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Taking Time Off From Work: The Best-Kept Secret To Growing Your Business


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How To Grow Your Business By Working Less with Casey Cheshire

Many entrepreneurs start out as a one-person show. They wear every hat, from bookkeeper and maintenance manager to salesperson and head of HR.

And it’s our experience that many business owners get so used to doing it all, even once the business is running smoothly, they’re convinced they still have to run the whole show.

At some point, though, they hit a ceiling. You can only work so hard and so long before your energy plummets and your business plateaus.

They’re tired, distracted, unproductive, and their creativity has fallen by the wayside. On the personal side, weekends and family holidays, friends, and favorite activities and interests have long since given way to work.

How do you stay on the growth track but get back your personal time?

It’s called a Free Day.

Dan Sullivan, Strategic Coach founder and creator of The Strategic Coach Program, says Free Days are the first step to entrepreneurial growth and success.

One of the first building blocks entrepreneurs learn when they come to Strategic Coach is a time system that’s designed specifically for entrepreneurs. It’s made up of three types of days, each with its own purpose: Free Days, Focus Days, and Buffer Days. But the most important one is the Free Day.

Unlike most time systems, our Entrepreneurial Time System is designed around the fact that in order to have high energy, to be focused on what’s most important, and to be creative in all your thinking, you must be well rested and have a clear mind.

Taking a Free Day doesn’t happen when you’re exhausted, or even just tired. It happens when you’ve scheduled, planned, and protected your Free Day so it truly is free—and then you actually take it.

Discover more about The Entrepreneurial Time System® that Casey Cheshire learned in his first Strategic Coach workshop and made his immediate focus — with immediate results. Download your free copy of The Strategic Coach Approach to Time Management.

Here’s how it works.

A Free Day is a 24-hour day from midnight to midnight, where you take time off from work—no business-related activities like checking in with the office, no email or phone calls, not even business reading.

Free Days are solely for activities that relax and rejuvenate you. For some people, it’s reading or going to a great movie and out for dinner. For others, it’s hiking or biking or a day at the spa.

You can imagine that once you’ve got the hang of taking true Free Days, the natural result is that you’ll be more creative, more focused, more productive, more confident—and a whole lot happier.

Time focused on the right things.

New to Strategic Coach, Casey Cheshire runs Cheshire Impact, a consulting firm in Nashua, New Hampshire. They help clients maximize their marketing automation and better manage their customer relationships, and as Casey says, “We have a blast.”

With his company firing on all cylinders, Casey still felt like he had a handle on taking time off from work. However, it was crystal clear to him that he personally could be doing so much more to grow his business by making the best possible use of his time. He knew that real growth could only happen if his time was focused on the right things, which needed to be planned out and scheduled—and the schedule had to be “king.”

Casey knew he needed a system.

Always be intentional.

At the recommendation of a friend and mentor, Casey signed up for The Strategic Coach Program. In his first workshop at Strategic Coach, Casey was introduced to The Entrepreneurial Time System, and he started to think about how he could use it to transform his “time dilemma.”

He learned about the three different types of days and, to his surprise, that the first and most important type of day is the Free Day—taking time off from work.

It took a bit of a shift in thinking, but the idea of taking Free Days before a big project, meeting, or presentation in order to be fresh and at his most creative resonated with his plans for a much bigger future—and in light of this, with his goal to make the best possible use of his time.

Casey had also noticed over the years that people who are really successful are exceptionally intentional about everything, including their time. He made the decision that his focus for the next 90 days until his second workshop would be on Free Days. He would take them seriously—and intentionally.

“The most intentional people win,” Casey explains.

Theory into practice.

Shortly after his workshop, Casey planned a family vacation to Disney World with his wife and kids.

“I had always felt that I was pretty good at taking time away from work, and everything was going well until the day I decided I was going to make one phone call. Just one call. What could go wrong? Well, it ruined the whole day—for everyone. I was upset by the call. My family was mad at me.

“Luckily, we salvaged the vacation and the call didn’t ruin everything. But I remember thinking, ‘Wow, that was only one phone call. How could that possibly happen?’ Well, I broke the rule. It was a hard but valuable lesson.”

Practice makes perfect.

Dan Sullivan, when he heard Casey’s story, gave him full marks for setting the whole vacation up properly to have great Free Days, but Casey made a common mistake.

The voice of experience, Dan explains, “Casey took one phone call, and that took him right out of the magic of Free Days.

“When you say you’re going to have a Free Day, but then you say you’re going to take just one phone call, it never works. It isn’t just five minutes. You’re thinking about it for a couple hours beforehand, then if the call doesn’t go the way you want it to, you’re thinking about it for the rest of the day, or longer. I’ve heard the story hundreds of times, and it’s always the same story with the same ending.

“When you’re on a Free Day, be completely free. That’s a true Free Day.”