"How Do We All Sign Our Work?" - Ann Handley, Author & Keynote Speaker - How Stories Happen #3
When so many people are excited to create a higher volume of content, shouldn’t we think more about what gives our work greater power? That’s what our guest today understands better than most, and she draws that power from everyday moments she hunts out, like a squirrel finding nuts in the yard.
Meet Ann Handley—she’s a best-selling author, a pioneer in content marketing, and a popular B2B speaker with a knack for imbuing ordinary moments with extraordinary meaning.
Ann reveals her morning routine, her idea capture system, and most importantly, her process and practice of becoming a word-class noticer of stories during a time when so many people simply stuff a screen in their face or turn to cheat-sheets to produce generic content.
In this episode, we dissect a signature story shared to her newsletter, Total Annarchy, which she sent to just over 50,000 readers. We zero in on a pivot point in the middle that makes the work resonate, and we find plenty of existential debates that unfolded in her writing process.
Together, we discover how to connect with an audience on a more personal level and leave a lasting impression, ensuring your stories aren’t just heard but felt. The best part? You don’t need to experience anything groundbreaking for your words to hit hard. But you do need to become a noticer.
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Episode Resources:
⚫ Follow Ann on LinkedIn: https://www.linkedin.com/in/annhandley/
⚫ Check out her website and subscribe to her newsletter here: https://annhandley.com/
⚫ Read Ann’s book, Everybody Writes: https://annhandley.com/everybodywrites/
🔵 Follow Jay: https://www.linkedin.com/in/jayacunzo/
🔵 Subscribe to Jay’s newsletter: https://jayacunzo.com/newsletter
🔵 Learn about Jay’s coaching and consulting: https://jayacunzo.com/
🟢 Created in partnership with Share Your Genius: https://shareyourgenius.com/
🟢 Cover art designed by Blake Ink: https://www.blakeink.com/
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Episode Transcript
This has been generated by AI and may contain errors.
This is how stories happen, where experts, entrepreneurs, creators, and communicators dissect a single story piece by piece. We hear how they found it and developed it, how it might improve and how they're using it to build their business and leave their legacy. What does it take to resonate and differentiate without all the hollow stunts we see online?
I think it starts by mastering our creative craft. And on this show, we try to get closer to the actual crafting. I'm Jay Akunzo. I am Anne Hanley, chief content officer of Marketing Profs. I am an author. I am a speaker. I am a friend of Jay. what else could I possibly want in this life?
[00:03:00] Jay Acunzo: Shouting aficionado? I think I would add that to your list.
[00:03:05] Ann Handley: That did come in hot, didn't it?
[00:03:07] Jay Acunzo: I love it. That's great. That's why we do this. It's because we get to talk to people that, you know, Make us feel excited and over the top. Uh,
[00:03:14] Ann Handley: I thought you were going to say, we do this so people will yell at us, which is, you know, not untrue. Yeah.
[00:03:19] Jay Acunzo: Please yell at me.
Um, I
think a lot about the importance of a creative practice as in like a thing I do that is pretty much for me.
I'll be and I would like some people maybe to pay attention to it, but it's every week, every other week on a deadline. I am making a thing. The train's leaving. I'm on that. What is the shape of your creative practice right now?
[00:03:42] Ann Handley: The shape of my creative practice is generally writing specifically. It's around my email newsletter. is that what you mean? Yeah.
[00:03:53] Jay Acunzo: Yeah. Yeah.
Like the projects that you would say are the through lines that drive you, the little engine that could underneath what people might pay you
[00:04:01] Ann Handley: I don't respond to nuance J You're gonna have to like tell me exactly what you want from me and how you want
[00:04:06] Jay Acunzo: All right. From the top. What do you do, Anne? Write. Oh God, this is going to be painful. Can you say more about this writing of yours?
[00:04:15] Ann Handley: So the reason why my email newsletter is my practice is because it does a few things for me. Number one, in the four plus years that I've been publishing it, it has allowed me to not only become a stronger storyteller and stronger writer, but also a looser one that has more joy in what I do.
And that is true because I have more fun, I take risks, I don't take myself so seriously as a writer, which was always a big hang up of mine, especially because I come from the journalism world. Which is so serious and you've got to be able to back up at a moment's notice anything that you publish or produce or say.
So that practice has been such a gift for me in so many ways. My audience thinks it's a gift to them. I get emails every single other Sunday when I publish the newsletter. Thank you for doing this. You have no idea what I get out of it. I I get a lot out of it. The truth is I do it
for me.
