Living on the margins is not something you put on a resume.
Most of the time it’s not considered an asset in any area of life. The only upside (“s/he knows a lot about life”) often ends up being a backhanded compliment, or an expression of pity.
The truth is that being an outsider is terribly lonely, even if you are good at switching between people and environments.
For example, one thing that gives me credibility in a workplace (a fascination with quick translation, and assessing complex ideas/tasks) makes for a difficult experience socially. I can talk all day about work and be fine, but I’m way too intense and think-y to feel comfortable in most social situations. Of course I’m fairly good at blending in, but that’s different from actually feeling like you belong somewhere.
Over time I’ve learned to embrace being strange, but there’s still plenty of friction. I went on a date a couple of months ago and the woman I had a beer with labeled me a “formal hippie” (whatever that is), and said I was too serious and a snob because I’d mentioned that I wanted to spend my time with people who were passionate about something in their lives.