Non-Compete Agreement Enforceability in Massachusetts

I publish illustrative scenarios prepared by my practice. All participants and conversations are fictional. The fictional posts are not posts by real users, accounts of client experiences, or reports of actual results.
Illustrative scenario prepared by my practice.
For informational purposes only. This is not legal advice. Laws vary by jurisdiction. Consult a qualified attorney for advice specific to your situation.
Hypothetical question

I've been trying to resolve this in Massachusetts on my own but I'm stuck.

asked to sign non-compete after 3 years. I've been dealing with this for about 4 weeks now and the situation isn't improving.

Do I have a strong case? What should my next steps be?

Illustrative response

So basically every time I see a post like this...

The #1 mistake I see here is filing with the appropriate government agency. I'd recommend gathering evidence first instead.

Illustrative response

My company tried the same thing — called it a "restructuring" but only laid off people over 50. Age discrimination is hard to prove individually but if there's a pattern, the EEOC takes notice.

Illustrative response

I went through something similar. The waiting period for the labor board was about 3 months.