There is a particular kind of leader who never needed to raise her voice to be heard in the room. Janet Levine has spent more than six decades proving that authority is not something a person seizes. It is something a person earns, one relationship at a time, by paying attention to people others overlook. Journalist, elected councillor, anti-apartheid campaigner, author of six books, and educator to thousands of students across twenty nine years at Milton Academy in Massachusetts, Levine has moved through worlds that rarely intersect. What connects them is a single, stubborn conviction: that the people doing the work deserve the credit, and the person in charge should be the last one reaching for it.
A Political Education in Johannesburg
Levine was born in Johannesburg at a time when the machinery of apartheid was tightening around every corner of South African life. She began publishing in national newspapers while still a teenager, an early sign of a career that would blend journalism with activism long before the two were treated as compatible. Through the 1970s she wrote a column for The Sowetan, becoming the only white journalist to hold a regular slot in a Black newspaper between 1978 and 1981, an assignment that placed her inside conversations most white South Africans of her generation never entered.
Her political career began in earnest in 1977, when she was elected to the Johannesburg City Council as a member of the Progressive Federal Party, the parliamentary home of the anti-apartheid campaigner Helen Suzman. Levine would go on to run one of Suzman’s election campaigns, coordinating four hundred volunteers in an effort to keep a rare opposition voice inside a parliament built to silence it. On the council itself, Levine filed motions to open civic institutions to all races and worked closely with Black trade organizations, eventually helping to launch a taxi drivers’ cooperative that gave Black commuters an alternative to a transport system designed to exclude them.
“You chose the crew to sail the ship. Let them hoist their own sails,” she says of the leadership instinct that carried her through those years, a philosophy she credits to standing back and letting a team claim its own results rather than folding every achievement into her own record.
Those years in municipal politics were rarely comfortable. Levine was a public representative inside a system explicitly designed to keep power in white hands, and every motion she filed to desegregate a civic institution was a small act of friction against that design. She was, by her own account and by the accounts of those who covered South African politics at the time, a crusading freelance journalist who had become an elected official almost by accident of conviction, holding office in a string of anti-apartheid organizations alongside her council seat. The taxi cooperative she helped launch, which would later be known as Ma-Afrika Taxi Ltd, was a practical response to a transport system that had been built to strand Black workers far from the jobs and services white Johannesburg took for granted.
She served on the council until 1984, when she emigrated to the United States. Three years later she published Inside Apartheid: One Woman’s Struggle in South Africa, a political memoir that drew attention from The New York Times Book Review, The New York Review of Books, and Terry Gross on NPR’s Fresh Air. Kirkus Review called it a grim and compelling account of life inside what it termed the belly of the beast that was apartheid, a description that captures the book’s refusal to soften its subject. The memoir remains one of the more intimate accounts of what it took to oppose a regime from within its own institutions, written by someone who had done exactly that.
The Model That Changed the Way She LED
If Levine’s political years taught her to fight for a seat at the table, her second career taught her what to do once she got there. In 1986 she joined the English department at Milton Academy in Massachusetts, where she would teach philosophy and literature for the next twenty nine years. It was there, immersed in the daily work of managing classrooms, faculty teams, and the founding of the school’s National Educators Institute, that she encountered the Enneagram, a model of personality with nine interconnected types.
“Discovering the Enneagram was my defining moment,” Levine says. “The more I studied the model, the more I could see how it worked in groups. There is a natural inclination of transference in choosing people for your team. Most teams land up with mini me-s.”
That observation became the foundation of her leadership philosophy. Left unchecked, she argues, most leaders unconsciously recruit people who think exactly as they do, which narrows a team’s perspective at the precise moment complexity demands the opposite. Levine began urging leaders to draw deliberately from each of the Enneagram’s three major groupings, a practice she believes produces teams that see problems, and their solutions, from genuinely different angles.
The insight was compelling enough that Levine wrote two books applying the model outside her own classroom. The Enneagram Intelligences: Understanding Personality for Effective Teaching and Learning, published in 1998, was nominated for the Grawemeyer Education Award and has since been translated into several languages, now considered a standard text in Enneagram studies. She followed it in 2003 with Know Your Parenting Personality, extending the same framework from the faculty room to the family home. Both books grew out of the nonprofit she founded during this period, the Transforming Teaching Workshops, through which she was invited to lead programs internationally, along with the Enneagram Teachers Association in the Narrative Tradition, which she also established.
“I still believe that the Enneagram can revolutionize education,” she reflects, with the frankness of someone who knows an idea arrived before the world was ready for it. “The time for the Enneagram was not yet ripe.”
Levine sees empathy and emotional intelligence not as soft additions to a leader’s toolkit but as the entire mechanism through which the Enneagram becomes useful. Understanding that a colleague’s instinct toward conflict, or toward withdrawal, or toward perfectionism is a pattern rather than a personal failing changes how a leader responds to it. It replaces frustration with curiosity, which is, in her experience, the difference between a team that fractures under pressure and one that holds together.
“They play a major role,” she says of empathy and emotional intelligence in leadership today. “With a personality model like the Enneagram, you have an exquisite tool to apply emotional intelligence and empathy with your team.”
