One way to resolve the outsider-insider dilemma is to look for an outsider with inside knowledge of the business.

ECONOMIST: Company bosses

While in grad school, I continued to work on all sides of the fashion industry, always feeling like an outsider doing inside observational work, and with a hyper-awareness of the power of aesthetic manipulation and body consciousness.

FORBES: The "Thinking Person's Stylist": NYU's Anna Akbari

He is an outsider on the inside.

NEWYORKER: The Hot Spotters