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Is there a word or short phrase for this? I have a cell in the back of my head insisting that it's "[something] pain".

The person who feels this way tries to wear their outcast status as a badge of honor, without letting other people realize that they are trying to do so. They are quietly trying to get themselves compared with those great geniuses of history who just wanted to fit in but, because of their genius, could not.

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You want to highlight this poseur's objectionable affectation? We've got a lot of words for inauthenticity.

How contemptuous do you want to be?

To say he's an aspiring outcast suggests, to me, that the harm is relatively minor.

To say he's a professional outcast underscores the artifice of his behavior with a little more irony.

  • I'm starting to think that perhaps there's no great answer to this question but this answer comes pretty close. – Aurast Sep 15 '15 at 17:14
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I think that in the context you are describing masochist , with the following connotation, may fit:

  • (In general use) the enjoyment of what appears to be painful or tiresome: isn’t there some masochism involved in taking on this kind of project?

(ODO)

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Perhaps martyrish or or martyrly? Also, masochistic, because of your use of the word "pleasure."

If pleasure isn't a necessary component, then perhaps contrarian, egoistic, egotistical, self-conceited, vainglorious, or self-important.

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If you're looking for a word to describe someone that is pretentious and countercultural, I think Bohemian would fit well. It tends to be used more for artists, though.

Maverick is similar and can be used more generally.

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Try pariah. It actually means "outcast", but when used sarcastically means someone who has affected this status.

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