Ann Handley! AI and Creativity!🧠How Ann Handley Uses AI...| Ep. 386

1 Aug 2025 · 21 min

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Podcast Summary: Do This, NOT That: Marketing Tips with Jay Schwedelson

Episode Title

Ann Handley! AI and Creativity! 🧠 How Ann Handley Uses AI... | Ep. 386

Podcast Overview "Do This, NOT That!" is dedicated to providing marketers with vital insights and strategies to enhance their marketing efforts. The episodes focus on actionable advice that can lead to significant improvements in marketing practices, blending behavioral science principles with creative approaches.

Episode Highlights In this episode, Jay Schwedelson talks with Ann Handley, a renowned writer and marketing expert, about the intersection of Artificial Intelligence (AI) and creativity. The discussion includes the impacts of AI on writing and marketing, and how to maintain a human touch in creative processes.

Key Discussions and Insights

  1. AI and Human Creativity
  2. Fear of Becoming Robotic: Ann expresses concern that humans may become more robotic rather than machines becoming more human.
  3. AI Misuse: Many creators make the mistake of relying on AI too early in the creative process. This could lead to a loss of original thought and creativity.
  1. Best Practices for Using AI
  2. Deliberate Use: It's crucial to use AI intentionally rather than as a default. Ann suggests it should assist in aspects that do not require deep creativity, such as administrative tasks.
  3. Creative Wilderness: Writers should spend time developing their ideas independently before incorporating AI, as creativity thrives in a less structured environment.
  1. Challenges in Copywriting
  2. Boring Content: There is a growing trend towards dull, formulaic content influenced by AI. Ann discusses the rise of “AI trigger words” like "unlock" and "discover," which contribute to this problem.
  3. Job Security for Copywriters: Concerns about AI replacing copywriting roles are discussed. Ann believes that while AI will change the field, the need for original thought and quality writing remains essential.
  1. Personal Use of AI
  2. Ann shares her personal experiences using AI for feedback on her writing. She uploads drafts to AI tools for encouragement and constructive criticism but emphasizes the importance of human creativity.
  1. Reading and Continuous Learning
  2. Ann advocates for reading as a tool for maintaining creativity and developing critical thinking. She suggests a challenge of 30 minutes of reading daily to rewire the brain.

Key Takeaways

  • AI as a Tool, Not a Crutch: Use AI to enhance productivity but maintain personal creativity and authenticity in content creation.
  • The Human Touch is Irreplaceable: Readers and consumers increasingly value content that feels authentic and not generated by machines.
  • Continuous Growth: Regular reading and storytelling are essential for personal and professional growth in the creative field.

Conclusion The episode underscores the importance of balancing AI's efficiency with the irreplaceable value of human creativity. Marketers and writers are encouraged to leverage AI as a supportive tool while prioritizing their unique voices and perspectives.

Additional Resources

  • Ann's Newsletter: [Total Anarchy](https://annhandley.com/newsletter/) - A must-read for insights on writing and marketing.
  • Jay’s Social Media:
  • [YouTube Channel](https://www.youtube.com/@schwedelson)
  • [TikTok](https://www.tiktok.com/@schwedelson)
  • [Instagram](https://www.instagram.com/jayschwedelson/)

Subscribe to the podcast for more actionable marketing tips and insights.

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Transcript

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0:01Welcome to Do This Not That, the podcast for marketers. Each episode is packed with quick tips. They're super short, and at the end, we have some fun. Let's jump into it, and thanks for being here. 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 is the first chief content officer in the world. She's a Wall Street Journal bestselling author. Her book, Everybody Writes, is basically the Bible for anybody who touches a keyboard for a living.

0:39She built Marketing Profs into one of the most respected marketing education platforms on earth. And her newsletter, Total Anarchy, is the only email that you actually want to read about stuff on Sunday mornings. She's amazing. And you are here. Thank you. Oh, thank you, Jay. You know, I always have such a great time talking to you. So I don't know why we don't do this more often. Oh, wait, we do. Because this is like the fifth or sixth time I've joined you. So hey, I'm so happy to be back. Do you actually have friendship bracelets on by the way? I don't. I'm such a liar. I know it's so embarrassing.

1:18You caught me. But I will. I'm a terrible human being. Yes, I get so excited every time I get to talk to you because you have such a fresh perspective. You say words that sound smart. And I love it all. So I want to jump right into it i saw this mit study mostly because i read your newsletter 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 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...

2:02That's amazing. Stupid and garbage are like the two words that I think Jay Schwedelson. 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. And so, yeah, that's what they found. That's what they said. There were a little bit of some points with that study that don't make it apply universally. For example, sample size was super small. It took place at an Ivy League institution. It was on the experiment, the research was very, very narrow in its scope. So there's a host of problems with it, I think, 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 careful.

