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

Summary

Podcast Summary: "Do This, NOT That: Marketing Tips with Jay Schwedelson" Featuring Ann Handley

Episode Title: AI and Creativity!🧠How Ann Handley Uses AI... | Ep. 386
Release Date: August 1, 2025
Host: Jay Schwedelson
Guest: Ann Handley

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1. Introduction to Ann Handley

The episode kicks off with Jay Schwedelson warmly welcoming Ann Handley, lauding her as the "Taylor Swift of writing" and highlighting her impressive credentials, including being the first Chief Content Officer globally and a Wall Street Journal bestselling author. Jay emphasizes Ann’s influence in the marketing education sphere and her acclaimed newsletter, Total Anarchy.

Jay Schwedelson [00:01]:
"Listen, if you don't know Anne, I don't know who you are. She is the first chief content officer in the world..."

2. Discussing the MIT Study: Is AI Making Us Stupider?

Jay introduces a controversial MIT study suggesting that ChatGPT may be diminishing human intelligence. Ann critiques the study's methodology, pointing out its limited sample size and narrow scope, yet acknowledges the broader concern that over-reliance on AI could potentially erode critical thinking skills.

Ann Handley [01:46]:
"Chat GPT is making us stupider, can make us all stupider if we're not... humans are becoming more robot."

3. AI’s Impact on Creativity and Decision-Making

The conversation delves into the delicate balance between leveraging AI as a creative assistant and the risk of it undermining human creativity. Ann emphasizes the importance of not defaulting to AI usage too early in the creative process to preserve the organic generation of ideas.

Ann Handley [03:35]:
"Creativity isn't efficient. And that's the point."

Jay concurs, highlighting the fear that productivity gains from AI might come at the expense of genuine creativity.

Jay Schwedelson [04:54]:
"I think that's the problem is that for the sake of productivity, we're losing creativity."

4. Strategies for Intentional AI Usage in Content Creation

Ann advocates for a deliberate approach to integrating AI into content creation. She suggests using AI for mundane tasks, such as drafting email reminders, while reserving the creative and impactful aspects of writing for human effort.

Ann Handley [05:17]:
"Don't use it as a first draft of your email newsletter. If what you want to do is connect your human heart with the recipient's human heart, be very intentional."

She warns against the default use of AI, which can lead to homogenized and robotic content, detracting from the personal touch that resonates with audiences.

Ann Handley [07:19]:
"Let it be lo fi. Let it make, you know, make it clear that this could only come from you."

5. The Future of Copywriting in the Age of AI

Addressing concerns about AI replacing copywriters, Ann remains optimistic. She argues that while AI will become a tool to enhance writers' abilities, the intrinsic value of original human thought and creativity will ensure that writers remain essential.

Ann Handley [09:38]:
"I don't believe that writers will even have be a job... there's always value in original thinking."

Jay shares his fear that businesses might undervalue human writers, leading to reduced hiring, but Ann counters that such short-term thinking will ultimately give way to the enduring need for authentic content.

Ann Handley [13:12]:
"I think it helps writers level up in ways that they should level up. I think it sets the bar to be Higher."

6. Ann Handley’s Personal Use of AI in Writing

Ann reveals her practical use of AI in developing her upcoming book. She experimented by uploading her manuscript to AI tools like ChatGPT and Claude to garner feedback, which she humorously describes as "gaslighting" when the AI overly praised her work despite its flaws.

Ann Handley [14:15]:
"I uploaded the rough draft manuscript to both ChatGPT and Claude... It gaslit me so hard."

This anecdote underscores the potential pitfalls of relying too heavily on AI for constructive criticism, highlighting the necessity for human discernment in the creative process.

7. The Importance of Reading and Cognitive Discipline

Transitioning to personal habits, Ann emphasizes the significance of sustained reading in an age dominated by digital distractions. She shares her practice of dedicating 30 minutes daily over 90 days to rewire her brain towards focused, deep reading as a form of "radical resistance" against the ever-present pull of AI and digital notifications.

Ann Handley [17:51]:
"Sit down for 30 minutes a day. Focus your brain if you can. It's a lot harder than it seems."

Jay relates by discussing his own reading habits and the value he finds in immersing himself in diverse and challenging literature to escape routine thoughts.

Jay Schwedelson [19:23]:
"Part of my every day has to be, no matter what."

8. Final Thoughts and Encouragement

In the concluding segments, Jay praises Ann’s newsletter, Total Anarchy, encouraging listeners to subscribe for high-quality content. Ann expresses her appreciation for the insightful dialogue, reinforcing the episode's themes of balancing AI usage with maintaining human creativity and intellectual engagement.