[00:05:15] Jay Acunzo: Yeah. Oh, I love that. I love, love, love that. I've stopped trying to make sense of like, is the work for others or is it for me? I'm like, it is for me, but that's where it starts. And then it's for others, but it's mostly for me, but I am giving it to you, but I want, I want to help you, but I'm also helping me.
And I'm like, you know
what? Maybe this isn't a question worth trying to make sense of anymore.
I'm just going to go and make something.
[00:05:35] Ann Handley: yeah, and I think the goals are different. You know, it helps me in ways that it doesn't help the audience. And that's good, and that's been a revelation for me in the sense that You know, so how does it help me? All the things that I just said, it helps me become a stronger writer. I'm more relaxed.
I have more fun. I have more joy in my writing. And as a result, more joy in my life. I feel better about myself as a creative person. So that's what I get out of it. But what I'm delivering and what the audience gets out of it is. All the things that we want to do. I'm sharing stories. I'm helping them become stronger communicators, stronger writers, stronger marketers sometimes.
So all of those things are actual takeaways that they're getting out of it. Like I'm, I'm packaging it up in a little takeout container and they're carrying it back to their own lives. And so that's, a gift that I do give them, but the gift that I give myself is You know, I was gonna say equally as important.
I mean, it's almost more important because if I didn't love
what I was doing, I wouldn't be
to be able to deliver those little takeout containers to anyone.
[00:06:40] Jay Acunzo: as you were talking about how the writing has changed or how you feel about the writing. Over time doing the newsletter, I was thinking about. when you ride a bike and you have training wheels and then eventually you don't, or when you have a coach, playing basketball, teaching you the mechanics of taking a jump shot, and then eventually you just go out and freely shoot. There's this like freedom that you feel to not just do the thing, but experiment with it and have fun with it and make it better and make it your own. That really only comes with practice. I'm curious about. Let's play those metaphors. I just used of riding a bike and basketball forward a little bit. I think a lot of people, they just want, what's the right mechanic?
Like, give me the story structure. And then it's like a template. I could almost print out and fill in my material beat for beat and all these things. And I find. That's where I really struggle to explain myself to others. Like, Jay, what, how did you construct this and shape this and all that stuff? And I'm like, I don't know.
I just know that I worked really, really hard to get to the point where that is the type of thing I didn't have to think about. So it's almost like the goal of my practice is in part, and there's many benefits, to stop thinking about what I'm writing and just sort of like feel my way towards something that I'm doing.
Good. And not need the written abstract structure, bulleted outlines, or, you know, mechanics of it all. Like the, the training wheels come off, the coach is not in my ear and I'm just able to sort of react and be in the moment. Is that a journey you've been on? Did you start by going, here's the story structure, here's the outline, here's the repeatability, and now you're just winging it?
Or, I guess what I'm scared to ask you, Anne, is like, Are some of these frameworks and externalized structures and stuff kind of bullshit for people who just go and make stuff?
[00:08:24] Ann Handley: Yeah, that's an interesting question. I don't think it's bullshit. I mean, I think a lot of what I try to give to an audience, When I think about someone sitting down on a Sunday morning to open up my newsletter, or really anything that I do, I mean, it could be a story that I deliver from stage, but, you know, just to keep it simple and talk about that simple, you know, construct of a newsletter, when I think about that person.
I do think about how can I give them something that is going to be helpful to them if they feel overwhelmed. Like, for example, a lot of people will, the feedback I get is, Oh, that's so masterful the way you, told this story. I get there? is kind of what they're asking, but really what they're saying is I can't do that.
What I really want to do is tell them, yes, you can, you can do it. Part of it is, as you say, showing up and doing the work and putting the training wheels on and then taking them off and just flying down the road and skinning your knee every once in a while until you really get less wobbly and solid and you're able to.
ride upright. So part of it is that, but part of it, I think there's a step before that, which is what are those training wheels? So I really want to help people bolt those training wheels onto their bike to use this analogy again. because I, I do think that that's scary. I never had anybody
do that for me.
And in a way that felt like. I related to it, and so the relatability piece of it is really important to me. I want people
to feel like it's not scary. You can do this. Yes, I want to empower you, and here's a way how. And here's a way that I have thought about it. Yeah, I have, transformed beyond it. But, you know, at the same time, you've got to know the rules in order to break them. And so I think just the ability to sort of understand play around a little bit with the training wheels on, with the frameworks and all the things that we talk about. I do think it, is very helpful to people long term.
Yeah.
