The Man Who Couldn’t Stop Going to College

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.

“I believe that people are like trees,” he said. “I hope I am a sequoia. I want to grow for as long as possible and reach toward the highest level of the sky.”

Against a backdrop of pervasive cynicism about the nature of higher education, it is tempting to dismiss a figure like Bolger as the wacky byproduct of an empty system. Then again, Bolger has run himself through that system, over and over and over again; it continues to take him in, and he continues to return to it for more. In fact, there is reportedly only one person in the United States with more college degrees than Bolger, and the vast majority of those came from universities within the state of Michigan (no disrespect to the Broncos, Eagles or Lakers). Because Bolger is just 48, and Michael Nicholson, of Kalamazoo, is 83, Bolger could surpass him, according to back-of-envelope math, as soon as 2054. In other words, Bolger is on a plausible track to becoming the country’s single most credentialed individual — at which point, perhaps, he could rest.

A proposition: No one more fully embodies the nature of elite American higher education today, in all its contradictions, than a man who has spent so much time being molded by it, following its incentives and internalizing its values. But what are those values, exactly? Of course, there are the oft-cited, traditional virtues of spending several years set apart from the rest of the world, reading and thinking. You know: the chance to expand your mind, challenge your preconceptions and cultivate a passion for learning. In this vision, eager minds are called to great institutions to reach their intellectual potential, and we know these institutions can perform this function simply because they are called Harvard and Yale.

That may be the way a prestigious education works for some, but probably not most. A 2023 survey of Harvard seniors found that 41 percent — 41 percent! — were entering careers in consulting or finance. The same percentage were graduating to a starting salary of at least $110,000, more than double the national median. Last year, the most popular majors at Stanford were economics and computer science. The ultimate value of college for many is the credential, guaranteeing a starting spot many rungs up the ladder of worldly success: Nothing you learn at an elite university is as important as the line on your C.V. that you’ve paid hundreds of thousands of dollars to type. And if you were feeling cynical, you could argue that the time you spend applying to college will affect the rest of your life more than anything in particular that happens while you’re there.

“It is only when we forget our learning that we begin to know,” Thoreau observed, famously, after his experiment in simple living. (Though, rich of Thoreau: he went to Harvard.) In a much different, much opposed way — one involving central heat — Bolger has spent the past three decades conducting his own half-mad American experiment in education. He has drunk deeper at the well of the university than almost anyone else. What does he know?

In 1978, Bolger was 2, riding in a Buick Riviera in Durand, Mich., when the car was hit by a drunken driver. He was basically fine, but his parents were seriously injured, and his mother, Loretta, spent months in the hospital, ending up with a metal plate in one of her legs. She had to leave her job as a schoolteacher. Bolger’s parents’ marriage disintegrated. His mother could be difficult, and his father, an engineer and patent lawyer who represented himself during the nasty divorce, was emotionally abusive. Bolger and his mother began splitting time between their comfortable home near Flint and his grandfather’s ramshackle farm in Grand Haven, which was so drafty they sometimes curled up by the wood-burning furnace.

Bolger’s mother spent much of her money in the ensuing custody battle, and her stress was worsened by her son’s severe dyslexia. In third grade, when Bolger still couldn’t read, his teachers said he wouldn’t graduate from high school. Recognizing that her boy was bright, just different, his mother resolved to home-school him — though “home” is perhaps not the right word: The two spent endless hours driving, to science museums, to the elite Cranbrook Academy of Art outside Detroit for drawing lessons, even to the Smithsonian’s National Air and Space Museum in Washington. At night she read to him: epic works of literature like “War and Peace” but also choose-your-own-adventure books and “Star Wars” novelizations.

The pair passed days in the library at Michigan State University, watched campus speakers in the evening and ate free at the receptions afterward. Sometimes, rather than drive the two hours back to Grand Haven, they would sleep in his mother’s pickup truck somewhere in East Lansing and do the same thing the next day.

“I saw the university as a home,” Bolger says.

Bolger wore secondhand clothes and had only one close friend his age. Yet he felt he was on a grand adventure. At 11, he began taking classes at Muskegon Community College. Still reading below a third-grade level, Bolger needed his mother to read his assigned texts out loud; he dictated papers back to her. At 16, he enrolled at the University of Michigan, moving with her into an off-campus apartment. He recorded his lectures so he could listen to them at home; his mother still read to him. Majoring in sociology, he graduated with a 4.0. He was 19.

Next, Bolger decided to apply to law school because of his admiration for the consumer advocate Ralph Nader, whose crusade for safer vehicles resonated with Bolger after his accident as a toddler. He was administered the LSAT questions orally and was admitted to Harvard, Stanford and Yale.

