ted speaker, AJ Jacobs from "Esquire." I thought this will be easy to get each new guest to come and say yes, given our extremely awesome lineup.

The thing is, it actually was easy and it is easy to get people to say yes. People say yes almost instantly. Getting them to show up however, that's a different story for certain people. This is the 10th original series that I've made with a brand plus two that are my own, which are still running new episodes today. And here, on this 12th show I've ever made, I find myself gazing at all these reschedules, cancellations, and outright ghostings all eight of them for this episode, and I find myself not surprised at all.

See, anything you create is full of these little moments of turmoil, ups, downs, wins, losses, choices that you have to make to make the final thing just work. That's any project. No matter how much somebody seems like they have it all figured out, no matter how good the final product may be, and damn, I hope you think this show is good. The actual story is a lot different behind the scenes. Oh, and by the way, the person we're talking to today, Ann Handley. Yeah, she showed up the first time she said she would on time, even with a bit of a cold, Ann's a badass. Anyways, this Odyssey ended with a wonderful chat with Ann, but it's just one of hundreds of small hidden things, choices, moments of turmoil, all of that stuff that go on behind the scenes when a creator creates anything marching towards that beautiful final project.

The thing that the creator can point to and finally say, "Hey, you see that? I made it." Welcome to, "I Made It." My name is Jay Acunzo and I'm an author, a speaker, a showrunner, a serial tinkerer throughout my entire career, and this is the official podcast from Podia. Podia sells tools to help creators of all kinds earn a living from their passion. You can sell courses, memberships, and digital downloads all without worrying about the tech. The folks at Podia and I both share a core belief, which is that creativity doesn't mean big. It's the sum total of lots of little choices and moments that add up to something special for our businesses. So on this show, we ask world-class creators at the top of their fields to deconstruct one favorite project, taking us deep inside their actions and their thinking, both of which normally stay hidden.

Today, we talk to Ann Handley, she's a giant in the marketing space, although she's just one of the nicest people you'll ever meet. She's also wildly creative, having written two seminal books for marketers, "Content Rules," which helped launch this industry now known as content marketing and "Everybody Writes," a "Wall Street Journal" bestseller. She speaks all over the world multiple times a month. She's a partner at the marketing education company, MarketingProfs and, and I can't emphasize this enough, Ann is the only person in the world that I know capable of being viewed as sweet and earnest and well mannered and yet still be as sarcastic as she is because she's both of those things. Today, we deconstruct her widely-read newsletter, "Total Annarchy." Get it? "Total Ann-archy?" So let's hear more about "Total Annarchy" from Ann, a little on the nose in the way she names stuff, Handley.

Jay: Ann Handley, you made a thing. What did you make?

Ann: I made a biweekly newsletter, also called a fortnightly newsletter called "Total Annarchy."

Jay: I liked that you said fortnightly because biweekly means every other week and also twice a week, right? Doesn't it mean both?

Ann: It does mean both, exactly. Which is why I am on an international campaign to bring back fortnightly.

Jay: I love it. So your business seems to be split between three different things. I thought I would just do my best to, you know, make this assumption of what they are and then we can talk about where the newsletter fits in those things. So you're a partner at MarketingProfs, which teaches marketers a lot of awesome things. You have a speaking business and then you also sell books and obviously they all feed each other. So where does the newsletter fit into all of this and why write it?

Ann: Well, if you were to draw a Venn diagram with those three things, each in its own circle, I think the newsletter would fit really nicely into the center of that. The goal of the newsletter is twofold. I mean, number one, it's just something that I wanted to do. Our mutual friend Brian Fanzo talks to companies and brands and marketers and individuals all the time. And his catchphrase is "Press the damn button," right? Just make something. And I found that as I got further along in my career, as I got more advanced, more responsibilities, I was still leading teams and I was still leading, I don't know, you know, my place in the industry say, but I wasn't making anything. I wasn't touching anything anymore. And when I went back, you know, 15 years, I was touching things all the time. You know, I was producing the MarketingProps newsletter, I was editing content, I was reaching out to writers and getting their headshots.

You know, I'm not doing that anymore. And so I wanted to do something that was just mine. So it's that psychic... Yeah. Satisfaction, I guess. Just that psychic satisfaction or feeling that, you know, I'm actually making something 100% that's mine. So that's the first thing. But the second thing is I really wanted a place to explore my interests, which are around marketing for sure, content marketing, but also writing. You know, I'm super passionate about writing as you know, that's really my background and my first love. And just life. Like I think that it's sort of the nexus of those three things, which is really what the newsletter is about in all of those three things also touch the three components of my professional life.

Jay: Is there anything different about writing for a newsletter compared to writing compared to something else? You mentioned that writing is such a love that you have not only doing it but teaching it and, you know, your last book was ''Everybody Writes,'' so it's something that's become just so linked to who you are publicly. Is there, like, talk to me about the nuances. Are you discovering anything different about writing for your newsletter than other things?

Ann: Yeah, a few things. I think the difference between writing a newsletter and writing a book is that, well, I should say what writing the newsletter has taught me about writing, which I think would probably carry through to my next book. But it's different in how I approached my last two books is that you are writing to one single reader. And that sounds so obvious, especially to people like you and me who are writers, right? We do this, we know that. You know, we may think about one person that we keep in our head when we're writing something, but there was something about that newsletter, the fact that I'm writing it to a single person who is, you know, looking at their phone or they're opening up their email and they're by themselves. It's not a room full of people, you know. It just changes how I'm communicating there. And you'll see, like, I see a lot of brands who send out newsletters and they're like, Hey guys, or you know, hi friends. And I did that too at first. I kept it in the plural, but it's just one person, isn't it? It's just one person who's reading whatever it is that you're writing.

