When James E. Ryan (Law '92), the University of Virginia’s next president, served on the law faculty here, the school’s third-years paid him their highest tribute. They chose him to give the charge to the graduating class. He spoke about time and happiness, organizing the secret to a life well-lived into five habits: make time, take time, steal time, don’t waste time, and cherish your time.

You can hear echoes of those themes in a speech Ryan delivered nine years later, his now-famous 2016 commencement address at the Harvard Graduate School of Education, where he remains dean through the academic year. With that same ability for distilling complexity, he offered five essential questions to ask in life, plus a bonus question at the end, to achieve true happiness.

While the law school charge garnered Ryan the plaudits of his listeners, the ed school address got him that and more than 10 million online views. His enumeration of the questions came in the last seven minutes, which made for a wildly popular video clip. Ryan then turned the speech into a book—the acknowledgments say it took some prompting—and it promptly became a New York Times self-help best-seller, taking its title from essential question No. 1: Wait, what?

The choice of phrase goes to the essential Ryan, the way he’s able to offer profound and serious insight without taking himself too seriously. Most of the examples in his speeches and in his book come from his own life and often at his own expense.

On the importance of asking the right question to get the right answer, he tells of how he tried to meet his future wife at a law school party. Instead of asking her for her name, he loses his nerve and introduces himself to her dance partner. Then he tries to cover by flattering the guy about his class participation. “All I can say is, please don’t judge me,” he tells the commencement audience. His point: Don’t ask “Are you Norman?” when the truth you seek is, “I’m Katie.”

“He is wickedly funny,” says UVA Law Dean Risa L. Goluboff, Ryan’s former colleague and a good friend. “But it’s not a mean funny. It’s a generous funny.”

Ryan was introduced as the next president of UVA in September. Dan Addison

Funny isn’t funny without good timing, and Ryan’s is impeccable. Just a month after the violent rallies that turned Charlottesville into a hashtag, and less than a month before UVA would begin celebrating the turn of its next century, Ryan stepped out of the shadows of the Rotunda’s South Portico and into the morning sun of Sept. 15 to greet the public and accept his appointment as the University’s ninth president.

Ryan’s return to Grounds—his official start date is Oct. 1, 2018—caps a nationwide search to replace current University President Teresa A. Sullivan, who formally announced Jan. 20 her plan to step down next summer. His name arose early in the search process.

That came as no surprise to Drew Gilpin Faust, the president of Harvard University, who placed a winning bet on Ryan four years ago as the unconventional choice to run the country’s top-ranked education school. “As soon as I heard that Terry Sullivan was stepping down,” she says, “I thought, ‘they’re going to come after Jim.’”

It stood to reason. Ryan, 51, checked a lot of boxes contained in the job description. He matched a preference for someone with UVA ties; he graduated first in his class at Virginia Law in 1992 and returned six years later to spend 15 years of increasing responsibility, accomplishment and popularity on the law faculty.

The position description made sure to warn all comers of the rapidly compounding challenges of higher education. Ryan could write books on the subject, and has on related topics, including his well-reviewed Five Miles Away, a World Apart, using a stark contrast in Richmond-area public schools to illustrate an analysis of the disparities in American education. As someone who has devoted his career to social justice and educational opportunity, Ryan also possesses the credentials and credibility to move UVA forward on matters of race and affordability.

And, in the quest for a charismatic leader who can articulate a vision, UVA has found someone who doesn’t claim to have all the answers but can ask some pretty engaging questions. As Frank M. “Rusty” Conner III (Col ’78, Law ’81), the rector of the Board of Visitors who co-chaired the search, told the Cavalier Daily, “We were looking for … two characteristics. One, go find the person with the biggest mind and go find the person with the biggest heart. And that’s what we did.”

Ryan is set to begin his UVA presidency in October 2018. Dan Addison

The central theme in Ryan’s story goes back to those remarks he gave UVA Law’s Class of 2007. “Don’t waste time by being afraid,” he told the 3Ls that April. “You’re going to feel a lot of pressure to conform, whether in your workplace or in your neighborhood, in raising your kids or in creating your relationships. Don’t be afraid to do what you think is right. Don’t be afraid to speak your mind. Don’t be afraid to do what you think is fun, to do what you think might work, to do something that hasn’t been tried before. … Happiness is risk’s reward. Boredom is fear’s.”

