Thirty years is a long stretch with the same stylist. It's possible your stylist thinks he knows you so well, he isn't convinced that you'd be happy with a drastically different look. Or, as happened with my stylist of 20 years, he might have fallen into the rut of executing the same cuts over and over to his clients.
If your cut isn't making you feel attractive when you catch a glimpse of yourself in a mirror, it might be time to shake things up a bit. When I hit my early sixties, I left my long-time stylist and took my "classic" bob into a salon filled with youngsters. I told the young stylist she could do whatever she wanted to my hair as long as (1) she didn't color it and (2) didn't give me an "old lady" cut.
I can't say that first cut and stylist were a resounding success, but it was the kickstart I needed. Over the next two years, I played with different lengths, cuts, products (gels, straighteners, thickeners, pastes--you name it, this formerly wash and wear senior tried it) and, yes, stylists. Most of the cuts were OK and a few were eye-openers (some great and some not-so-good), until I finally settled on my current style--a fringeless, inverted, side-parted, wavy bob that is very short in the back and long on the top and sides. With product, I can make my hair look dramatic or sedate--sleek, spikey, or curly.
Hair grows back, so I figure it's not a bad way to shake off those growing older doldrums. You are a very pretty woman in your current cut, but, if that cut doesn't make you feel good about yourself, then it's time to do something. Maybe you'll go back to your tried-and-true cut after a fling with something new, but, even if you do, you'll see yourself in a different light. Plus, it was fun viewing myself through the eyes of young stylists who wanted to make an older woman look current and stylish--even to the point where I seriously started thinking of putting a purple streak in my greying locks!