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Key Takeaways

• Balanced AI Integration: Use AI as a tool to enhance efficiency in mundane tasks while preserving human creativity for impactful content.

• Maintaining Authenticity: Intentional use of AI ensures content retains a personal and authentic voice, avoiding the pitfalls of homogenized, robotic outputs.

• Value of Human Writers: Despite advancements in AI, the unique value of original human thought and creativity remains irreplaceable in the field of writing and marketing.

• Cognitive Discipline: Engaging in consistent, focused reading habits can counterbalance the distractions of digital life and AI influence, fostering deeper cognitive skills.

• Future of Marketing: The coexistence of AI and human creativity will likely elevate the standards in marketing, pushing professionals to innovate and refine their craft.

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Notable Quotes

• Jay Schwedelson [00:01]:
  "Welcome to do this. Not that. The podcast for marketers... Why? Because we have the Taylor Swift of writing here."

• Ann Handley [01:46]:
  "Chat GPT is making us stupider, can make us all stupider if we're not careful."

• Ann Handley [05:17]:
  "Don't use it as a first draft of your email newsletter... be very intentional."

• Ann Handley [14:15]:
  "I uploaded the rough draft manuscript to both ChatGPT and Claude... It gaslit me so hard."

• Ann Handley [17:51]:
  "Sit down for 30 minutes a day. Focus your brain if you can. It's a lot harder than it seems."

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This episode offers a profound exploration of the interplay between AI and human creativity, providing actionable insights for marketers striving to harness AI’s benefits without compromising the essence of their creative endeavors. Ann Handley’s experiences and perspectives serve as a guiding beacon for navigating the evolving landscape of content creation in the digital age.

Transcript

[Jay Schwedelson]

Welcome 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 Ann 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 best selling author. Her book Everybody Writes is basically the bible for anybody who touches a keyboard for a living. She 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.

[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.

[Jay Schwedelson]

Because this is like, it's never enough.

[Ann Handley]

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?

[Jay Schwedelson]

I don't. I'm such a liar.

[Ann Handley]

Lies.

[Jay Schwedelson]

I know. It's so embarrassing. You caught me. But I will. I'm a terrible human being. Yes. 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 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?

[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 that'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, some points with that, 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 a, the, the experiments, the, the research was very, very narrow in its scope. So there was, there's a host of problems with it, I think, from a research standpoint, but I think the point still holds that ChatGPT can make you stupider, can make us all stupider if we're not, if we're not careful, you know, and the fear has always been that the machines are going to 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, becoming more robot. Like, you're a writer, you're a creator, and you use AI to, 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?

[Ann Handley]

Yeah. 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 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, you know, for, for. 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 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 because I think that's the problem is that for the sake of productivity, we're losing creativity, right?

[Ann Handley]

That's the fear. Yeah, exactly.

[Jay Schwedelson]

So what do you do about that, though? Are you saying, do you. Do you say internally? Because every company on the planet, I was like, we need to use AI every stupid meeting on the planet. Right. So do you, do you literally think you need to have guardrails within your, you know, content creation process and say, okay, 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.

[Ann Handley]

Yeah, well, I don't think there's going to be any company on this planet that's going to 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. 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, 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. 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. 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 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, that I am proud of. And so I think we need to think about, like, do we. 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.

[Jay Schwedelson]

Well, 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 swung 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' written by A.I. i mean, are we at that point or is it not there yet?

[Ann Handley]

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. 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. 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, 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, use these words, go in 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, the elongated dashes that, you know is coming from AI I 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.

[Ann Handley]

Yeah. There's another study that came out recently that, that doc out of that and 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? Yeah. Then we just saw these, like, sort of AI like trigger words.

[Jay Schwedelson]

I hate it. Like discover. Like we're all Magellan. Like, who cares? What are we discovering? I, I, I, I literally can't take it. 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 gonna start avoiding certain aspects of marketing careers?

[Ann Handley]

God, I hope not. You know, somebody, I wrote a post yesterday or the day before. I forget yesterday about no Friday. Who cares, Anne. Who cares what day it was? This is my. This is like my little OCD thing.

[Jay Schwedelson]

I want to keep talking about which day. That's compelling.

[Ann Handley]

Are you sure that's.

[Jay Schwedelson]

This is what everyone wants to know is what day was it?

[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 Main or mountains or whatever. But it did great so that, you know, don't follow best practices unless you know or write your own best practices, I guess. Anyway, the point of me sharing that with you is that I talked about something that I call thoughtstepation, which is that when you invite AI into the process too early, habitually, that over time, you'll develop what I call thoughtstepation, 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. A kind of laxative, I guess. And I'll. I'll leave the metaphor there because this could get really gross real fast. What was your question?

