Somewhere along the way, adulthood convinces us that we should know what we’re doing before we begin. We start believing that confidence and readiness are the same thing. We tell ourselves that before changing careers, starting something new, pursuing an idea, or stepping into a different chapter, we should feel fully prepared. The problem is, when I look back at the most important moments in my life, I can’t think of many that started that way.

A few weeks ago, I had the opportunity to reconnect with a group of college friends I hadn’t seen since graduating from USC. We came together under difficult circumstances. One of our fraternity brothers had passed away unexpectedly, and for many of us, it was the first time we’d been in the same room in more than thirty years.

What surprised me wasn’t how much had changed. It was how much hadn’t.

Within minutes, the same personalities emerged. The same stories resurfaced. The same dynamics that existed when we were eighteen years old somehow found their way back into the room. As the evening went on, the conversation drifted back to those years and the decisions that felt so significant at the time.

What struck me was how many of us shared the same memory. We all thought everyone else had it figured out. We assumed the people around us were more confident, more certain, and more prepared than we were. Looking back, it’s almost funny. The people I viewed as confident admitted they were just as unsure as I was. The people who seemed to have a plan were figuring things out one decision at a time.

Sitting there thirty years later, I realized that what I had mistaken for readiness was often just movement. People weren’t acting because they felt prepared. They were acting because life kept moving forward, and they moved with it.

That realization stayed with me because, over the same month, Stella had wrapped up her semester abroad in Copenhagen while Gigi just finished her first year at NYU Tisch. Watching both of them navigate those experiences reminded me how much uncertainty we expect young people to embrace. One moved to another country. The other moved across the country. Both spent their time navigating situations they had never experienced before.

And yet, at no point did I expect either of them to feel ready.

How could they?

There is no amount of preparation that fully prepares you for living abroad for the first time. There is no guidebook that tells you exactly how to build a life in New York City at eighteen years old. The experience itself is what teaches you how to do it.

What strikes me is how willingly we extend that grace to young people and how rarely we extend it to ourselves.

Somewhere between college and adulthood, we stop seeing uncertainty as part of growth and start treating it as evidence that we shouldn’t move. We assume that if we don’t feel ready, we aren’t ready.

But those aren’t the same thing.

Looking back, I can think of plenty of moments when I felt confident enough to take the step. I can’t think of many when I felt ready.

Moving to New York. Starting my own business. Getting married. Becoming a parent. Taking on leadership roles. None of those chapters began with certainty. They began with enough confidence to begin and enough trust to figure out the rest along the way.

Confidence says, “I’ll figure it out.”

Readiness says, “I already know how.”

One moves your life forward.

The other is one of the great illusions of adulthood.

“Your 50” is a 50-week reflection series about realigning, activating, and expressing what comes next.