Four Leadership Lessons from my Last Surf Session of 2022
It was Boxing Day, a day for family, but the swell and tide made it perfect conditions to surf a secret spot along the Pacific coast south of San Francisco. I hadn’t been able to make the last outing and had been envious of my friends’ stories of the long rides on this isolated break. The clincher for my decision to go? … the spot is named Dragons.
Lesson One: Find Your People (… who make you better)
I’ve surfed with these friends for years, a group of designers, data scientists, and tech people with a shared love of the ocean. One of us had a passion for finding secret spots. He researches and scopes them out for years and then, when the conditions are just right, he’ll suggest a field trip. We’ve been known to rappel down cliffs in search of the best, most uncrowded wave. We share an easy camaraderie, the ability to catch up with each other’s lives and work even if it’s been months since we’ve seen each other. And we share the thrill of watching others catch a beautiful wave or wipe-out in a punishing hold-down.
I’m the worst surfer in the bunch, amongst the oldest and the weakest physically. Yet surfing with these friends makes me better. They keep me going when it’s hard to motivate getting up at 5am and pulling on a wetsuit to jump in the freezing Pacific.
There’s never a bad session… even if you can’t make it out to the lineup through pounding Ocean Beach waves or when you get skunked. These are my people, my tribe of crazy adventure-seekers. Surfing with them pushes my limits, and expands my horizons to try secret spots.
So look for the people like you, who support you in new adventures and bring out your bravest self. And hope that you too make them better.
Lesson Two: The Best Way to Get from A to B Might not be a Straight Line
That secret spot, Dragons, is a reef break. You sit at the take-off point and choose to go left or right down this peaky A-frame. The best surfers ride down the line and then paddle back around to the starting point. I mostly wipe out and end up in a pile of whitewash maybe a swimming pool’s length away from the take-off point. The seemingly fastest way back from point A to B is a straight through the whitewash. But paddling against heavy whitewash is like being on a hamster wheel of continual exertion with zero movement. The only way to get back is to paddle sideways, away from the whitewash, towards a channel of clear water that gets you back to the takeoff point.
This is counter-intuitive. When I’m in a panic because I’ve just wiped out, I often keep hopelessly running in place trying to take that straight line from point A to Point B. After 5–10 minutes of struggle, the self-awareness usually kicks in and I try another path rather than single-mindedly pursuing a dead-end path.
So, if the shortest, most direct way doesn’t seem to be working, take a pause, consider the range of perspectives and and make a different choice.
Lesson Three: Ocean Conditions are Unpredictable
That day it was a big swell, big enough so that the nearby Maverick’s legendary break was going off. But it was long period, which means that there is a long time of waiting through placid waters before the next set of waves comes through.
The conditions changed drastically that day. In the span of 30 minutes, I was:
Fighting my way through endless whitewash
Frantically duck-diving the front face of a towering wave to make it through to safety on the other side
Sitting around shooting the shit with my friend, admiring the sunrise sky, and maybe starting to get a little bored
The ocean is a shapeshifter. Yet you have to stay on your toes because the conditions might change at any moment. This is similar to leadership in a chaotic, modern world. We believe we have some semblance of control, yet the only thing we have control over is our ability to keep on going / trying and our own mindset. Everything else is unpredictable.
Lesson Four: Focus on the Process, not the Outcome
Many people have a vision of surfers up and riding down the line, effortlessly controlling the board as they fly through the water. But that day, I was skunked and got zero waves. I was exhausted after the long paddle out from shore to reach the faraway reef, and then churned by too much whitewash.
Yet it didn’t matter.
What stays with me is sitting by the mysterious take-off point seemingly in the middle of the ocean. It was a boil of water that gurgled, hissed and spit like an underwater dragon trying to send us secret messages, the namesake of this Dragon’s spot. It started out eerie, but soon became comforting as the boil marked the take-off point where we’d paddle back towards the consistent A-frame wave.
I’ve spent many years of my life and work focusing on the outcome — that OKR, that promotion, that job offer. And time after time, I remember the feeling of accomplishing the outcome and still feeling empty. Often I would reset the milestone and move the goalposts in pursuit of the next outcome. Instead, I now try to focus on the process. The beauty of paddling out to a new spot and staying present to the dragon’s hissing. Or the continual learning that often happens with each new work project or each new boss.
That last surf session at Dragon’s was the most apt wrap-up for this year of growth where my intention for the year was, courtesy of Hamilton, ♫ I will always be satisfied.♫
I wish you the most satisfying of 2022s as we collectively look forward to dreaming in 2023.