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📼 Small Talk

Most Gen Xers Are Using AI All Wrong

Here's why I think that's a mistake (and how to fix it).

Jonathan Small's avatar
Jonathan Small
Jul 30, 2025
∙ Paid

I made this mistake once. I’m not gonna make it again.

Back in the late 90s, I was working in magazines when this thing called the internet came along. At first, we didn’t take it seriously. The web team? That was the JV squad stuck on the 9th floor. The ones not good enough to be in print.

That aged about as well as an open can of LaCroix.

Had I had the foresight to understand what the web was becoming and actually spent time learning, I might not have been so blindsided when print magazines imploded.

I’m fine now. But it was a humbling learning curve.

So when I saw a recent Pew study showing that only 23% of Gen Xers have ever used AI, I felt that same sick feeling in my stomach.

Another major technology shift that could change everything. And Gen Xers are going to roll their eyes and cop a ’tude.

I get it. Yet another thing we have to learn.

Enough already.

We lived through the shift from vinyl to cassettes to CDs to DATs to DVDs to Spotify.

From typewriters to desktops to laptops to iPads to iPhones to… chip implants?

We have to do this again? Fuck me.


The way I see it, Gen X’s relationship to technology falls into three buckets:

The Analogs

These are the people still walking around with iPhone 7s and a sense of pride about it. They write checks. They don’t do social media. They are very upset about AI’s impact on the environment.

The Hybrids

They’ve adapted, reluctantly. They’re on Slack, but they hate it. They’ve used ChatGPT once or twice but weren’t impressed. They say things like, “It’s stealing from real artists.” They’re quick to give up when the results feel generic.

The Early Adopters

These are the ones testing the tools. Not because they like it, but because they don’t want to be left behind. They’re poking under the hood of ChatGPT or Claude, trying to figure out how this stuff fits into their work.

I used to be a Hybrid. But on AI Tip, I’m not just adopting it, I’m taking it home, feeding it snacks, going outside and playing catch with that shit.

Why? Because I don’t see a future where this technology isn’t a major part of our lives. And I can either snicker at it and hope it goes away, or learn to work with it to make my life bearable.

Someone once said:

“AI won’t replace you. A person using AI will.”

Thanks to the wise choice I made in my early 20s to be a creative, I still have a good 15 to 20 years of work life ahead of me with no pension or safety net. And I’m not about to let some Millennial call me a dinosaur because I don’t know how to write a prompt.

Who’s with me?


Here’s my offer to you. I teach a three-hour class for newbies on how to use AI effectively. Nothing fancy. Nothing that will leave you annoyed and wanting to throw a sneaker at the computer screen.

I give you the basics to make AI your own, almost free intern who is lightning fast, eager to please, and never complains about work-life balance.

But who’s also as dull as a robot unless you tell it exactly what you want.

What You’ll Learn:

  • How to prompt AI, so it helps you out.

  • The single most important shift in mindset that makes AI useful for creatives

  • The 5 biggest mistakes people make when using ChatGPT (and how to avoid them)

  • Why writing with AI is not “cheating” — and how to keep your voice intact

  • The difference between bad prompts and smart instructions

  • How to brainstorm, structure, and edit using AI like an almost free intern

  • Real-world examples of using AI in writing, teaching, and content creation

  • A simple, repeatable framework that makes AI work for you — not the other way around

My video walks you through how I use AI in my creative work — researching, editing, brainstorming, and emails.

I created this class because I wanted to take one and couldn’t find it anywhere else.

If you’re a paid subscriber, you’ll see the full video below.

If not, this might be a great time to upgrade.

$5 a month.

That’s less than a movie ticket…in 1985.

👇 Unlock it below.

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