Throughout his career, Ryan has lived out his own advice, at least four times making the bold choice over the safer, more conventional one.

That’s how he came to UVA for law school in 1989. It was a year after he had graduated Yale summa cum laude, majoring in American Studies—and a year after he had won admission to his first choice, University of California, Berkeley, School of Law.

Rugby had intervened. He played for Yale, made the All-New England team, and had the chance to play on tour in Australia and New Zealand after graduation. He tried to defer his law admission by a year. When Berkeley said no to Ryan, Ryan said no to Berkeley. He spent six months Down Under, then rounded out the year as a children’s ski instructor in Colorado and a Catholic services volunteer in Appalachian Kentucky.

Ryan reapplied to Berkeley during that year, but he also broadened his list to include UVA. Then he got a call to come interview for a prestigious, full-ride UVA Law Hardy Cross Dillard Scholarship. Ryan was honored and also basically broke. His immediate concern was how to pay for a trip to Charlottesville. The admissions dean told him to worry not.

The story captures a couple things about Ryan. For starters, there’s his obsession with athletics. “I will play almost anything with a ball involved,” he says. In addition, he skis, mountain bikes, and regularly runs the Boston Marathon, completing this year’s at a 7:01 minutes-per-mile pace.

Ryan’s willingness to say no to Berkeley shows something else about his makeup. Sure, given his undergraduate credentials, he probably didn’t need to worry about getting readmitted, but it still took courage for someone who grew up working class in Midland Park, New Jersey, the first in his family to go to college, to allow his education to get sidetracked. That he did so shows his sense of perspective, to borrow from one of his five big questions, on what truly matters in life—such as a onetime shot in your early 20s to scrum in Oceania.

Further validating the bold choice, it was at UVA that Ryan, after his early awkwardness at the dance, met the woman he’d marry, Katie Homer (Law ’92). Frosting on the future wedding cake: During law school he got to play for Virginia Rugby.

Example 2 of Ryan’s road less traveled by came when he began his law career. After a series of prestigious internships and clerkships, culminating in his clerking for U.S. Chief Justice William H. Rehnquist in 1993–94, Ryan could have made millions in any major legal market. Instead he accepted a two-year public interest fellowship in Newark.

The third career crossroads came during his 1998–2013 tenure on the UVA Law faculty. By three accounts, he was on track to become dean. Ryan says he really doesn't know if it would have been his for the asking, but offers: “I thought about it. It was an attractive possibility.”

But a different possibility captured his imagination: Around 2011, Stanford University called to see if it could consider the education law scholar for education dean. He didn’t get the post—a friend says he was the runner-up—but it got Ryan to thinking, and it mentally prepared him to accept Harvard’s job offer two years later.

(When that call came, one snag, Faust and Ryan both remember, involved assuring Ryan he’d be able to find a home where he could keep his chickens. Hence the family’s move from rural Virginia to the Massachusetts countryside.)

The fourth example is the current one: Ryan’s choosing to detour from his success and prospects at Harvard. In the midst of his consideration for UVA’s presidency, Ryan became viewed as a possibility for Harvard’s. In June, six months after Sullivan made public her decision to step down, Faust announced hers. Just as Faust suspected UVA would approach Ryan, Conner acknowledges his UVA search committee had real concerns Harvard would do the same.

Harvard law professor Michael J. Klarman agrees with the logic. “I wouldn’t go so far as to say he would be the front-runner, but it’s clear that he would have been one of the leading contenders,” says Klarman, whose friendship with Ryan goes back to when Ryan was one of his students at UVA Law School and later a colleague on the faculty.

Says Ryan, “I don’t know whether that’s true or not.” He was already far down the line in his talks with UVA by the time the Harvard search got under way. More to the point, as he has repeatedly demonstrated, he’s not one to reach for a rung simply because it’s in front of him. Or, as he says, “I don’t aspire to be a university president, generally, but I’m intensely interested in being the president of UVA.”

