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How Entrepreneurs See Their Summer Vacations

This post is written for entrepreneurs everywhere. Vacations for entrepreneurs are critically important. I’ve started to view my summer vacation as an annual benchmark that helps me see the progress in my business growth.

Author: Jeremy Harrison

Updated: July 2, 2019

When we were first married, my wife and I headed to the Outer Banks of North Carolina as newlyweds for a week at the beach. That summer beach week has turned into a beloved annual tradition. It’s a great chance to shut it off and relax, read books in a comfy beach chair, and basically do nothing for a week.

But since starting my small business in 2006, I’ve viewed my summer vacations a little differently. For an entrepreneur, it’s not “paid time off” like you’d enjoy in a typical job. Right?

Vacations for entrepreneurs are critically important. Your business can quickly consume you, as it has for me too many times over the years. Without seasons of rest, you will burn out. 

My summer vacation has sort of become an annual benchmark that helps me gauge the progress in my business growth. 

Here’s a timeline of my first several beach vacations after launching my startup… 

2006 – YEAR #1

My business was four months old, and I was a solo operation. I went on vacation after pushing through a huge project that consumed several weeks of my time. I got paid for my work, then we immediately left for our vacation. Since I had been so consumed with completing a huge project before vacation, I hadn’t been doing sales activity. When I returned, I was running out of cash quickly and didn’t have enough work secured. My mailbox was empty, my checkbook was emptying, and I was afraid I was going to have to shut it down just four months after starting the whole thing! Oops! Needless to say, more work came, but I think I probably sounded like a desperate salesman for a while after getting back from my first vacation as an entrepreneur.  🙂 

2007 – YEAR #2

Went on vacation and had my first full-time employee, one month into his job.  He was designing and coding sites while I was gone. My work in sales and project management stopped. But unlike 2006, it was nice to know we were doing billable work while I was away, so I could resume projects upon my return and bill for finished work.

2008 – YEAR #3

Went on vacation and had both a designer and a project manager moving projects forward. Only the sales and billing activity stopped, but 2008 was so much better than 2007. 

2009 – YEAR #4

Went on vacation and had all those folks from 2008 keeping things humming, plus an office manager doing billing—I was the sales guy at the time, and my sales activity took a much-needed break. 

2010 – YEAR #5

Went on vacation and had a newly-hired sales guy bringing in new sales while I was away… FINALLY everything kept running and I think they probably got more done without me there!


Entrepreneurs, enjoy vacation.Ever since, the complexity of the business has grown, but the capability of our amazing team to handle it has grown even faster.

In fact, I’ve found that when I’m on vacation, our cash situation always gets unexplainably better. It’s a running joke at the office. Big sales get closed, and big project invoices get finished and paid while I’m shut down. It’s awesome.

Our office manager used to joke that maybe I need to make a monthly trip someplace so our cash keeps flowing at max speed. Do you think she’s trying to tell me something?  🙂 

This post is written for entrepreneurs everywhere.

Wherever you are in this timeline, take time to shut it off and ENJOY VACATION! You’ve earned it. 

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