Time off is an important part of time management.

2 Strategies For Taking Effective Free Days as an Entrepreneur

Dan Sullivan
6 min readFeb 20, 2020


Do you find it hard to transition between Free Days?

Do you have trouble removing yourself from your business, even for just 24 hours?

If so, you’re not alone. As entrepreneurs, we often get so caught up in our work that it becomes difficult to fully detach on days off. I call this phenomenon the “Free Day Flip,” where we are forced to go from “work mode” to “couch potato mode” overnight. Turns out that’s easier said than done.

The importance of Free Days

Strategic Coach is unique in that it is one of the only coaching services for entrepreneurs that truly focuses on time spent not working. And one of our core principles around time management is the concept of Free Days

For those that don’t know or that need a refresher, a Free Day is a 24-hour period (from midnight to midnight) where you do absolutely no work. The core purpose of a Free Day is relaxation and rejuvenation.

To the average person, this might seem straightforward. But for entrepreneurs, this may pose a challenge. It can be difficult or close to impossible to fully remove yourself from your business for even 24 hours. And while it might seem trivial, the importance of taking time off truly cannot be understated…

Contrary to what some entrepreneurs may think, Free Days actually allow you to be more productive with your time overall. I’ve been taking 155 Free Days each year for 30 years, and I find that I am so fresh when I get back to work that I am super productive. I’m able to accomplish far more than I would have if I kept working day in and day out.

(And yes, you read that right — I take 155 Free Days per year. That’s 22 out of 52 weeks of the year, and I get more done each year than I did before I started this routine.)

I’ve also found that Free Days give me perspective on what is truly important and urgent in my business. Entrepreneurs often feel like everything they’re doing is urgent and necessary. I used to feel that way too, but it’s often untrue.

When I first started Strategic Coach, there was a moment where I had planned to take two weeks off. I wanted to cut it down to one week because I had some work that I needed to finish, but I decided at the last minute to go ahead and take off the full two weeks.

Before I left, I wrote down everything I had planned to do in that one week timeframe on a slip of paper and put it into a folder. I had about 15 things on the list. I left for the two weeks, and when I came back, I realized that almost three quarters of my list was completely irrelevant. I no longer needed to do those activities, they were no longer important, or someone else had done them for me.

That left me with three tasks that I actually had to complete immediately. I got them done that day because I was refreshed and ready to be productive. Taking that extra week off had virtually zero impact on my business and the things I needed to get done.

I could go on about the power of Free Days, but that’s not what this is about. I’d like to discuss two major tips that can help you make the most of your Free Days (and make sure they happen in the first place).

Two rules for effectively taking days off

The reason entrepreneurs struggle with taking time off is simple: they don’t have a system in place that allows them to comfortably step away from their business, so they feel forced to keep working even on their days off. Whether they think their business will fall apart without them or they don’t want to let their team down, the end result is the same — entrepreneurs simply cannot stop working!

So, the question then becomes… How do you set up a system that allows you to completely remove yourself?

There are two general strategies that I use which I think will help any entrepreneur reading this.

1. Get clear on what activities need to be completed before you leave.

When I found it hard to take Free Days, I realized it was because I never actually clarified when I was supposed to stop working. I had so many things on my plate and I kept working through them with no clear end in sight. When a Free Day came around, I didn’t feel like I could take it because I was always in the middle of something.

The first step when taking a Free Day should be to get clear on what needs to be accomplished before the Free Day arrives.

If you have a goal of what activities you want to accomplish before you leave, then you can relax on your Free Day knowing that you’ve completed everything you set out to accomplish. If you fail to do this, you’ll either never take a Free Day or, if you do, you’ll be thinking about all of the things you didn’t finish — and more than likely, you’ll start working on them again.

2. Plan out what you’re going to do on your first day back.

If you implement the first rule, there will still be something in the back of your mind throughout your time off. “What am I going to do when I get back to work?”

Just like you set a goal of activities that need to be completed before you leave, it is imperative that you plan your first day back before you begin your time off. It doesn’t even matter whether you do those things on your first day back or not. What matters is that you know there is a plan in place for when you get back to work.

This serves two purposes. First, it allows you to totally free up your mind so you can fully relax and rejuvenate without getting sidetracked about what you should be doing when you get back. Second, it means that when you do come back to work you’re not starting from zero. It allows you to be incredibly productive when you get back because you can get right into doing instead of trying to decide what you should be doing.

Getting into the right mindset

The other important part about taking time off is getting into the right headspace. Entrepreneurs are always thinking about their businesses, and shutting that off is difficult without a clear strategy.

My strategy is simple. I read fiction. I love reading business-related books just as much as any entrepreneur, but I’ve found it’s best to avoid them on Free Days. They’re just going to get you back into the working mindset.

In particular, I like murder mysteries and stories with some international intrigue. I like Lee Child, Daniel Silva, Jonathan Kellerman, Michael Connelly… I like these authors because they can rope you in from the first paragraph. There’s no ambiguity, no psychological stuff — it’s just an interesting story that I can get excited about diving into.

During a week of Free Days, I’ll easily get through three or four fiction books.

Creating YOUR Schedule as an entrepreneur

Now, at this point, you may be thinking… “Dan, that’s great for you — but I can’t take 155 days off and I don’t even like reading fiction books!”

You’re right. What works for me may not work for you. I like certain books and certain settings. You might not want to read on your Free Days, and that’s perfectly fine. We all lead vastly different lives and have vastly different businesses. As such, you’ll need to do some experimenting to create an approach that works for you.

For some, this can be a constant learning process. Shannon Waller, who has been taking Free Days for years, recently discovered that she needs her Free Days to be completely unscheduled if she wants to truly relax and rejuvenate. And there are many other specific things I do with my Free Days that I failed to mention here because they likely will not apply to everyone.

In the end, you’ll need to find what works for you. I recommend trying some of the methods I’ve described here, but remember that the goal is to simply focus on relaxing and rejuvenating during your time off — and not focus on work.

Good luck.

I hope this article triggered some new ideas about how your spent your time as an entrepreneur.

Thanks for reading,

For more guidance on time management for entrepreneurs, Download The Entrepreneurs Guide To Time Management to learn how to work less while making more money!

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Dan Sullivan

World’s foremost expert on entrepreneurship in action. Co-founder and President of The Strategic Coach Inc. Find out more: https://www.strategiccoach.com