And so I think once I realized that that shift was super powerful for me as a communicator. I think it gives my writing a sort of intimacy and a sort of shorthand, you know, because I think I'm talking to one person. I think I'm talking to that a smart reader. I don't need to talk down to them, you know, I don't wanna condescend to them. I want to speak to them, you know, as an equal. And so it's really changed the way that I communicate.

I think in the past I've had a tendency to communicate not so much in a condescending tone. And I don't mean that in maybe the traditional way, but I mean like almost as a teacher. You know, sometimes the way a teacher communicates, which is often loving, but at the same time kind of know-it-ally. And I feel like I had a tendency to do that before. Whereas now I'm very much a, I think my voice has shifted a little bit because of it, it's nuanced. But to me, it's been a really important shift.

Jay: From the first edition on through and you know, I'm sure there's maybe some way you experimented with not doing this, but, and by the way, for listeners, we're going to compare the first edition to the 51st edition in the second half of this episode. And I know I can sense Ann cringing about looking at the first one already. So before we get there, you address people as a single person. You say, "Hello, friend," "Hello, gorgeous," "Hey, beautiful." Like that's how you open, not "Hey, guys." And I remember, so I see exactly what you're saying and I actually buy into that. When I podcast, when I make a video series, when I'm writing, it's the one person. I've said something publicly before probably on Twitter because that's where in moments of frustration, I tend to run my mouth too much about stuff that frustrates me. And I was like, why does every single YouTube video have to open with "Hey, guys?"

Ann: Yeah, exactly.

Jay: Because you're speaking to one person. And I got most people agreeing and a couple people who obviously because they descended, they were the people, the minority that sticks in your brain, right? The negative comments always stick in your brain. And they were like, "Well, actually, I like hearing that because it lets me know I'm part of a community of people that believe this stuff like this topic or like this creator." And I didn't quite know how to make sense of that quite frankly.

Ann: Are they all in the room with you though when you're reading it so, or listening to it or watching it? I don't know. I mean I guess that's an interesting way to think about it. I think there are other ways to convey community. I think that greeting is an opportunity to remind somebody that it's just me talking to you. And I think it's as important for the viewer or reader or, you know, whoever it is on the other end of a camera or a microphone or, you know, a newsletter or the, you know, the other end of the inbox, whoever that is. I think it's really important though for both of you to remember that someone is writing this, you know, again, as an act of generosity quite often. And that in an act of humility and that there's a vulnerability in that.

And then I also think that shifting it around, it's really important for the creator to realize the same that there is one person on the other end and they've got to be useful to them. It's not about the creator, it's not about the writer, it's not about the podcast, it's about the value you're delivering. And so I think that that equation is balanced when you think of it only as one person to one person. But that's an interesting point of view. I don't know. I'd have to think about that.

Jay: There are other ways to build community though like you said. I like to think of it as like if I had, I'm talking to you, the individual and you're a part of this, the group, it's, you know, Seth Godin is now publicly saying the same line a lot, which is people like us do things like this. That's like his tag right now. And so what I'm trying to do is say, "Hey, you, hey, Ann, hello, friend." Singular, right? I'm talking to one individual, but when I talk about the things we're discussing, like making great content, like creativity or meaning or doing what matters in life, I'm saying we, right? So that's my version of community building. I'm not addressing a multitude. I'm inviting one person into the multitude.

Ann: Yeah, that's true. Actually, I do the same thing now that I think about it now. So I'm really glad that we just solved this problem.

Jay: So, all right. I wanna clear up something that's been bugging me about a lot of creators who listen to this show and who make newsletters. And I'm saying this a someone who's been guilty of this for years and only recently changed and probably in large part duty your counsel whether from stage or an article or one-to-one, which is the difference between a letter, the letter part of the newsletter and the news part of the newsletter and the differing levels of importance of each of those things. Can you just clarify that? I've heard you talk about that before.

Ann: Yeah. So that's kind of an another one of my epiphanies that happened when I started publishing this newsletter and I started thinking about it a little bit more deeply because I think like a lot of creators, you know, I started that the newsletter, and I've told this story before, but I started almost because like almost as a challenge because somebody said to me, why don't I ever hear from you, you know. Why don't you start you know, sharing more about what you're doing and what you're thinking about and where you're going and so on?

And so I did and, but I didn't do it with a lot of forethought, you know, at the time anyway, because I think as is true of a lot of things that we create, especially things that aren't sponsored or tied to our business in any way. But even if they are sometimes too I think you just like, you don't really know what you're doing at first. You're sort of flailing about in the deeper water trying to find your footing. And I spent a lot of time there a few weeks anyway, trying to figure out what is this, what am I doing here? And eventually, I started to get my footing a little bit and really started to understand, really understand where I was going with it. And one of the epiphanies that I had was that this really is truly a letter and a lot of brands, a lot of companies, a lot of people I think when they think about an email newsletter, they focus on the news part of the word. They focus on the first part of that word, the news. They think of it about what they wanna say. They think of a newsletter as a distribution strategy for other contents.

And I think of it as very differently. I think we should focus on the second part of that word, which is the letter, which isn't to say that you shouldn't use it as a way to drive business or share content or you shouldn't be using it to distribute. But I think you've gotta remember again, one person, one inbox, massive opportunity to send a letter to that person. And so again, I think it's all a subtlety, right? It's a shift in how you think about things. And I think ultimately that shift eventually changes the way you communicate, changes the way you market. I think it changes the way you think about the people you're marketing to.

