How to Take a Vacation When You Run a Small Business

For small business owners, taking a vacation — at least one where you don’t spend the whole time tethered to your smartphone or computer — may seem nearly impossible. Here’s what you need to do so you can relax and enjoy the time away from your business.

Running a business? Think you can’t get away for vacation? Or, do you worry that if you do go on vacation, you’ll need to spend hours hunched over your laptop in your hotel room or take endless business calls while you’re on the beach or sightseeing? All while your family fumes at your inability to leave work at home?

You’re not alone. According to a study published by Ondeck Capital, only 57% of small business owners planned to take a vacation. Furthermore, a report published by the Xero accounting software company found that 85 percent of small businesses owners admit to working while on vacation, with 60 percent checking in proactively at least daily.

The good news is that owning a small business doesn’t have to prevent you from taking a vacation and enjoying time away from your small business. But, as much as I’d love to tell you it’s possible to totally unplug yourself from your business while you go on vacation for a week or two, I can’t.

That’s because I’m one of those small business owners who won’t leave for any kind of trip without my smart phone and my laptop. But even though I check in on things while I’m gone, I’ve learned ways to minimize the time I spend working. Here are strategies I use that you can use or adapt for your needs.

Prepare your business in advance for your vacation

The key to making your pleasure trip a real pleasure is to prepare customers and your employees for your absence.

If you have individual clients who work with you, personally (instead of working with any of your employees), alert them in advance to your vacation schedule and that you will be unavailable to do their work during your vacation.

If you have clients who tend to wait until the last moment to have work done, tell them you’re going to leave (or be will be unavailable) starting several days before you actually plan to leave for vacation. That way, you won’t have to deal with their last-minute requests when you want to be packing and getting ready to leave.

Tell them you’ll be back at work two or three days after you actually get back, too. Doing so will give you time to catch up and get back in the swing of things before dealing with clients and new issues.

Don’t schedule anything to go “live” (for example, a new website, a major website redesign, big mailing, big ad campaign, etc.) right before you leave or while you’re away. The reason: you don’t want to be dealing with last-minute problems or mistakes as you’re about to get on the plane, or when the family is waiting for you to get in the car so you can start exploring the national park you chose to visit.

Be sure you have all your important contacts and their phone numbers in a single file on your computer and on your smartphone. It can be helpful to have a paper copy, too, in case your electronic device breaks, gets stolen, or the battery dies when you’re not in a location to charge it. Having this list readily available will save time if you need to contact any of these people to handle an emergency while you’re away.

For peace of mind, take paper copies of your boarding passes, car, hotel and tour reservations, and any other details of your itinerary. Sometimes referring to a piece of paper is just quicker and easier than finding an address and phone number on your phone or computer. For convenience and quick access, stack the documents in a small folder in the order you’ll use them, and keep it in your purse or carry-on. That way, if your phone battery dies, you can still board the plane or get to your hotel without hassle.

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Prepare and train your employees for your absence

Over the years I’ve learned that if there’s anything in your office that could possibly break down or go wrong, it will do so while you’re away. If the office Internet connection is going to go out, it will happen when you’re gone. If your business website is going to go down, it will do so while you’re away. Par for the course are equipment breakdowns, shipping snafus that anger your biggest customer, and just about anything else that demands urgent attention.

A number of years ago, for example, I was in Arizona on a business trip when I got a call from one of my employees telling me that a lot of water was leaking from the ceiling onto her desk. But, it wasn’t raining outside. The desktop computer tower under the desk was right below the leak on the desktop. I had her turn off and unplug the computer (fortunately it hadn’t gotten wet yet), and then call the building manager. The problem turned out to be an issue with an air conditioning duct that ran through the ceiling above her desk.

After that incident, I made sure my employees had a list telling them how to handle various problems and emergencies when I wasn’t available.

On the list were things like:

Steps to take if any of the computers won’t start in the morning, when to call in help, and who to call.
What to do if the Internet connection goes out, including where the router and cable modem were, what to look for, how to reset them, and when to call in the cable company for help.
What to do if the company website appears to be down, how to be sure, (i.e., that it’s really the website that’s down and not the office Internet connection), and who to call to troubleshoot and fix the problem.
When to call the person responsible for building maintenance in the office building, and what her phone number was.

I assigned responsibility for handling problems to one employee, but let the others know that if that person was out of the office, they could and should handle any problems that needed immediate attention.

In addition to that list, I made sure that outside resources we regularly use for programming and hosting knew each other’s names and contact info so they could work together to fix any emergency situations without me having to give them the go-ahead.

To avoid having employees send me multiple emails every day, I told them what kinds of things I wanted to be notified about and when. Unless there was a really urgent and important matter, I asked them to send me one email at the end of the day briefly summing up anything I needed to know about before I got back. Everything else was to be printed and put on my desk for my attention when I returned.

Set vacation rules for yourself

All the advanced planning in the world won’t help if you allow yourself to be sucked into work on your small business every day. To avoid that, set a time of day and a time limit for checking in on the business. Choose a time of day when you’re likely to be just hanging around the hotel room anyway — say a half-hour early in the morning and perhaps another 45 minutes in the evening when you return from dinner or evening activities.

To avoid being hacked, be wary of using public or hotel Wifi connections. The best option when not on a private connection is to use a VPN (virtual private network). Several major antivirus software companies offer VPNs. Check with whichever antivirus software company you use to see if they have that option.

If you can possibly avoid it, do not call forward your business line to your cell phone. Have employees pick up your calls for you, or use a VOIP (Voice over Internet Protocol) service provider like Grasshopper or RingCentral to capture and retrieve voice mail messages. If you use a virtual office, use their voice answering service if one is available.

If at all possible, avoid sending or receiving contracts or other important faxes while you’re away. You want to be able to read and review them in detail, not while you’re rushing to get out the door to get on the tour bus.

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Don’t spend time posting to or reading social media accounts while you’re gone. If posting to social media is part of your daily business routine, create and queue up the posts in advance with a tool like Hootsuite, or have a virtual assistant or employee create and post them for you. Save those great photos you took to post when you return. Posting vacation shots saying “We’re have a great time here” could make your home a target for burglars.

Finally, remember, the less time you spend connected to your business while you’re away, the more you’ll enjoy your vacation and benefit from it.

Disclaimer: The content on this page is for informational purposes only, and does not constitute legal, tax, or accounting advice. If you have specific questions about any of these topics, seek the counsel of a licensed professional.