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MEA CULPA

My Biggest Mistake in Life Is This

Let’s get into it.

Joanna ColesChief Creative and Content Officer

PublishedApr 13, 2026, 12:26 PM EDT

UpdatedApr 13, 2026, 12:50 PM EDT

Updated Apr 13, 2026, 12:50 PM EDTPublished Apr 13, 2026, 12:26 PM EDT

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It’s somewhat unnerving when a friend calls out of the blue and asks to discuss your biggest mistake.

We serve on a board together, so my mind briefly raced through the usual corporate anxieties. Had I done something unwittingly wrong? Approved something unwise? Driven down the share price with an ill-timed remark?

But that wasn’t what he meant.

Instead, he began by confessing one of his own mistakes, fair to say a catastrophic one, which led to what remains the largest hack in American corporate history.

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The friend in question was Michael Lynton, the former chief executive of Sony Entertainment. And the mistake he was referring to, of course, was the Sony hack, a cyberattack that nearly destroyed the studio, toppled executives, led to U.S. sanctions against North Korea, and permanently changed how corporations think about digital security.

A decade on from the fallout, Michael told me he was writing a book partly to exorcise the experience and partly to explore the nature of real mistakes—the kind that genuinely shape lives. The book, written with his co-author Joshua L. Steiner, is called From Mistakes to Meaning: Owning Your Past So It Doesn’t Own You; it’s out now and, unless you have never made a mistake, is worth a read. Definitely.

The premise is simple: most people don’t talk about their real mistakes. Instead, they offer the polite cocktail-party versions—the humblebrags where someone claims the most embarrassing moment of their life was sitting next to Leonardo DiCaprio and asking what he did for a living.

(True story humblebrag alert: I once hugged Justin Trudeau, thinking he was a friend’s son because I knew he looked familiar. These things happen.)

But Michael wasn’t interested in that kind of story. He wanted the real stuff. Which led to the arresting question he put to me: what was my biggest mistake?

Like most people, I’ve made many. The trick with big mistakes is that you often don’t recognize them until later, when you finally have enough distance to see the shape of your life clearly. When I sat down to think about what might make a helpful chapter—an exercise that involved a fairly rigorous interview with Michael, his co-author and a psychologist—I realized something I had not quite said out loud to myself before:

My biggest mistake was not having more children.

I have two sons, and mostly I adore them. But truthfully, I wish I’d had more. A bigger family. A louder, messier house. And the deeper mistake was this: I never really questioned the cultural assumption that surrounded my generation when we were entering the workforce, that a career was inherently more fulfilling than motherhood.

To give this some context, I can still remember my first interview for a job in journalism on Fleet Street in London. I passed the editor my résumé. He tossed it aside, leaned forward and said: “You’re under 30 and you’re a woman and I need both of those. You can start as soon as possible on the three-month trial.”

My point is the opportunities opening up for women at that moment were historic, and my generation were thrilled to seize them.

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Fleet Street itself was still a strange mix of feminist opportunity and entrenched sexism. After work, the journalists would move, almost en masse, to the legendary El Vino, a dark, low-ceilinged, wood-paneled bar that dated back to the 1700s. Women were technically welcome. But we weren’t allowed to order drinks. Or pay for them.

Men had to order. Men had to settle the bill. Perhaps my small smattering of female colleagues and I should have responded by boycotting the tobacco-stained bar on principle. On the other hand, it was saving me quite a lot of money —though I suspect a fair amount of the receipts found their way onto expense accounts.

That contradiction captured the era perfectly. Women were being invited into the newsroom, but not quite trusted with the wine list. And the broader cultural signals were clear: the world was opening up and we should seize the opportunities. The alternative, motherhood, was dull, exhausting and faintly old-fashioned. Like a cardigan you’ve left behind.

The ambitious women in the magazines we pored over were editors, lawyers, producers, bankers, and journalists. Not mothers of four. Motherhood was something you might get around to later, once the real business of life was underway. Babies could wait. Careers, travel, ambition, independence—these were the things we were encouraged to grab with both hands.

What there wasn’t, at least in the culture I was breathing at the time, was any real suggestion that motherhood might turn out to be among the most meaningful parts of life. That you might love it. That you might actually be good at it. That a big family might bring a depth of satisfaction no promotion ever quite matches. And biology, of course, was not consulted.

That realization—my own very non-humblebrag mistake—is something I discuss in more detail in our podcast conversation:

And I would love to hear from readers about theirs. Not the cocktail-party humblebrags. The real stuff. The stuff that makes up a life.

This article was originally published on Substack. Want to read more from Joanna Coles? Subscribe to PRIMAL SCREAM.

Joanna ColesChief Creative and Content Officer

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