2:52The fear has always been that the machines are going to become more human, right? 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. So, all right, going down that path a little bit, becoming more robot-like, you're a writer, you're a creator, and you use AI as a partner, as an assistant, as a whatever. how do you use it in a way that assists you and doesn't kind of like take the place of you, especially as a writer and creator?

3:35Yeah. So, you know, I talk to a lot of marketers all the time, you know, some advanced in their careers and some brand new and the wrong way to use AI, I believe. And first of all, like, you know, I'm not, I'm not dictating it either way. Like I 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. But in general, I think it's a mistake to fire up AI by default. Instead, I think we need to be more deliberate in how we're using AI. And so for that, I mean, 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.

4:19Because if I do, it starts to almost lay the tracks for me to write and create and think in a certain way. Instead, I need that wilderness. 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. So, okay, so that's really important because I think that's the problem, is that for the sake of productivity we're losing creativity right yeah that's the fear yeah exactly so what do you do about that though are you saying do you do you say internally because every company on the planet everyone's like we need to use ai every stupid meeting on the planet right so do you do you literally think you need to have guard rails within your you know content creation process and say okay we're going to 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?

5:17Yeah, 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, to use AI to save time when it doesn't matter, and then spend that time to make something really great. 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 want to do is connect your human heart with the recipient's human heart.

5:57So I think we need to be very intentional about how we use it and not just use it as a default. 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 worried about. I think AI has vast potential. There's lots of great stuff about it. but it can really help people who don't write naturally, who don't feel like natural writers. Like, yeah, it can help you unlock your ideas 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.

6:31And 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 am proud of. And so I think we need to think about, how do we maintain the joy in what we create and that feeling in what we create? Because again, creativity is not efficient. We can't make it more efficient by adding on AI. Well, I agree with you totally about the joy aspect too, because creating something is really, it's powerful. It's how you grow as a person. And do you think that the pendulum has now swung so far with all the AI stuff that we as recipients, as readers, as consumers of the content, that we want more stuff that's not written by AI?

7:15I mean, are we at that point or is it not there yet? Yeah, I mean, 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. and let it make, you know, make it clear that this could only, this could only come from you and that you are, you are creating it. 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.

7:56And 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, then I think it's, it's a sign that you need to back off the AI a little bit. You know, it's so funny. So we've been year for years, we used to talk about spam trigger words, 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 commonly that when we see it, we actually are not reacting to it or things like M dashes, you know, the elongated dashes that you know is coming from AI.

8:28I think it's funny that it's like AI spits the same garbage back to all of us. I mean, how many subject lines start with the word unlock? It's like, what am I, a locksmith? It's ridiculous. Yeah, there's another study that came out recently that documented that. It showed how it's changing the way that we're communicating too because it's putting words like unlock and delve. What was another one? Yeah. Yeah, we just saw these sort of AI trigger words. I hate it. Like, discover. Like, we're all Magellan. Like, who cares? What are we discovering? 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 because you're so close to it like are we is there gonna be a whole generation of copywriters that don't become copywriters 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 going to start avoiding certain aspects of marketing careers god i hope not you know somebody I wrote a post yesterday or the day before, I forget, yesterday about, no, Friday.

9:30Who cares, Ian? Who cares what day it was? This is like my little OCD thing. No, I want to keep talking about which day it was because that's compelling. Are you sure it wasn't? That's the content. This is what everyone wants to know is what day was it? Yeah, no, it was Friday. And I'll tell you why. Because there's 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, especially during the summer, right? Because people are gone. They're on vacation already. They're off to the East in New England or off to the Cape or they're off to the Maine or mountains or whatever, but it did great.

10:04So that, you know, don't follow best practices unless, you know, write your own best practices, I guess. Anyway, the point of me sharing that with you is that I 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. Like it doesn't even allow you to think without feeling like you need AI as a kind of laxative, I guess. And I'll leave the metaphor there because this can get really gross real fast. What was your question?

10:44I got so distracted. I'm still stuck on stepation. Can you just do a whole thing just on stepation and different things you could add as the prefix of stepation? Oh, yeah. Yeah. I think there's a lot there. Is there? Yeah. I mean, there's some book down the road that should be called stepation. And then it's all the different things that could go with that. It's a good keyword to own, honestly. You're immediately going on GoDaddy as soon as this ends. and you're going to try to register that that's amazing it's like oh geez who oh it's subject line oh no they got to it first exactly exactly so all right let's go off super random topics now um ai in your personal life do you i mean me and chachipati are besties wait i just remember what your question was oh good one of us sorry this is i this is you can tell it's been a morning thoughts to patient the reason i started talking about that somebody wrote on as a comment said that well i don't believe that writers will even be have be a job 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 because it's just like that just guts me so hard and number one i don't believe that's going to 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 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 the job, are writers going away?

