December 16, 2021

Donor Spotlight: An Interview with Amy Gross

By the mid-2000s, Amy Gross was, by any conventional measure, sitting on top of the world. After decades at the helm of several major magazines—from Vogue and Elle to Mirabella—Amy was editor-in-chief of O, The Oprah Magazine, earning a very good paycheck and enjoying unparalleled access to celebrities and leaders in the arts, entertainment, fashion, sports, politics, and business, including her own media-mogul boss, Lady O herself. And yet… Amy’s life wasn’t focused on what she wanted to do most—meditation. “I basically wanted to devote more time to practice and let it be the main road—the highway—of my life,” she recalls.

So, in March of 2008, Amy bid farewell to the magazine biz and enrolled in a Mindfulness-Based Stress Reduction course Jon Kabat-Zinn offered to healing professionals wanting to incorporate mindfulness into their work and lives. Soon, her MBSR training and then teaching became another way she dove deeper into practice. Amy’s history as an IMS yogi, however, goes back further. She sat her first IMS retreat, Joseph Goldstein’s 10-day Vipassana retreat, in 1995, and she sat two successive Three-Month Retreats between her jobs at Elle and O. In addition to teaching meditation, Amy has contributed to the insight world as an IMS donor and thought partner, and she served two terms on the board of directors at the New York Insight Meditation Center.

Recently, John Spalding, IMS’s Director of Partnerships and Communications, spoke with Amy to learn more about how she became a meditator and made her way from magazines to meditation, as well as what she thinks about online programs and has missed most about in-person retreats.

How did you come to meditation?

Freshman year at Connecticut College, I picked up these little books about Zen in the campus bookstore. I’m sure I didn’t understand them—they talked about “the void” and what could I possibly have understood about the void? But just reading the sentences in those little paperbacks was incredibly quieting. When I graduated, I got a job at Glamour in New York but I was always on the lookout for places to practice. A friend would call me and say, “Some Tibetan monks are leading a powa initiation at a midtown hotel—do you want to go?” And I’d say sure. Or somebody would say, “A famous Zen teacher from Japan is teaching at some apartment on Sutton Place. Are you interested?” Sure. A weekend retreat at a gorgeous zendo in upstate New York?  You bet. Whatever came along, I was up for it.

Years passed with me reading about Buddhism and dipping into a wild variety of experiences but, as I told a Buddhist-oriented friend at lunch one day, the time had come to stop reading and start sitting. I needed a teacher. A week later she left a phone message: “Found a teacher for you—Joseph Goldstein will be teaching at Omega.” I immediately booked the weekend, and immediately after, I signed up for Joseph’s 10-day Vipassana retreat. So now I had a teacher—in fact I had two: Joseph co-taught the Omega retreat with Sharon Salzberg. And the summer before, at a symposium on Buddhism and Psychotherapy I discovered a young psychotherapist named Mark Epstein, reading from his first book, Thoughts Without a Thinker. I was the editor at Elle Magazine at that point, and I thought, I have to get him into the magazine. (He later told me I was the first person to interview him and take him for lunch.) I was so impressed with him that halfway through the interview, very unprofessionally, I asked if he’d be my therapist. Fortunately, he said yes. So that was the beginning for me of getting seriously devoted to this process of “lightening up,” as Joseph calls it, waking up, emerging from the fog of reactive behavior.

And all this time you were building a high-powered career in the magazine world, at publications including Vogue, Elle, Mirabella, and Oprah’s O. How did you juggle that with your meditation studies?

I didn’t grow up planning to float around New York wearing Manolo Blahnik shoes and being the editor of anything. I’d been pre-med and grew up thinking that being a doctor, relieving pain, promoting healing, was the best thing you could do. I fell into magazines, and without fire-in-the-belly ambition, I enjoyed my jobs as jobs rather than my life’s work. I remember sitting in my huge office on the 44th floor, overlooking the Hudson river, and thinking, I’m making more money than I ever imagined, and I would rather be earning $10,000 a year writing a newsletter at a retreat center.

I’m living your dream, Amy!

[Laughs.] Soon after that epiphany on the 44th floor, I did walk out of my job. I wrote about that exit for Newsweek, how a few of my editors took me out for tea that day. I sat there stunned by my own possibly rash behavior but after an hour or so I noticed a strange feeling rising in my body and realized it was bliss. I was free. Joseph’s reaction to my news was, “That’s wonderful! Now you can do the three-month retreat.” Which I did, and the next year’s too, and was signed up for a third but in 1999, O Magazine invited me to join as editor-in-chief. I stayed for eight years, continuing to use most of my vacation time for retreats at IMS. For years I thought of meditation as a side road, but I was more and more recognizing it as my guiding path. By 2007, I felt that the job was getting in the way of my life. I let the company know I wanted to leave and I asked Sharon what she thought I should do with all the time I would have. She recommended that I do Jon Kabat-Zinn’s work—teach Mindfulness-Based Stress Reduction. Uncanny woman! Years before, reading Jon’s book on MBSR, Full Catastrophe Living, my reaction had been: This is my work! He was offering a secularized Buddhism with special emphasis on the intention to relieve pain and promote healing. A few months after I retired, Jon was giving a seven-day MBSR workshop for doctors and other health professionals with Saki Santorelli [then the executive director of the UMass Medical School mindfulness center Jon had founded]. That was my first step, and it was everything I wanted it to be.

After the MBSR course, what was your next step to becoming a meditation teacher?

I took the first teacher training course, at UMass, and then the second, and apprentice-taught with a couple of very generous and experienced MBSR teachers. I began to teach on my own and continued going on retreats to deepen my practice. I taught the full 8-week course as well as workshops I adapted for different groups—for the New York Times, the School of Visual Arts, a New York Insight “graduate” course, a NYC prep school, a retreat for journalists I co-taught with Saki—all wonderful experiences but after 10 years or so, I wanted more space, less doing. So I whittled teaching down to a drop-in group for older people, run by a community center that Sharon had introduced me to in 2011. Now we’re doing it on Zoom, and instead of a small group in a small room, we reach 40, 50 people who never could have imagined they’d be: a) meditating and b) doing it on zoom. It’s been amazing and joyous.

What is your perspective on the challenges and opportunities of the shift to teaching meditation online?

I’ve been part of a lot of magazine startups, where you’re really inventing something, designing or redesigning the architecture of a magazine. That’s the most thrilling thing for me: what does this magazine want, need? Zoom and other online platforms invited us to the same questioning, to reinvent. How do you transform your center, your content, into an intimate online presence? How do you make a zoom call a sangha? How do you keep the flavor of your sangha? It’s just remarkable how centers have responded and the response they have received, and the sense of intimacy that can be created in a Zoom environment. There is nothing like being together in person, but there’s no question that we should all be tremendously grateful for what technology has allowed us. It’s given us access to teachers all over the world. Everybody is available. It’s been almost dizzyingly rich. So much to see, hear! But at the same time, I have this image of coming back to IMS and setting down my luggage in the lobby, then pulling out my pillows, taking off my shoes, and walking through the upper room to find a seat in the hall … and feeling the quiet, that thick quiet that permeates your body. I can’t wait.

What does it mean to you to be an IMS donor?

The existence of IMS is vitally important to me. In my experience, it is a unique institution, and uniquely consistent with everything my practice has taught me to value, kindness above all, integrity, purity of motivation….  It’s the city on the hill for me. Every time I go and take my seat there, I’m filled with rapture. I’m filled with rapture sitting here talking to you about it.