[00:10:24] Jay Acunzo: her creative platforms, overall premise, like what's the big idea that you explore and you own. And then we were working on a couple of stories like line by line. And we started with this like four part story structure. And I remember she showed up later to another coaching call and she was like, I didn't use that structure, but here's what I made. Like, do you think it's okay that I didn't use it? I'm like, no, it's, great. Like, the point of these things is not. To cling to them. The point is to like sort of use them almost like a, an old school, rocket ship, you know, a spaceship that had those like big, big tanks that would fall away, like it's to get you going and then you want them to fall away. It's like being in one of those like spaceships and the structure that I gave you falls away. Like I don't want people I work with or teach to have to cling to it forever and ever.
I just sort of want them to sense their way forward naturally over time. But yeah, to your point, maybe you need that structure guidance early.
[00:11:18] Ann Handley: Yeah. No, I think that's true. I mean, I've never seen an adult riding with training wheels. it's a similar approach. what we do is we help you bolt on the training wheels and then we want you to take them off. I can't take them off for you. I want you to take them off.
[00:11:33] Jay Acunzo: Do you have a system,
speaking of like feeling your way forward versus like putting regimented frameworks and systems to things, do you have a system for collecting and organizing ideas and story threads and all the material you're taking in all the time that eventually becomes. Fodder for your newsletter, for your speeches, for your books, for your social content.
[00:11:54] Ann Handley: Yes, absolutely, I do. If I didn't, I don't know how I would function as a writer, as a storyteller, as a communicator. don't really even know what that would look like. So, yes, as I'm speaking to you now, I'm standing in my tiny house behind my house, and I'm watching squirrels just run around the yard, and I don't know what they're doing.
They seem very busy. there. Some of them have stuff in their, in their cheeks. It looks like, and they're, they're digging little holes in the ground and they're putting stuff in there. Others are, are just like climbing trees outside the windows. I am that squirrel. I am constantly scurrying around looking for things that entertain me, that I think are useful, that make me laugh.
And then what I do with them as I'm going throughout my day, the. Art of looking at them. Art sounds kind of pretentious, but looking for those moments, looking for those little nuts that delight me in one way or another makes me pay attention to things a little bit more aggressively.
It just tunes me into
my daily life in a way that is so beneficial to any creative person. for example, when I'm at the grocery store or in the line at the post office, I try not to look at my phone, which is all of our tendency, right? You're standing there. Oh my God, this line is a million people long.
And so what do you do? Like you put this phone right in front of your face and I start scrolling threads or Instagram or something like that. And so I don't do that. I try very vigilantly to not do that, but instead listen to snippets of conversation. around me. And sometimes it's, you know, it doesn't lead anywhere, but sometimes it does.
And it, you know, if it makes me smile, then I make a mental note to keep that little nut in my head. And then the next morning I start every morning by writing longhand in a notebook. I don't write in a way that is appropriate for anybody else to, to read. you know, I write just stream of consciousness sometimes.
, you know, it's just messy. There's no punctuation. I'm just kind of like, sometimes I, I add some doodles in there. I'll do some drawings, but all that to say, that's my repository for all things all things story, like that's where I store all of those nuts.
And that becomes sometimes oak trees, sometimes nothing. Like sometimes they're just sort of dead, but nonetheless, there is some value to just tuning into your life. And it just makes me laugh. And sometimes, by the way, I'll find something that I wrote a while ago inside a journal and I'll connect it to something else that happened just last week.
So that's the other
thing that can happen is that over time, you can start to build this sort of catalog of things that have happened that, oh, you know what? That reminds me of that thing that happened when I was waiting in line at the registry of motor vehicles, you know, and so, There's this just sort of this wonderful richness of stories and moments that happen in your life that you can ultimately draw on.
Sometimes, by the way, I just want to tell a story. there's something in
my notebook that I think is hilarious, like really specific example. Weirdly, it involves a squirrel also, but I saw a squirrel eating a piece of pizza.
In a tree in my neighborhood, when I was out for a walk, I was walking my dog, Augie, walking down the street, and I look up, it was April, so there was no leaves on the trees just yet. They had that sort of, angry, scaly little, like, bud on a maple tree that looks like teenage acne. You know, it was like that.
And it was in the tree, I saw a squirrel up there, literally eating a piece of pizza, and he was holding it by the sides. Not by the crust, like a human would. He was holding it by the sides, but he was eating it like from the tip. it was just amazing. It was just such a moment. So I thought about that for the longest time.
I have to figure out a way to share this story. I wanted to tell that story so badly because it was so weird and because it actually happened and it delighted me so much. And it just took up so much brain space. It just took up permanent residency in my brain to the point where it was just lounging around on the couch.
It had, you know, it had redecorated the place. It was like, it literally was in my brain. It was like, I live here now.
