If you are currently the owner of a small business, the term “vacation” probably sounds like a foreign word. As the person who is running the whole show, you probably worry that the moment you take a summer vacation, your whole operation will come falling down. In this article, we will try to help you do the impossible: taking a summer vacation as a small business owner.

While a small business owner taking time off might seem to be an impossible dream, there are likely many things you can do to get the break that you deserve. In fact, according to most studies, regularly scheduling vacation days can provide tangible benefits to your business.

Vacations reduce stress and can also help you become a more productive business owner. Additionally, by offering vacation time to everyone within your ranks, you will be able to retract—and retain—some of the most talented individuals available. Though work is an important part of your life, it is important to remember that it is merely that—apart.


1. Identify The Least Busy Time Of The Year

Even if your business operates year-round, there are still probably times of the year that are much busier than others. For example, accountants are usually busiest around tax season (spring) and retail companies are usually busiest near the holidays. By setting your vacation for immediately after your busy season, you can minimize the impact of your absence.


2. Give Advanced Notice To Your Most Important Clients

As long as you can communicate clearly and let your clients know your plans early on, planning a vacation should be much more manageable. If you can tell your clients “I’ll be out of the office at the end of this month, please let me know if you need anything before then”, you’ll likely get a reasonable response. This may even be a good opportunity for an unexpected selling point.


3. Plan Vacations Well In Advance

The further in advance you can plan your vacation, the easier it will be to take it. Imagine if an employee said to you, “I am planning to go to Hawaii in August of next year”, you would easily be able to prepare for this. The same principle still applies when it is a boss speaking to their employees.


4. Cross-Train Your Top Employees

There may be skills that, as the owner of the business, only you can do. However, with the right training, your top employees can likely fill in your shoes. Because your absence will eventually come up (business trips, roadshows, etc.), having a “number two” to take your place will certainly be a valuable thing.


5. Consider Allowing Your Entire Team To Take Off At Once

If you sincerely don’t believe that your business can continue operating in your absence, then it might be best to give your entire staff some time off at once. Closing the doors to your business will likely have a much smaller impact on your bottom line than you initially assume. Once everyone has had a chance to relax and rejuvenate, your collective moral will be higher and you’ll all be more productive.


6. Choose A Vacation That Is Already Near A Holiday

As you have probably noticed, whenever there is a federal holiday in the middle of the week, the entire business world (well, except for maybe hospitals) operates a bit more slowly. In 2019, for example, the Fourth of July was on a Thursday. Planning your vacation for this specific week would have a minimal effect on your bottom line. Thanksgiving, Christmas, New Years, Memorial Day, and Labor Day are all often weekday holidays as well.


7. Set An Automated Message For Phone Calls And Emails

Instead of feeling the urge to respond to every email and phone call coming your way, take a moment to set an automated message explaining to clients and that you are on vacation. In this message, you can include an alternative contact number (such as another employee) as well as the date you plan on returning. This will help keep anxious clients at ease.


8. Sort Out As Many Details As You Can In Advance

The key to going on a stress-free vacation is to plan as many details in advance as you possibly can. If you are like many business owners, you likely have a constant sense of worry, no matter whether there is a problem at hand. By knowing the things your future self is likely to worry about—did I remember to send that email? Will someone be able to sign for that shipment? Is there anything major that I’m forgetting about?—you will be able to have adequate answers that can put your mind at rest. Making a detailed checklist (that you can bring with on your vacation) will be a tangible piece of evidence that says “yes, this was actually taken care of.”


9. Give Yourself A Break—the World Isn’t Going to End Without You

One of the problems faced by many business owners is that as soon as they leave their operation, they immediately want to return and make sure that everything is okay. Go ahead and take a deep breath—things are going to be just fine and the world will not end without your presence. It may be helpful to turn off your phone and computer altogether. After all, the purpose of a vacation isn’t to be constantly worrying about your business. The purpose of a vacation is to get some much-needed relaxation and enjoy the fruits of your labor.



You’ve been working hard for years—now it is time for you to finally take a break. Though taking a vacation may seem like something that will interrupt the course of business, it is something that almost all business owners can reasonably do. Keep this handy checklist in mind, kick your feet up, and enjoy the moment.

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Andrew Paniello | Andrew attended the University of Colorado and earned degrees in Finance and Political Science (Philosophy minor). He is currently a freelance writer with a primary emphasis on business topics. In his free time, Andrew enjoys playing piano, painting, hiking, and playing basketball.