Why your AI is like the movie, “50 First Dates”

(Formerly The AI-Powered Business Advisor)

_{Issue #7 — February 17, 2026}

There's a movie (you've probably seen it) where Drew Barrymore wakes up every morning and doesn't remember the day before.

Her boyfriend, played by Adam Sandler, has to re-introduce himself. Every. Single. Day. He shows up, explains who he is, reminds her of everything they've built together... and by the next morning, it's all gone. He's a stranger again. She has no memory of the life they're building. It's a romantic comedy called 50 First Dates, and when it came out in 2004, everybody laughed.

Here's what that has to do with you.

If you've been using AI to help build your consulting business, there's a decent chance you're living in that movie right now.

You open a fresh chat, type in a request, get something generic back, tweak it, close the window... and the next day you do the whole thing over again. Your AI has amnesia. And you're Adam Sandler, showing up every morning with flowers, hoping today will be different.

I hear it on almost every group call I run with my clients.

Smart people. Experienced professionals. Twenty, thirty years in their industries. They know AI is powerful. They've read the articles, watched the videos, maybe even paid for a course or two. And when they sit down to actually use it... they get frustrated. The output sounds like it was written by a college intern who Googled your industry five minutes ago.

So they either keep fighting with it, spending more time editing the output than it would've taken to just write the thing themselves. Or they give up and decide AI isn't for people like them.

Both conclusions are wrong.

The problem isn't the technology. The problem is how you're using it. And the fix is simpler than you think.

Here's what I've learned after months of building inside Claude every single day. Writing curriculum, developing frameworks, creating client deliverables, drafting newsletter copy, analyzing call transcripts. Hundreds of hours of real work, not tinkering.

AI is not a search engine. It's a colleague. And you have to treat it like one.

Think about it this way. If you walked up to a stranger on the street and said "write me a sales page," you'd get something useless. They don't know your business, your clients, your voice, or what makes your approach different. But if you sat down with a trusted colleague who had read your positioning statement, understood your ideal client's frustrations, and knew what made you different from every other consultant in your space... that colleague would hand you something sharp, specific, and worth using.

That's the difference between opening a blank chat and working inside a system.

Let me tell you what actually changed things for me.

I was updating a module in my Launchpad program. I've been refining this curriculum for months now, and I was deep into a session with Claude... restructuring a lesson, tightening the script, rebuilding the slides. About halfway through, Claude just... stopped. Ran out of gas. Couldn't finish. I got a message that essentially said "I can't complete this."

I was furious. I'd spent an hour getting to that point, and now I had half a lesson and a dead conversation.

But here's the part that surprised me. Instead of starting over, I opened a brand new conversation and said something like, "Listen. You're killing me, Smalls. You keep dying in the middle of the work. Why is that happening, and how do we fix it?"

And Claude went back through those old conversations, analyzed what went wrong, and essentially said: "You're asking me to do too much in one session. I have enough capacity to build the script and structure, or the slides. Not both. Let's split the work into two processes."

That conversation changed everything about how I use AI.

Not because of the specific fix. But because of what it revealed. I had been treating AI like a magic box. Put a request in, get a finished product out. And when the magic box failed, I blamed the box.

What I needed was a system. Not a better prompt. A system.

So here's what I built, and it's what I now teach my clients to build.

One home base. A single master project where all your business-related AI work happens. Not scattered chats across different tools. One place where the AI knows who you are, who you serve, and how you work. Every conversation inside that project can read your core documents. It's like giving your colleague a permanent briefing folder.

Think of it this way. Your project has context files that sit there permanently. Your positioning statement. Your ideal client avatar. Your voice and style guidelines. Every single time you start a new working session, your AI already knows the answers to the questions that matter most. It doesn't have to ask, and you don't have to explain.

That's how you cure the amnesia.

But here's the thing... the briefing folder only works if you keep it clean. Four to six documents is the sweet spot. More than that and you start diluting the signal. Your AI is like that goalkeeper one of my clients described on a call last week. A seven-year-old who can put his knee on the ground or open his arms, but if you ask him to do both at the same time while yelling at the striker... he freezes. Too much context overwhelms the system just like it overwhelms a person.

So you keep it lean. The right context, not all the context.

Then you work in task-specific sessions. One conversation, one deliverable. Writing a LinkedIn post is one session. Drafting an outreach message is another. Reviewing a call transcript is another. You don't try to do everything in one marathon conversation, because the AI loses focus the same way you would if someone kept changing the subject in a meeting.

And when you produce something great... when a session gives you an output that really nails your voice, your positioning, your client's pain... you capture what worked. You ask: "What did we do differently this time?" And you fold that lesson back into your system so you don't have to re-teach it next week.

The system gets smarter every time you use it. That's the opposite of amnesia. That's compound interest.

The consultants I work with who build this system and actually use it every day... they stop fighting with AI and start collaborating with it. Their outputs sound like them, not like a template. Their positioning shows up in everything they produce without having to re-explain it. And the time they used to spend starting from scratch every Monday morning gets redirected toward the work that actually generates revenue.

It's not about being an AI expert. It's about being organized enough to let AI be useful.

Near the end of the movie, Lucy says something that stops you cold. "I don't know who you are, Henry... but I dream about you almost every night." Even without her memory, something stuck. Something deeper than what the conscious mind could hold.

That's what the right system does. It gives your AI the one thing it can't create for itself. Continuity.

Drew Barrymore's character couldn't help her amnesia. It was a medical condition. Your AI's amnesia is a design choice. And you can fix it this week.

Dale

Want to dive deeper? Check out these related articles:

👉  The Prosperous Consultant | Issue #6
👉  The Prosperous Consultant | Issue #5

You might also find these interesting:

🔎  The Trust Reckoning: The Shadow Side of Force 1
🔎  Client Value Journey: Stage 1 – Aware

P.S.: When you're ready, here are more ways I can help you...