Surviving the Shift - The AI blues

If you’ve been in marketing for a decade or two you’ve already survived big shifts: desktop to mobile-first, mass media to targeted advertising, outbound marketing to inbound marketing, etc.

Each shift shook up how you market, but AI is starting to change who can do the work, how fast it gets done, and what skills actually matter.

And this shift is dramatically faster. Faster in a way that makes you question whether your brain is still running the current version of the operating system. You get comfortable with a tool and, two days later, it feels like you’re explaining Myspace to a teenager.

This creates the illusion that everyone else is up to speed and you’re lagging behind.

Execution used to be the edge. If you could actually do the work -- write, design, build -- you stood out. Now “pretty good” is everywhere. It’s like decent coffee: once rare, now unavoidable.

And that’s a strange thing to watch if you spent years honing your craft. There’s no ceremony when a skill loses leverage. Experience still matters, just less. You’re not automatically ahead … you’re just earlier, trying to update your skills without discarding the parts that still work (taste, judgment and deciding what’s worth doing in the first place).

All this logically leads to compression: fewer people doing more … value clustering around the people who can aim all this capability in the right direction.

Which leaves us in an odd spot today. Still expected to perform while the ground shifts under our feet like a treadmill that occasionally changes speed just to keep things interesting.

Maybe I’m overthinking it. Wouldn’t be the first time.

Or maybe this is just what it feels like to go through a major shift while still being expected to hit deadlines and sound like you know what you’re doing.

Probably both.

The only thing I’m reasonably confident about is that the advantage is moving. Away from grinding, toward choosing. Away from doing, toward deciding.

Would you pay $4,500 for one of my books?

 In 2022, one of my books was turned into the artwork below by Mike Saijo. 

First he deconstructed my book "The Words and Wisdom of Will Rogers". Then, using copy machine toner, put a portrait of Will Rogers over the pages.

The title of the piece is Portrait of Will Rogers, 2022 and it's for sale for $4,500.

 

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Thanks to Patrick Combs. If he hadn't brought this to my attention on LinkedIn, I might never have known of its existence.

Creative Hoarding

 A lot of being creative isn’t about divine lightning bolts or some muse whispering in your ear. 

It’s about noticing things other people skim past. That weird crack in the sidewalk that looks like a map of Italy. The way someone in line at the grocery store hums just off-key enough to make it sound intentional. The shadow on the wall that looks like a hand reaching for something it can’t quite touch.

Most folks let those things slide by. They don’t mean anything. They’re background noise. But if you’re wired a little differently, you snag them. You tuck them away. You build a kind of junk drawer in your head full of odd shapes, overheard phrases, smells that made your eyes water.

And then, when you’re staring at the blank page, or the canvas, or the meeting room whiteboard, that junk drawer cracks open. The thing you thought was useless? That becomes the spark. Creativity isn’t conjuring something out of thin air. It’s remembering that you already collected the raw material, and having the guts to mix it together in a way that feels new.

So yeah, maybe it’s less magic and more hoarding. Except instead of stacks of newspapers and old toasters, it’s the little moments no one else bothered to keep.

AI would never smoke a cigarette with you.

Great headline, huh?

On March 22, 2026, this letter, handwritten by Shane Hegde (CEO & Co-Founder of Air), was published in the New York Times. 

It’s his argument that after nearly a decade working with 250,000+ creatives is AI can generate, resize and optimize 1,000 brand variations in seconds … but it can't decide what's worth making. That part still requires a person with judgment and taste.

Read the full text of the message below.

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For more thoughts on AI and the creative process:

Don't Let AI Kill Your Analog Intelligence

Why Every Copywriter & Content Writer Needs an AI Usage Policy 

Generative AI: TO BE (a tool) OR NOT TO BE (a tool)?

The Adolescence of Technology 

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The full 3/22 message:

AI would never smoke a cigarette with you.

In life we long for simple stories, and these days the headlines deliver:

“AI will replace you.”

Each week, there’s a new AI startup that claims its product will make creatives obsolete. Photographers, videographers, graphic designers, illustrators: highly specialized individuals who have spent decades turning crazy ideas into something everyone can visualize.

If anyone should be buying into this narrative, it’s me.

In 2018 my friend Tyler and I started a tech company called Air. We told investors that every company was becoming a media company. And, if true, every company would need an engine to scale their creative work.

Over the last eight years we’ve raised $70M to build this engine.

Today, nearly all of our product resources have shifted to build AI centric features. Our best engineers spend most days evaluating AI written code. But after nearly a decade working with over 250,000 creatives, I’ve built a rather rigid, shockingly unorthodox belief:

AI will never replace creative work.

Creative work starves for originality.

A person decides where the story begins, which frame feels right, or whether the work should even continue to exist. The best pieces of content require doubt and indecision.

The difference between a creative and a machine is this obsessive anxiety.

Artificial intelligence is trained to find patterns and recommend the most common answer. The machine aims for objectivity. It can generate images, resize assets, translate languages, and optimize performance.

It’s always correct, but it’s not always right.

AI would never tell you to slow down.

It would never argue that further introspection might change the work.

You won’t find AI smoking a cigarette at 9AM on Howard and Lafayette. Only a beautifully inefficient mind would believe cancerous reflection could improve its work.

Over the coming months every company you know will be reshaped into an unrecognizable form. Smaller teams. More machines.

But the organizations that survive will require human beings who are willing to take risks. These people understand that letting what they love kill them is a uniquely human trait. Their illogical texture for life is something machines can’t compute.

At Air, the value of our product is shaped by a creative’s direction.

We use AI to help them scale their work, but deciding when, where, and how to deploy this technology remains defiantly human.

The best creative work is always an argument.

I’m around if you want to share yours.

 - Shane   s@air.inc  419.902.7392