[00:16:01] Jay Acunzo: Oh my gosh, I love that. I'm a little bit hungry now. Maybe I need to go outside and find some
[00:16:06] Ann Handley: Oh, and shoot a squirrel. Yeah. Yeah. I thought you're going to say have some pizza, but why would you do that now?
[00:16:10] Jay Acunzo: No, when you have delicious squirrel meat just waiting for you right there. Woo! This show is early in its run. And it also might be late in its run because it might go away because of stuff like this. Let's save it with a great story, a story that you brought to us. It's from your newsletter. And we were kind of going back and forth
about like, what kind of story should we tell?
And here's a few examples. And there's different things you did in each of these and stakes involved. And we picked this one because I think Well, for me, anyway, it's emblematic of the type of story you like to tell that I've seen from you. So I did want to put that on display and better understand it.
[00:16:52] Ann Handley: Mm hmm.
[00:16:52] Jay Acunzo: two, you said, you know, it's kind of like a challenge to myself. How do I make a story that's like ultimately about me and kind of like a, Semi nothing moment I experienced into a story that people care about, that has stakes, that maybe ties to the lessons that people are used to hearing from me. so I just want to set it up that way. And when you're ready, I'd love to hear this story, which you titled in your great newsletter, total anarchy. You titled this story or the subject anyway, want to unpack this box with me. So, and when you're ready, take it away.
A package arrived last Tuesday. The return address was a bookseller. Probably a review copy of my book, I thought. I get a lot of unsolicited review copies from publishers. I left it on the dining room table. A few days later, I opened the box.
[00:17:40] Ann Handley: Not a review copy at all, it turns out, but a copy of Letters of E. B. White. I could read the title through its clear bubble wrap packaging. There was a note on top that said it was a gift from Harry Morton from Lower Street in the UK. I'd spoken at his event a few weeks prior. Harry had lightly stalked me, it seems.
He'd discovered that I am a fan of E. B. White's. Author of Charlotte's Web, Stuart Little and Half the Duo who wrote The Elements of Style. The latter was my inspiration for everybody writes from his office in London. Harry had tracked down a copy of E B's letters from a used bookseller in California.
The seller included this note from Harry. What's better way to say thank you for teaching us about the value of making content that matters, then with some content that matters, Harry? So thoughtful, right? The thing was, I already owned a copy of Letters of E. B. White. A few summers ago, I'd found my copy in a bin at a main library book sale.
The book I found looked hungover. Jacket torn, pages disheveled. It looked like E. B. White's letters had been up all night on a bender. I bought it from the library for the bargain price of 1. I didn't unwrap the copy from Harry. I need to get a knife to cut through the layers of bubble wrap and packing tape.
We'll do that later. And just now I unwrapped it and wow. Wow. Wow. Wow. This book. Yes, I have a copy already, but this book, this book, this copy, it's a first edition. It's signed this book. is signed by the author, by E. B. White himself. E. B. White touched this book. E. B. White inscribed it in black pen in a scrawling, spidery hand.
This copy is not hungover. This copy is pristine. in near perfect condition since 1976, its publication date. He likely signed this then, E. B. White. He would have been 77. I can't emphasize the thrill it gave me. E. B. White touched this book. He signed this book.
And now it's mine. Maybe you're like, big deal. But from the story of your own life, think of a person you admire. Imagine that you hold an icon or a symbol. Or the art of that person in your hands right now. Imagine that adult you is suddenly connected to the child. You who first connected to wonder felt its spark and then felt it ignite something in yourself too.
Imagine holding a symbol of something that made you who you are today. Imagine that. And that's how it is for me. Now, standing in the dining room, holding a book. That my literary hero also held in 1976, 48 years ago. I am holding a book touched literally by the person whose words first touched me. The person who inspired me to want to be a writer too, back when 8 year old me was sitting on my twin sized bed in my childhood bedroom reading Charlotte's Web for the very first time.
In the age of writing robots, an age where machines are only going to get better and faster at creating content at scale, the question I've been obsessed with lately is this. How do we sign our work? Whether we use AI in the process or not, it's never been more important to ask. How do we signal to an audience that this is ours?
How do we show our reader that we touched this? What can we sign? Here's the reality. We might use AI, but the value of marketers increasingly comes in the things that cannot be automated. The value of creatives comes down to how well we can do things that do not scale. The value of our work comes down to how much artful creativity it has.
Slight side rant, I will slap any elitist who says that any of us are not artists. Maybe smack them with this two pound, 768 page letters of E. B. White. Creativity is about possibility, solving problems differently, and showing up in memorable ways, considering out of the box alternatives, and then shredding the box entirely and refashioning it to construct something brand new.
