May 15, 2026
Making sense of mistakes
Alum author encourages self-awareness, graceby Allyson Irish
For many years, Joshua Steiner ’83, P’17, ’19, operated with the philosophy “repress for success.” Moving on from mistakes quickly, putting his head down, and focusing on work enabled him to graduate from Yale and Oxford, co-found two investment firms, and land a spot on Andover’s Board of Trustees. What it didn’t do was provide him with the tools to process hard experiences.
“I would have been far healthier and happier if I had allowed myself to talk about mistakes,” Steiner said in April during a candid conversation with Dean of Studies Caroline Odden P’26, ’28, at All-School Meeting.
The visit came amid a flurry of media attention on his first book, “From Mistakes to Meaning: Owning Your Past So It Doesn’t Own You.” Written with his friend, former Sony CEO Michael Lynton, the book provides a structured way of assessing mistakes through personal vignettes shared by successful executives, artists, authors, and others.
Find someone you trust and talk your mistakes to death.
”
Steiner, far right, and co-author Michael Lynton, far left, appeared on Good Morning America to promote their book. (Courtesy photo)
Steiner’s “big mistake” occurred in his late 20s when he was chief of staff for the U.S. Department of the Treasury. During this time, President Clinton was being investigated for questionable real estate and financial dealings as part of the Whitewater Scandal, and Steiner’s personal letters and diary were subpoenaed—both of which contained references to colleagues and the scandal itself.
After surviving scrutiny across global media, Steiner kept his job and moved on. For many years he attempted to ignore this embarrassing past incident, making jokes about the scandal and trying to forget. But during COVID, Steiner and Lynton had the opportunity to dive more deeply into their past; the pair realized that a book focusing on mistakes could give others permission and a framework for talking about their own misadventures.
While on campus, Steiner dined with student leaders and attended two classes during which he shared research from the book, including various ways that students can learn to have a healthier relationship with their own mistakes, have them sting less acutely, and ultimately make fewer of them.
Steiner acknowledged that Andover can be a difficult environment, and students can often feel overwhelmed. Thankfully, today’s culture is more open to conversations about things such as therapy, mental health, and wellness, and students have more support, such as the new Wellness Council.
His advice to students: recognize that mistakes reveal hidden aspects of your personalities, have empathy for yourself and others, and truly listen when a friend opens up to you.
Top photo: Neil Evans
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