The Art of a Great Question

I’m not sure if most people get scared of being “too comfortable.”

But I do. And when I feel this sensation of getting too comfortable, I know it’s time to make a drastic change.

Cal Fussman felt the same way when he was 22. Before he became a master interview. Before he spoke to Muhammad Ali, Jeff Bezos, Serena Williams, Al Pacino and 500+ others...he was living in St. Louis. He loved it... but he knew he had to leave.

And I’ll tell you why…

Tenor.

No one wants tenor at something that lacks love. (For clarification purposes, Cal wasn’t a professor or a teacher. But tenor still applies.) He knew that if he stayed only a few more years his life would be fixed.

Stale.

“I would’ve known everything that would happen for the rest of my life,” Cal said.

Why?

He was scared he’d never leave.

He realized he would be working at the newspaper, writing the same article for the rest of his life.

He didn’t see this as luck. He saw it as a reason to go somewhere else in all areas of his life.

If Cal never left, this conversation would have never have happened.

The moment he drove out of town is where his story begins...

Cal drove to New York City. Where he worked as a writer at a small sports magazine.

He told me he’d found a passion. Not a job, but a PASSION.

“This was life,” he said.

He woke up everyday wondering who he was going to meet and where he was going to go. And he’d ask himself, “What great thing is going to happen?”

“I felt like the whole city was mine,” Cal said.

He was on the ground floor of a new career. And he was being sent everywhere.

‘The Steelers are going for their 5th Super Bowl ring. Go cover it,’ his boss would say.

It was great. Until Newsweek pulled the plug.

“Did you cry?”

He needed to find a job, but where?

“Anything else would just be a job. There was no passion. No life,” Cal said.

I remember feeling like I’d lost everything (family, money, all my relationships at work). I called my insurance company. I bought a bigger life insurance plan. I was ready to kill myself.

I didn’t have a big dream like Cal. I didn’t look at the opportunity. I was stuck in the middle of a rain cloud and the light in my life continued to dim.

So I wrote it all. I wanted to expel it from my body. It went online. I posted for days. And then it became 10 years. Then it became more.

Cal found his 10 year outlet, too.

He went to Europe.

“I had this romantic vision in my head,” he said.

He had no plan. Only an idea of what he imagined it to be. And he got addicted.

“I got addicted to the feeling of not knowing. I just fell in love with this idea of waking up in the morning not knowing what was going to happen. And this was 24/7,” Cal said.

He’d gotten a taste of this at the magazine, but this was so much more.

This is how Cal got his superpower.

Let me explain.  

Cal woke up every morning with no clue where he was going to sleep that night. He needed people to take him home and give him a place to stay. After awhile he got really good at this.

“I bought a ticket. And I got on a bus not knowing where it was going. I get up the steps and start walking down the aisles, looking for an empty seat. And I know this is a crucially important decision because I gotta find somebody just by reading their face,” he said.

He had to figure out in those 30 seconds who would trust him. (And who he would trust.)

“I needed that person to invite me home,” Cal said. 

Every day, he was indulging in knowing as little as possible about how his experience was going to unfold. This was how he got passed around the world.

Because he figured out how to superconnect.

Then I pressed him. “Can ANYBODY listening right now learn this skill?” It’s a lot harder now. Especially with the endless supply of knowledge we have.

Maybe the person sitting next to the empty seat has headphones in. We’re now connected somewhere else.

How do we get back to indulging in now?

Cal started asking questions to survive.

It grew into a fulfilling career. And eventually blossomed into an expertise.

That’s how Cal Fussman became one of the greatest interviewers of all time. Now he’s interviewed an estimated 500 of the most iconic people.

He asks the question no one else is asking. And gets the best answers.He completed his initial 10,000 hours without the world seeing. By traveling, by getting by.

I think we might be losing this art of asking a good question.

What happened to the conversation?

Everything is scripted. The conversation has been replaced by the glut of media and gotcha journalism. We’ve stopped looking for the interesting story. We’re too focused on the likes and the follows.

We know all the answers now. 

“If you’re looking at the laws of supply and demand, the supply of answers is filled. We got answers up the gazoo, but how many great questions do we have? How many people who ask great questions are left?” Cal said.

Have we lost our curiosity?

Are we losing the ability to connect with one another?

I hope not. 

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