Anne Handley is not here to bash AI—she actually uses it—but she is here to warn us about what happens when we use it too early, too often, and for the wrong reasons. Jay Schwedelson gets into it with Ann Handley about how to stay creative when AI wants to take over your brain, what’s really at stake for writers, and why being a good marketer still means sounding like an actual person (even if it’s a sweaty, messy one).
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Subscribe to Total Annarchy—Ann’s free newsletter on writing and marketing that’s actually worth reading.
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Best Moments:
(01:31) Why she’s more afraid of humans becoming robots than robots becoming human
(04:00) The biggest mistake creators make when using AI
(05:15) A smart rule of thumb for where AI should save time
(07:15) How we’re being trained to accept boring content—and how to fight back
(08:08) The rise of AI trigger words like “unlock” and “discover” (and why they’re ruining copy)
(09:00) Are marketers avoiding copywriting as a career now?
(11:18) The case for “thoughtstipation” and why prompt engineering is not the future
(14:00) The very human way Ann used AI to review her book draft
(17:30) Her 30-minutes-a-day reading challenge and why it rewires your brain
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Transcript
Jay Schwedelson: I'm very, very, very excited. Why? Because we have the Taylor Swift of writing here. Yes, we do. I'm wearing friendship bracelets. Who's here? We have Anne Hanley. Listen, if you don't know Anne, I don't know who you are. She's the first chief content officer in the world. She's a Wall Street Journal.
Jay Schwedelson: Bestselling author. Her book Everybody writes, is basically the Bible for anybody who touches a keyboard for a living. She built marketing props into one of the most respected marketing education platforms on earth. And her newsletter, total Anarchy is the only email that you actually wanna read about stuff on Sunday mornings.
Jay Schwedelson: She's amazing and you are here. Thank you.
Ann Handley: Oh, thank you Jay. You know, I always have such a great time talking to you, so I don't, I don't know why we don't do this more often. Oh, wait, we do. 'cause this is like the, like
Jay Schwedelson: It's
Ann Handley: the, the fifth or sixth time I've, I've, uh, joined you, so, hey, I'm so happy to be back. Do you actually have friendship bracelets on, by the way?
Jay Schwedelson: I, I don't, I'm such a liar.
Ann Handley: Oh, lies. Lies. You're already gaslighting me.
Jay Schwedelson: I know. It's so embarrassing you caught me. Uh, but I will, I'm a terrible human being. Um. Yes. I, I, I get so excited every time I get to talk to you because you have such a fresh perspective. You, you say words that sound smart and I love it all. So I wanna jump right into it.
Jay Schwedelson: I saw this MIT study mostly because I read your newsletter. I, I saw this MIT study that said chat GPT is making us stupider, which is not, I don't have a lot of room to, to move there. So is that true? Is it making us stupider?
Ann Handley: Yeah, well that's what the MIT study says, and it's like, I know that stupid is kind of your word. Like you use that a lot. Not that you're dumb, stupid, but you do use that word a lot. I, every time I see the word, I kind of associate it with you. Again, not because of your mental acuity, but because
Jay Schwedelson: That's
Ann Handley: know.
Ann Handley: Stupid and garbage are like the two words that I think Jay sch wetson. Um, but yeah, that's what MIT said, and I actually think that was in the headline. It's like, basically chat gpt is making us stupider. Um, and so yeah, that's what they found, that's what they said. There were a little bit of, um, some, some points with that, with that study that don't make it apply universally, for example.
Ann Handley: Sample size was super small. It took place at an Ivy League institution. Um, it was on a, it, the, the experiment, the, the research was very, very narrow in its scope. So there was, there's a host of problems with it, I think, um, from a research standpoint, but I think the point still holds that. Chat, GPT can make you stupider, can make us all stupider if we're not, if we're not careful.
Ann Handley: Um, you know, and the, the fear has always been that the machines are gonna become more human, right? That, that robots are going to be ruling us. But I actually think that I'm more scared of the opposite, which is that humans are becoming more robot-like. So to me that's the conversation that that research really opened up.
