The AI Advice Trap: Why Context Matters

@mitch.social

“Mitch, that’s the third time you told me not to incorporate.”

I sighed. “But you’re not listening to what I’m saying.”

The potential client shook her head. “I’m comfortable doing what ChatGPT is recommending, but I appreciate your help.”

“I’m not sure what AI is telling you, but there’s a lot more to consider than just setting up a business entity.”

She smirked. “Hey Mitch, thanks but no thanks. AI is going to replace all you lawyers.”

Six months later, my phone rang.

“Hey Mitch, what do I do now?”

I leaned back in my chair. “What do you mean?”

She let out a long breath. “All I wanted to do was protect my personal assets from business liabilities. Now my new lawyer and accountant are telling me I have to file new tax returns, business licenses, get new separate business insurance, enter into new lease and purchase agreements as a corporation, and about a dozen other things I never thought of. The time and money with all of this is killing me.”

I nodded. “I told you earlier that based on your situation, you didn’t need to incorporate right away. A simple business liability insurance plan would’ve covered your concerns without adding unnecessary legal and financial burdens. For you, incorporation was overkill.”

“But ChatGPT told me it was the best way to start and run my business.”

“I get it,” I said. “But everyone’s situation is different. Did you ask about the steps and responsibilities you’d need to handle every year after incorporating?”

Silence. Then, “No. That never crossed my mind. The multiple tax returns, state filing fees… it’s crazy. Can you help me unwind my corporation so I don’t have to deal with all of this?”

I chuckled. “Did you ask ChatGPT what your options are now?”

She sighed. “I did. It told me to comply with all legal requirements or—” she hesitated “—contact an experienced lawyer to help me shut it down and get my life back.”

“Well then,” I said, “you’ve made the right call. Let’s get things fixed.”


This happened last week. (Details tweaked for privacy, but you get the gist.)

AI is amazing. Truly.

I’m a fan. A big one.

But context? Context is everything.

AI is only as good as the inputs you give it. Feed it incomplete info, and you’ll get advice that’s… well, let’s just say, not quite right for you.

So, if you’re leaning on AI for guidance, do it wisely. Give it the full picture. The details. The nuance. Because the best advice? It’s not just smart—it’s tailored to you.

Best,

Mitch

mitch.social
Mitch Jackson ⚖️

@mitch.social

30+ years of fighting for equality—trusted lawyer, fearless advocate. I share political commentary on breaking news 👉 https://mitch-jackson.com/substack (it's free)

🔗 https://linktr.ee/mitchjackson

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