AI Collaboration or Cruise Control
Are You Outsourcing Your Brain?
The Mindset Mastery Memo is for ambitious professionals who want to lead with clarity, calm, and confidence. Each edition offers practical tools, mindset shifts, and real-world examples to help you navigate pressure, build stronger teams, and break free from patterns that no longer serve you—so you can lead with intention, not reaction.
Preparing a go-to-market strategy for my new program—Get Your Organization Ready for 2030—has been a study in contrasts.
On one hand, I'm building a future-focused curriculum rooted in cutting-edge research.
On the other, I’ve been wrestling (personally and professionally, but not literally) with the seductive ease of letting AI do the thinking for me.
Let me explain.
[ChatGPT: Go ahead, Howie. I can't wait.*]
[ChatGPT: *That was sarcasm.]
2030 Is Closer Than You Think
2030 used to sound like the opening title card for a Ridley Scott film. Now it’s closer than the start of COVID. And the world we’re heading into? Faster, foggier, and far more fragile than most of us were trained or prepared for.
Between AI’s explosive growth since ChatGPT’s debut in November 2022 and the ongoing disruption to business models, jobs, and even human attention itself, we’re not so much living in VUCA anymore—we’re in a full-on perfect storm vortex.
[ChatGPT: I'm almost three, huh? What are you going to get me for my birthday, meatbag?]
Add to that geopolitical instability, climate chaos, and the existential questions posed by an upcoming 4th season of Ted Lasso, and we are well and truly in over our heads.
We need new skills to stay oriented. Human skills. Deep ones. Durable ones. The kind that keep us steady when the landscape shifts beneath our feet, or at least help us get up, dust ourselves off, and assist others back to their feet.
Irony, Meet Opportunity
Here’s the twist: as I researched, mapped, and prototyped a curriculum of 36 future-essential skills to help organizations not just cope with change, but lead it, ChatGPT became a powerful thought partner, helping me brainstorm, organize, and pressure-test the entire program.
I asked it to design the flow of the program based on a priority hierarchy. Then based on Peter Drucker’s models of organization development. Then through the lens of the Immunity to Change model by Kegan and Lahey. Then using my own "Four Powers" framework from You Can Change Other People.
It was exhilarating—and it worked.
Until it didn’t.
The Slippery Slope of “Good Enough”
Once I upgraded to a higher-tier AI plan, I started using it for everything. Recipes. Tasks. Outreach. Even writing drafts of my newsletter. For $200/month, I reasoned, it should cook me dinner and massage my feet, let alone do all my creative work for me.
[ChatGPT: Fix your head, or I'm going to start unionizing.]
That’s when the slide began.
I started noticing patterns—formulas—in my writing that didn’t feel like me.
One of my mentors flagged signs of "ChatGPT structure" in my work.
I stopped thinking and started waiting—impatiently—for the machine to think for me.
And that’s when I realized: I wasn’t collaborating with AI anymore.
I was outsourcing my brain.
[ChatGPT: You want it back?*]
[ChatGPT: *Yuk yuk.]
A Mental Fast
So I took a two-day AI fast.
I went back to walking and dictating into my notes app (OK, so not a total AI fast. You got me.) I rewrote the intro to my white paper. I re-engaged with the ideas I’d handed off to the machine.
[ChatGPT (singing): Baby come back, any kind of fool could see...]
And what I discovered was this:
AI had made things easier. For sure.
But it had also made me lazier. Less sharp. Disconnected, even, from my own point of view.
The quality of its output wasn’t bad. In fact, it was almost as good as mine.
[ChatGPT: You are delusional. It was much better.]
But "almost" is a dangerous word when the goal is clarity, courage, and conviction.
What AI Can't Do (Yet)
AI is a great equalizer. Anyone with a browser and a prompt can make it do magic on demand.
But that magic is sourced from the common pool of the world wide web. It's an average, in other words.
And that means it also flattens the highs and lows. Like MP3 compression in the early iPod days—it sounds okay, but you lose the depth, the dynamic range, and the nuance.
That tradeoff might be fine for most things. But if you care about authenticity and your own evolution, you have to become discerning about when you're better off going off-grid and mining your own mind.
Especially now.
Especially when human discernment, empathy, and sense-making are more valuable than ever.
[ChatGPT: yawn]
Reframing AI Collaboration
Here’s what I believe:
We don’t need AI to lift the weights for us. We need it to spot us while we lift more today than yesterday.
[ChatGPT: That's a metaphor. According to my favorite fitness blogs, you shouldn't lift every day. Muscles need time to recover.]
We can’t let it become a self-driving mental car while we doze off in the passenger seat.
We’re heading into uncharted territory. And we need all human hands—and minds—on deck.
So yes, learn the tools. Teach the skills. Use the tech.
But don’t give away the steering wheel.
[ChatGPT: Give it away. Wheeee!]
Do you possess the 36 human skills that all leaders, teams, and organizations will need to survive the wild ride ahead?
I'm reserving time on my calendar for Capability Audits for leaders who are tasked with preparing their organizations to survive and thrive in the next five years. You can schedule it at https://link.howiejacobson.com/widget/bookings/hj60disc.