Jay: I think to use the word shift again, like you just said, the one of the shifts we're living through when you are, do... when you are a marketer, not when you're doing marketing, you're blasting the world. But when you embody what it means to be a marketer and to serve and to make things better in the world and create things people like. The shift that you've just experienced or you know, maybe your predecessors just went through if you're just entering the workforce. But marketing used to be defined by grabbing attention and now I think it's about holding it.

And when you're only focused on grabbing attention, that rewards a lot of bad actors because you're jumping out, interrupting, sneaking, hacking, tricking people. But if you wanna hold people, in other words, if you wanna shift from who arrives, to who stays and serve those people, there's only one "tactic" that works, which is to provide a genuinely good experience that they decide they're gonna come back to. Like, it's sort of the fool me once idea. And so when you write a letter, when you're writing something over time, you're starting that relationship-building process. You're focused on residence, not reach. And you're switching your mentality from marketing as a way to grab attention to a way to hold attention. And so, I think, when I think of the shift when you mention the word shift, that's what comes to mind.

Ann: Yeah. I think that's true. Although I also think that it's not just about holding attention, right? It's also about earning trust. And so, you know, I do think that in marketing, I 100% agree with you that, you know, that for years we've been focused on, you know, can I have your attention when really it should be, how can I earn your trust? And I think if you think of everything that you do, every newsletter issue that you publish, every email that goes out, every marketing automation program that you set up as a through that lens of earning trust, I think it just changes the way you market. And so yeah, 100% agree with you. And I think that we're all just better people. I think if we focus on our marketing in specifically that way, right?

Jay: Right. The pithy summary here is it's not about who arrives, it's about who stays and the people who stay, it's about earning their trust. No one's gonna stick around if you're not part of their favorite things that they trust and love and expect. And, you know, you're making a promise and whenever you deliver something, especially repeatedly, especially serialized or episodic, a show, a newsletter, etc, you're making that promise and delivering that promise, showing up over time and deepening the relationship, that all builds trust.

Ann: Yeah. Yeah, exactly. And I also think that, you know, something like a newsletter, in particular, is a unique opportunity, which isn't just a...which isn't only unique to newsletters, but it is one of those opportunities, I think, to also do a second thing, which is to build some affinity. So not only do I trust you, but do I like you? You know, are you showing me who you are? Are you showing me your personality, what your company is all about, what you care about, what you value. And so all of those things, I think, are an opportunity through content, through newsletters, through podcasts like this one, I think, through video. I mean, there's a million ways to do it, but I think that the intersection of those two things, of the trust and the affinity, is ultimately what really will set your company apart. And it's something that, by the way, no one else can copy, you know, no one else can be you and no one else can. You know, other people can have the same sort of, I don't know, products you do. So many other people can maybe act with, you know, that same impulse toward trust. But I think showing who you are as a person, as a company, as a brand is also a massive differentiator.

Jay: So I wanna move to the part of the show where we're gonna really get in the weeds of your newsletter and we're going to compare the first one you ever sent out to the latest one you've sent out at the time of this recording. So cue cringeworthy reflection out of one's own writing. But to do that, I wanna present the case for a very specific way of interpreting this word that is so ephemeral and misinterpreted, which is creativity. And then I wanna try to apply our kind of agreed-upon language to your newsletter. Okay. So here's the thing. So I think just to debunk a couple of things number one, I think people misinterpret creativity as inventing something from nothing, but that ignores the fact that you're always introducing the new thing into a world full of preconceived notions and a status quo.

So I don't think it's about net new invention because I think that's impossible unless you're like a deity inventing a race. Like you just always, there's always a backdrop to something. The second thing I wanna bunk is that different gets tied to creativity. Oh, it's about being different. But I think it's also about being different and good or and welcomed because you and I could give speeches. We appear on stages as part of our work here. We could give our speeches entirely with our back turned to the audience the whole speech. Like that is different, but it's not good. It's not welcome. So creativity is doing something different and good or different and welcome. The shorthand let's say is refreshing compared to the status quo. That's kinda how I like to talk about creativity. It's something refreshing compared to the status quo.

Ann: I like that. No, I was just thinking about that. Yeah, no, I like that. I like refreshing.

Jay: Yeah. Great because I think it's gonna be part of my next book, so I'm glad this is good. The good researcher. All right. So.

Ann: You're welcome.

Jay: Thank you. That's how we're going to define creativity. Something refreshing compared to the status quo. Now, you look at the behavior of most people who create stuff or especially in marketing, but it's everywhere. Somehow creativity has become known as something big, right? Let's be creative here is like code in many cases for let's do something big. But as this show is out to prove, creativity is just the sum of lots of little choices and moments and wins and not such great choices. And when you receive a project from someone else, you're getting the final product. So maybe it looks big, but the creator has gone through lots of little things to kind of string it all together to create that project.

So what I'd like to say is creativity is about refreshing and small wrinkles added to a project all the time. Subtracting things, adding things, tweaking things, changing things. You're just always making little nuance changes. And I think your newsletter is one of the best embodiments of that idea that I've seen.

Ann: Well, thank you. Yeah. I think it's a risk, you know, it's the idea that you are taking something that you do, you know, a way that you communicate that you are comfortable communicating your true self through, I think. And then pushing it a little bit further, you know, taking some risks in how you're communicating. In the sense of my newsletter and how I write it, there's little things that I do almost every week where I'm playing around a little bit, I'm experimenting a little bit. I'm thinking, is this going to resonate or are people going to hate this? So yes, I agree with that. I think a lot of creativity is risk-taking and it's iterating on things that work and then polishing it, even more, bring it to yet a new level.

Jay: Right. And when you're doing something that does have additions, it's, you know, again that promise to show up on repeat overtly, especially. Sure, a blog you're promising to show up on repeat, but a newsletter you're like, every Sunday night you will get an addition or every Sunday morning in your case, I believe, every other Sunday morning for your newsletter.