As to the why of that, you can find some answers in Ryan’s far-reaching five-plus-one questions. They provide a framework for understanding the principles that drive him. They also give an early read on his leadership style and how he’s likely to approach his new responsibilities.

Wait, what?

Ryan’s first essential life question, “Wait, what?” takes its inspiration from his children—Will, a Harvard sophomore; Sam, who starts Yale next fall; Ben, a high school junior; and sixth-grader Phebe. Depending on the circumstances, it’s uttered in disbelief, protest or when reality intrudes on inattention. Ryan calls “wait, what?” the root of all understanding.

He learned the lesson of pause-to-understand in his early days of leadership at Harvard Ed, he says. “I confess I didn’t have much of a vision when I began,” he writes in the book. “Not having answers, much less a vision, made me nervous at first, to the point of despair and occasional panic.”

He laughs in hearing the words read back to him now. He says those first several months taught him to trust “that if you ask enough questions, and listen carefully to the answers, you’ll eventually have the answer to the key question of ‘What is your vision and what are your priorities?’”

It’s how Ryan will approach the scope of the institution that awaits him, he says. “The biggest ‘wait, what?’ moment is just the size and complexity of a major university compared to a school,” he says. That’s especially the case at UVA, where all the schools and other operations combined still make up roughly half the enterprise when you factor in the UVA medical complex.

“He’s going to be a first-rate and successful president,” says John T. Casteen III (Col ’65, ’66, ’70), UVA president from 1990 to 2010. There will be a learning curve in spite of all Ryan’s years in Charlottesville. Casteen says, “To know well the law school is not to know the University.”

Ryan is already preparing to plunge into life on Central Grounds and the inimitable UVA undergraduate experience. While the president’s residence on Carr’s Hill undergoes a previously scheduled renovation, Ryan plans to move into Pavilion VIII on the Lawn. (Where his chickens end up, he says, remains under negotiation.)

“If you look at his writings, his teachings, his speeches, it is all about the student experience,” says UVA rector Conner. “And it’s all about engagement with the students.”

Before he officially starts, Ryan will need to prove a quick study on the University’s upcoming capital campaign, a multibillion-dollar what that can’t wait long. It will take up a large portion of the new president’s time, Conner says, but he benefits from having so much of the infrastructure already in place.

John C. Jeffries Jr. (Law ’73), Ryan’s former dean and colleague on the UVA Law faculty as well as a member of the Board of Visitors search committee, sees Ryan as a natural in this part of the role. Donors “want to believe they’re contributing to success, that what they’re doing is supporting achievement,” Jeffries says. “The most important thing in fundraising is to inspire that belief. He’ll be great.”

To his point, Ryan notes he’s just wrapping up a Harvard Ed campaign that has raised $280 million against a $250 million goal.

I wonder ...

Ryan’s second essential question, “I wonder …” isn’t a question, but it prompts the asking of some of life’s most incisive. It’s a call to curiosity and an invitation to question the status quo—asking “I wonder why” to understand the present nature of things and “I wonder if” to explore better possibilities.

As both insider and outsider, Ryan is particularly well-positioned to wonder about the whys and ifs of UVA. Says Jeffries: “He’s essentially an inside candidate, but with an overlay in the perspective of having seen the nation’s best university function, and being part of that. That’s a powerful combination for us.”

Casteen encourages Ryan to question assumptions in organizing his administration. “You don’t want the president to accept the structure in place,” he says. You want him to question it and critique it.

The “I Wonder …” chapter is the most poignant part of Ryan’s book about life’s essential questions. Raised by loving adoptive parents in a stable home, he set out at age 46 to learn about his biological mother. His incurious assumptions melt away as he learns the story of a young Irish immigrant who falls in love with a man she doesn’t know to be married with children. The adoption records tell of her crying in the hospital, knitting her baby the sweater he wears when she turns him over to the adoption agency, and how she prayed for him each of the preceding nine days. Through a rapid succession of events, Ryan meets her, and learns that she has prayed for him every day of his life.

“This is not a story about changing the world, of course, but it did change my world, in a remarkable and meaningful way,” he writes. He uses the example to encourage introspection.

