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How to Take a Real Vacation While Running Your Business

How to Take a Real Vacation While Running Your Business
Image credit: Paris | Flickr
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Vacation anxiety is real -- and for good reason, as anything can happen when you aren't in the office. Back in 2008, I experienced my own living nightmare when my point of sale systems’ server crashed, closing our stores indefinitely.

It’s events like these that encourage many startup and small business owners to deal with vacation anxiety by simply not taking vacation. According to OnDeck’s Small Business Owners Survey, only 9 percent of the 200 business owners who participated planned on taking a full two-week vacation. Sixty-one percent indicated that they would take a one-week vacation and 26 percent said that they'd take a few days off. Not only is it common for small-business owners to not take vacations, but they are known to worry profusely when they do take one. Of those who do take time off, 67 percent planned on checking in with work at least once per day.

With so many advances in technology, it is possible to thwart vacation anxiety -- at least partially -- and go on a relaxing getaway as things running smoothly while you're away.

Related: 5 Reasons Why Your Team Needs You to Take a Vacation

Here are five surefire tips to take the stress out of managing a small business while you’re away, drinking piña coladas and kicking back on the beach.

1. Choose the right person to step in for you.

Before even thinking about the technology that you’d like to use to help manage the shop while you’re away, the first thing that you should consider is selecting one of your trusted employees to stand in for you. Having a reliable stand-in who knows your business inside and out can help bring peace of mind while you're on vacation. Ensure a smooth transition by going over both routine and unexpected tasks along with the appropriate procedures.

2. Communicate your expectations.

A lot can happen in a day. Before relaxing by the pool, run through different scenarios and consider how involved you’ll be if they happen. You should also gauge how your departure may affect your team. Do they expect you to check in regularly? Will your stand-in have absolute authority to make decisions? What constituents an emergency?

These are all good questions to ask before committing to your getaway. Clarify your expectations in advance so that your team back home knows how and when to reach out to you.

3. Set boundaries for yourself.

Just as you must set boundaries with your team, set boundaries for yourself. Forty percent of travelers agreed that their smartphone is the most important item they take on vacation, with more than two-thirds reporting they use their devices every day. And though they’re off hours, checking work emails is the most common smartphone activity. Let’s face it: It’s not a vacation if you’re glued to your phone. If you've committed to checking in via email just once per day, pick a time and stick to it. Simple routines will ease your anxieties while still giving you the break you need. That said, avoid the temptation to check in more frequently. If you've prepared your team well, they won't expect an immediate response.

Related: You Need a Real Vacation (And So Do Your Employees)

4. Stay in the loop with web-based collaboration tools.

If your team uses a web-based collaboration tool such as BaseCamp, Trello, Asana or Evernote, use it to stay in the loop -- but within the boundaries you've set for yourself. With access to these kind of tools you can troubleshoot in real time without being tied down to your brick-and-mortar location. You will soon realize that your vacation anxiety was unfounded and that your stores are running just fine in your absence.

5. Schedule a 'hangout.'

As prepared as your stand-in may be to manage the shop while you're gone, a crisis could prove difficult to handle without your input. In some cases, meeting face to face, even if just for a few minutes, may be all that's needed to calm down employees and turn the situation around. Google Hangouts is the perfect tool for live video chats. You can use Google Hangouts on computers, laptops, tablets and smartphones.

Running a business on vacation is just one of the many challenges business owners face, but like most things, with a little bit of planning and preparation, it can be done. 

Related: How to Vacation Like a Boss