From Lawyer to Island Caretaker

When people ask Alan Rilla, caretaker of Spectacle Island, how to get a job like his, he laughs and tells them, “You can’t.”  Alan, a former lawyer and corrections specialist, has been responsible for overseeing this Boston Harbor island for six years.  It’s a job he applied for, along with 200 other people, after reading an article about the open position in the Boston Globe.  For six months of the year he has the island more or less to himself.  During the other six months, he entertains 85,000 visitors from all over the world.  He  describes it as “the best job in the world,” and appears to be a very happy guy.

But let’s get back to the law part.  Alan grew up in a close-knit Italian neighborhood in the Berkshires.  An internship in the Public Defenders’ Office after college turned him on to the law, and he applied to law school.  Most people never left his neighborhood, so his going to law school was a big deal not only for his family, but also for his entire community.  After a few years with the District Attorney’s office, Alan switched to private practice and joined the most prestigious firm in his county.  One of his first clients became the most lucrative in the firm’s history, and Alan had a pretty comfortable life mostly serving that one client for several years.  When the client was acquired by a larger company, Alan decided not to follow the job out of state.

As he tells it, “When I was a Master of the Universe, and had moved into a big house, my father would come by and say, ‘You know what the problem is with this big house and all these toys you have?’ I’d say, “No, what’s the problem with all these things I worked so hard for?’ And he’d say, ‘They can’t love you back.’”

When his father got sick, Alan thought about that conversation and decided to downsize.  He spent the last two years of his father’s life caring for him, and then worked on projects he liked.  An opportunity to testify at the State House on reforms to the corrections system led to an opportunity to work with Sheriff Michael Nash, whom Alan describes as an “icon.”  Alan spent eight years working in the corrections system, developing juvenile justice programs that won multi-million dollar federal grants and became models for other states.

Alan’s corrections work ended in March 2005, when his attempt to calm down a disturbance at the jail led to some inmates throwing him off a second story balcony and breaking his neck. Nearly a year later and well into his recovery, he read that Globe article and applied for the caretaker job.   Alan’s not sure what he’ll do when his term on Spectacle Island ends in 2016, and that doesn’t bother him at all.

Readers, have you ever applied for a job that seemed totally unrelated to your prior work?  If so, why?  If not, why not?

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