[Jay Schwedelson]

I'm still stuck on stipation. Can you like, can you just do a whole thing just on stipation and different things you could add as a. As the. The prefix of station.

[Ann Handley]

Yeah. Yeah.

[Jay Schwedelson]

I think that there's a lot there.

[Ann Handley]

Is there?

[Jay Schwedelson]

Yeah. I mean, there's some book down the road that's gonna. Should be called stipation, and then it's all the different things that could go with it.

[Ann Handley]

It's a good keyword to own.

[Jay Schwedelson]

Honestly, you're immediately going on godaddy as soon as this ends, and you're gonna try to register that. That's amazing.

[Ann Handley]

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. AI, in your personal life, do you. I. I mean, me and Chatgpt are besties.

[Ann Handley]

Wait, I just remember what your question was.

[Jay Schwedelson]

Oh, good one. Of us.

[Ann Handley]

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 somebody wrote on as a comment said that well, I don't believe that writers will even 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. Cause it's just like that just guts me so hard. And number one, I don't believe that's going to happen. 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 that 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? 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, no Gohan and shift.

[Jay Schwedelson]

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 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.

[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 chatgpt first like cannonballed into our marketing pool and then suddenly all these companies were like, yay, free content. We don't need writers anym. We don't even need mediocre writers. Like we'll just have ChatGPT 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. 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. And so, yeah, I don't think it's going away. And I think ultimately, even if there. There's sort of this bumpy period, I think ultimately we'll come out the other side.

[Jay Schwedelson]

I'm all in. I hope so. I agree with that. All right, now I want to know in your personal life, because ChatGPT is my only friend other than you. So do you. Do you use AI? Do you. I mean, how do you. How do you. How does Ann 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. I first talked about this idea on the main stage at content marketing world 2016, gave 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 ide. 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 going to quit writing and just become a prompt engineer. I don't know. Like, 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. The rough draft manuscript to. To both ChatGPT and Claude, and I was like, just tell me what you think of this book. But be kind in 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. It gaslit me so hard. Jay, like, 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? And as you say, if. If AI is like, is. Is your only friend. Like, it's. It's least a friend. Who is going to support me. So, yeah, I appreciate it. I love it. Yep.

[Jay Schwedelson]

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. By the way, another thing that you put in your newsletter recently, which I actually, I think because of AI in doing more is, is reading books. I've always read books, but now I'm like, like, so focused on it because I'm like, I think I'm 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. And 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. And Ann Hanley is a captain book person on Earth. Are you a sample person, sample download, or you go right in?

[Ann Handley]

I go right in. But you know, I don't read on a Kindle. I, I, I use like, I read on a physical book. I've 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 a, and like, just the ability to use it for sketching. So I've thought about that. But, but yeah, right now I'm, I use actual books. And so I don't do any sampling. 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, 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.

[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, like, for 90 days.

[Ann Handley]

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, like my, I walked on My daughter on the, on. 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 look down and she has her phone propped up and I was like, all right, good. I'm glad you're reading, like sort of.

[Jay Schwedelson]

Right?

[Ann Handley]

I mean she was.

[Jay Schwedelson]

Book is near so she was available.

[Ann Handley]

If you needed her. So yeah, it's. 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, it's almost become an act of radical resistance. Just, 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 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 gaslighter at that point. 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 slow, smart act of reading is, is radical at this point.

[Jay Schwedelson]

I love it and that's a huge. It's part of my every day, has to be, no matter what.

[Ann Handley]

What are you reading right now?

[Jay Schwedelson]

Yeah, yeah, I'm reading the Lioness of Tehran. It's really good. It's about the whole. How Iran changed over the years and all this stuff.

[Ann Handley]

It's really. Oh wow, that's awesome.

[Jay Schwedelson]

So yeah, 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 stuff.

[Ann Handley]

Yeah, same, same. Yeah, like I'm a big, I'm a big fiction person. I try to find, try to find just a story that I can lose myself in. First of all, because I love stories and I'm sort of a natural storyteller, but for the same reason I just sort of want to get out of my day to day and you know, like you, I'm a massive reality fan, reality TV fan and so I'm also a fan of reality in general, now that I think of it anyway. 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 records, 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 going to put in the show notes. It is called total anarchy. If you go to annhanhandley.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. And thank you so much for being here.

[Ann Handley]

So great as always. So thanks, Jay.

[Jay Schwedelson]

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 market 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 Daymond, John, Martha Stewart, and me. GuruEvents.com check it out.