5 Unexpected Lessons Learned on My Chesapeake Bay Sailing Vacation

My wife and I just ended a sailing vacation with friends on the Chesapeake.  As a responsible entrepreneur, I was planning on working a few hours daily.  I planned to wake up early,  check in on things and disconnect to enjoy the rest of the day.

Very little went as planned.  On day two of my trip, I woke up early to get things done and discovered my laptop died.   It put me into a a panic.  Now as I look back on it with my new laptop fully configured,  I have to admit that:

• My business did OK given I wasn't available.
• My clients are NOT in an uproar.
• I had me a little fun.

Here's what I learned from this experience.

Lesson 1: I need to leverage my team better.

This was a working vacation by design.  Given what I have in the works, I don't yet have the luxury of completely disconnecting.  At the same time, I expect way too much of myself.  I schedule myself for too much with or without a vacation and don't put my team to task the same way.

The laptop breaking aggravated the situation.  The last four days of my trip, I couldn't get online.  What I know I need to do is admit my shortcomings and identify what I can have others on my team do.  It's so obvious, but after all these years, I still don't delegate enough.  I haven't struck the balance between what I can and must do, and what I should be assigning to my team.

Lesson 2: I have a really good team.

I have a very capable team.  My top team member Danica's been with me five years.  During this time she has learned a lot and I have learned that there are things she does a lot better than I do.  As soon as the laptop died, I jumped on the phone with her and assigned two urgent task that needed to get done right away. With little explanation, she took them on and both got done.  Then I went through the rest of the list and assigned them to her to get done or to assign to other team members.

You know what?  Just about everything got done.  I had a few customers that experienced delays, but nothing became a crisis.

Lesson 3:  I have really good (and understanding) clients.

I hold myself and my team to very high standard, but sometimes I pretend I'm the online marketing superman.  I act as if I had 24 hours of daily productivity and I find myself saying, " "Of course I can get that done right away." too often.  That's so stupid.

There were several clients I had to call and explain the situation.   In every situation, they were understanding.  Things outside our control happen and given that we normally deliver as expected, they saw this as the exception.  And they appreciated that I had a plan to get their issues address with a "Plan B" that met their needs.

Lesson 4: I need to behave more like a CEO.

One on my college buddies on the trip with saw what was happening and asked me a few questions about how I run my business.  He's known me an long time and very quickly said, "You need to start acting like a CEO."  He was right.

All to often, I'm the one rolling up my sleeves reviewing websites, configuring automated email  sequences, and doing the work myself.  I have to put a stop to this. I have do a very capable team.  I need to enlist them to change this.  In the past, I have done this and they have eagerly jumped in to do the work.  There's no reason why they wouldn't do it again and further replace what I'm doing today.

Lesson 5: I need to enjoy my vacations more.

My vacation's behind me and I do feel refreshed.  I slept in my own bed again, feel good and like that I'm back to my regular routine.  The vacation did what it was supposed to do.  It got me out of my head sharing time with my wife and friends.  It recharging the batteries so I can return to work rested and at my most creative self.

Let me know what you are doing to delegate and make your business even less dependent on you than it is today.