The easiest way is this - just start.
There's no perfect way to start challenging the status quo. You either keep doing things the same way or you don't. But maybe that's not very helpful advice. Try this - ask "What would someone who challenges the status quo do in your position?"
Do some role playing and try to put yourself in someone else's shoes. The amazing thing is that pretending to be someone else can produce real changes in behavior.The video below will explain more on this subject.
So what would someone who wasn't afraid of challenging the status quo do? When you find the answer - try to do that.