What makes someone look cool?
Think about someone cool. Maybe a friend, a classmate, a relative, a celebrity. What made them look cool?
I’d never really thought about this until I took my first surfing lesson.
I was at a work conference in, of all places, Hawaii. I generally find the big, convention center conferences a waste of time so I seek out smaller, more intimate ones where I can learn and discuss things directly with others in my field. This one just happened to be in Hawaii, so how could I not go?
The first day was everything I’d hoped for. Despite my jetlag, I was fully engaged and couldn’t write fast enough in my notebook all the ideas I wanted to bring back after.
The morning of the second day was open and we were encouraged to explore the area. I decided to take a surfing lesson. I’d never surfed before. What better place to start than the white sand and blue water of Hawaii?
I showed up at the location with one other brave conference attendee. There was a tiny beat up shack near the beach with some sand covered surf boards leaning against it. It seemed like the meet up spot.
A tall, thin man in board shorts and a rash guard shirt emerged with a cup of coffee in his hand. “I’m Lenny. You guys doing the lesson?”
Aside from being a bit older than I expected, Lenny looked exactly the way I pictured a surfer. Long, sun bleached hair. Tan, leathery skin with faint, sunglasses-shaped stripes wrapped around his eyes.
He handed us our own rash guards and pointed us to two surf boards laid out on the sand. We told him neither of us had ever surfed before. “OK, let’s go over the basics”, he said.
“The most important thing to remember when you are surfing is to look cool.”
We both laughed, figuring this was his go-to surf instructor joke. His face didn’t change. He was serious.
Then he proceeded showed us the basics — how to lay down on the board, where to place our hands and feet and how to paddle. He showed us how to pop up on the board by placing one foot forward and swinging the other through. Then came the “look cool” part.
“When you pop up, keep your eyes on the shore and your knees bent. Do it cool.”
There was that word again. I wanted an actual lesson, but he kept talking about looking cool. What did that even mean? Why would I worry about looking cool as a first time surfer just trying not to fall off my board?
I ignored the cool part and focused on the handful of actual surfing advice he gave.
We walked our boards out to knee depth, hopped on our bellies and paddled out. He swam effortlessly alongside, talking about everything but surfing. He’d been in a band. He moved here from San Diego a few years ago. His son had just graduated from college.
I wondered how that information would help me surf.
He spotted the first wave and pointed me toward the beach. When it got closer, he told me to start paddling, then gave my board a firm push. I paddled as hard as I could.
“Pop up!”
I tightened every muscle, swung one leg forward under me, the other leg in front of that one. I gritted my teeth and tried to lock my body to the board. Then I fell off. The board flipped over my head and the strap attached from the board to my ankle pulled me in every direction. I’d failed my first attempt. I gathered my board and proceeded to paddle back out to Lenny.
“You gotta do it cooler, man!”
That’s it? That’s what you tell me?
I was annoyed and wondering how I could get my money back or find a different instructor when Lenny pushed me into the next wave. Same result. I fished my board out and paddled back to Lenny.
“Look man, when you pop up, keep your eyes on the shore and do it cool.”
I ignored him and stuck with my approach of trying to muscle my way onto the board, falling off every time.
Finally, mostly out of muscle fatigue, I tried it his way. I let my body relax, sunk into my stance, totally present in the moment, pretending to look cool. I cruised all the way to the sand and looked back at Lenny. He was pumping his fists in the air.
I paddled back out. “That was cool!” I said. Lenny high fived me and pushed me into the next wave. Another success.
After many more successful pop ups, I walked back to my hotel, trying to unpack what had just happened. I thought about cool people. Denzel Washington was cool, but why? The Fonz from Happy Days was cool, but why? Ken Griffey Jr. was. cool, but why?
Every cool person I could think of had three qualities. They looked relaxed, confident and fully present in the moment. They didn’t seem to be worrying about the past or the future. Could it be that simple?
Supposedly if you smile, you instantly feel happier. Maybe coolness worked that way?
I’ve thought about Lenny a lot over the years. Every time I felt nervous about speaking in front of a crowd or trying something new, I’ve tried to do it cool. It helps me stay in the moment. It gives me confidence. It helps me relax. It’s a surprising hack that’s served me well.
Next time you are nervous about something, take Lenny’s advice.
“Do it cool!”