Faust remembers this profound personal journey unfolding as she talked regularly with Ryan in recruiting him to Harvard Ed. Along the way, he shared updates with her. “All of that has made him, I think, such a grounded person about what really matters and about what values are, what opportunity means, how people reached a hand out to him in various ways through his life.”

It’s there and throughout his book and his speeches that one sees a very personal side to UVA’s next president. “He’s very emotionally open and available,” says Goluboff, the law dean. “That’s part of what makes him a great leader. He feels things, he feels them deeply, and he expresses it and articulates it.”

Couldn’t we at least …

Of all Ryan’s questions, “Couldn’t we at least” is the most tactical. It’s a way to find common ground, agree on some basic first steps, so people of different views can collaborate toward a solution. Or, as he told the 2016 graduating education students at Harvard, “This is the question to ask that will enable you to get unstuck.”

Ryan tells how an African-American law school classmate took that approach in seeking to overcome the class’ self-segregation. Theodore W. “Ted” Small Jr. (Law ’92), now a lawyer in DeLand, Florida, formed a circle of five white and five black students to get together once or twice a month to talk about race. “At the beginning it was hard and it was awkward, and everyone was a little bit nervous,” Ryan recalls. “You’re worried about causing offense. You’re worried about being offended. But what happened over the course of probably 2½ years that we kept this group together is that we all became incredibly comfortable with one another and had a lot of really honest conversations.”

Among the more remarkable feats on Ryan’s resume are his clerkships with judges well right of his own political sensibilities, first Nixon appointee J. Clifford Wallace, the chief judge of the 9th U.S. Circuit Court of Appeals, and then Rehnquist, the Nixon U.S. Supreme Court appointee whom Ronald Reagan had promoted to chief justice. Rehnquist was known to pick talent and temperament over ideology in choosing his law clerks, and showed a strong preference for UVA graduates. In a warm tribute upon Rehnquist’s death in 2005, Ryan told the law school’s Virginia Law Weekly, “I think the tendency to assume that those with whom you disagree are ‘bad’ or somehow intellectually or emotionally deficient is rampant. My year with the Chief cured me of that tendency and helped me and my co-clerks understand that it is possible to have deep personal affection for someone with whom you disagree, and to genuinely admire that person.”

Klarman saw that generosity of spirit when he and Ryan served together on the UVA Law faculty. He remembers Ryan’s genuine friendships with his ideological opposites. After Klarman joined the Harvard Law faculty, and had heard Ryan was a candidate for Harvard Graduate School of Education dean, he wrote a recommendation letter to Faust, one he has never shared with Ryan. “In a way that I could never manage myself, Jim can disagree with someone without the disagreement becoming personal or rancorous,” Klarman wrote. “More than once, I’ve seen him break the tension in an appointments committee meeting with a deftly timed joke or self-deprecatory comment.”

True to “couldn’t we at least,” Ryan’s management style is that of consensus builder, and a highly persuasive one. Faust says the outsider she brought in to take over the ed school was not a disrupter. “He’s quite the opposite. He wins people over,” she says. “He’s just integrity all the way through. He’s straightforward. He’s a winning personality. And that enables him to move an institution forward and inspire people to follow.”

Ryan comes to UVA from Harvard’s Graduate School of Education, where he is the dean. Courtesy Harvard University

How can I help?

The importance of Ryan’s next question is its phrasing: “How can I help?” Just that it’s phrased as a question, as opposed to the declarative, “Here, let me help,” supplants arrogance—thinking oneself a savior—with the respectfulness of deference. As Ryan said in his famous commencement remarks, “How we help matters as much as that we do help, and if you ask how you can help, you are asking, with humility, for direction.”

It helps explain Ryan’s accepting the UVA job offer in the aftermath of the August 11–12 hate rallies on Grounds and in Charlottesville. Jeffries says the search committee had real concern the turbulence could make it harder to pry Ryan away from Harvard.

Ryan says the opposite was true. The events made him think of the Harvard baccalaureate remarks Faust delivered after the 2013 Boston Marathon bombing. She titled it “Running Toward,” in homage to the man in the cowboy hat who plunged into the crowd to help and later explained, “My first reaction was to run toward the people.” In her speech Faust offered that as a way to live one’s life. “It means running toward not just your own dreams but running toward where you can help. As Martin Luther King Jr. wrote 50 years ago this spring, ‘I am in Birmingham because injustice is here.’”