At Yale Law School, Bolger floundered. The method Bolger and his mother had devised to cover reading assignments fell apart: There was so much of it, and it was so detailed. Bolger’s age made him a kind of celebrity on campus, and not in a good way. Classmates found him bombastic and insecure. “He was 19, and I suppose he acted it,” says Andrea Roth, now a law professor at the University of California, Berkeley, who was friendly with Bolger at the time. Bolger failed two classes his first semester and dropped out.

To attend Yale, Bolger had deferred a master’s program in sociology at Oxford, so in 1996, he moved to England. There, he thrived under the tutorial system, which reminded him of home-schooling. Then he just kept going, embarking on an odyssey through the Anglosphere’s great universities, during which he improved his reading but still leaned on his mother. From Oxford, he went to Cambridge, where he took a master’s in sociology and politics. After three years in Britain, Bolger moved to California, where he studied for a master’s in interdisciplinary education from Stanford, and then quickly to New York, where he got another master’s, in the politics of education, as well as a master’s degree in real estate development, both from Columbia, in a single academic year. He found time in the summers to work toward a master’s of arts in liberal studies from Dartmouth. He slept four hours a night.

And he kept on stacking degrees: a master’s in design studies with a real estate concentration from Harvard; a master’s in international development from Brown; the “coexistence and conflict” master’s from Brandeis; a master’s from Skidmore, where he studied “positive psychology”; all culminating in his doctorate in design, focused on urban planning and real estate, from Harvard in 2007. More recently, Bolger has done a trio of M.F.A.s in which he said he learned how to write “in a compelling narrative way,” “how to communicate stories in a compelling and gripping way” and how to delve deep into “the different genres of writing.” He has worked as an adjunct or visiting professor at more than a dozen colleges to fund his endless pursuit of learning.

One thing Bolger has not seemed to learn over the years is to introspect. Why has he driven himself to this extent — to place himself over and over in the kinds of impractical programs young adults enter to wait out a bad economy or delay the onset of adulthood à la National Lampoon’s Van Wilder? Many of us love learning, too, but we don’t do what Bolger has done; we listen to history podcasts on our commutes or pick our way through long books in the minutes before sleep. Despite all his degrees, Bolger has never sought a tenure-track job — only a few of his degrees would even qualify him for such a position — and he has never really specialized.

Unless you consider putting together a killer college application a form of expertise, which both the market and Bolger do.

Over the past 35 years, acceptance rates to the United States’ most elite universities have shrunk to about 6 percent from nearly 30 percent. Students, frightened by those numbers, are applying to more colleges than ever and making these numbers more frightening in the process. At the same time, overtaxed counselors don’t have the time to help as much as applicants and parents want. The rise of so-called holistic admissions, which look beyond grades and test scores, has also contributed to a sense that there is a “secret sauce” to getting into exclusive colleges and turbocharged demand for people who can demystify it.

After he got his doctorate in 2007, Bolger became a full-time private college-admissions consultant. “No other consultant has Dr. Bolger’s record of success,” reads his website — a claim that is difficult to verify, yet one that many people seem to believe. Four years with Bolger runs at least $100,000. (In the world of elite college coaching, this isn’t exceptional: A five-year plan from the New York firm Ivy Coach costs as much as $1.5 million.) Over the past 15 years, he has developed a coaching style he compares with that of Bill Belichick, Mr. Miyagi and Yoda.

On a humid morning late last summer, Bolger saw clients in an upstairs room at the ‘Quin House, a modish Back Bay members’ club in an ornate Commonwealth Avenue limestone. He has a home office in Cambridge but prefers to work as much as he can out of the private clubs to which he belongs, including the staid Union Club, opposite Boston Common, and the Harvard Club, which feels loosey-goosey by comparison.

That day he was meeting with Anjali Anand, a sunny then-17-year-old who was in Boston for the summer to do research at Boston University; and Vivian Chen, also 17 at the time, also sunny, also in Boston to study on B.U.’s campus. Anjali and Vivian faced a brutal fact: For young strivers of the American upper middle class, credentials and a can-do attitude are no longer sufficient for entry into the top tiers of the U.S. News and World Report college rankings. These accomplishments must be arranged into stories so compelling that they stand out from the many other compelling stories of the teenagers clamoring for admission.

And so Bolger devoted the meetings to teaching self-narrativization, particularly as it relates to the all-important essay component of the application. He encouraged the high-achieving Anjali to be vulnerable. “Someone who is 100 percent confident with no hesitations isn’t as compelling,” he said. “This is why there are more movies made about Batman than Superman.” With Vivian, he tried to connect her desire to become a dentist to a deeper narrative thread.

