You just wrote it yourself - he has an enormous desire to be praised, so much so that he completely fails to notice just how much he lacks a connection with literally anyone or anything (Michael is of course a comically over-emphasized example). This is the key to understanding the "clueless" or the "educated gentry" ladder, they are unhappy with being in "labor" but lack the balls/intelligence/true desire/luck/whatever else to be the "elite", so they come up with alternative scoring rules. Why do you think writing an op-ed in the NYT is so highly desired in that ladder? The other ladders don't dabble in praise, they either want their jobs to satisfy basic life needs (labour) or want ever-growing power with minimal regard to others opinion (elite), more specifically others opinion is only relevant insofar as it is a stepping stone on the path to more power.
Maybe your (and sibling's) comment along with mine illustrate two sides of the same coin. I think Michael is interested in status mostly as a path to connection. The dreams he talks about, if I remember correctly, center around having a family and a nice life, not prestige or power or winning. That's part of why I think the "Michael Scott" analogy is such an awkward fit for the middle ladder proposed in the article. My recollection of the series is that Michael is actually pretty satisfied with his status in society, but not his status relative to the people around him. If Michael dreams of writing an op-ed in the New York Times, it's because he hopes it will make Oscar like him or something.
