On a sunny morning in early March, Tom Slocum, a 57-year-old ski bum in Telluride, Colorado, walked up Tomboy Road, a popular hiking route that winds above the north side of town. An avid athlete and skier, Slocum moved to Telluride in 1984, a couple of years after graduating college. Like many ski town residents, he’d worked several jobs over the years, in hotels, mostly. Over the last five or so years, he’d grown frustrated with his life—presumably by the fact the he was a middle-aged man living in a small caretaker’s unit behind a multimillion dollar home, struggling to get by in one of the country’s most idyllic ski towns.

As he’d grown into middle age, his body had begun to break down, and he wasn’t able to enjoy all of the activities that h...

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