I never went looking for a mentor.
In 1995, I was working as the lead tech guy for an internet startup, Tripod. I spent an inordinate amount of time with the company’s two cofounders, one a recent college grad my age, loaded with charisma and ambition, and the other, a distinguished college professor, a World Bank economist with a desperate desire to leave academia and work in “the real world”. I loved both men and both drove me mad in equal measure, but Dick Sabot, the professor who was my fathers’ age, was the friend I gravitated to.
As chairman of the company, Dick’s responsibilities were wide-ranging and general, but centered on the corporation’s strategy, fundraising and future directions. The company was my life, and I spent countless hours talking with Dick about where we were going and how best to get there. At some point, Dick asked me for help editing a letter to investors, so I could ensure the discussion of technical matters was correct. Gradually, I found myself writing and editing much of Dick’s writing for the company, helping steer the company through countless discussions and arguments with Dick and Bo, his co-founder. I would occasionally joke that I’d taken on an additional job as assistant to the chairman, but mostly I was thrilled at the chance to work on our most important projects and our hardest decisions.
It literally didn’t occur to me that Dick was mentoring me until a year after we sold the company. Dick no longer needed my help understanding the technical aspects of business, which were now part of a vast publicly traded company and well beyond my understanding. And yet we had developed a habit of meeting every week in his living room for breakfast. I would bring muffins and fruit juice and we’d talk about our parent company, the business he wanted to start next, the nonprofit I was starting. He became the chairman of the board of my nonprofit, giving us an excuse for our regular meetings, but our conversations were wide-ranging, about different ways to make the world a better place, about his and my decisions to live in the rural community we both loved, about how to live a good and meaningful life.
My nonprofit bloomed then crashed. His new business grew and then collapsed, first with a heavy snowfall crushing the warehouse where all the inventory was stored, then with embezzlement by his CFO. I washed up on the shores of academe, becoming a researcher at Harvard’s Berkman Center. As I flirted with returning to school and earning a PhD, Dick made the case that I’d always learn more in the real world than in a classroom.
And then he died. While Rachel and I drove to his farm to have dinner with Dick and his wife, he had a massive heart attack while working out at the college gym. I’d brought a block of marzipan for him from a trip to Armenia, and I left it with his wife as we hugged, sobbing, in the parking lot of the hospital where he died.
If I was too dense to notice when Dick began mentoring me, I didn’t miss his absence. My work was going well – Rebecca and I had launched Global Voices, I was developing my voice as a writer and learning a new way to shape the world, this time through philanthropy, working with Open Society Foundation. But I found myself second-guessing every decision, wondering how to pick a path to follow without someone older and wiser to talk through my choices with.
My closest friend at the Berkman Center was David Weinberger, a funny, kind and generous writer who’d produced the most cogent book I’d encountered on what the internet was and why it was important, Small Pieces Loosely Joined. We shared drafts of our blog posts and argued about the future of the internet, and when I talked to him, I felt less lost.
And so I asked David whether he would be my mentor. And he said no.
More precisely, he said, “I don’t want to be your mentor. I want to be your peer.”
It was one of the hardest and kindest things anyone has ever said to me. But he was right. And we remain dear friends, reading each other’s work, propping each other up when we face hard moments, offering each other advice and counsel. It’s a very special relationship to me, but it’s different from what Dick and I had, more symmetric and subtle. I learn from David every time I speak with him, but I don’t show up at his house with juice and muffins.
It took me several more years to realize that it was time for me to close the loop. I was teaching at MIT, advising a cadre of brilliant graduate students on their research, when I noticed I was spending at least as much time talking about their aspirations and their fears as I was about their research. I’d assumed that at some future date, when my hair had grown sufficiently grey perhaps, I would magically develop a store of wisdom that I was ready to pass down to the next generation. But I’m still young, still an idiot most of the time, and still desperately trying to grope my way through life, unsure of where I’m ultimately going. But somehow listening to these amazing young people and occasionally offering my thoughts and opinions appeared to be helpful to them, and so I’ve kept doing it.
In the process, I realized that Dick hadn’t started sharing his work with me in a subtle attempt to educate me about business and leadership – he’d asked me to help him write and think because I was good at those things and I helped make his work better. And I don’t advise students because MIT pays me to – I advise students because they’re brilliant and creative and because talking with them makes my thinking sharper and better. And I do it because I care about them and when they succeed, it gives me a sense of pride and accomplishment that I never imagined I could feel about work I hadn’t done with my own hands.
This fall, at a moment where I was feeling particularly dark about my decision to teach at MIT, my students and staff did something marvelous for me: they nominated me for the Martin Luther King Jr. award, MIT’s institute-wide award for leadership. Thanks to their profoundly generous letters of recommendation, I won, and while the handshake from the university president, the check and the trophy were nice, the prize was the pile of recommendation letters my students handed me. I sometimes send students the letters of recommendations I write for them, because I think it’s important to let people know how you really feel. And my students let me know that they valued me as a professor, an advisor, a friend and a mentor.
I never went looking for a mentor. Now I’ve found dozens. Sometimes they’re wise elders whose examples I try to learn from. At least as often, they’re young people whose passion and energy helps maintain my passion and energy. The best part about these young mentors is that I’ve got them fooled – they think I’m mentoring them, when in truth, they’re mentoring me.