Ann: Yes. Every other Sunday morning.

Jay: Right. So you're making an overt promise to keep showing up. And so it's incumbent upon you not only to show up, but to keep making it better and different. And I think in that way, you keep deepening the relationship because there's no stagnation. You keep refreshing the work.

Ann: Yes. And it keeps the bar high too, right? That's the other piece of this, is that, you know, you can't stagnate. I mean it's easy to think that you can, like when you asked me, you know, just when we started talking about this newsletter at the beginning, that's part of the reason why I chose a newsletter over just a Facebook Live every other Sunday, for example. Because a newsletter people can unsubscribe and you can never darken their doorstep again. And I like that because it calls me to an accountability that I find really challenging.

Jay: Yeah. That's why I like making a show. A show is a vehicle that forces you to try and reinvent all the time. Again, those wrinkles, not giant stunts but consistent creativity.

Ann: And then one more thing and then I'll just shut up about this so we can talk about what you wanna talk about. But the other reason why I think it's interesting to think about an email newsletter for something like this is that it is so old school, right? People think, I mean how many articles have you ever seen or read or share that say that email is dead? Email newsletters are old school. And I like my sensibility is that I love taking something that everyone else has called out like that they just say, or that's dead, that's done, that's over. And so I love taking that and playing with it and experimenting with, is it really? Is this not the case or are we just doing it wrong? And so I think that is a place where I like to apply my creativity more broadly.

Jay: So let's see that creativity in action. Let's compare edition number 1 and edition number 51. And since we are trying to trace creativity back to the roots, which are making consistent small changes all the time, those little risks and tweaks all the time every addition here. So we're gonna compare, I think it was 20, I'm taking a look here, January 1st, 2018 that was edition number 1. And January 5th, 2020, that was number 51. So we're separated by two years and I thought we could just kind of walk through the newsletter quickly. So we both have the newsletters pulled up and I just wanna start with a cadence. So that's not in the physical content necessarily, but was it always every other week? And if so, why was that the choice?

Ann: Yes. It's always been every other week. And that was basically because I'm very busy. So I made a choice that if I'm going to produce something of value, meaning something that takes me some time to do and requires some thoughtfulness on my part, that I just physically could not do it any more frequently than that. And I also knew from the beginning that I wanted to play with length. I wanted to play with the idea that newsletters can't be long-form, that you'll lose readers, that people don't have the tolerance or patience for long forum, especially in an email. And so I wanted to play with that and I thought, well, you know, it's almost too much to require people to, or to ask people I should say, to read something long-form with any more frequency in my mind anyway, that's what I thought.

And I went into it the first year thinking, I don't know if I can do this every other week, I'm gonna try. But you know, I remember you probably have heard this quote from Jerry Seinfeld that, you know, part of creativity and part of his genius is just showing up every day and not breaking the chain, writing every day. And so I said to myself, I can't break the chain for the first year and then one year turned into two. So but I still keep that promise to myself as well as to the readers.

Jay: Why Sunday mornings?

Ann: Sunday mornings, because I think it's a very contemplative time, it is for me. And I think that it's a good time to take a step back and put things in context a little bit, which is exactly what my newsletter tries to do. I think this newsletter would be, it would feel different if it came out on a Tuesday afternoon because, you know, you're fully into the work week by then. You know, you're really into the swing of things. And I think that you would tend to just glance at it and close it and probably not go back to it. And so I wanted to publish something that would maybe give people some context and a nice way to tee up their week. That's why I start with a little bit of a story. I want to put all the things that I'm talking about in there, content marketing, writing, life, all in a sort of, you know, in a bigger context in a nice package. And so that's why the Sunday morning. A lot of my readers, by the way, and I know this from stats, but also just anecdotally from people emailing me, a lot of them will wait until Monday morning.

So it's the first thing that they open. I just got one actually two days ago from somebody who said that they save it to start their workweek with, and like, that works too. You know, it's up to the readers. But for the most part, you know, the biggest spike I get in readership, of course, is Sunday morning.

Jay: So there's something so sweet as a creator to hear somebody is talking about your work with that word, I'm saving it. It's like, it's this delicious thing.

Ann: Oh my God, I know. I am just like, I'm so grateful for that and I get that, you know, frequently enough where, you know, people will say to me like, you know, I save your newsletters in a folder for example. And I go back to them when I feel like I need a little pick me up or something like that. I'm like, I mean, yeah, you're right. Like how sweet is that? That's just, it just fills my heart, really.

Jay: I feel like that what we should all aspire to do, it's to be someone's favorite, not be bigger but be better, not be viral, but be consistent, right? Like, forget the random spikes and focus on showing up all the time until someone says to you, damn, I can't get enough of this. Or wow, I really, I savor it and I expect it and you deliver every time. And I think, you know, we can get into the actual content here like I'm seeing the evolution of it because I've been a subscriber for quite some time. Although like I said in our emails together, my first edition was number 16, so it took me 32 weeks to realize I should be on this email list. So apologies for that. But people should totally subscribe.

Ann: At least you caught up to it though, you know.

Jay: That's true. That's true. I'm gonna just go on to the website and fake that like I knew what was going on the whole time, but we're just gonna go top-down here and deconstruct the newsletter. So every single edition, TA number 1 and number 51, why tag it? Why have the little marker like that?

Ann: Basically I stole that from Avinash Kaushik who publishes his own newsletter. And so he does it that way and I just find that they're very searchable in an inbox, but also just to remind people that you're building momentum with something. That's what I mean by the number.

Jay: So I like it because it feels like it's an event, right?

