I’d say the biggest obstacle is that a requisition for someone at your level is just really hard to get. It’s hard to convince people that we need an expensive gray beard. Without a requisition at your level some companies have a policy that they won’t talk to you because they don’t want to leave you with a bad experience (sounds like bs but this is true). The view isn’t entirely just financial. People at your level…
I'm often challenging my leaders because I believe they work for me, e.g. their job is to make my life easy. I usually get away with it simply because I've been here long enough to know how projects usually unfold.
As our workforce gets younger and younger (we don't generally hire graybeards either) I start wondering how I fit in - I don't want to ever become a manager so I guess I have to fake it with the skinny jeans!