Raising a teenager sounds scary. I think a part of the problem is that parents now are trying to guide their children just as their parents did with them. Not realizing that the world has changed and that the parenting approach should change according to what the world is now.
I think that is exactly what you are trying to do, so that's good.
It's not that scary, but sometimes I'm worried about the level of confidence of my child... but that is probably normal for all parents... And I remember that my parents didn't give too much sh*t about my stuff, and I survived... So, I suppose that he will also...
On the other side, I agree that times are different now than they were 20-30 years ago... and children have different things that trigger their emotions... So, it has to be handled in a different way...