How Do You Take a Working Vacation and Still Catch a Break?

how to take a working vacation

When you’re standing at the helm of a thriving small business, stepping away for a quick vacation often seems impossible.

As a result, less than half of small business owners opt to take any time off work at all. Yet even those bold enough to get out of the office every so often grab an average of just five days’ vacation per year. Believe it or not, that inability to switch off is hurting your business — not helping.

According to a recent Gallup poll, small business owners who don’t take any vacation days are far more likely to be unsatisfied with their standard of living, and also struggle to maintain any sort of balance between their work lives and personal lives. Work relationships and daily performance will inevitably suffer, too.

Bearing that in mind, it’s crucial that you get yourself out of the office and enjoy a semi-regular change of scenery. Even if you’re unable to unplug completely, it’s totally possible to take a relaxing vacation while still getting a bit of work done.

To help you get started, here are a few tips on how to take a working vacation:

How To Take A Working Vacation

1. Rearrange Your To-do List

Big projects tend to be a huge vacation barrier for small business owners. After all, any big marketing campaign, research and development exercise or production cycle requires constant attention — and so it can be nearly impossible to manage those projects from abroad. That’s why you should be planning your vacation well in advance in order to work around thorny projects.

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Pick some dates you’d like to escape from the office, and ensure those days don’t interfere with crucial projects you may have scheduled. Likewise, don’t be afraid to push an important exercise back until after you’ve had your vacation.

2. Get Stuff Done Before You Leave

Unfortunately, current deadlines aren’t going to magically disappear just because you need a bit of fun in the sun. In order to make the most of your time off and minimize the time you’re going to have to spend working on your vacation, it’s important to get as many tasks done as possible prior to your departure.

If you’re not going to have constant access to WiFi, get all of your online research done before you leave the office. Likewise, if you’re going to need access to files on a shared drive, be sure to transfer them onto your personal devices beforehand. These sorts of little tasks will make a world of difference when you’re away.

3. Limit Yourself to Basic Tasks

The whole point of taking a working vacation is to relax. If you’ve brought a gaggle of stressful and time-consuming tasks to do, you won’t enjoy a single minute of your time off. Bearing that in mind, you’ve got to limit yourself to basic tasks like checking emails, following up with key employees or checking analytics. Whatever you do, don’t get sucked into a long conference call or trying to chase down a lost delivery.

4. Pick a Schedule and Stick To It

If you can’t get around doing a few more complex tasks while on vacation, be sure to stick to a firm schedule. If you need to check in with the office, do it at a set time every day. More important still, let employees know this is the only time of day they will be able to catch you in real time. Likewise, you should set out a strict deadline each day to drop what you’re doing and get back to enjoying yourself. This is particularly crucial if you’re away with family members. Kids grow up fast, and so you’ve got to let family time be family time.

5. Choose a Dedicated Work Space

In order to maximize your productivity while working on vacation, it always helps to choose a dedicated work space. Visiting the same coffee shop each morning, or consistently using the kitchen table in your hotel room will help to simulate a more typical working environment. In turn, that simulation should go on to increase your productivity and get you back to enjoying yourself that much quicker.

6. If You Can’t Provide Good Feedback, Don’t Provide Any

When you are checking in with employees every so often, one of the worst things you could possibly do is to respond to their work with a two-word text message or a short and cryptic email. Complicated employee tasks may require complicated conversations; therefore, if you haven’t got the time or the will to walk your team members through detailed instructions or subtle mistakes, don’t bother trying at all. If feedback can wait until you’re back from vacation, don’t try to get to it before.

At the end of the day, no two businesses are alike. Bearing that in mind, no two working vacations will be the same, either. It’s crucial that you set some time aside beforehand in order to think about what it is you’d like to achieve by going on vacation, and what you’ll need to accomplish while you’re away.

But either way, you’re only shooting yourself in the foot by locking yourself in the office all day. Do yourself a favor. Get out there and get a bit of sun. Your sanity and your business depend upon it.

Do you have any additional tips on how to take a working vacation, maybe something that’s worked for you?  Please share in the comments below.

Working Vacation Photo via Shutterstock

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Nash Riggins Nash Riggins is a Staff Writer for Small Business Trends and an American journalist based in central Scotland. Nash covers industry studies, emerging trends and general business developments. His writing background includes The Huffington Post, World Finance and GuruFocus. His website is

2 Reactions
  1. #4 is the biggest hurdle from my experiences. It takes discipline.

    Also, if you’re not hiring & training employees that you can trust with vital tasks, maybe you need to reconsider your hiring and training practices. If you’ve got the right people, trust them.