With so many contexts functioning in self-reinforcing ways, I'm wondering how it's ever possible to develop a new context?
There are often temporary contexts which serve as entries into these robust, self-perpetuating contexts that appear to defy change. Rather than simply join into a current context, there are phases of initiation to make the transition successfully.
Do those transitions have to be painful like a fraternity hazing, getting tagged as a newbie or being assigned to a special group of inept recruits?
Initiations sometimes begin uncomfortably in order to shake up the preconceptions, break the clinging to the past and disrupt any over-confidence of those in process. Once that purpose is accomplished, transitions are orienting and challenging. The process helps people realize they can do things they've never done before. They discover new abilities to recognize, understand or respond to situations that they could not have foreseen in themselves. They acquire new ways to feel confident enough to take more risks, test their limits and explore unknowns.
Does everyone succeed that goes through a well designed initiation?
No, that's not the intention. It's meant to be a test of individual commitment and endurance. Those that fall out during the process we're kidding themselves, doing it to impress others or trying to be someone they're not. Initiations are crap detectors that work really well. Those that get through it respect the ordeal and each other for what's been revealed in each of them.
What's the most overlook concern in creating contexts for initiation into other contexts?
Timing issues. Herding everyone through the transition at the same time defeats the purpose. Individuals are getting tested before they are ready to face it without making excuses. The initiation generates false evidence about who has got the right stuff and who cannot hack it. When each individual comes through a transition when the time is right, each can be challenged by the obstacles and confident in the outcome. This intermediary context has the right effect.