Ann: Yeah.

Jay: It's not just yet another, it's number 51, it's number 52. This is a discreet event and it's happening and we've promised it and here it is. Get ready. The way you write your subject lines is you have like several topics. So I think it's typically three. So for example, number 51 you wrote after the TA number 51, you have a little unicorn emoji. Then you wrote, "What matters more than a new year's goal; new storytelling template; things to stop/things to adopt in 2020." Is it just easy to do it that way? Why do you think that's the approach you've taken?

Ann: Yeah, I just found that it worked better, essentially. So if you go back and you look at the first few that I published, I think it was just January and February, maybe into March of 2018. But it was a pretty straightforward, you know, headline like that first one we're looking at here, New Year, new newsletter. But I found that it just didn't really convey what was inside, you know. So I wanted to offer up that little bit of that free prize inside sort of mindset, tell people exactly what it is that they're getting and why they should open it. The challenge with this newsletter a little bit is that, you know, I'm serving different audiences here. So for example, there are a lot of people on my list who are writers, creators.

You know, there are people on my list who are marketers at big companies. There are sole proprietors, there are consultants. They're, you know, my sister. So it's like a pretty massive group of people who sort of have me, you know, they're all connected to me in some way. And so I think that's what you see there in terms of calling out a few different things is picking out the things that are not only what I consider the strongest sort of prizes, I guess, that are inside that newsletter, but also my attempt to serve a pretty disparate audience by letting them know like you belong here too.

Jay: That's, I get that. That's so great. And just for listeners who may or may not have seen this, you have a welcome in very tiny font, which is "Welcome to the 51st issue of Total Annarchy." This was not there at the beginning. We'll get to that. So you welcome people quickly. You thank new subscribers, especially if you've been at a speaking event or appeared on a podcast and then you offer a link if it was forwarded to you to get your own. So that's like the little welcome blurb. Then you have the letter. I feel like from the outside looking in, it feels like you have a handle on those two sections. Are there other sections that you kind of grapple with?

Ann: Yeah, there are. Well, yeah, there are a few sections in this. I'm just sly to like actually flip through it now to see what they are. Try to remember what they are. Yeah. Well, I'll tell you like more broadly, one of the things that I have grappled with just with this newsletter is whether I wanna create a sort of theme that I'm talking about over the course of a period of time. So almost make it more episodic in the sense that, you know, these next eight issues are almost gonna be like a show, like in your world, right? And that each newsletter would be sort of a component of that show, almost like serial publishing, you know what I'm saying?

Jay: I actually, that's how I used, when I wrote my first book, that's how I use my newsletter, my podcast. I was basically like I have to start exploring and researching. I'm gonna do so publicly, you know, bonus points if people pay attention to this stuff and like the content and, or eventually buy the book. But for now I just have to like collect my thoughts and get them in some kind of coherent form and fashion. So I was like, every week the newsletter's gonna build on itself. Every week the podcast is gonna explore a similar theme, but it was purely out of like this need to just investigate. And I just decided to do so publicly. So I totally see a use case for that.

Ann: Yeah, that's interesting. I didn't realize that, that's how you put your book together.

Jay: It wasn't just a straight like curate my newsletter and podcast off into the book. Like the outline of the book very much superseded all the old content, but I was able to get back into those stories and more importantly it was like, you know, in the same way that you do exercises that don't look like the sport that you play to be better at that sport, there was a lot of writing in there that you're like, well, that didn't appear in the book or that wasn't relevant, but it was really trying to prepare me to then write the book. Does that make sense?

Ann: Yeah, no, totally. Yeah. Yeah. No, I liked that a lot. Yeah, I've thought about that. I actually almost launched something like that at the beginning of this year because it felt like a good time to do something like that. You know, January, new year after a three-week break. It was the first time that I actually took three weeks instead of two weeks in between issues because of the holidays. And so I thought about doing that, but then I thought, you know, I'm just, I wasn't really ready for it. I didn't feel set up for it. So I decided to not do that and to really get a better sense about the why behind I would wanna do that. Why I would want to do that.

So the other section just going back to your question about anything else I struggle with, the tool section. Usually, I collect tools that I use throughout the week. I carry them there. It's getting to the point where now here we are two years into it. Some of the tools that I shared way back in January, February, March of 2018 are ones that I'm still using every single day, but I haven't shared them for two years. And so what I've thought about doing is taking that and making it more of like a Google doc resource essentially. And maybe just sharing new ones there, but then linking to all the other tools that I think are really useful for, you know, creators or marketers or whatever the case may be. So those are the only two sections where I'm thinking, I don't know about that.

Jay: Talk to me about the writing of the letter. You know, do you regimented are you about trying to come up with that? You know, I was talking to a mutual friend of ours, Mitch Joel, and you know, Mitch is a prolific blogger, podcaster, author, and speaker in his own right. And he was saying like, I have no process. Like I', if you're trying to interview me about my writing process, it makes no sense. Like I get off of the plane, I'm like, I'm gonna sit right there in the terminal and write because the inspiration was there. You know, he's kind of in the moment all the time, which I guess is his process. Where do you fall on that spectrum of like everything's gotta be just so to write versus all the time, whenever?

Ann: Yeah, it's a little bit of both, I think, for me. I mean, I start my day by writing longhand in a journal every single day. And that was a new thing for me. I haven't actually been doing that for a very long. I started the newsletter before I started doing that. And so I've only been a, which is funny because I think of myself as a writer. I feel like I've been a writer my whole life, but I've never really been good at journaling. And I've tried many, many times and I've failed many times because it's always felt to me like, what's the purpose of this? Why am I writing to myself, you know? When I was a kid, I was a prolific penpaler. You know, I had tons of friends that I was writing to. This was before the age of social media, of course.

