You're Asking the Wrong Question

Ask this one instead.

My family and I were sitting in an Italian restaurant in Turks & Caicos, where we’d flown to spend some time together in the wake of publishing Save Your Asks. It was pretty deserted in there, and the wait staff was mostly standing around, clearly counting the minutes until they could go home.

But our waiter—he was different. An amazing name, I thought, as I read his name tag: “Johnly.” He had the biggest smile, and I could immediately feel his energy. My wife, Julie, and our daughters were equally enthralled with Johnly. We started talking, and as he brought our various courses, we were in what I call the race to the middle, which is how fast and effectively you can find common touch points between you and the other person. I learned Johnly came to Turks from Haiti to get his degree in hospitality and is one of 11 kids and now has 3 jobs.

By the time dessert rolled around, I knew I had to ask it. I knew I need to go there. The most important question you can ask the person sitting across from you. I said, “Johnly, we’ve gotten to know each other pretty well here. I want to hear from you. What’s your dream?”

Yes, this is the most important question to ask for a genuine connection: “What’s your dream?”

Not “What do you do?” That’s the worst way to open up a conversation. Most people don’t actually enjoy what they do, and are trying to untether their identity from their jobs. And for whatever reason, we forget our dreams, we don’t know what our dreams are, or we don’t believe that pursuing our dreams can actually be a way to live. We find ourselves making uncomfortable small talk, failing to tap into the universe of opportunities that can explode before our very eyes when we truly connect with each other.

If you feel the energy with another person, it comes down to this one question: “What’s your dream?” Or it can be as simple as, “What fires you up?” Once you get to that point, things change. Walls come down.

Anywhere I go, it can happen. I feel the energy, and I get to that question. And it’s not just business connections; I might have an interaction with someone at the grocery store. But it was my interaction with our waiter in the Turks & Caicos that was such a profound moment for me. It helped me figure out that my purpose has evolved to be much bigger than just inspiring connecting. It's actually more nuanced: my purpose is to help uncover people's dreams and then to become a catalyst in them pursuing those dreams.

“Mr. Chris,” Johnly said, “I’m gonna tell you. I have two dreams. My first dream is to save enough money to buy a plane ticket to go back to Haiti to see my mom and family. My mom, she is not doing that well health wise. And my second dream is to move to the U.S. and work in hospitality.”

As he went to get our dessert, I turned to Julie and said we had to make the first dream a reality. When Johnly returned, I said: “I’m going to take care of your ticket to Haiti. So you can focus on your second dream.”

Johnly burst into tears and told us how grateful he was. Several months later, Johnly and I text nearly every single day. I’m working on the visa for him to work in the U.S. What’s in it for me? I truly want to make dreams a reality for people.

You don’t have to buy a plane ticket for anyone. You don’t even have to buy a cup of coffee. But when you allow your heart and your mind to open up to the limitless possibilities of this life, you begin to see connections. They’re electric. So when you begin to feel that energy from another person, ask them their dream. Ask them what fires them up, and see what happens.