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

Do This, NOT That: Marketing Tips with Jay Schwedelson l Presented By Marigold

GURU Media Hub

Growth, Education, Email, Business, Revenue, How To, Entrepreneurship, Marketing, Profit, B2b, B2c

5 • 715 Ratings

🗓️ 1 August 2025

⏱️ 21 minutes

🔗️ Recording | iTunes | RSS

🧾️ Download transcript

Summary

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 our 100% FREE + VIRTUAL EVENTS! ->

Guru Conference - The World's Largest Virtual EMAIL MARKETING Conference - Nov 6-7!

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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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MASSIVE thank you to our Sponsor, Marigold!!

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Transcript

Click on a timestamp to play from that location

0:00.0	Welcome to Do This, Not That, the podcast for marketers.
0:06.1	Each episode is packed with quick tips.
0:08.3	They're super short, and at the end, we have some fun.
0:11.1	Let's jump into it, and thanks for being here.
0:14.7	I'm very, very, very excited.
0:16.6	Why?
0:16.9	Because we have the Taylor Swift of writing here.
0:20.6	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
0:39.6	she built marketing profs into one of the most respected marketing education platforms on earth
0:44.2	and her newsletter total anarchy is the only email that you actually want to read about stuff
0:49.2	on sunday mornings she's amazing and you are here thank you oh. Oh, thank you, Jay. You know, I always
0:55.8	have such a great time talking to you. So I don't, I don't know why we don't do this more often.
1:00.5	Oh, wait, we do because this is like the fifth or sixth time I've joined you. So hey, I'm so
1:07.7	happy to be back. Do you actually have Frontier bracelets on, by the way? I don't. I'm such a liar. Oh, lies. I will. I will. I will. I will. I know. It's so embarrassing. You 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.
1:29.3	So I want to jump right into it.
1:31.3	I saw this MIT study mostly because I read your newsletter.
1:35.3	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 move there.
1:43.3	So is that true? Is it making us stupider? Yeah, well,'t have a lot of room to move there so is that true is
1:44.8	it making us stupider yeah well that's what the MIT study says and it's like I
1:49.8	know that stupid is kind of your word like you use that a lot not that you're dumb
1:53.3	stupid but you do use that word a lot every time I see the word I kind of
1:57.2	associate it with you again not because of your mental acuity, but because
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