Thinking about why people need an expert, this is manifest in Rabbinic authority or medical authority.
Two answers I heard are, either people want the truth and believe an expert has more knowledge (in particular in a specialized field), or people want to avoid responsibility.
Given these answers I am not sure how to move forward, how to help people take control of their own life. Clearly there is a hesitancy on both counts, but you can't tell someone to just take control, you know more than you think, or take responsibility its good for you. Rather I believe there is something underlying the need for expert opinion.
I think the need for expert opinion, external authority, emanates from a need for feedback, supervised learning, sensory deprivation being painful people look for external feedback.
It should be possible to teach people to appreciate unsupervised learning. Measuring the model not the target result. Measure the information representation not the maximization of a function.
