365 Squarey Monsters: What If You Just Said Hello?

Sunday, August 16, 2026

What If You Just Said Hello?

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Finding the Courage to Say Hello

A few nights ago, I walked into a cocktail party where I knew only a handful of people and did something that once would have made me very uncomfortable: I introduced myself to strangers. By the end of the night, those simple hellos had led to conversations and connections I never could have anticipated.

Starting a conversation can feel intimidating, especially with someone we don’t know. But conversation is a skill we can practice — and in a time when so many people are hungry for connection, being the person willing to say hello matters more than ever.

👉 See how great connections start with a conversation

Becoming an Ex-Shy Guy

I was a shy kid, and my first retail job at Dadsons haberdashery in Queens was a frontal assault on that shyness. Selling clothes forced me to approach strangers, make them comfortable, and learn how to gab — sometimes with a little humor to break the ice. Those lessons followed me to St. John’s Home for Boys and, eventually, to my first flower shop.

The simple skill of starting a conversation has shaped much of my life. A stranger can become a customer, a customer can become a friend, and a brief conversation can become a relationship. But someone has to start it.

👉 How a shy kid learned the value of saying hello

What makes us happy, successful, and fulfilled? After a year of conversations with fascinating thinkers and leaders, one answer keeps coming back: relationships. In the second installment of Power & Impact’s Leadership Lessons, I revisit conversations with David Brooks, Arthur Brooks, Dan Ariely, and John Rivers about how connection shapes our happiness, our outlook, and the lives we build. Listen to The Relationship Advantage.

IN CASE YOU MISSED IT: When we hear about a medical breakthrough, we rarely think about the years of work that made it possible. Andrea Lopez lives that process every day. In last week’s Celebrate Your Story , she shared her remarkable journey into cancer research, explained how CAR T-cell therapy is changing lives, and discussed why great mentors can change a career. Watch our conversation.