Building Consensus, Not Followers
Ask Levine what separates a leader who merely delivers results from one who leaves a lasting mark, and she does not talk about vision statements or bold strategy. She talks about fairness.
“Leaders who do not have favorites, who pay equal attention to each member of the team,” she says. “Leaders who listen, rather than talk. Leaders who build consensus will have lasting impact.”
It is a philosophy that runs directly against the instincts of what she calls the take charge, forge ahead leader, the kind who marches forward assuming a team is falling in line behind. Levine learned otherwise the hard way, and the lesson stayed with her.
“When you turn your head, no one is there,” she says of that discovery. “That was a great lesson and observation for me.”
Trust, in her view, is built the same way regardless of the room, whether it is a newsroom, a city council chamber, or a faculty meeting. It requires a team assembled from different personalities and points of view, paired with a genuine willingness to hear them out.
“At the risk of repetition, you need a team built with different personalities and points of view,” she says, “and the knowledge that their opinion and input will, at the risk of repetition, be at the very least listened to.”
She is equally direct about what technology cannot replace. As artificial intelligence reshapes entire industries, Levine argues that listening skills, the ability to build positive feedback, and the patient work of steering a group toward consensus will only grow more valuable, not less, because a machine can process information but it cannot make a person feel heard.
“Working hard to lead the group to consensus, so that everyone can be part of the solution,” she says, describing the leadership skill she believes will matter most in the years ahead, “or at least know that their point of view was heard.”
Levine traces this same thread through every sector she has worked in, from journalism to civic government to education to consulting. The settings changed constantly, from a segregated council chamber to a New England faculty lounge to the conference rooms where she now advises other organizations. The underlying material, in her experience, did not, and adapting her leadership style to fit each new arena has, she says, required real shifts in approach but never a change in the fundamental model she trusts.
“People are people, and each person has an Enneagram type,” she says. “Once you know and understand and apply the model you will find ways to amalgamate a team, build camaraderie, intuitively know how to frame your message.”
A Storyteller Returns to the Page
In the years since retiring from Milton Academy, Levine has turned her attention back to fiction, the form she says lets her carry South Africa’s history to readers who never lived through it. Her 2023 novel, Liv’s Secrets, follows a Jewish family that immigrates from Lithuania to South Africa and is swept into the country’s upheavals across the twentieth century, a story she has described as partly drawn from her own extended family’s history. The novel arrived two decades after her first work of fiction, Leela’s Gift, published in 2009.
The past year, Levine says, has been dedicated largely to promoting that novel, an experience that introduced her to corners of the publishing world she had not expected to navigate.
“I have learned about the GIG economy, scammers and scamming,” she says, “as well as interacting with wonderful, interesting, supportive and efficient people.”
That chapter is closing. Levine is now at work on her seventh book, a new novel titled The Awakening of Diya Sharma, and is simultaneously halfway through a memoir that picks up where Inside Apartheid left off, tracing the leadership positions she has held since, including her work founding the Transforming Teaching Workshops in the United States. She is candid that the project may take time to complete, and that much of what readers eventually learn about her later career, including the specific organizations and leadership teams she has advised, will likely surface first in that memoir rather than in an interview.
It is a fitting instinct for a writer who has spent a career translating lived experience into published work almost as it happened, from teenage newspaper contributions in Johannesburg to a political memoir written within years of leaving South Africa. Her essays and articles have appeared in The New York Times Sunday Magazine, The Boston Globe, and The Yale Review, a body of freelance work she has sustained continuously alongside her books, her teaching, and her advisory work.
“I feel a shift coming, as I pivot from that project to try to have another novel published,” she says. “I’m also halfway through writing my memoir and want to continue.”
She remains an active book reviewer for the New York Journal of Books and continues to accept invitations to speak with book clubs, a format she says she particularly enjoys because it puts her back in direct conversation with readers, the same instinct for listening that has carried through every stage of her career.
“My website is a good place to start,” she says, when asked how readers might follow her work. “Reading my books is another way to connect. Send me an email. I particularly enjoy connecting with book clubs.”
What Levine Wants the Next Generation to Know
For all the ground she has covered, from a whites only Johannesburg council chamber to a New England classroom to the pages of six published books, Levine resists the idea that leadership is a single, teachable formula. She prefers to point to literature. Asked about the most common misconception surrounding leadership, she reaches for Shakespeare.
“Some are born great, some achieve greatness, and some have greatness thrust upon them,” she says, quoting As You Like It. “All true. And the Enneagram will help you understand all three types of leaders in precise detail.”
It is a fitting note for a career that has itself taken all three forms. Levine was thrust into leadership on a city council built to exclude people like her allies. She achieved it again in a classroom, building an institute from nothing. And in her writing, greatness has simply been a byproduct of showing up, decade after decade, to tell the truth as she saw it.
Her closing message to aspiring leaders is characteristically unadorned, three instructions delivered without embellishment, the same plain confidence that has carried her from a Johannesburg newsroom to a Massachusetts classroom to a writing desk where two more books are taking shape.
“Persevere. Dream big. Believe in yourself.”