12:37Is 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. No, go on and shift. No, my fear is that the job, the person is needed, but that companies are going to think it's not needed. And so they're not going to hire for the role because they're going to think it's an unnecessary job. And I mean, that's kind of the top down thing that I worry about it, because I believe the need is there. I just think you have a bunch of doofuses that will think it's not needed anymore because that happened.

13:12But 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 ChatGPT first like cannonballed into our marketing pool, and then suddenly all these companies were like, yay, free content. We don't need writers anymore. 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 sets the bar to be higher which i think is great for writers and for marketers um and so yeah i don't think it's going away and i think ultimately even even if they're sort of this bumpy period, I think ultimately we'll come out the other side.

13:59I'm all in. I hope so, I agree with that. All right, now I wanna know in your personal life, cause Chachamiki is my only friend other than you. So do you use AI? Do you, I mean, how does Anne use AI? In my personal life? Yeah. 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. I first talked about this idea on the main stage at Content Marketing World 2016.

14:43We have a keynote speech on it in 2016. And then my thinking evolved over time, things progressed, and I started thinking about it in a slightly different way through a different lens. All that to say, by the time the book comes out in 2026, it will be 10 years. 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. I could be the idiot writer who just is deciding that I'm going to quit writing and just become a prompt engineer. I don't know. I'm not sure if this is any good anymore. But that said, how I use AI in my personal life, I uploaded the book, the rough draft manuscript, to both ChatGPT and Claude.

15:24And 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 of it anymore. Like I've done that already. Like I've already asked it to pressure test ideas and to push back. And it gaslit me so hard, Jay. Like this is brilliant. This is such a great idea. You are so smart. all right, 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? And as you say, if AI is your only friend, like it's at least a friend who is gonna support me.

16:07And so, yeah, I appreciate that. I love it. I love it so much. No, and 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. 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 what you think about this. So I'm a sample person, meaning like I'll go on my Kindle sample, sample, sample, sample.

16:42And then I get to the end of the sample. I'm like, is this the greatest book I ever read? No, it's not. I'm not going to buy it onto the next. and I read like 10 samples before I get to one book. And I found that's stupid because some books take a little while to get into or whatever. Anne Hanley is a captain book person on earth. Are you a sample person, sample download, or you go right in? I go right in, but I don't read on a Kindle. I use like, I read on a physical book. I thought about getting a scribe because I've had a few artist friends who tell me that it's a really nice mix between a Kindle and just the ability to use it for sketching.

17:18So I've thought about that. But yeah, right now I use actual books. And so I don't do any sampling, but I do, I give a book 50 pages. If it doesn't grab me at 50 pages, unless there's a very specific reason that I'm thinking it, I'm reading it like for research or something like that, which happened during the research of this book. 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. 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 like 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 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 looked down and she has her phone propped up and I was like all right good I'm glad you're reading like sort of right she was book is but also she was available if you needed her so um yeah you've got to train your brain you've got to 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 almost become an act of radical resistance.

18:47Just 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. And give yourself grace. It's like if you can only make it 20 minutes, okay, you've done 20 minutes. Good job. I will be your AI gaslighter at that point. I just want people to think about how do we counter some of this always-on, accelerated pace of life. i think you know that the slow smart act of of reading is is radical at this point i love it and that's a huge it's part of my everyday has to be no matter what are you reading right now yeah yeah i'm reading uh the lioness of tehran um it's really good it's about the whole how uh iran changed over the years and all this stuff it's really wow that's awesome so yeah um i try to read things that are really outside of my everyday because it lets me kind of like not think about just the regular 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 want to get out of my day to day.

20:02And you know, like you, I'm a massive reality fan, reality TV fan. And so I'm also a fan of reality in general, not I think. And so yeah, it's like I want something that's different from that too. I love it all. Listen, if you want to get good book recos, you could read Anne's newsletter, because Anne's newsletter is my favorite newsletter on the planet. It's way better than mine. I'm not just saying that we're going to put in the show notes. It is called Total Anarchy. If you go to annhandley.com, you can register for this thing for free. We're going to put in the show notes. We're going to promote it anywhere, everywhere.

20:38Ann, thank you so much for being here. This was so great, as always. So thanks, Jay. All right. We'll see you soon. You did it. You made it to the end. Nice. But the party's not over. Subscribe to make sure you get the latest episode each week for more actionable tips and a little chaos from today's top marketers. And hook us up with a five-star review if this wasn't the worst podcast of all time. Lastly, if you want access to the best virtual marketing events that are also 100 % free, visit guruevents.com so you can hear from the world's top marketers like Damon John, Martha Stewart, and me. Guruevents.com.

21:20Check it out.

From the publisher

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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Check out Jay’s YOUTUBE Channel: https://www.youtube.com/@schwedelson

Check out Jay’s TIKTOK: https://www.tiktok.com/@schwedelson

Check Out Jay's INSTAGRAM: https://www.instagram.com/jayschwedelson/

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