Jay Schwedelson: So, all right. Going down that path, a little bit of becoming more robot like, uh, you're a writer. You're creator, um, and you use AI to, as, as a partner, as an assistant, as a whatever. How do you use it in a way that, um, assists you and doesn't kind of like take the place of you, especially as a writer and creator?
Ann Handley: Yeah. So, you know, I talk to a lot of marketers all the time. You know, some. Advanced in their careers and, and some brand new and. The wrong way to use AI of, I believe, and first of all, like, you know, I'm not, I'm not dictating it either way. Like I should caveat this by saying, whatever works for you to get the work done, to do work you're proud of, then good for you.
Ann Handley: But in general, I think it's a mistake to fire up AI by default. Instead, I think we need to be more deliberate. How we're using ai. And so for that, I mean, you know, for, for all, I guess I'll just speak for me, but I think I speak for a lot of creative people when I say this, is that I don't invite AI into the process too early, because if I do, it starts to almost lay the tracks for me to write and create and think in a certain way.
Ann Handley: Instead, like, I need that wilderness. Like I need to be able to feel a little frustrated by ideas and thoughts, and I need to ultimately be able to sort of bring and weave them together. AI can make us more efficient, but creativity isn't efficient and that's the point.
Jay Schwedelson: So, okay. So that's really important. 'cause I think that's the problem is that for the sake of productivity, we're losing creativity.
Ann Handley: Well, yeah. I mean, that's the fear. Yeah, exactly.
Jay Schwedelson: what do you do about that though? Are you saying, do you, do you say internally? 'cause every company on the planet, everyone's like, we need to use ai. It's every stupid meeting on the planet, right?
Jay Schwedelson: So do you, do you literally think you need to have guardrails within your, you know, content creation process and say, okay, we're gonna use ai, but not until we've gotten to, you know, this point in the process, do we go and ask if this thing stinks?
Ann Handley: Yeah, well, I don't think there's gonna be any company on this planet that's gonna tell you like, don't use AI here, use it here. And I think it's incumbent on all of us as individuals, as creators, as writers, as creatives. I mean, however you identify. Um. To use AI to save time when it doesn't matter, and then spend that time to make something really great.
Ann Handley: You know, let AI write your email reminder, for example, but don't use it as a first draft anyway. Don't let it write the first draft of your email newsletter. If what you wanna do is connect your human heart with the recipient's human heart, you know, so. I think we need to be very intentional about how we use it and note, not just use it as a default.
Ann Handley: I think there's a lot of companies and a lot of people who are just using it by default, and so that's what I'm, that's what I'm worried about. I think AI has vast potential. There's lots of great stuff about it. It can really help people who don't write naturally, who don't feel like natural writers.
Ann Handley: Like, yeah, it can help you unlock your ideas and, and unlock your voice, but. I think there also tends, there needs to be a point where we say like, this does not serve me as a person long term. It's not helping me grow. And it's not, you know, it's not helping me create something that I believe is important, that I want to have impact that I, um, that I'm proud of.
Ann Handley: And so I think we need to think about like, how do we, how do we maintain the joy in what we create and, and that feeling in what we create. Because again, creativity is not efficient. We can't make it more efficient by adding on ai.
Jay Schwedelson: Well, I, I agree with you totally about the joy aspect too, because, you know, creating something is really, it's powerful. It's how you, you know, how you grow as a person. And do you think that the pendulum has now sw. Along so far with all the AI stuff that, that we as recipients, as readers, as consumers of the content that we want more stuff that's not written by ai.
Jay Schwedelson: I mean, are we at that point or is it not there yet?
Ann Handley: Yeah, I mean.
Ann Handley: I think that the human always stands out, you know, like you see it on LinkedIn, like I'm sure you've had this experience too, Jay, where it's like you can tell a robo comment on your post by something that's actually written by a person. Like, you know, let it be lo-fi, let it make, you know, make it clear that this could only, that this could only come from you and that you are, you are creating it.
Ann Handley: Um, and so I think we do crave those experiences. You know, again, I worry about a world not where. The robots start to become human, but the humans start to sound like robots. And so if you're sounding like a robot, if you're not sweating enough in what you're creating, again, if it's the right move for you, then um, then I think it's, it's a sign that you need to back off the AI a little bit.