So, how do we sign our work? By kindling the warmth of our actual human voices in whatever we create with a focus on building and sustaining relationships with the pounding pulse of people within an organization with a focus on sharing who we are, not just what we do. So walk with me into the future.
Two blog posts are side by side. Both offer the exact same content. Two newsletters arrive in your inbox, both contain similar value. Two copies of the same book sit on your shelf. One is signed, one is not. Which do we read, open, and treasure? Which do we engage with the most? Which do we remember? We engage with the one that feels like it was signed.
The one that feels like it was touched by someone, anyone. I want that someone to be you.
Damn. done. How did it
[00:23:19] Ann Handley: That's a, that's a
[00:23:19] Jay Acunzo: It's a good fucking story. Yeah.
You said when we were debating which story for you to bring to the show that this is one where you kind of had to make sense of how to tie this story about you and,
you know, a nice moment that you experienced, to the audience and what they're going through in in
their work.
Is that something that you decided and figured out with clarity? Like, aha, that's how, and then you wrote it? Or were you like, I don't know how, but I know that while writing it, I'll figure it out.
[00:23:47] Ann Handley: It was a pizza swirl moment where this book arrived and It happened exactly like I said. I opened it, but because I added the detail that it was in bubble wrap, so that you knew that I could see the cover, and that you, standing right beside me, which is how I imagine the reader always is, that you and I together, we see the cover, we know what it is, and we're like, eh, like throw up a shrug, move on with our lives.
I got to go get a knife if I'm going to open it. I don't really care. So, that sort of ambivalence was the sort of, uh, the tension in this, right, where I didn't care about it until suddenly I did. Suddenly we did. Like, I'm bringing you along with me. So, to go back to your question, that tension was the piece that when I started to think about it this was a story that I wrote in my notebook.
I started to think, this is exactly the kind of ambivalence. That so many of our readers in a marketing context, a context also have for our work, you know, they're just going to scan. They're going to look for the most important bit. a lot of marketers, I think, approach the content that we're creating with that same sort of ambivalence in a way it's like, well, it's good enough.
And I am constantly pushing against that tension. And when I thought about why I wasn't excited about this, it's because I didn't, Like, I literally was not excited because I didn't realize that E. B. White had touched this. And so that metaphor of touching it physically and then touching it emotionally or making sure that our fingerprints and footprints are all over it, that was the connective tissue between this book arriving that I was excited about so much.
And flipping it in a way that could make any reader excited about it and give them a take away, start to help them bolt those training wheels onto their, their own bike to continue that metaphor. So it was a little
bit of both. It was some internal processing going on that as I was writing it in my notebook, like when I first wrote about it in my notebook, it was a straight story just about like, holy wow, I can't believe Harry Morton.
Uh, here you go, Ed. I was like, wow. Thank you so much. I was so excited, but it wasn't until I, you know, it took up residence in my brain again. This is another story that moved in for a little bit
and it wasn't until I started to think about it that I started to realize, oh, what's interesting about this to me is that he touched it.
But what's interesting about. content, like I'm using that word on with air quotes. What's interesting to me about content that I relate to is that it feels like I know the person who this came from, and that just
cascades throughout all of our work in marketing. You know, that's why I talk about your frontline matters more than your subject line, who you are and how you're showing up and how you do the work is what I'm interested in.
And what I
think the direction that we as marketers should be moving in in an age of AI, but even setting that aside. I still think it's the best way to think about marketing in 2024.
[00:26:49] Jay Acunzo: Your from line matters more than your subject line.
I love that. You know, you can multivariate A B tests, do any number of types and styles of
tests that you want to that subject line. If it's coming from you, and that's the reason I open it, congratulations, you're where we all want to be.
And it's where we all need to be.
I think this has become urgent, you know, a lot of the stuff that you and I have talked about for many years and, and you know, many more years than me, mostly cause you're just ancient, you're
[00:27:14] Ann Handley: Yeah, I know.
[00:27:15] Jay Acunzo: super old. No problem. No problem. I've learned from you. I was trying to compliment you.
And in doing so I did the opposite, which kind of describes most of the conversations that we have. so me as a young child, I say this and as, someone who's on the way out, let's face it, uh, you say this a lot. The person, the quirks, the personality we're, we're exhibiting it here. and all the messy things that make you, you, like it's in some people's minds, not everyone, but some people's is, but yeah, that's a nice to have. Like, give me all the other stuff first, right? The technical, things that look like repeatable checklists and best practices and all that.
