What I learned about leadership from 1 week at sea with 7 entrepreneurs

What I learned about leadership from 1 week at sea with 7 entrepreneurs

By Nathan Seaward

Last week, Derick Deal and I lead a group of powerful entrepreneurs on a sailing trip through the Greek Islands. Here’s what I learned.

1. People want to be lead and I love leading! I used to have a story that it wasn’t ok to love leading. That it somehow meant you were power hungry or domineering or something.
What I discovered was, I love leading and that’s ok. People want to be lead and I’m a good leader.

2. Vulnerable leadership still feels scary as shit. As someone who has all of their darkest secrets splayed out across the internet, I thought I would be comfortable with vulnerability. But it’s called vulnerability for a reason. It’s always uncomfortable.
I chose to lead by being open and vulnerable. That meant sharing when I didn’t know how to lead people in a particular moment. It meant speaking up when I was struggling with someone’s way of being. It also meant yelling direct orders in the moment when something on the boat had to be done immediately. All of these were inherently uncomfortable but powerful forms of vulnerable leadership.

3. Pilots are leaders. By definition, a pilot leads a plane, it’s crew and its passengers from one place to another. It involves holding a bigger picture of everything that’s going on around you and deciding what needs to be focussed on in each moment. We call that situational awareness. It also means listening to and sharing just the right amount of information with the right people so they can feel safe and perform their role effectively.

4. We all need more adventure in our lives. To me, adventure is doing things where you don’t know what’s going to happen. Everyday on our sailing trip, we set off on an adventure, not knowing what might happen or where we were going to dock for the night. It was so exciting for everyone. It’s a reminder that in your business, you don’t need to know what’s going to happen next and that’s what makes it fun.

5. Powerful structures allow magic to happen. We created a number of structures for the week. The first: We encouraged everyone to eliminate or minimise their phone use for the week. Second: Everyone had to be on the dock, ready to go at 6.45am every morning. Derick lead everyone through 1 hour of physical activity and then I lead a 1 hour meditation. We then took some silent reflection time and shared our insights over breakfast. That meant everyone had done 5 hours of PT and meditation by the end of the week. Third: Set some agreements. On the first day we discussed how we wanted people to show up. The fact that on a boat, things always go wrong and that’s ok.

This powerful container allowed the magic to happen naturally. Deep connection, open conversations and a shit ton of fun.

6. Learning how you learn might be the most important thing you ever discover. 
My lowest form of understanding is via audio. If you try to explain something to me just by speaking to me, you’ll see my eyes begin to glaze over. Derick has learned to spot this and finds it hilarious.

Here’s how I learn:
– Watch somebody do the thing.
– Try the thing myself. Make mistakes.
– Sit down quietly and read more details about how to do the thing.
– Try again and perfect the thing.
– Teach somebody how to do the thing.

Sailing gave everyone the opportunity to explore their own learning styles.

Teaching people how to sail allowed me solidify the concepts for myself.

7. We are drowning in information and starving for connection. Everyone commented how much they loved the community feel that was created on the boat. Some said they’d been looking for this type of community their whole life.

It was a place where you could share without judgement. Have deep and vulnerable conversations at any time and not be shutdown.

I believe this connection was created by taking away a lot of normal stimuli. The phone, the news, work problems, emails, family disputes. We are drowning in information.

The reality is, we had 7 people living in an intimate, tight, messy environment for a week. There was nowhere to hide. No place to avoid intimacy and connection with others. No way to numb out and distract yourself.

We created a good old fashioned hang out with a bunch of cool people and their hearts and souls began to sing again.

Derick and I had a hunch that adventuring with a group of powerful people would create something special. We were right.

Our next adventure begins in Northern Norway on October 16th and will be co-lead by the powerful Shelley Paxton, former CMO of Harley Davidson.

If you’re interested, reply to this email with “NORWAY” in the subject line.

P.S Whenever you’re ready . . . here are 3 ways I can help you create an extraordinary life:

1. Join my Community of Game Changers

For the past year, i’ve been curating a community of game changers. Entrepreneurs and coaches who want to impact people and the planet in new and innovative ways. We are a supportive group committed to deepening our missions and lifting each other up when things get tough. If you’re interested in joining, contact me now for more information.

2. Come on an adventure
From sailing the Mediterranean to safariing through Africa, I love to take people on adventures! I believe that adventuring stimulates us in new ways, helps us grow and gives us more connection everyone. If you want to join my next entrepreneur adventure, check out the adventure section now

3. Work with me privately
It’s no secret that the best way to create an extraordinary life and business is to work directly with someone who’s already done it. I’m looking to work with an entrepreneur that’s ready to become world class in everything they do. Is that you? Learn more here