From Mistakes to Meaning: Owning Your Past So It Doesn’t Own You

By Michael Lynton and Joshua L. Steiner

Simon & Schuster, February 2026/272 pages

Reviewed by Paul Deegan

February 2, 2026

In late 1992/early 1993, I worked in the Clinton presidential transition office in a nondescript building on Vermont Avenue, five blocks from the White House. I was assigned to the economic policy team.

Initially, there were fewer than a handful us. As the inauguration approached and the team grew, many interesting people arrived: Bob Reich, who went on to become Secretary of Labor; Goldman Sachs Co-Chair Bob Rubin, who would head up the National Economic Council and later become Secretary of the Treasury; Blackstone Vice Chair Roger Altman, who became Deputy Secretary of the Treasury; and World Bank Chief Economist Larry Summers, who joined Rubin and Altman at Treasury, later becoming secretary himself.

Among my fellow twenty-somethings, two were standouts. One was McKinsey consultant Sylvia Mathews (later Mathews Burwell), who became Rubin’s chief of staff and eventually a cabinet officer in her own right under President Obama, then the first woman President of American University.

The other was Josh Steiner, who became Altman’s chief of staff at Treasury and later held the same role under Lloyd Bentsen.

Steiner and his friend Michael Lynton, who’ve both lived through high-profile controversies, are now telling those tales and turning their experience into invaluable advice with From Mistakes to Meaning: Owning Your Past So It Doesn’t Own You.

Before I get into the review, let me share some reflections about Josh that may offer context for the book. Before he came to the transition, I heard that a superstar was joining us. Steiner had been chief aide to Timothy Healy, the Clinton confidant and Jesuit priest who was president of the New York Public Library. This was a prestigious position in the New York power sphere, held previously by George Stephanopoulos.

Josh was handsome, whip smart, unfailingly kind and courteous, hardworking and faithful. For such a superstar, he was modest and a little shy. He was the kind of guy you’d want your sister to marry.

After the inauguration, my move to the White House and Josh’s move to Treasury, as the Whitewater real estate scandal grew, his stress and strain were evident, though he always carried himself with great dignity and composure. Sadly for Josh, and the country, the government career of one of the most able and competent people I’ve ever met ended abruptly and in controversy, and that story is a key part of this book.

From Mistakes to Meaning begins by recalling when Lynton, who was CEO of Sony Entertainment at the time, called Steiner in a panic back in 2015. In response to the release of the Seth Rogen-James Franco film The Interview, which Lynton had green lit, his company had been hacked by the North Korean government, and thousands of documents were posted by WikiLeaks.

It was a story (to use the polite word) of unprecedented cultural-geopolitical-cyberespionage magnitude, and it swallowed the news for days. In the middle of trying to manage the crisis, Lynton realized that his own private emails to his family could come out.

Lynton called Steiner because, at the height of the Whitewater investigation, Josh’s diary had become public for a passage in which he had written that the White House had put “intense pressure” on Altman — a Clinton friend — to remain involved in the handling of Whitewater from Treasury.

When Josh told Congressional investigators that the diary was not an accurate portrayal of events, he was labelled “the kid who says he lied to his own diary”.

All of us have made mistakes. Steiner and Lynton perform a public service with this thoughtful book, delivering a master class in coming to terms with and overcoming them.

Steiner writes, “In the same way that banks used to build imposing facades and grand halls to assure customers about their stability and solvency, everything about the Treasury architecture gave off a sense of probity and endurance. I tried to channel that vibe as I read my subpoena. As I realized that it required me to preserve and produce all my papers, letters, calendars, files, and diaries relating to the Whitewater scandal, my mood deteriorated.”

When confronted by the WikiLeaks dump of his emails, Michael Lynton realized how the single decision of green lighting The Interview had impacted not only his life but the lives of the people he loved. And, when what he’d written in his diary about the White House’s handling of Whitewater became public in a way he felt compelled to deny, Josh Steiner regretted both the writing and the denial.

While those events from years ago provide for an interesting read, it is the deep introspection, lessons learned, and larger applications that make this book a must-read.

Steiner and Lynton go beyond their own experiences by working with Alison Papadakis, director of Clinical Psychological Studies at Johns Hopkins, who provided the academic research to guide their exploration.

They interview people like Malcolm Gladwell, who candidly share their own mistakes. They note: “Interviewing Malcolm Gladwell made us anxious. Who wants to interview someone who interviews people for a living? If you host a cooking show, you probably wouldn’t invite Ina Garten as your first guest.”

Gladwell revealed that in 1978, he set a new Canadian record in the boys-under-sixteen 1,500. Yet he quit running and told the authors, “I engaged in an act of self-sabotage at fifteen and have regretted that decision through much of my adult life…One of the biggest mistakes that I’ve made.” Steiner and Lynton conclude, “For Malcolm, running was about racing, and racing was about winning. It’s the perspective of a perfectionist.”

Steiner and Lynton offer practical advice on how to avoid such life-altering choices or, if you’ve already made them, how to process them in the most useful way possible.

On how to talk about mistakes, they developed a clever acronym – DUET: disclose, unpack, empathize, and trust. On disclosing, the pair who felt shame during their own struggles point to the words of Bernard Baruch, the famous financier and presidential adviser, “I have known men who could see through the motivations of others with the skill of a clairvoyant; only to prove blind to their own mistakes. I have been one of those men.”

They recommend unpacking mistakes by examining them in a three-act structure: what happened during, before, and after the mistake. “If you demonstrate empathy to yourself and the people with whom you’re talking, it will encourage the kind of disclosure that can lead to beneficial change,” they wisely observe.

Perhaps one of the book’s most important observations is, “The people with whom you’re closest will know that your mistakes do not define you. Indeed, we believe that if you trust them with your honesty, it will deepen your friendships just as it did ours.”

The penultimate chapter is titled, How to Make Fewer Mistakes. It begins with a quote from Charlie Munger of Berkshire Hathaway: “I’ve made my way in life by making fewer mistakes than others. I’ve just avoided them. If you try to be consistently not stupid, instead of trying to be very intelligent, you’ll end up being wise and make fewer mistakes.”

Easier said than done, as the authors point out, before offering the following advice: First, take a deep breath. Second, balance between making decisions instinctively and acting more deliberately. Third, focus on what not to do.

After all their research, interviews and years of self-reflection, the authors came to conclude that they really had two problems, “We didn’t know what had driven our mistakes, and we didn’t want to let out what little we knew and felt.” Growing up, they write, “We were taught to focus on those attributes that drive success—bravery, focus, selflessness—and suppress those emotions that thwarted advancement—fear, ambivalence, compassion.”

All of us have made mistakes. Steiner and Lynton perform a public service with this thoughtful book, which delivers a master class in coming to terms with and overcoming them.

Clearly, this is a book these two men had to write, and we should all be glad they did. On a personal note, I hope Josh goes back into government at some point, as he now has even more to offer the American people.

Paul Deegan, CEO of Deegan Public Strategies, was an executive at BMO Financial Group and CN Rail, and he served as Deputy Executive Director of the National Economic Council in the Clinton White House.