Benjamin B. Bolger has been to Harvard and Stanford and Yale. He has been to Columbia and Dartmouth and Oxford, and Cambridge, Brandeis and Brown. Over all, Bolger has 14 advanced degrees, plus an associate’s and a bachelor’s. Some of Bolger’s degrees took many years to complete, such as a doctorate from the Harvard Graduate School of Design. Others have required rather less commitment: low-residency M.F.A.s from Ashland University and the University of Tampa, for example.

Some produced microscopically specific research, like Bolger’s Harvard dissertation, “Deliberative Democratic Design: Participants’ Perception of Strategy Used for Deliberative Public Participation and the Types of Participant Satisfaction Generated From Deliberative Public Participation in the Design Process.” Others have been more of a grab bag, such as a 2004 master’s from Dartmouth, for which Bolger studied Iranian sociology and the poetry of Robert Frost.

He has degrees in international development, creative nonfiction and education. He has studied “conflict and coexistence” under Mari Fitzduff, the Irish policymaker who mediated during the Troubles, and American architecture under the eminent historian Gwendolyn Wright. He is currently working, remotely, toward a master’s in writing for performance from Cambridge.

Bolger is a broad man, with lank, whitish, chin-length hair and a dignified profile, like a figure from an antique coin. One of his favorite places is Walden Pond — he met his wife there, on one of his early-morning constitutionals — and as he expounds upon learning and nature, it is easy to imagine him back in Thoreau’s time, with all the other polymathic gentlemen, perhaps by lamplight, stroking their old-timey facial hair, considering propositions about a wide range of topics, advancing theories of the life well lived.

And there’s something almost anachronistically earnest, even romantic, about the reason he gives for spending the past 30-odd years pursuing college degrees. “I love learning,” he told me over lunch last year, without even a touch of irony. I had been pestering him for the better part of two days, from every angle I could imagine, to offer some deeper explanation for his life as a perpetual student. Every time I tried, and failed, I felt irredeemably 21st-century, like an extra in a historical production who has forgotten to remove his Apple Watch.