I need that first. And like all this, and stuff or J stuff that's nice to have, or that's for some people. And I think what we're living through right now is a moment where like, People are realizing like, no, that is the work and it's grown urgent.
[00:28:06] Ann Handley: yeah, I absolutely believe that it's urgent.
I mean, the reality is, I have felt this way for years. I mean, even predating AI, but AI turns up the heat that much more. I think it's so critical for us. as people as forget about marketing and creatives for a second. I think it's important for us as people to foster that kind of connection to the work and through our work.
So those 2 things, and that's why I think it's so critical for us to. Create things that could only come from us. And, you know, I've been talking about this for, you know, a long time, like since 1942. Apparently, I didn't know I've been around that long, but apparently I have. But no, I've been talking about this forever.
at the dawn of content marketing, I know that you share this mindset. I talked a lot about how it was important to. Not just create more and more stuff, which was what the SEO, camp was saying.
You just need more and more stuff to rank higher. And therefore you'll get, you know, that mindshare from anyone searching for you. And then that quickly was dispelled when all the SEO people like, no, no, no, actually Google is, it will penalize you if you do that. So don't do that. I've been always like pushing against this idea that just create more and more stuff and who cares about the quality of it like I've been talking about the importance of quality for a very long time And also evolving the message and so increasingly I think that there has never been a more Important time there's never been more urgency to use your word.
I think it's absolutely true But also I think it's always been the case. I think we've always been pushing against this idea that Good enough is good enough and that more is more and more is better. I've never bought into that, mindset and I feel like there are more people that are truly, understanding that.
and
so, yeah,
I do think it's incredibly important, but. I will say I don't think it's just a now situation. I think it's always been the case, but as I said, it definitely feels like it's only getting like the, the heat is, turned up to high underneath us. And I think it's just more important than ever.
There's this moment in the middle of the piece that I wanted to ask you about, because it's something I personally have struggled with. Like I see certain storytellers and usually it's not in a business context. Usually it's, I don't know, a documentarian or filmmaker or someone who's telling stories in, you know, more of like a, hate the entertainment verse education dichotomy.
[00:30:31] Jay Acunzo: And I think it's, that's a false. Decision you have to make with your work, but people who would identify as entertainers, I think these people are prone to sharing a story simply to share the story and any kind of lessons or insights or frameworks or teaching is kind of implied, right? Like maybe they know they're there as a storyteller and they give you space to kind of synthesize yourself. an example being like my favorite storyteller, Anthony Bourdain, he wouldn't spell it all out for you at the end of an
episode, he would kind of give you a line or two of voiceover or a final quip from a subject and then let Moments linger through b roll and music and
you're left with like your feelings and your thoughts. So there's that approach And I find a lot of storytellers. I love do that Then there's the approach that you know, I do a lot and you did here Which is I do have to take a moment here and acknowledge you the audience And what you're learning or going through head on in kind of plain language So here's the moment I wanted to ask you about where you did that maybe you're like big deal But from the story of your own life, think of a person you admire. Imagine that you hold an icon or a symbol or the art of that person in your hands right now, So
you kind of plant the audience in your story much more overtly than some other storytellers. And it's always something I wrestle with. And I just wonder like your relationship to those two approaches, if that's ever crossed your mind.
[00:31:47] Ann Handley: Yeah. I do think about that quite a bit and It's funny that you, zeroed in on that moment because I did have a thought when I was writing this. Do I even need that section where, because the section before it ends with, me freaking out, EB White touched this book, like he touched it and now it's mine.
And that moment where I was like, Holy wow. I thought about not. Bringing the reader or inviting the reader and his or her skepticism to the stage when I say, like, maybe you're like, big deal, like, obviously, I'm inviting the skeptic into the room in that situation. I thought about not doing that and then going straight into, in the age of writing robots, you know, how do we sign our work, which is the next section down.
So I thought about skipping over that completely, but here's why I didn't, because that section of, I don't know, what is it like, maybe. Five or six paragraphs of where I'm inviting the skeptical piece of you into the room is critical. I think to making it clear that yes, this is my personal story about E.
B. White and inviting the reader to then consider their own hero in their own lives. So I realized I needed that because I needed a transition from this happened to me to. Imagine if this happened to you, and this person is probably not E. B. White for you, but who is it for you? And that's a section that sticks with people.
And I know this because, you know, one of the things I do in my work constantly is invite, um, Readers to write back to me, to
literally hit reply and tell me what resonated. Now. I don't say in there. There's no specific trigger. Tell me who that person is for you because that would be cloying and it would also take people out of the story too much.
