The other 'AI': author Ann Handley on analog intelligence

Chief Word Officer learns to fear "thoughtstipation"

👋 Eleanor and Kenn here! Thank you to everyone who signed up to this newsletter and is eager to explore AI and writing with us. It feels like we're still in a messy middle where it's hard to distinguish between hype and fatalism. We hope that the conversations we feature here will help illuminate a path forward.

🧠 Before thoughts, a request!

Is there anyone we should speak to about AI, creativity or writing? Any great resources or links we should feature? Reply to this email.

✍️ On to the show…

This newsletter’s first interview is with Ann Handley, WSJ best-selling author, speaker and digital marketing innovator who has a deep love for the written word and believes that everyone can be a writer. I was so excited for this conversation, having followed Ann’s work for several years now.

Ann has not shied away from using AI (her own AI is named, aptly, ‘Annalog’), but she believes strongly in cultivating time and attention away from tech as a way to maintain lucidity and produce true insight. Below are three takeaways followed by our conversation, edited for clarity.

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Key takeaways from my interview with Ann Handley

• The power of the “other AI” (analog intelligence): Ann starts her day by writing on paper for a few minutes. Analog thinking and writing help you stay connected to your own thoughts and the world.

• Beware of thoughtstipation: Over-reliance on AI can override our natural thinking process. Listen to yourself before you invite AI into the process to maintain the human touch.

• The “from” line vs. the “subject” line: In the AI age, there are a million tools to optimize email subjects, but none that can replicate an authentic relationship with your audience.

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EW: I love that you’re not a Luddite! Many people are doomsayers about AI but have never actually used it.

AH: We love the black and the white. I think that's where the conversation around AI has very much bifurcated as well. It's the best thing ever, or it's terrible. It's the downfall of civilization. What I'm advocating for is something that is more nuanced, and sometimes nuance doesn't sell because people want to get enraged about either the positive or the negative.

I know that this technology is here to stay. What does that mean? We need to use it in thoughtful ways that work for us based on who we want to become and based on our own identities — whether we identify as creatives, innovators, or people who just want to take care of our own mental health.

AI can be incredibly helpful, but we need to not forget that the human component is so important. The irony is that if you talk to the AI companies, they will champion this idea that ‘Make sure you keep the human in it,’ but they're frustratingly non-specific about how we actually do that.

EW: What does your view on AI and its limitations mean for your everyday writing practice?

AH: Every morning, before I doom scroll on my phone or before I fire up my laptop and start responding to emails and processing, I sit down just for 15 minutes, sometimes 10, sometimes five, and write something that struck me the day before. It can be an oddball thing that I observed. It can be something funny. It can be a conversation I had, a conversation I overheard.

Why do I do that? Because it does two things for me. It taps me into my life more tangibly. There's such a temptation when you move through your day to be staring at your phone. But I intentionally don't do that because I know I need to find a story that I can write down tomorrow morning. I have been doing this for about four years now, and it has plugged me into my daily life in a much more important way.

The second way that I preserve balance between analog intelligence and artificial intelligence is that whenever I sit down to write, whether it's a LinkedIn post or my fortnightly newsletter that comes out every other Sunday, I don't start with AI.

The AI companies will tell you, ‘The best thing about AI is that it speeds up the process.’ I don't think that's the value of AI, because that is getting in the way of our thinking. Over time, that can lead to what I call thoughtstipation, which is this sort of mental constipation caused by an over-reliance on AI tools. We're outsourcing our thinking, and our thinking is giving us our ability to reflect on what's going around us, to create, but also to be in touch with our own thoughts and ideas and our own selves.

That ability to trust yourself, and the ability to listen to your own thoughts and ideas before you invite AI into the process is such an unlock. It's the way that we maintain that human touch that even the AI companies will tell you that we need to maintain. I think it allows us to focus our attention and our curiosity and our connection with ourselves as creatives, but also with the world around us.

EW: When you do switch on the AI, what does that look like?

AH: Typically, I will write four drafts of everything that I publish or produce. That's true even if it's a LinkedIn post, which sounds like total overkill. But I'm a writer, and I love the feeling of words.

The first draft is pretty much always analog. I take a notebook and I will write out what I'm thinking about or what I want to write about. I'm not writing pages and pages; sometimes it just looks like a bullet list.

Then, I take that, and I fire up either Word or a Google Doc, and write a first draft, then let it sit for a little bit. There's something magical that happens when you let it sit overnight. It's like an avocado. It ripens on the counter. The next day, I come back to it, and I usually will go through it again, just myself.

