Over the years, whether as a General Counsel, public company executive, or “lawyer friend” on speed dial, I’ve been asked the same types of questions on repeat:

• What should I think about before signing this contract?

• When do I actually need a lawyer, and when can I handle it myself?

• How do I protect my IP without slowing things down?

The answers aren’t always simple, but they don’t have to be overwhelming either.

That’s why I’ve decided to share some clear, approachable ways to think about your legal and business strategy.

As market uncertainty continues to swirl and potential layoffs loom across industries, I’ve seen a surge in calls from friends and colleagues facing job instability. Whether it’s an unexpected termination, a looming demotion, or questions about severance, it’s clear that many are navigating these waters for the first time and often, without a map.

As margins get tighter and legal budgets come under the microscope, one question keeps coming up from founders, operators, and fellow executives:

“When do I really need to hire a lawyer?”

This week on my “lawyer friend” series where I tackle real legal scenarios I get from friends and clients, I’m diving into a deceptively simple document: the Non-Disclosure Agreement (NDA).

If you’re an investor, entrepreneur, freelancer, or work with intellectual property (aka: most people), NDAs are likely a routine part of your professional life. But here’s the problem: most people don’t actually read them.

Thinking about jumping into freelance, consulting or fractional work?

You’ve got the skills. You’ve got the clients. Now make sure you have the legal foundation to protect yourself and your business.

One of the most common questions I’ve been getting lately:
“Can I use a contract form from ChatGPT or online?”

Short answer: Sort of, but proceed with caution.

Between our social media habits and the rise of AI, people are waking up to the risks of sharing their lives, ideas, and images online. Whether you're a creator, founder, freelancer, or just someone who posts family updates to Instagram, your personal brand is now public facing. And that means your digital footprint, i.e. photos, voice, likeness, and original work is at risk of being misused, remixed, and monetized by others.

Here’s the good news: with a little bit of awareness and a few diligent habits, you can significantly reduce your exposure and take better control of your online presence.