In my defense of labels, I claimed that, “Will’s implicit label is “label-avoidism.”  Adam Ozimek at Modeled Behavior explains the unique intellectual dangers of this label:

[T]o define oneself as, for example, “of no party or clique”, as Andrew
Sullivan does, creates in others a social expectation of holding
beliefs that defy parties and cliques. You may not be expected to take
particular and easily predictable positions on every issue as you would
if you had a politically well-defined label like, say, paleolibertarian,
Christian conservative, or pro labor democrat.  But you are expected to
regularly take positions that are idiosyncratic.

Take Will for example. He is one of my favorite writers and I think
he has a great talent for peering deeply into an issue. But nowadays I
expect Will’s self-description as stridently not-a-libertarian who still
steadfastly holds some libertarian positions to mean he will be boldly
rejecting libertarian positions somewhat regularly, and embracing them
other times. Will’s label as a label-less individual is perhaps even
more central to my expectations of him than ever, since this has become
an important issue to him that he wishes to persuade us on. “Look at
me”, Will seems to be shouting sometimes, “I am no longer beholden to
libertarianism!”. I don’t begrudge him his new found freedom, and am
glad he feels unburdened of a bias, but it is a label he is wearing

Ozimek continues:

Perhaps Will’s rejection of a label, or I should say his embracing of
the label “label-less”, is the most effective way for him to minimize
his biases. For me, I think I feel the most pressure or bias from my
“idiosyncratic” label, and my “neoliberal” and “libertarian” labels
help counter that by aligning social expectations of my beliefs to what I
approximately consider to be the truth, and so regularly believe. But
“idiosyncratic” isn’t a political ideology, it’s an adjective. And try
as we might we cannot label ourselves as “adjectiveless” or be
“adjectiveless” people and writers.

If I were Will, I’d spend less time preaching against labels and more time trying to publicly bet overconfident labelists.  And I’d take great joy in goading, “Since you say you know, and I say I don’t know, you should at least give me 2:1 odds.”