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

ECONOMIST: Company bosses

He's the insider-outsider who represents the synthesis of the much admired elegant skill-based Spanish soccer culture and the hardscrabble, passionate English lower-league ethos.

WSJ: Hot Managers Moyes, Martinez Look to Future

We admired him as a fearless outsider and a cunning insider, a pal of J.

NPR: Roth Rewrites History with a 'Plot Against America'

First of all, did you consider yourself and insider or an outsider?

NPR: Book Examines Covering the Race Beat

Mr. Greenberg is an outsider by virtue of not being a psychiatrist but an insider by virtue of serving as one of the investigators involved in field-testing some proposed diagnoses on actual patients.

WSJ: Book Review: DSM-5 | The Book of Woe | Saving Normal

The outsider, not knowing what the insider knew, would make a lot of mistakes and chase down a lot of rabbit holes.

NEWYORKER: In the Air

Obama's selection of a reliable insider and budget expert for the critical Treasury job and not a prominent outsider with broad business or Wall Street experience is yet another sign that he intends to actively pursue his economic-policy objectives in his second term, including raising more tax revenues from the wealthy than agreed to in the fiscal-cliff deal.

NPR: THE RESET: Obama Picks Familiar Faces For 2nd Term

The price that the outsider pays for being so heedless of custom is, of course, the disapproval of the insider.

NEWYORKER: How David Beats Goliath

Sure, there continued to be some mystifying close-mindedness one wonders if a certain ESPN NBA Insider will soon become an NBA outsider but Collins's announcement didn't provoke the type of meltdown it had long and ludicrously been predicted to provoke.

WSJ: Jason Collins's Slam Dunk