Pushing back against 20 years of stagnation

I managed to finish that career plan that had been giving me trouble. Right before sending it on to my manager, I removed those couple of paragraphs where I proposed that I lead a group that is contrarian by design. That was my surrender to staying within the safety limits of my organization. I felt that it was particularly pertinent to do that at this phase as my manager is one of the most conventional people in the organization. He cautioned me against taking on a moderately risky project (where most of the risk was really in the visibility of the project, a failure in this case would have been more costly than a failure on a similar by lower profile project). I'll need his support going forward. I didn't see the value in threatening that support for no real benefit.

I'll need to take some other steps to firm up his support tomorrow. He sent me an email asking about the status of one of my (very minor) projects. He's scared that we might get noticed. Rapidly responding to unreasonable demands is often viewed as a desirable trait in my group. Let other people set the priorities. i know that his fears are unfounded because I actually asked about the project timing. We're nowhere close to  being on the critical path for this project. He doesn't know that because he's relying on second hand information that is pretty incomplete.

I'm trying out this plan where I force myself to notice my assumptions. Asking about the project timing is one way that I have broken out of some common group think (just rely on the information handed to you from the person making the request without asking any follow-up questions). My manager's been doing this kind of thing for something like 20 years. Who am I to challenge all that experience. But he's probably been doing his job pretty much the same way for 20 something years. He found a way that gets the job done and he hasn't done anything to change that approach in all of those years. He has 20 years experience doing his job one way. He never notices his assumptions. He doesn't notice that's he's not seeing the whole picture.