{beacon} Workweek Newsletter
Callie and Daniel Reece write in this week and I touch on doing things for the first time
Adam Ryan
May 17th, 2026
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Hey all,

Thanks to the New York crew for having lunch this week with me. It was fun to catch up and see Alex continue to be the best dressed guy around.

Callie and Daniel Reece are our guest writers this week. Thought provoking and relatable, I love both pieces.

With that, let’s dive into it.


WHAT'S TOP OF MIND

1) Why Everyone Feels Burnt Out on AI Already

By: Daniel Reece

It might be hard to believe, but convos around AI are still in their early stages.

Yet, so many people are already saying they’re tired of talking about it!

To be fair, I don't blame them whatsoever. I've been one of those people too, since I've written so many articles about it at this point, but I recently came to a realization...

The current AI inputs are what is causing this general feeling.

What I mean is, people are all rotating the same recycled conversations:

“Will it replace jobs?”

“How do I prompt better?”

“Is it ethical?”

Super important, sure, but these are still surface-level and you've probably already had 100 discussions like this.

That repetitive surface-level thinking leads to boring conversations, pretty much every time now. 🫩

Here’s what I think happening:

AI is nothing more than a multiplier. It doesn’t create interesting ideas so much as it amplifies the ones you already have.

So if your inputs are boring, your outputs will be too.

This is where creativity comes in (arguably my fav topic). Right now, most people are wildly out of mental shape in this department...but that's a different rant and explanation.

💡 Fun fact: A popular NASA-backed study shows ~98% of kids test at “genius-level” creativity.

By adulthood, that drops to ~2% because people stop using it.

Creativity is a muscle that most people haven’t trained in years, then AI shows up...

…And instead of rebuilding that muscle, we try to outsource it.

This is where I believe that everything starts to feel the same.

The people who are doing interesting things with AI right now?

The way I see it, they’re literally just more curious humans. :thinking_face:

They’re learning random, fun shit and following weird interests.

They're letting their brain connect dots that don’t “make sense” on paper.

And that’s the unlock that being intentional about creativity gives you.

Your creative hobbies shape the way you think about everything, including AI.

So if the conversation feels boring, train your inputs.

Do stuff that satisfies the creativity your inner child had so much of.

Because AI will only ever be as interesting as the person using it.

2) Large Language Models

By: Callie Myers

I've loved reading everyone's takes on AI in Top of Mind these last few weeks (btw who knew we had so many great creators amongst our operators at WW!). The theme across these that's stuck with me most is how many of you have learned to steer AI with your own taste, judgment, and vision.

That points to something I believe pretty strongly, which is that in the future, there will be two types of people. There will be those who use AI to think for them, and those who use AI to learn. Passive acceptance vs. cognitive direction.

Like many here, I've experienced the benefits of automations and efficiencies from AI. When I “vibe-coded” my first data dashboard, I was pumped, and also amazed by how far AI had come in the last 12 months alone.

But as a deep generalist, none of my interactions with AI energize me as much as when I use AI to learn.

There's a tense conversation happening, especially in higher ed, about how AI can undermine learning, and it absolutely can if you use it that way. But I've also experienced firsthand how it can supercharge learning when you lean on your curiosity.

I'm the kind of person who, when I can't sleep, will start a Wikipedia rabbit hole on how the members of one of my favorite bands MUNA met and end up two hours deep on the Satanic Panic. As technology has evolved, I've used all of the tools to feed my curiosity: regular search engines, Wikipedia, TikTok, YouTube, etc. AI didn't create that habit, but LLMs are the best tool I've ever had to pull on a curiosity thread endlessly. I've spent Focus Wednesdays at work going deep with Claude on B2B go-to-market pricing and positioning, asking the “why” questions and the “where did this start” questions over and over until I've really internalized the concepts. I've spent car rides home through Austin traffic using Claude voice to learn about geopolitics and weather patterns.

I've learned so much in so much less time. The combination of having access to all of this information and being able to ask follow up questions in natural language lets me go deeper than I ever could before. It really is democratizing access to knowledge in a way that hasn’t been reinvented since the advent of the internet.

And the part that actually makes me emotional when I think about it is that everything AI knows was created by humans. Every business framework, every insight, every weird, beautiful, horrifying, gross thing it can teach me, humans did that. And what I learn then helps me create new things with my own human point of view. Using AI to learn is using AI to access more of what other humans have already figured out. That feels very different from using AI to skip the figuring out entirely.

The one non-negotiable when learning this way is to be skeptical. Check sources and push back. AI sounds more confident than Wikipedia ever did, so if you're already practiced at fact checking people IRL, you're trained for this.

Point is, as cognitive offloading gets easier and more seductive, I think it matters that we notice which mode we're in when we reach for AI. Are we outsourcing the thinking and the creating, the part that makes us human, or are we learning and taking something with us to supercharge our own thinking and creating?

Rule of thumb: stay curious, stay skeptical, and stay human.

3) Doing things for the first time

This past week I was at The Newsletter Conference with a bunch content platforms, publisher, and large creators. As with most conferences, I found myself baffled how far behind most people are when it comes to realizing where the puck is moving.

The insights and daily conversations we have at Workweek are months, and in some cases, years ahead of others.

At times, that is a huge advantage. Other times, it makes life a lot harder.

If anyone is doing something for the first time it's incredibly hard. First newsletter sent, first event, first sales call, etc. Even if you have a great blueprint or training, the second time you do something is SO much easier than the first time.

It's to a whole new level if that thing you're doing has no blueprint or training.

That was something I was thinking about this week. Most of the industry talks in the word subscribers. It's the common language. But it's also the lowest common denometer. And as our values state, we should avoid it. Why? Because it's lazy. It's misleading. And leads to worse outcomes.

As we start to build out our own creator tooling, it's really important that we emphasize WHO is subscribed and not how many.

There are ways we can do this like what % of banks are subscribed to FTT or what % of the Fortune 500 subscribe to TMM or what % of health systems read Hospitalogy. That's an easy thing to understand and, ultimately, is what drives any business forward.

But it's not language people use. It's not what they're used to. We will have to spend a lot of energy to ensure we educate the market, including advertisers, what this means and why it matters.

It's a fun challenge and one we are leading in terms of narrative. It also is why we're set up to win in the long run. But from here to there doing something for the first time is hard!


QUESTION OF THE WEEK

What's something you've done in your career for the first time that you found the 2nd or 3rd time SO much easier than the first time?


Thanks for giving it a read. Make it a great one.

Adam

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