Ann Handley's Power Lunch: Meet Her 5 Guests

About this article:
Our Field Notes series shares in-the-trenches, first-person perspectives from the frontlines of marketing, creativity, and leadership. These reflections are shaped by lived experience and challenge the status quo — offering fresh ways of thinking about the work.

An Imagined Gathering on Attention, Craft, and the Quiet Work That Endures

We’re in Lake Como, seated around a table at a restaurant I can’t reveal the name of—it’s that special.  It’s me and five others: people and ideas shaping how I’m thinking lately about how good work actually gets made, how meaning accumulates, and why attention and focus have become the scarcest resources we have. 

At the center of the table is A.I.—no, not that AI, but the more important Analog Intelligence: the ability to think clearly, creatively, and humanly in a world optimized for speed, automation, and scale. It’s a reminder that thinking is a full-body sport—it needs our hands and hearts as well as our heads.  

Analog Intelligence sharpens judgment, she tells us. As the soup is served, she points out that preserving it is a competitive advantage. Writer Annie Dillard is all in on this idea. She tells a story about a well-known writer who is collared by a student on a college campus. “Do you think I could be a writer?” the student asks this famous writer. “Well,” the writer replies, “I don’t know… do you like sentences?” The student is stunned. Sentences? The writer goes on to describe a painter they once knew.

When asked how he became a painter, the painter said: “I liked the smell of the paint.” I suspect many of us became communicators, writers, and marketers because we like sentences. We, too, like the smell of the paint. 

I encourage Annie to tell this story because for us writers and communicators now, it's easy to write with an A.I. companion hovering—like a happy-headed golden retriever dropping tennis balls at your feet under the guise of helping you do what you used to do on your own. What you used to need to do on your own. 

So you don't use AI, you say. So walk without the retriever trotting alongside. Okay. But you still know it's there. 

I feel a weird grief in that. Something personal and important has been interrupted—or turned into something we now have to protect. 

 If I sound like I'm being precious about writing, I am. 

 It doesn't mean AI doesn't have value. I’m not a hater.  

 But it does mean we're in a new era where part of our job isn't just to write—but to decide when not to invite the golden retriever to trot alongside us. Because writing is thinking: We need to give ourselves time to think. And because: 

 We like the smell of the paint. 

Annie nods. She doesn’t say more; she’s already moved on to the oysters. 

Next to Annie, Nike and Formula 1 newsletters are sharing a chair, because I couldn’t choose between them. In a world obsessed with speed and scale, two brands practically defined by speed and scale chose one of the slowest moves in the book: a newsletter. Not just a newsletter either… but one focused on storytelling. 

What I love most is the newsletter part (big fan of newsletters), but also the restraint. Both launched last year without splashy promotion, influencer activations, or a single press release. They are less interested (at this point) in scale than they are in building something worth showing up for before trying to grow it.  
 
That’s a brave move, I tell them, pressed as they are awkwardly together on a single dining chair. It takes actual meatballs to stand in a room and say, We’re not here to rack up numbers; we’re here to nurture something real. Nike and F1 just ordered the polpette. I couldn’t have written that moment any better. 

George Saunders laughs at the wordplay, then explains to Annie Dillard that polpette is the Italian word for meatballs. He’s here to laugh at my jokes and also for his radical commitment to revision, humility, and clarity—and for the generosity with which he shares his craft, with students and through his own Substack newsletter.  
 
Saunders talks endlessly about how long it takes to get things right, and how often our first clever impulse is wrong. We need more of that energy in marketing: permission to stay longer with an idea, to trust that resonance comes from care, not cleverness.  

And because I’m feeling bold, I’m absolutely shooting my shot with Taylor Swift. Not as a pop icon, but as a study in sustained creative mastery and generous leadership.  
 
Taylor understands craft, audience, and reinvention at a level most brands only pretend to. Her analog instincts are sharp in this digital world: storytelling, pattern recognition, emotional specificity, long arcs. She writes thank-you notes to her staff and seals them with wax!  
 
She’s shaped how I think about building bodies of work—not moments—and about treating an audience as collaborators, not targets.  

This is a group that together celebrates quality over velocity. Resonance over reach. Craft that compounds. Which is why they’re here: I’m less interested in what performs well this week and more curious about what still matters five years from now. 

There’s lively tension at the table: Taylor challenges my skepticism about scale. Nike and F1 challenge my instinct to slow everything down. Analog Intelligence hands me a Blackwing pencil, while Annie Dillard (who is both a painter as well as a writer) wonders if I’ve ever painted a first draft? George glances at her, intrigued.  

I thought we’d get together to talk about marketing. But during this lunch I’m thinking increasingly about leadership. Of our programs, of ourselves.  
 
Right now, the real leadership skill is less about strategic direction-setting and more about attention stewardship—deciding what deserves care, time, and protection.  

We all need to get sharper at creating conditions where good work can happen, and braver about resisting the false urgency that erodes it. I’m pushing against the idea that moving fast is the only way, or that relevance requires constant, always-on visibility. 

Also, we just got the tiramisu. The gang gets ready to tuck in.