Jay Schwedelson: You know, it's so funny. So we've been year for years. You, we used to talk about spam trigger words. You use these words, go to the junk folder, and that kind of like went in the toilet. That's not true anymore. Whatever. And now there's these, you know, these words that AI gives you back most common. That when we see it, we actually are not reacting to it.
Jay Schwedelson: Or things like m dashes, you know, the, the elongated dashes that you know is coming from ai. I think it's funny that it's like AI spits the same guard back to all of us. I mean, how many subject lines start with the word unlock? It's like, what am I a locksmith?
Ann Handley: Yeah. Yeah. There's another study that came out recently that, that documented that and said, it showed how it's changing the way that we're communicating too, because it's putting words like unlock and, and delve. What was another one? Um, yeah, then we just saw these like sort of ai, like trigger words. Um,
Jay Schwedelson: hate it. Like discover, like we're all Magellan. Like who cares? What are we discovering? I, I, I, I, I literally can't take it. Um, so do you think, and this is for, I don't know how many copywriters are out there listening or aspiring copywriters, but I'm just curious 'cause you're so close to it, like. we, is there gonna be a whole generation of copywriters that don't become copywriters?
Jay Schwedelson: You're like, well, I can't go into that industry. Do you feel like this whole like AI is taking my job in marketing and people are gonna start avoiding certain aspects of marketing careers?
Ann Handley: I hope not. You know, somebody, I wrote a post, um, yesterday or the day before, I forget. Um, yesterday about. Friday. Who cares, Ann, who cares what day it was? This is my, this is like my little OCD thing. I
Jay Schwedelson: No, keep this. I wanna keep talking about which day it was. 'cause that's compelling.
Ann Handley: Are you sure? It.
Jay Schwedelson: the content. This is what everyone wants to know is what day
Ann Handley: Yeah, no, it was Friday. And I'll tell you why. Because as a marketing lesson in this, I do have a point, which is that everybody says, don't put up a LinkedIn post on a Friday during, especially during the summer, right? Because people are gone, they're on vacation already. They're off to the, at least in New England, they're off to the Cape or they're off to the Maine or mountains or whatever.
Ann Handley: But it did great. So that's, you know, don't follow best practices unless. Or write your own best practices, I guess. Um, anyway, the, the point of me sharing that with you is that I talked about something that I call thoughts to patient, which is that when you invite AI into the process too early habitually that over time you'll develop what I call thoughts to patient, which is kind of a blockage that you get in your brain.
Ann Handley: Like it doesn't even allow you to, to think without. Feeling like you need AI as a, a kind of laxative, I guess. Um, and I'll, I'll leave the metaphor there 'cause this could get really gross, real fast. Um, what was your question?
Jay Schwedelson: I I'm still stuck on sta Can you, like, can you just do a whole thing just on sta and different things you could add as a, as the, the
Ann Handley: Oh, yeah, yeah, yeah.
Jay Schwedelson: that there's a lot there.
Ann Handley: Is there.
Jay Schwedelson: Yeah. I mean, I, there's some book down the road that's gonna, should be called Sta and then it's all the different things that could go with
Ann Handley: It's a good keyword to own, honestly. Uh,
Jay Schwedelson: You're immediately going on GoDaddy as soon as this ends. And you're gonna try to register
Ann Handley: stipulation. It's like, oh, geez. Who? Oh, it's subject line. Oh, no, they got to it first.
Jay Schwedelson: exactly. Exactly. So, all right, let's go off the super random topics now. Um, um, AI in your personal life, do
Ann Handley: Oh wait. Hold on.
Jay Schwedelson: mean, me and Chacho Patt are
Ann Handley: Wait, I just remember what your question was and, alright, sorry. This is, I, this is, you can tell it's been a morning thoughts to patient. The reason I started talking about that is because somebody wrote on, as a comment said that, well, I don't believe that writers will even be have be a job.
Ann Handley: Instead, every writer will be just become a prompt engineer. And I just like, died instantly on the spot. Just became like dust and bones and I just collapsed into the floor. 'cause it's just like, that just guts me so hard. And number one, I don't believe that's gonna happen. Um, and number two, I just think that's, it's a ridiculous premise because what you're saying there essentially is that you know, no one will want to read your original thoughts anymore.
