Ask Jade - October 2026: Spooky Legal Mistakes Vol. 2
October 1, 2026
October 2026: Spooky Legal Mistakes Vol. 2 – More Real Legal Horror Stories
It’s October. You know what that means: scary legal stories.
These stories are real. The names aren’t included, but the legal consequences certainly are.
Story One: The AI Hiring Tool
A business owner used an AI hiring tool to screen applicants.
No disclosure. No bias audit.
One rejected applicant filed a complaint with the Illinois Department of Human Rights. Under the new law, that’s legal exposure.
She didn’t even know the rule existed.
Story Two: The Brand She Didn’t Own
A consultant paid a designer to build her entire brand. Every invoice was paid on time.
But there was no intellectual property assignment agreement.
Two years later, a licensing deal fell apart because, legally, the designer still owned the work.
Paying for something does not mean you own it.
Story Three: The Trademark Filed Too Late
A wellness brand spent three years building her name and following.
She never filed a trademark.
Someone else did first.
She received a cease-and-desist and had to fight for her own brand.
Story Four: The Outdated Severance Agreement
A business owner used an old severance template. The employee signed it.
Months later, a claim was filed, and the confidentiality clause was unenforceable under updated Illinois law.
Old templates don’t account for new rules.
Story Five: The 50/50 Partnership
Two business partners opened a fitness center together.
They went in 50/50 and split the income and expenses 50/50. They used an online operating agreement.
One partner ended up doing all the work. The other was still entitled to 50% despite the lack of effort because the operating agreement didn’t address it.
Don’t Let This Be Your Story
None of these business owners were reckless.
They were busy.
And underprepared.
Don’t let this be your story.
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