Denise was sitting on my patio in New York this summer, a perfectly ripe cherry in one hand and a bit of dark chocolate in the other, when we started talking about the very first time we worked together.
We were laughing about a moment that changed everything for her — and how wild it is that she almost didn’t mention it.
She’d tossed this little story into our original half-day strategy session like it was no big deal…
“When I was 8 years old, I skipped our family Disney vacation because it interfered with the Jerry Lewis Carnival I’d been planning for a year.”
And then how I wouldn’t let that juicy bit slip by…
What the what?! What drives that? Where else does this show up? Say more!!
That’s when it hit her: she wasn’t just someone who “likes to get things right.”
She was a striver. A tinkerer. A relentless refiner.
And while that served her in some places, it was suffocating her in others.
That realization — in our first 30 minutes together — cracked her entire strategic innovation session wide open. It shaped every decision we made after that, in all the right ways.
ChatGPT would never know to ask those questions.
You probably wouldn’t casually think to share that story in a prompt.
And even if you did, AI wouldn’t know what to do with it.
Because AI isn’t curious. It’s confident.
Which is exactly how it ends up handing you some dude’s 2022 funnel strategy— the one with the yacht emoji subject lines and the “crush your launch” energy— dressed up in your tone, like it belongs in your business.
That’s the difference between a chat window and a true thought partner.
Everyone’s Using AI. That’s Not the Problem.
It’s helpful. No argument there.
It’ll brainstorm ideas. Polish a paragraph. Even write a pretty decent launch email while you refill your coffee.
The problem isn’t using AI.
It’s what we’re starting to use it for.
The Problem? Treating AI Like Your Business Coach.
It’s not just helping you brainstorm webinar titles or rewrite your About page anymore.
You’re asking it what to build. How to scale. What to charge. Whether your 6-month mastermind should be a 12-month mastermind — with a VIP tier and retreat in The Algarve.
And then — because it sounds smart and has a confident tone — you treat the answer like gospel.
But AI doesn’t know you. It doesn’t know what lights you up or burns you out. It doesn’t hear the hesitation in your voice when you say, “It’s fine, it still works.”
It doesn’t catch the quiet ugh under your breath when you describe your client load. It doesn’t know that you’ve been trying to pivot quietly without scaring off your best clients. Or that you’re secretly craving more whitespace, more substance, more something — but you can’t quite name it yet.
AI can’t read the room. It can only read your prompt.
And unless that prompt includes the full backstory, the buried dreams, the part you’re afraid to say out loud — you’re going to get a smart-sounding plan for someone else’s business.
Probably dressed up in your tone. With your favorite emojis. And the same generic advice it just fed a thousand other business owners yesterday.
Helpful? Sure.
Strategic? Not even close.
It Feels Helpful. That’s the Trap.
The illusion is seductive.
AI gives you speed. Structure. Certainty.
But you don’t need another plan that looks good on the screen. You need something that feels like yours.
That 6-figure mastermind it just spit out? Might be exactly what you shouldn’t build.
AI will help you scale the thing that’s already wearing you out — and call it strategy.
BTW, the average AI tool?
It’s regurgitating ‘strategy’ pulled from dusty internet archives.
Meaning: That hot tip it just gave you? Probably recycled from a bro-marketer’s launch plan that was already stale when BeReal was still trending.
Neatly rephrased. Dressed up in your tone and matching emojis. But still outdated — and not designed for you.
AI Doesn’t Know When Something’s Off. You Do.
It doesn’t notice the hesitation in your voice when you describe your current offer. Or the flat tone when you say, “It’s fine, it still works.”
It doesn’t ask what you’re tired of. Or what you’re trying to talk yourself into one more time.
AI can’t see the nuance, the energy leak, or the half-truth you’re hiding behind smart copy and solid revenue.
That stuff only comes out in real conversation. When someone’s paying attention — to what you’re saying, how you’re saying it, and what you’re avoiding.
You’re Not Asking the Right Questions. And That’s Normal.
A few months ago, my friend Nika and I found out we’d both tried that “What are my blind spots as a business owner?” prompt we heard about on a podcast.
As she started reading her results out loud — I nearly choked on my Werther’s. (Okay, Grandpa. But still.)
“You could play bigger, you spend too much time perfecting, you’re not behind but….”
Um. Same. Word for word.
We’d both been walking around thinking, Wow, this thing really gets me — when actually, we’d just been handed the same generic self-help salad dressed in our own brand tone.
That’s the trap: AI makes bland advice sound bespoke.
So you treat it like insight — and keep making business decisions based on templates that have been repackaged more times than a launch coach’s favorite swipe file.
Meanwhile, you’re sitting there thinking:
- Maybe I’ll try a mastermind model.
- Maybe I’ll turn this into a retreat.
- Maybe I just need to raise my prices.
AI nods enthusiastically and helps you plan the whole thing.
Slides, email sequence, 6-month calendar — done by lunch.
But here’s the thing: You’re not designing something new. You’re just remixing the same tune with a different beat.
Because unless you shift the bigger questions — about what you actually want to build, why it matters, and what no longer earns its keep in your Stripe account or sanity — you’ll keep recycling the same stuck story.
AI won’t stop you.
It’ll just wrap your latest detour in your brand voice and call it a breakthrough.
This Isn’t About Smarter Prompts. It’s About Smarter Insight.
That’s why you need a strategic thought partner.
Someone who doesn’t feed you canned prompts and leave you there. Who doesn’t regurgitate what worked for someone else’s business model in 2021.
Who asks the questions you didn’t even know were there — and then notices what opens up when you finally answer them.
If you don’t want AI to replace you, don’t build a business that sounds like it already has.
Because the second your work blends in, you become just another voice in the blind spot buffet.
And that’s not why you started this. You didn’t pour your soul into this business — sweat it, obsess over it, sacrifice for it — just to wind up with a strategy that sounds like it came from a chatbot trained on bro’ marketers in Patagonia vests.
You built it to be distinct. Undeniably yours.
So why would you hand over your life’s work to a tool that will never understand the depth of your story — or care how it ends?