Ann Handley: We'll just be using ai, let AI. Gather up what other people have said and summarized, and then we'll just regurgitate it out. Like what is the value in that? And so I do think there will always be value in writing because there will always be value in original thinking, in creativity and us as people. And so when people say, you know, is writers is, is is the job, are writers going away?
Ann Handley: Is the job going away? No, I don't think it will. Does it mean that we won't use AI in some capacity in those roles? Of course we will, but I don't think that the job is going away. Okay. Sorry. Now go on and shift.
Jay Schwedelson: No, my fear is that the job, the person is, is needed, but that companies are gonna think it's not needed. And so they're not gonna hire for the role 'cause they're gonna think it's an unnecessary job. And I, I mean that's kind of the top down thing that I worry about because I believe the need is there. I just think you have a bunch of doosies that will think it's not needed anymore.
Jay Schwedelson: 'cause that
Ann Handley: but don't you think that's a short term knee jerk? Like that's what I think because I think we saw this at the very beginning, right? Where when chat GPT first, like cannon balled into our marketing pool, and then suddenly all these companies were like, yay, free content. We don't need writers anymore.
Ann Handley: We don't even need mediocre writers. Like we'll just have chat GPT do it. And I think that that's, that's not the way to go. I think that that was proven to be not a good idea pretty quickly. Um, I think it helps writers level up in ways that they should level up. I think it, it sets the bar to be higher, which I think is great for writers and for marketers.
Ann Handley: Um, and so, yeah, I don't think it's going away. And I think ultimately, even if it there, there's sort of this bumpy period. I, I think ultimately it will come out the other side.
Jay Schwedelson: I, I'm all in. I hope so. I agree with that. Um, alright. Now I want to know in your personal life, 'cause me, Chacha is my only friend other than you. Um, so do you, do you use ai? Do you, I mean, how do, how do you, how does Anne use ai?
Ann Handley: in my personal life.
Jay Schwedelson: Yeah.
Ann Handley: All right, so right before we started recording, I told you that I just finished the first draft of a new book that I've been working on for the past. I mean, I've been actively writing it for the past year and a half, but the idea I've been evolving for 10 years, or by the time the book comes out, it will be 10 years.
ge at Content Marketing World:Ann Handley: And so I'm very, very close to this idea. I don't even know if it's any good anymore. It could be to use your word, total garbage. You know, I could be the idiot writer who just is like deciding that I'm gonna quit writing and just become a prompt engineer. I don't know, like I'm not sure if this is any good anymore.
Ann Handley: But that said, how I use AI in my personal life. I uploaded the book, the the rough draft manuscript to um, to both chat GBT and Claude. And I was like, just tell me what you think of this book, but be kind and the be kind. Part of the prompt was important because I'm sort of past the point where I can take any criticism, any of it anymore.
Ann Handley: Like I've done that already. Like I've already asked it to pressure test ideas and to push back and it, it gaslit me so hard. Jay this is brilliant. This is such a great idea. You are so smart. You are gonna just change the world. And was I being gaslit? Yes I was. But I am here for it because what writer just doesn't need somebody in their corner all the time?
Ann Handley: And as you say, like if, if AI is like, is is your only friend, like it's, it's at least a friend who is gonna support me. So yeah. I appreciated that. Um, yeah.
Jay Schwedelson: I, I love it so much. No, and I, I, I, I always tell it, is this a good idea? And then yes. Oh my God. That's the best thing of all time. And by the way, another thing that you put in your newsletter recently, which I actually, I think because of AI in the last year or so started doing more is, is reading books.
Jay Schwedelson: I've always read books, but now I'm like. Like so focused on it. 'cause I'm like, I think I'm gonna come a doofus if I don't like read even more. So I have a personal question to ask you, uh, what you think about this? So I'm a sample person, meaning like I'll go on my Kindle sample sample, sample sample, and then I get to the end of the sample.