During the brief news conference on the Lawn following the announcement of his selection, and just a month after the violence in Charlottesville, Ryan took a question about how those events affected his decision. “I watched it unfold online,” he said, “and as I was watching this and I was thinking about this job, the idea of running toward kept running through my mind.”

As a practical matter, Ryan will be exercising deference during the current academic year by virtue of distance and his day job of Harvard dean. His official Oct. 1 start is more than a year after the announcement of his hire and two months after Sullivan completes her term on July 31.

Details of the transition continue to be worked out. Meantime, Ryan plans to take advantage of his year as an outside observer. At his request, University senior managers have started sending him briefing materials. Ryan says he expects to visit Grounds regularly, with increasing frequency next semester, over the summer, and up to his scheduled start. “There are also some issues that will affect my presidency more than President Sullivan’s presidency, and she has been incredibly welcoming of my being involved,” he says.

For Sullivan, this has been a deliberate choice. “My objective is to make this as smooth and seamless as possible so that Jim has a running start, and I’m still running when I hand the baton off,” she says.

While she’ll be available to him as much as he’d like, she will exercise a scheduled leave by spending a couple of semesters at the University of Texas-Austin, refreshing her knowledge of demography for when she begins teaching it at UVA. “It is important to leave town, because the new president deserves an opportunity to get traction without having you hang around,” Sullivan says, noting Casteen extended a similar courtesy to her.

What truly matters?

The fifth essential question, to ask yourself “What truly matters?” carries the authenticity of how Ryan has steered his own life—the 22-year-old who knew law school could wait but rugby in Australia wouldn’t, the would-be law dean who would instead lead an education school, Harvard’s rising star who’s running toward a UVA he sees poised for something even greater.

Ryan shows a focus on what truly matters in the balance in his life—his professional achievement, his discipline as an endurance athlete, his personal touch in relationship building, his devotion to educational opportunity, and his emphasis on family in his book and in conversation.

“Everybody I know who’s had Jim’s level of success pretty much has to work all the time. Jim obviously works hard, but he also knows what’s important,” says Harvard’s Klarman, Ryan’s friend for almost 30 years. “It’s just a really impressive thing, both to realize the importance of balance and then somehow to be able to execute it, by figuring out what’s important and what you need to do, and what’s crap.”

That September morning on the steps of the Rotunda, Ryan explained why the presidency of UVA is something that truly matters to him. “I know this sounds cliché, but I honestly care most about making a difference in the world, and I believe in the power of this institution to make the world a better place.”

In general terms, he told Virginia Magazine, that means “students feel like they’ve had a life-changing experience,” faculty members feel “like they’ve been able to do their very best work while at the University,” and alumni “still feel a deep connection to the University.”

“I think if you can get those things right, you will have a University that is widely considered to be the very best public university,” he says.

Even so

The payoff to Ryan’s “Wait, What?” speech comes in the bonus question he offers at the end. If you live your life asking, “Wait, what?” “I wonder…” “Couldn’t we at least?” “How can I help?” and “What truly matters?” then you can answer “I did” to this line from the Raymond Carver poem, “Late Fragment”:

And did you get what you wanted from this life, even so?

Ryan puts the emphasis on the “even so,” because it acknowledges our lives are imperfect. It captures, he writes, “the reality that pain and disappointment are inevitably a part of a full life, but also the hope that life, even so, offers the possibility of joy and contentment.”

The narrator in the Carver poem answers “I did” because he can call himself beloved. Were it his nature, and it is not, Ryan could make a good case for himself.  “Everyone who has worked with Jim Ryan has affection for him,” says Jeffries, an esteemed member of the law faculty since 1975. In that Harvard recommendation letter, Klarman described Ryan as “one of the most likeable people you would ever want to meet—sincere, witty, modest, generous, and utterly dependable as a friend and a colleague.”

In accepting the UVA presidency Ryan has taken on a daunting assignment, but when he arrives on Grounds next academic year, he will have the advantage of a huge store of goodwill, even so.

S. Richard Gard Jr. is editor of Virginia Magazine.