Sometimes at that point, I will invite AI into the process. For example, if something is feeling a little fuzzy to me, I'll use AI as a sounding board, almost a second brain. I have a very good friend who has trained his AI to think like him, which I can see the value of. But for me, the value is getting input from somebody who doesn't think like me.

I'll spar with it a little bit and ask it to challenge me on some points, but honestly, sometimes I just need a little gaslighting. I know it's ridiculous, because it's a machine, but you know what it's like — you're working on a novel, a blog post, or a landing page, and you can feel so alone and so in your head. I've never had anybody in my life who is that patient with me, who will read what I wrote and go, “Yay!” Maybe my mom when I was a kid, but that was about it? We all need a little encouragement and gaslighting as creative people.

EW: What excites you, and what makes you scared about AI?

AH: If there's anything that AI has reminded us of, it’s how important writing is. Some people will use AI to barf out a landing page and call it good. But I also think that there's another segment of people who will suddenly realize, “Wow, words actually do matter, and we don't want to just use [AI] to create AI slop. Instead, we want to create something that feels special, that can only come from us.”

In some ways, AI is ushering in more respect for writing than ever before. I think because, ironically, AI can enable a slower, more intentional approach if we use it right.

What scares me about it is that writing is hard, and I'm just as lazy as the next person. I see the allure of firing up AI and offloading our brains.

EW: How do you see AI impacting marketing, and how do you see leaders reacting?

AH: It's harder and harder to get people and audiences to come to your website. So what does that mean? It means that the rise of brand is going to be paramount for all of us in marketing. We're already seeing that in a lot of different places. Creativity, brand, storytelling: all of those things are very much front and center for a lot of forward-thinking leaders right now.

There are a lot of different components coming into play here that will inform, ultimately, not just good writing, but storytelling and a stronger brand. That has to do with the kinds of emotional connections that you're making with your prospects and your customers. Where does that emotion come from? It comes from great writers.

EW: I think this connects to what you’ve said about the “from” line being so much more important than the subject line in an email.

AH: There are a million tools that can help you optimize that subject line. I could fire up AI right now and say, “Give me 20 great headlines or subject lines for this newsletter.” But there are no tools that can help you optimize the ‘from’ line, because that's all on you and your relationship with your audience or the recipient of your email.

It's not specific just to email. It actually relates to how we're showing up for our audiences and our customers across everything that we're doing. The more that we can form those connections with our customers, the more they will not just buy from us, but the more they'll be thinking about us.

There's some great research out of the LinkedIn B2B Institute that says that 95% of people are not in the market for you at any one time. In other words, only 5% of your possible addressable market is actively in market for you. Pair that with research out of Bain and Google that says that when we finally choose to buy, 90% of us will go with a very short list of whom we already know.

That means that you've got to be connecting with people emotionally, so that when they're ready to make a decision, they go, “Oh, you know who we should talk to? This company.”

I don't think you get into that short consideration set by constantly talking about yourself and pushing features instead, it's about showing up consistently in ways that will feel recognizable and connective to those you ultimately seek to serve or sell to.

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Kenn's corner

🌅 I’m struck by Ann’s decision to be analog at the start of the day. It points to a truth so deep that we fail to notice it. It now takes a deliberate effort to be analog when for those of us, d’un certain age, it used to take a deliberate act to go online. (Open a computer, fire up a modem, wait…)

💡What other aspects of human cognition has changed when technology or behaviors around the technology change? Obviously, our sleeep cycle is vastly different than most of history due to electric light. (We used to have two phases, now just one.) Perhaps the shift in the Middle Ages from communal reading out loud to private, silent reading? It enabled new ideas. But did we lose community? (Read more—aloud with others—here and here).

🌍 I’m just back from the UN’s “AI for Good Summit” in Geneva, where I found myself chatting with Nicholas Thompson, the CEO of The Atlantic. When I asked him, “What does journalism look like in the age of AI,” he immediately shot back: “Narrow it down: to the production of journalism? The reading of journalism? The journalism business market? The way you find your journalism?” His reply crystallized the profound range of changes taking place, which we’ll be exploring at CWO.

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Thank you for reading — your attention is precious! Until next week ☕️

How was AI used to produce this newsletter? Read next week’s email to find out: we’ll always disclose our AI use in the subsquent edition. Also, for those who care, there are two (intentional) typos in this missive—for your sentimental enjoyment!