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Leadership & Letting Go

Leadership & Letting Go

I’ve been a fan of all things nautical my entire life. Bodies of water, and the vessels for traversing them, give me a sense of unending potential for exploring and creating. The sailboat in particular captures my fascination, harnessing wind and waves, to push through open water.

In early 2016, I flew to Puerto Vallarta to take a week-long, basic keelboat certification course. Each day, we sailed out onto the Bay of Banderas, and my instructor, Shawn, taught me each part of the boat, all the points of sail, as well as how to tack, jibe, perform water rescues, and dock. Each night, I’d read and study the manual, learning all the knots, sailing rights of way rules, and nautical terminology.

By week’s end, it was time to take the certification exam, both on the water and on paper. When I aced the exam, Shawn suggested we go out for a celebratory sail and bring along the Spinnaker sail for extra fun.

Once out on the water, Shawn rigged up the Spinnaker (which looks sort of like a half of a giant balloon), while I tended to the tiller. Shawn looked back over his shoulder and said, “Things are about to get really interesting!” I remained completely relaxed and confident, having no clue what he meant.

The moment the wind filled the Spinnaker, the boat keeled over far to my right. I scrambled to get on the high side of the boat so I wouldn’t be dumped out. I grabbed the tiller with a tight grip, trying to control what was happening. My brain shut down, flooded with fear.

Shawn looked back at me and yelled, “Stop trying to control the boat! You are gonna capsize us!”

I had no idea what to do.

“Loosen your grip on the tiller. Open your hand, and let it bob back and forth inside your hand. Feel these waves. The boat will tell you what it wants to do.”

As a Class A Control Freak, this ran counter to every instinct in my body. I knew if I didn’t do exactly as he said, though, we would be in danger.

And so, because I had no choice to do otherwise, I let go. I 100% surrendered.

I sank into feeling the waves running beneath the boat, rising and swirling, pushing us this way and that. The tiller nudged me like a puppy to follow its lead. As I dropped into letting go, the boat immediately responded. It felt like we were surfing on the wave tops, smooth and fast.

Leadership & Letting Go

Shawn yelled up at the sky, “You’ve got it!”

Up until that moment, I had only intellectually understood what surrendering meant. Now I knew what it felt like in my cells.

Not unlike the boat finding its true power and stability over rough waters, I now had muscle memory for how to stop directing, controlling, or demanding certain outcomes. The only way forward is to let the boat (or the situation) tell me what it wants to do or be.

I’m coming to understand more each day just how much the ever-evolving and changing “Now” wants us to relax our grip on our predetermined destinations. This doesn’t mean that we sail in circles without any sort of a charted course. Rather, if we engage with our curiosity, responsiveness, agility, and creativity, we find ourselves leading from our core, not our clipboard.

Ultimately, this builds trust, engagement, and community among those in our organizations, teams, and enterprises. And even more importantly, we begin to have the kind of crucial conversations that coax true innovation and new thinking to the fore.

As wildly uncomfortable it is for me, embracing not knowing and releasing prescribed agendas connects me to the best version of myself and opens doors to synchronicity. It signals a playful energy to the Universe, too, which answers our courage and openness with evidence of magic made manifest.

Filed Under: Leadership

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