“Why the mouth and teeth?” Bolger asked.

Bolger said his business has enabled him to mix with “the 1 percent crowd.” In addition to his condo on Cambridge’s tony Memorial Drive, Bolger owns a house in Virginia and his family farm in Michigan. He has an Amex invite-only Centurion card. In 2016, he donated more than $50,000 to support Hillary Clinton’s presidential campaign, for which he received a special Jeff Koons print; more recently, he has donated more than $2,500 to the presidential campaign of Robert F. Kennedy Jr. He loves to attend celebrity talks: Bruce Springsteen, George Clooney, Joe Montana — anyone who, in his mind, defines a category.

Bolger carries about 25 clients at a time, but his most important pupil is his 9-year-old daughter, Benjamina, whom he home-schools and considers his best friend. Bolger models his daughter’s education after his own: hands-on, interactive, wide-ranging, lots of time in the car. (Bolger’s son, Blitze, is also being home-schooled, but he’s only 4, so there’s less to do.) His wife, Anil, who helps him recruit clients, is happy to let him oversee the liberal-arts component of their children’s education while she handles math and Chinese. Bolger is trying to be less intense than his mother, to emphasize the development of his daughter’s emotional intelligence. But one of his main pedagogical devices is still the field trip.

On another bright morning last summer, Bolger took Benjamina to Concord’s North Bridge, for a holistic lesson but also a lesson in holism. He was joined there by his friend Dan Sullivan, a fellow polymath, who has also collected a staggering number of credentials. (The 42 entries under the “Experience” section of his LinkedIn page include Ambassador at the Parliament of the World’s Religions and Colonel at the Honorable Order of Kentucky Colonels.) Bolger had planned a discussion around bridges and diplomacy. But he believes the world is “nonlinear,” and his habits of speech reflect this. There were digressions into history, comparative government, union organizing, car safety, Robert McNamara, the strength of triangles, the cryogenic preservation of corpses.

A composed, precocious and sweet girl, Benjamina followed her tutors across the bridge and to the bronze statue of a Minute Man, inscribed with Emerson’s “Concord Hymn.” There the three of them stood in contemplation, looking a little like a child star and her security detail.

“Was that shot actually heard around the world?” Bolger asked.

“I don’t think so,” Benjamina replied.

“Yes,” Bolger said. “So this is an example of a metaphor.”

​​After stopping in Concord for a bite, Bolger and Benjamina drove the two miles to Walden Pond. The pair sat on a wooden plank above the beach on the pond’s east side. Except for the sounds of teenagers flirting and retirees shifting in folding chairs, it was quiet. Bolger explained Thoreau, the woods, the essential facts.

“I don’t know if you find this inspirational or not,” Bolger said. “I have the ability to pretend no one is here.”

Benjamina made a skeptical noise.

“I guess I could do it for a week,” Bolger said. “A year just seems too long.”

Thoreau’s experiment made him one of the most important men in American history. Bolger’s experiment has, well, not done that. Instead, it has done something even weirder. To spend any time around Bolger is to feel that you have been enrolled in a bespoke, man-shaped university, one capable of astonishing interdisciplinary leaps, and it basically all hangs together — the way that any mix of freshman electives at a top university might complement one another, might rhyme, produce its own sort of harmony. It is unclear what, exactly, is at the center. But there are gravitational forces at work nonetheless.

Also, Bolger’s experiment has made him a wildly compelling father to a daughter who, it must be said, is exceptional. She is fluent in two languages, she is nice, she is funny, and last summer she performed Fritz Kreisler’s thorny violin piece “Sicilienne and Rigaudon” at Carnegie Hall with grace, élan and even wit. At the very least, Benjamina has on her hands the material for one of the all-time great college-admissions essays.

The day after their colonial field trip, father and daughter had lunch at the Harvard Club. Surrounded by dark wood and wine refrigerators, they ordered off the Veritas menu: Bolger had a B.L.T., and Benjamina had a hamburger with fries. The meat arrived on a bun with an “H” grill mark, for Harvard.

“Do you think the burger looks better because it has an ‘H’ on it?” Bolger asked.

Benjamina didn’t hesitate. “Yes!”

Source for illustration at the top: Photographs from the Bolger family; Arnold Gold/The New Haven Register, via Associated Press.

David Hilliard is an artist and educator from Boston. He creates narrative multipaneled photographs, often based on his life or the lives of people around him.