Like, I want them immersed in it. I got, I don't know, maybe 200 responses. No exaggeration. This person was, Lucy for me when I was a little girl and I read Anne of Green Gables or, this person was, R. L. Stein for me when I was a kid and I read this because I have so many writers and creatives on my list.
Most of them were authors, but not just like I had some people who were saying, you know, I have something from. Keith Richards from, when I bumped into him someplace and he signed this t shirt that I was wearing and it's like all kinds of creatives, you know, will find something in that story. And so all that to say, I think it's important to, you know, not just invite the skeptic into the room, but to challenge the reader to think about their own person.
And that, to me,
is what really made the next piece of it work. Because when I started talking about the writing robots in that point, without that transitional section in there. It would have felt like, oh, this is just like a marketing thing. Yeah, yeah, that's cute. And it would have been a good story, but I don't think it would have drawn the reader in quite the same way.
I'm always looking for those moments where, as I said, I can have the reader standing right beside me. I literally will think of it this way very often. If you were sitting across the table from me or beside me on the couch, What would you be feeling right now? And I want to articulate that so that they see a little bit of their own reflection in my
work, even when it's about me.
[00:35:10] Jay Acunzo: One of the calling cards that I feel like you have to people who know your writing is you talk about, my favorite type of story to tell is it seems similar to yours and you're such a master at it and which is you tell small stories with big meaning and those small stories. if there was a pie chart, I would say a very small sliver of the pie is about the demographic that you speak to.
It's about marketers and business people and entrepreneurs and authors, like, here's the story of someone who has your job title going through something that looks like your job. That's a very small percent of the pie. The bigger percent is, and it's far and away the bigger percent is, here's a thing I observed. Or that happened to me or that someone told me there is nobody here with the title of VP of marketing or content marketing manager or even author or writer involved in this story yet. You're here to be a better version of those things to read me. I know some of this is practiced You're the squirrel hunting for the nuts, and you've got a backlog of all these things. guess what I want to know is, like, what is it about telling the story? If you want the reader there with you, the shortcut seems to be, Well, this is someone who has your job title, right? And then you're automatically there.
That's not what you do. Why?
[00:36:22] Ann Handley: Because that's a case study. to me, it's the difference between just sharing a case study and weaving a story, crafting a story. The story piece of it, you know, we're talking about metaphors a second ago, and the story is essentially a big metaphor I use a lot of metaphors in my work, but in a very meta sense, the whole story itself is a metaphor for something, almost all the time.
And so I think it's the only way to engage someone emotionally is to speak to the person and not to the job title. I want them to think about how they're showing up in their jobs. Yes, but not just that. Like, how are you showing up in your life? How are you showing up for your kids, for your parents, for your siblings?
because here's the thing, if I give you a case study that's sort of soulless, bloodless, emotionless, maybe it does have some emotion. I shouldn't be so hard on case studies. but if I started it there, it would not speak to the person. It would maybe make you a better marketer, you'll become a better marketer, but you won't necessarily be a better person. But I think if you're a better person, then you will also be a better marketer, a better parent, a better sibling, a better, whatever the case may
be. And so I'm also just inherently much more interested in people than I am in marketing. I mean, marketing is what I do, but it's not necessarily who I am.
And I think that is true for so many of us. And I think that's actually part of the reason why so many of us fell into marketing. no one ever was lying in that twin bed at the time when I was reading Charlotte's Web for the very first time.
My reader was not lying on their twin bed thinking, God, I cannot wait to launch an ABM campaign. I cannot wait. That doesn't happen. That's not how we're wired. So many of us went into marketing because we love the creative aspect of it. And I'm speaking to that person and not just like there's lots of different people who are on my list, which is honestly a surprise to me.
There's a lot of homeschoolers who are on the list. There's poets, there's novelists. It's not just marketers. which is another reason why I rarely will speak just to a marketer. Like for example, in that story, there's this moment where I say, we might use ai, but the value of marketers increasingly comes in the things that cannot be automated.
Then I say the value of creatives comes down to how well we can do things that do not scale. The value of our work comes in how much artful creativity it has. The reason why I have those three categories is because that's kind of my, people .
in a broad sense. That's who's on my list, so I, I don't wanna speak just to marketers at the beginning, by the way, I did.
I don't anymore because I've now learned that my work doesn't appeal to just marketers. Ha
[00:39:01] Jay Acunzo: from the outset, you're doing something with that metaphorical approach to storytelling, where you say, you know, package arrived last Tuesday. The return address was a bookseller. You know, yes, you're talking about work, but it's a step removed from work. And then you start talking about E. B. White and your relationship to E.