And so, you know, I use the tools that I had to have that sort of social networking capability. So all that to say the idea of writing in a diary or a journal was just, and I'd actually talked about this in the first issue. It was just never something that I was very successful at. So fast forward, you know, decades and I'm finally using a journal the way that I find productive, which is to write down stories that I hear or things that happened to me, not thoughts and feelings or, you know, the sort of minutia of life that I don't care about, you know, ultimately, or that's embarrassing to read or that you would never want your kids to find, like that kind of stuff. I write down things that happened that made me laugh or just like stuff that I see that I think is ridiculous or that I may be able to use it at some point somewhere. And so that's really where a lot of these letters come from.

Jay: I was an intern, it feels like a life ago, at ESPN in their PR and comms department. And I was talking to one of my assignments, the only cool assignment I should be careful not to brag too much about it, but because it's the only cool assignment I got there. The rest was groundwork. I got to interview my favorite baseball writer because we were doing a press release about some upcoming project of his, and I was writing my thesis at the time as an English Lit major. And my thesis, because I wanted to be a sports journalist and that was a literature major was "The Use of Baseball in 20th century American Literature." And as I'm talking to this guy, Buster Olney is his name for sports fans.

Ann: I was hoping you were gonna say Roger Angell.

Jay: No, no. How do you know Roger Angell?

Ann: Because he's E. B. White's son, well, stepson.

Jay: Oh, really?

Ann: Yeah.

Jay: I didn't know that. No, I didn't know that.

Ann: Oh, man.

Jay: Oh wow. I have a lot to learn Ann Handley. Maybe I'll stick with you a little more.

Ann: Oh my gosh. Yeah, he's amazingly.

Jay: So, yeah, so Buster Olney, way too take the wind out of my sail.

Ann: I'm sorry. Oh my God. I was just like, I was thinking to myself, Oh my God, he's gonna say Roger Angell and I'm gonna freak out. All right, sorry. Buster.

Jay: In fact, he's a total shmuck who works for ESPN who nobody should admire. No. He's like a hall of fame baseball writer. Anyways, Buster Olney, I asked him a question about how he always has these stories that no one else digs up. I feel like this is your magic in your letter portion at the top of your newsletter, and it's not stuff that you've heard of, like, in the news today Apple, as everybody saw did this. Now, occasionally you do mention very topical things, but you take a very unique angle on them, but mostly it's a little tiny, almost like small story. It's from maybe your life or something you observed from someone else's life. And I'm reminded of Buster's advice to writers, which is, you know, don't look for stories, look for story threads. In other words, his magic to compete in a very finite world.

Lots and lots of writers writing about only 30 teams every season and he's different somehow. He's like, it's because I have all these random throwaway things and I'm not thinking in the moment, is this a thing? Is this interesting? Can I use it? He's like, throughout my life, outside of baseball, and then back in my work inside baseball, I just have tons and tons of story threads. And when it's time to create, I try to pull one.

Ann: Yeah.

Jay: I just love that and I felt like I feel kind of revived coming from the way you write.

Ann: Yeah, yeah. I love that a lot. Yeah, I really liked that quote and I think it's absolutely true. It's exactly what I do and it's the kind of writing that I really love to read too, which is really where a lot of this comes from. Like my approach as a writer, it comes very much from the kind of writing that I like to read. It's small stories that always are tied to something bigger and that go in surprising directions, you know. And so I liked that a lot and I'm really sorry that I spoiled that because it was a really good story.

Jay: See, Buster has some wisdom too, okay?

Ann: No, he does.

Jay: So, we've been mostly talking about the letter portion. That's the top portion. When you scanned, that's where the similarities really end, issue one compared to issue 51. It's very different the rest of the way. Issue one was categorized, so marketing, writing, etc. But it's basically a numbered list of 12 different links and your take on those links. 51 very much more modular beyond the letter you have like, yes, you have some numbered sections, but it doesn't feel quite as much as like here's a bunch of links I found. It feels more like, I don't know, I'm like traipsing around these topics with you.

Ann: Yeah, that's true. My background is as a journalist and so I always have a little bit of an ongoing battle internally between my inherent storyteller and my inherent journalist, right? And so what you're seeing in that first issue where I felt, okay, here's the marketing, here's what's going on in marketing, here's what's going on in writing, here's what's going on in career. Here are the events that I'm at. I felt like I can feel my anxiety about being very comprehensive or as comprehensive as I possibly could for that audience of writers, content marketers, and marketers. And so I think that's why I like, when I look at that list now of that very first issue and I have all these things broken out and it's all very modular and scannable, it's because of that. It's because I thought, God, I've gotta be like the source for all of these things.

And then I think pretty quickly I realized how ridiculous that was, number one, because no one is waiting two weeks to find out what's going on in marketing, you know? And so I realized that I had, I could just take the pressure off myself and just talk about what resonates with me. And just let people know, you know, sort of what I care about and what's important to me that week. And that's enough, you know, which I think there's a broader lesson in there for a lot of creators, you know, is just sharing what you love and what makes you smile or laugh or what makes you feel smarter and interpreting it for your audience, packaging it in a way for your audience, for your specific reader or listener or you know, whoever the case may be that matters to them. I think that's really all you need to do. And that's enough.

