The Sailboat Captain Advantage

A few months ago, I admitted something scary to my coach, Dave: ”My calendar is making me nauseous."

Something had shifted after a deep spiritual retreat I attended in January.

For context, for the last 15+ years, I've kept my calendar INCREDIBLY busy. It's not abnormal for me to take 14 meetings in a day.

In the early days of Ampush, I would do meetings from 8-6 and then work ‘til midnight. I was used to working hard.

I had regularly worked 70+ hour weeks in consulting and finance.

When I started my personal growth journey, I started to dig into why I worked so hard.

And I started to learn how much of my identity and personality was caught up in "being busy."

• I grew up with a strong value around hard work. Hard work = good; laziness = bad. This value has been helpful when balanced, but when taken to the extreme, it led me to burnout and feeling like I wasn't "allowed" to take a day off. It's made it hard to downshift.

• My enneagram is a type 7, "the enthusiast." At some very deep level, I keep myself busy to avoid feeling things, especially "negative" things, like sadness and fear. If I'm busy all the time, it keeps the anxiety at bay!

• I have a lot of attachments to success (and related money and approval/status). Once I learned that hard work got me into a good college, then good jobs… I got "hooked" on it. It's served me well.

For YEARS, I've been talking about slowing my calendar down. Doing less. And how I want that to be the case. 

Earlier this year, I put in place a system where I would give each company a "day”: Monday was GA day, Tuesday Aux day, etc. It seemed like a great plan. 

Focus for me, clarity for everyone on my calendar, etc. It started off great…

…But pretty soon, it didn't feel good. By my Wednesday date nights with my wife, I’d tell her I felt like I had already worked five days!

It wasn't working for a few reasons:

1. It created scarcity for the companies so people would LOAD my calendar up so as not to "miss" their day

   

2. If I had to miss a day due to business travel or personal reasons, it made it tough on the company

3. People felt "forced" to use me, which led to them creating reasons to involve me even when I was not needed

4. It led to my getting too involved with teams, which can be disruptive for CEOs

In general, it left me less energized, plus it was creating a lot of cardinal sins for leaders. As a leader, you always want the team focused on the customer and ideally never doing things "for the leader."

Because of the rigid schedule and designated time, too much was designed around me.

I've been talking for years about changing my calendar, but this time the nausea was telling me something important. 

I was no longer THINKING I needed to make a change — I was FEELING it.

It's common in spiritual circles to talk about BEING versus DOING. I have become addicted to doing! Being is kinda scary. 

But Dave (as he does) gave me a great analogy: the Sailboat Captain versus the Motorboat Captain.

At a high level, this seems obvious, but I wanted to explore (i.e., journal in public) even more on this topic. So, I turned to my friends, ChatGPT and Google.

Here is some of what I learned:

"They’re both excellent mariners, but the mindset, skills, and leadership style required differ quite a bit because of the nature of the vessel they command."

"Sailboat captains must possess a strong understanding of wind, currents, and sailing techniques, while motorboat captains focus on engine maintenance, navigation with charts and electronics, and maneuvering in various sea conditions."

So what does this mean for leadership?

The Sailboat Leader is the CEO who:

• Reads market winds and adjusts strategy accordingly

• Makes small, strategic moves that compound over time

• Builds systems and culture that work even when the they’re not actively steering

• Stays calm during storms, knowing when to wait and when to act.

The Motorboat Leader is the CEO who:

• Sets aggressive targets and drives hard toward them

• Relies on energy, activity and direct action to move forward

• Leads from the front with high visibility and urgency

• Powers through obstacles rather than navigating around them

Both styles can work, but they require different skill sets and work better in different conditions.

Now shifting from Motorboat Leader to Sailboat Leader is a scary shift for a super entrepreneurial, doer-type like myself. But let's take a step back. 

When we look at Ampush's success, was it all my hard work and daily grind?

Or was it the fact that I figured out Facebook was going to be the next Google and made a bet on it? Ok, maybe both — that's a hard one to discern.

But the two most successful GX companies, GrowthAssistant and Aux, BOTH of them received less work/doing from me than Kahani and Unbloat. (I'd estimate I worked 3x more on the two failed ideas.) 

Meanwhile, for both GA and Aux, they were good ideas, I found great people and I was of service to them (when and how they needed it).

This feels extremely clear. Despite keeping my calendar busy, the things that have led to GX’s success have been SAILBOAT things: find the right market, partner with an amazing person, stand up the business model, use my relationships to get customers, influence culture and direction.

So I'm already being both captains, and the sailboat guy is winning. The motorboat dude is just scared and spins his wheels.

So, what does this mean for me? 

1. Creating more space

I want to create more time to think, be and learn. What does this mean? I have to say “no” more when it comes to my calendar and ensure my time gets directed to the highest-leverage stuff.

2. Prioritizing better

I met a friend who runs a holdco recently and asked him how often he meets with the customers or teams of his portcos. He looked very confused. "Never, unless the CEO asks me to," he said.

I may not get to this level, but I think it’s a great litmus test.

3. Increasing presence and love

With more time and spaciousness, I want to be fully present for any conversation or meeting I'm in — that means I bring my head, heart and gut in a fully open way. That means I ask myself, "How can I serve this person?"

4. Depth over breadth

Similar to the successes of Aux and GA, going deep on fewer things will serve me better than being shallow on a ton.

What does this mean for you?

Think of this email as a chance to reflect on your own time, decisions and results. I'm not suggesting this shift for everyone. 

If you're in year one of your startup, it’s probably a bad idea.

But for almost any leader, there are probably times when it makes MORE sense to be the sailboat captain than the motorboat captain. 

Building those sailboat skills and knowing when to use them will make you a more effective and happier leader!

jesse