Out to sea – From fear to the mischief of loving it

In addition to my role as Chief Mischief Officer, this week I am part of a delivery crew sailing a 50 foot
Beneteau from Charleston, SC to West Palm Beach Florida.   
As a member of the crew I had to perform my
duties to the best of my ability and to support every other member of the
When we left at sunrise on the Friday after US
thanksgiving the temp was in the 30s, the Ashley River was busy with container
boats and the swells were from 9 to 12 feet. 
A member of our crew was understandably seasick.
Our Captain focused on getting us safely thru
the channel, steering clear of container ship traffic, and for a short time we had to leave the narrow
There was a moment where I
started to think of our crew, this adventure and compare it to my business

Just like a start-up there are moments where you
feel so out of control, one of your more seasoned leaders gets sick and
everyone picks up and supports each other… and you truly wonder if you will
make it and why you chose to do this. 
Yes, both at sea and in business the feeling of
helplessness can be quite overwhelming.
With 4 layers of clothing on, wrapped in
sleeping blankets, safety briefing completed, we took our individual
As we journeyed south we each persisted on
course most of the time.  As we sailed
thru Georgia the weather subsided and the swells dropped to 4-6 feet.  We all moved from concern and ill ease to
well being.  Hmmm…  the same feeling after you
raise your first round of funding or close your first few deals.  Yes it seems we are going to be OK after all.
After my 1AM to 3AM watch I journeyed down to
the main cabin for some seriously needed sleep. 
I wondered how my flat lander belly would do and much to my delight the
rhythm of the rolling seas lulled me into a delicious sleep. My final thought was
“wow, I am going to be a good first mate”. 
It was like my first CEO journey, when I
realized I knew and could do much more than I have ever been tested to do
before.  I fell asleep in awe at the
capacity of human beings, individually and in teams.
Saturday morning now 45 miles offshore from Saint
Augustine, our team is well.  Everyone is
rested, performing their duties, sharing stories. 
Our little crew has a new level of camaraderie
and capability and we are only half way thru the journey.  Fear has turned to enthusiasm and love for
our adventure.  I experienced a whole new
way of contributing and communicating. 
I tested my physical and emotional strength and
I know I’ll be a much better
business leader and friend from this experience.  
This experience was a delicious chance to become a better
version of myself – mischief at its finest.  
1028 AM ET Saturday November 29th.
Chief Mischief Officer and sometimes first mate.
Scroll to Top