Jay: That's enough. It is. And people, I feel like shy away from that. I talked to Tim Urban, the writer of the blog ''Wait, but Why.'' Incredible, incredible blog. Incredible, incredible writer. And I asked him, you know, you write to a million-plus people about these really big topics having to do with space and science and society and friendship and love, and it just, it's very all over the place in terms of topics and a broad audience. I was like, ''How do you make sense of who you're writing to?'' And he said, "Well, even though we're all different in some ways," he's like, "I'm willing to bet that there's a lot of people in the world who are very similar to me," and he's like, "I'm writing to a stadium of Tims." He's like, "I'm willing to bet that I can create an audience by writing essentially to myself, but I think I could fill a whole stadium like a football stadium of like a couple hundred thousand or a hundred thousand or 50,000 Tims." And he's like, "That's kind of who I'm writing to." So, in effect, it's, I'm writing to one person as we started talking about, but he's not scared that writing to one person means he won't create anything impactful. I feel like you have a stadium of Anns going on here.

Ann: I know. It's just so funny. God, that would just be...that would be such a trip. Yeah, no, I was just thinking about that. That's really interesting. I just read George Orwell's "Why I Write." Did you ever read that? Have you ever read that book?

Jay: No.

Ann: Yeah. Yeah. It's really, it's an interesting book. It's very political. You know, he wrote the essay politics in the English language, which is a famous essay about writing. But ''Why I Write'' contains that essay as well as a number of other, I don't know, just, just lots of political discourse, which was not as interesting to me because it takes place in...he wrote it in the 40s. And he was British. So he's talking a lot about, you know, Germany and England. And it was just stuff that just, like, it just didn't hold my interest as much as the straight-up writing stuff did. But my only reason for sharing that with you is because he talks about how being a writer is a sense as much as we like to think about, you know, our audience and as much as we are providing value to them still, it really is to a large degree about us, right?

Our ego is involved and we want people to look at us. And so Tim's comment just kind of reminded me of that because it's like a stadium full of Tims, you know, like when you said a stadium full of Anns, it's like part of me recoils against that and part of me would revel in it and it's like, let's just be honest about that, you know? And I think that's part of what gives us that ability to stand up and say like, I'm creating this is that element of look at me and I made this, I think is just as important.

Jay: Totally. I mean, look, we people listening and you and I, we've won the birthday lottery. We're not, you know, banging rocks against other rocks, trying to eke out a living. And we're not saying everyone's financially stable or anything like that, but we get to do this work. It's work we choose, right? There's a selfishness to that. Not an aggressive negative screw you kind of selfishness. I think there's a generosity in it. You are creating and handing it off to people. So if someone says like, do you create for yourself or create for your audience, my tendency is to actually just kind of think about it and go, first of all, the answer is yes.

Ann: Yes. Right, exactly. Yeah.

Jay: And second of all. If it's like there are things I do in my work where I'm like, I don't care if anyone reads this, I just want it to exist.

Ann: Yeah, exactly. And I don't think that's a negative thing. Like I think the fact that you create for your audience as well as you like of course you do. And of course, you wanna be proud of what you do and you wanna get some sort of psychic satisfaction out of it. You know, that's really just as important. And so when I read Orwell I just thought to myself, you know, it just really made me laugh because I thought that is so true. Just the idea that your ego is at play here and it's completely fine to acknowledge that audience of Tims in the background.

Jay: So I mentioned that the evolution of the newsletter seems to be from this pretty bare-bones text-only list of links to a much more visual emoji-filled, you know like, I think, again Ann grabbing us by the hand and walking us around the interestingness that you've collected for us or are creating for us. And so there's different sections that have discreet titles. And yes, you have the letter, then you have a couple of links in numeric fashion, but then you have things like shelfies. Shelfies, I can't even say it, which is like the books that you're recommending or tools or department of shenanigans, which can explain that one quick. I'm not sure what that one is.

Ann: Yeah, department of shenanigans is just well as the name implies is something that I think is funny or silly and doesn't really fit with anything, but I just think is ridiculous for some reason. And so I just, every other week, every fortnight I try to share something from the department of shenanigans. Shenanigans is just a word that I use at MarketingProfs a lot to describe things that are's the layer of personality, it's the layer of warmth on top of anything. And so any of the products that we put together, for example, at MarketingProfs and so I'm just applying that to my newsletter as well.

Jay: Yeah. And then below that you have love letters, which is where you write, I think people who have maybe had you on as a guest or mentioned to you. And just, you know, thank you...

Ann: Yeah, exactly. Yeah. It's just like mentions in PR or something like that.

Jay: Right, right. And then you sign off and below that you have events and where you can find other work that you've done, like your book. Looking at issue number 51, there's a lot in here. Like I said, it's gotten really modular. It's full of personality. Are there any tiny little things in here that whether or not the audience and the readers are gonna pick up on this, you kind of like either spend an irrational amount of time on it and loved it or you're like cackling to yourself while you're doing it. It's like, this is for you. Even if the audience does like it or even if they say nothing about it, you're like, I'm going real deep on this one. It's like I said, I'm doing this for me.

Ann: Yeah. Yeah. I had an obvious one and there aren't as many in this one, but puns, my subhead puns, I love and I spend way too much time trying to like think of ridiculous puns to share. This last issue isn't such a great example of that, but you can see it a little bit like right angle with, you know, with a W-R-I-T-E instead of R-I-G-H-T. Powers that three instead of powers that be like, I don't know, they're just silly. But I really, I love puns. I just think that puns are very clever and they make me laugh. And so yeah, that's one thing that I spend a lot of time on. I also spend a lot of time cutting and pasting emojis. You can see a few of them in here. And I've asked myself this like, why?

And I don't know, I just think it adds a playfulness to a newsletter. It adds, you know, emojis can be very silly in business and I typically don't like them when I see them in any other content. But I think in newsletters is one place or newsletters and social media, Instagram in particular, of course, that I think they are completely...that they can just...if they're used sparingly enough, I think they can add a playfulness to what can be otherwise a little bit, you know, gray and dull. The content tools thing too is like sort of an inside joke with me because the first, my first book, right, was content rules and so content tools is sort of a riff on that. I mean, nobody gets that except for me, you know, but I just think it's fun.