Jay Schwedelson: I'm like. Is this the greatest book I ever read? No, it's not. I'm not gonna buy it onto the next, and I read like 10 samples before I get to one book and I found that's stupid. 'cause some books take a little while to get into it. Whatever. Anne Hanley is like Captain Book person on Earth. Are you a sample person?
Jay Schwedelson: Sample download, or you go right
Ann Handley: I go right in. But you know, I don't read on a Kindle. I, I, um, I use, like I read on a physical book. Um, I've thought about getting a scribe because I've had a few artist friends who've to tell me that it's a really nice mix between a Kindle and a, um, and like a, just the ability to use it for sketching.
Ann Handley: So I've thought about that, but, um, but yeah, right now I'm, I use actual books and so I don't do any sampling, but I do, I I give a book. 50 pages. If it doesn't grab me at 50 pages, unless it's a, there's a very specific reason that I'm thinking it. Um, I'm reading it like for research or something like that, which happened during the research of this book.
Ann Handley: So, but I give it 50 pages. If it doesn't grab me, then like, it's life's too short to read bad books.
Jay Schwedelson: And your thing you said was, what was it? 30 minutes a day For how long? Like this is the challenge to people. You gave people
Ann Handley: For 90 days, 30 minutes a day, 90 days. See if it doesn't change your brain. See if it doesn't start to rewire your brain. Because I see this in my kids too. It's like, it's so tempting to just pick this up, you know? Um, like my, my, I walked on my daughter on the, uh, on uh, she was on the deck the other day and she was reading a book and I was like, oh, I'm like, this does my heart good.
Ann Handley: And I walked up to her and I gave her a kiss on her head and I'm like, I'm so happy to see you reading a book. And I look down and she has her phone propped up. And I was like, alright, well good, I'm glad you're reading. Like,
Jay Schwedelson: sort of right
Ann Handley: she was,
Jay Schwedelson: is near you.
Ann Handley: she was available if you needed her. So, um, yeah, it's just, you've gotta train your brain, you've gotta train your brain to step away from the things, the apps, the notifications, the ai, all of it. And so I do think that it's, uh, it's almost become an active.
Ann Handley: Radical resistance. Just sit down for 30 minutes a day. Focus your brain if you can. It's a lot harder than it seems if you haven't done it yet. Um, and give yourself grace. It's like if you can only make it 20 minutes, okay, you've done 20 minutes. Like good job. Like I'll, I will be your AI gaslight at that point.
Ann Handley: Like I just want people to think about how do we counter some of this always on accelerated pace of life. I think, you know, the, the slow smart act of of reading is. Is radical at this point.
Jay Schwedelson: I love it, and that's a huge, I, I, it's part of my, every day
Ann Handley: Oh, I'm so delighted
Jay Schwedelson: no matter
Ann Handley: Whatcha reading right now?
Jay Schwedelson: Yeah. Yeah. I'm reading, uh, the Linus of Teran. Um, it's really good. It's about the whole, how, uh, Iran changed over the years and all this stuff. It's
Ann Handley: oh wow. That's
Jay Schwedelson: Uh, so yeah. Um, I try to read things that are really outside of my every day because it lets me kind of like not think about just the
Ann Handley: Yeah. Yeah. Same, same. Yeah. Like I'm a big, I'm a big fiction person. I try to find, um, try to find just a story that I can lose myself in, first of all, because I love stories and I'm, I'm sort of a natural storyteller, but I, for the same reason, I just sort of wanna get out of my day to day. Um, and you know, like you, I'm a massive reality fan, uh, reality TV fan.
Ann Handley: And so, um. I'm also a fan of reality in general. Not I think of it, but anyway. Um, and so, yeah, it's like I want something that's different from that too.
Jay Schwedelson: I love it all. Listen, if you want to get good book Recos, you could read Anne's newsletter because Anne's newsletter is the my favorite newsletter on the planet. It's way better than mine. I'm not just saying that. We're gonna put in the show notes. It is called Total Anarchy. If you go to anne hanley.com, you can register for this thing for free.
Jay Schwedelson: Uh, we're gonna put in the show notes. We're gonna promote it anywhere, everywhere. And thank you so much for
Ann Handley: was so great as always. So thanks Jay.
Jay Schwedelson: All right, we'll see you soon.