B. White and all these things. it's almost like when you try to rip a bandaid, like, you know, my five year old has a cut on her knee, you go to rip the bandaid. If you're like, I'm going to rip the bandaid now, I'm going to count to three and I'm going to rip it on three, one, two, three, what's happening the whole time she's resisting, she's bracing, she's pushing back, she doesn't want to.
I think when we tell literal stories where it's more case study ask, or even a story that has a narrative structure to it and stakes, but it's about someone that has your job title or something like that. What's going on in people's brains is they're bracing, they're resisting. They're
like, but my boss, but my resources, but this, but that there's a lot of head trash in the way.
And as storytellers, we want them to be open to some kind of change, some kind of new approach, some kind of way of thinking or feeling or doing. And how do you do that? You kind of pretend you're taking a detour. So instead of going, I'm going to rip the bandaid on three, one, two, three, rip.
you rip it on two. so with this metaphorical story, it's even further in that direction where you're like. Hey, just calm down. Stress doesn't apply here. Job doesn't apply or come with me on this little personal journey. People go, okay, this is not about like me trying to get results
before I get fired Like, this is just a nice story. Oh, isn't this nice. It's warm and sunny here. And then you're like, aha, and here's the lesson
But they're more open to it at
[00:40:27] Ann Handley: Yes, yes, exactly, because you've
[00:40:29] Jay Acunzo: or bracing
[00:40:30] Ann Handley: Yeah, exactly, because you've, brought them along with you, because now they're standing beside you and they are vested. Mm hmm. They're able to recognize themselves. They're able to figure out like, wow, I see why it's important to her. And now I'm imagining why it's important to me as well.
So yes, all of that. Andvery often, what I love to do is to take a kind of hard left in my stories. So suddenly it's like, I'm going down the road one way and suddenly it's like, we're going to just go over. You didn't even see that coming. I didn't even signal. Okay. This is a kind of new evolution in my writing if you go back and read some of my early newsletters, would, you would knew where it was going immediately.
I've since
realized that it's a lot more fun to read when you don't, because suddenly I'll do a hard left and people are like, wait, what? And then when you bring it all back, people are like, yes. And then emotionally, they're just like, they're right there with you. They're cheering because they're like, yes, I knew this was going to come back.
And they're like sitting at the edge of their seats and you've got it. you're experiencing it together. And I love that moment so much. so much. I love that moment when people are like, wow, I didn't expect that. And that really packed a wallop, you know, I really felt that. And that's why I do it because I want you to be like, wait, what?
And then come back. Oh God, that was amazing.
the line that when I first read the piece and then when you revisited it today, hit me the hardest and definitely will stick with me is I think the line that if you're not the most proud of this line, you're at least, I think maybe feel this is the most significant because it's the point of the pieces. How do we sign our work? It's a very simple question. You
[00:42:08] Jay Acunzo: wrote it in one line, bold italics on its own paragraph, one line. how do we sign our work? I know how I signed my work. I can't necessarily explain it to you or even how I got there.I know there's people out there who are not in that position. I'm very privileged and also very practiced. you know, you're incredibly practiced and someone is listening, going, I want to sign my work, where do I even begin? What, would you tell them?
[00:42:36] Ann Handley: The most important thing is just to pick your head up, start paying attention to the world around you. part of what I write about is my experience, the things that form me as a writer, as a creative, as a communicator, as a marketer, but a lot of what I've honed has happened over the past five years since I launched that newsletter.
And that comes from looking up, looking around, tuning into my life, paying attention to those stories, writing down those small moments. Sometimes they ignite and become bigger moments and they connect to bigger things and sometimes they don't. But I don't know any other way to become a stronger communicator and to give yourself that advantage than to slow down and look up essentially.
So many of the marketers that I talked to and the communicators and entrepreneurs and all the people that I talked to, they start with sitting down at a keyboard. Putting their claws on the keys and just expecting, Okay, I'm going to write something. I'm going to write something. What am I going to write about?
And, you know, that's not the place to start. I think it's, you've got to take it back a few steps. and just tune into your life differently.
How Stories Happen was created by me, Jay Akunzo, and it's produced by Share Your Genius, cover art by Blake Inc. Learn more about these kind and creative humans and how they can help you by checking the links in your show notes. And while you're there, please explore my sponsor link. Big thanks to everybody supporting the show as a listener, a sponsor, or a partner.
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And pillar content to bring it to market. In other words, you're smart enough, you're expert enough, but maybe your IP isn't strong enough to differentiate. And if you feel that that's you, let's chat. Thank you so much for listening. I'm back in two weeks with another episode of the show, but until then, as always, keep making what matters because when your work matters more, you need to hustle for attention less.
See ya.