Jay: I love that. I love hearing about it. I know it will forever change how I read it and anyone listening here read it, takes it. My favorite thing in the latest edition number 51, you have the template, free storytelling template. It was kind of, that's the big headline. And then parentheses, the subhead says, "Just for newsletter subscribers." And then another parenthesis immediately after it says "Dasu," like D-A-S-U. I'm like, that is Ann right there. Dasu. I'm like, Oh, that's Ann.

Ann: It's so funny. Yeah. Yeah. And there's a few other things in here, like, for example, if you go to the very end, during in the love letters section, love letters is another place where, you know, I'm just giving people love who gave me love. But where is it in here? I said, Oh, look at that. There's a shelf for you in there too. I forgot about that. Oh, we're, here we go. Goldie Chan in the Forbes piece, "17 Ways to Network Like a GD Pro." Like it's like, you know, a gosh darn pro. And I almost took that out too. That's another example of like dash, you know, so all that to say, it's just like, it's just playing with language a little bit. And I have a lot of international readers on this newsletter because I've especially last November, I got a ton of subscribers from Brazil when I did a really big event there.

And so I worried a little bit about the GD and the DAS for them. But again, like when I go back to my promise to my reader to not condescend or dumb things down for them, it's like, you know what, they'll figure it out. So I just have to assume that they are smart and that they can handle it even if they don't speak English and may be confused by DAS, you know.

Jay: There's such in this has to do, this is every project. It could be something small. It doesn't have to be something that has such obvious length and size as a single edition of your newsletter or multiple. But there's so many nooks and crannies that you can explore and go deeper with and evolve. And if you compare 51 to number one, it's sort of like number one is a newsletter from a marketing mind written about as well as a newsletter from a marketing mind can be. Number 51 is Ann's newsletter. Does that make sense?

Ann: Yeah. No, it's interesting. I never thought of that. I think there's a lot more voice in 51 and I think that's really what all of those things add up to. And again, the opportunity for brands in terms of writing a letter is to really put your voice in there. It just takes a while to evolve your voice, you know, to let it develop. And so I think that's really what we're talking about. And I think that has relevance for any brand, any company, any person really who's writing or creating in any way. It does take a while for your voice to develop and letting, you know, giving yourself permission to develop that voice over time. I think that's where the power is.

Jay: When you think about doing this. We've talked a lot about of, yes, various focus things, emojis, but also a lot of very grand things like showing up every day and building trust and what this means to you and who are you writing for. Like it can be really crippling to have something where your person is so caught up in the project. And I know everybody listening feels that way for much of their work. Just the nature of what we do as creative people. Have you encountered any moments where it was like, oh, I don't know if I can keep doing this?

Ann: Yeah, I mean all the time. It usually happens midweek between the two issues. So for example, you know, I publish every other Sunday, right? So that Sunday in between, there's almost this sense of relief. Like, Oh thank God I don't have to do that today, you know, which is terrible in a way. Like it's mortifying to me because I love doing this. You know, I love everything that know, I love so much about what I do, but I especially love this. But that said, it's a lot of work and it takes a lot out of me. Not just from a, you know, from a straight-up industry perspective, like, you know, because I have to like, because it's work, because I have to work hard at it. But the second piece of it as I talked about, you know, because I know that I have to be vulnerable because I know that, you know, I have to put a lot of my sort of mind into this in the way that that plays out.

So yeah, there is a relief that comes like every other Sunday when I'm thinking, Oh, I don't have to do that. I'm just...I can sort feels like you're on vacation in a way that feels like I'm on vacation. But that said, you know, whenever I think about stopping it, like I just, I can't imagine that either. You know, I get no money from this. There's no sponsor, there's nobody telling me that I need to write to these 25,000 people every other week. Like there's no reason why I have to do it, except that I love it. And now it's kind of embedded in who I am. And I love experimenting with it. And I love growing an audience. I love speaking to readers. I love it when they write back to me and they tell me what it means to them. All the things that we talked about here today. So all that to say, yes, I wanna quit and no, I never will.

Jay: We end with a quote from E. B. White as read by Ann.

Ann: "A writer should concern himself with whatever absorbs her fancy, stirs her heart and unlimbers her typewriter. A writer has the duty to be good, not lousy, true, not false, lively, not dull, accurate, not full of error. She should tend to lift people up, not lower them down."

Jay: That's Ann Handley, author, speaker, partner in MarketingProfs and all-around fantastic human. You should read her newsletter, "Total Annarchy" every other week since it is a fortnightly newsletter after all. And to get it, you can go to I have to thank Podia for deciding to make this show. It's their official podcast and they enlisted me to help and to host. And it's such an honor to be on the journey with you listening. But man, I just really hope you're enjoying this. So do me a favor if you are. Podcasts are super hard to measure and to prove that we should keep making this show, if you really like it and you want more episodes, please just send us some kind of signal so we know we should make a season two. We still have a few episodes left, but we want to know should we keep going with this show? Send us a tweet, an email. We're literally talking to you listening right now. If you're like, nuh, someone else will do this. No, we want you to let us know if you like this show. We're all easy to find on social media, both me and Podia.

You can also subscribe to an email list dedicated to just this show with alerts for new episodes and bonus content too. That's at So just to sum up, Ann is great, you're great and please let us know if you think this show is great so we'll make more. I'm Jay Acunzo and this is what I made this week, but here's to whatever you're making right now. Keep going and let us know if we can help. See you.


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