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The Secrets to Actually Relaxing on Your Summer Vacation

Business owners often take their work with them, even on summer vacation. Learn to step away, and your kids and significant others may thank you.
Journalist, freelance writer
July 24, 2015

If you're like a lot of business owners, vacationing doesn't come easily to you. You calculate not just how much it'll cost, but how much money you may lose by not working on your business. You fear that your company won't be able to get along without you, or you may feel like going on a vacation is a sign of laziness.

But one could argue that your business isn't really successful until you can vacation without everything falling apart. (It's harder when you're a solopreneur, but taking a vacation may be even more important for you if you don't want to fall apart.)

If you're taking a vacation, good for you. Go guilt free, consider this vacation a badge of honor (not shame) and recharge.

Though vacations are necessary for you and your business's well-being, you are right to be wary during your wandering. Before packing your bags and rushing out the door, there are a few things you should do first.

Handle the Obvious Stuff

Tell your employees, vendors and anyone who matters when you're leaving on vacation, and when you'll be back. Unless you're leaving someone in the lurch, they'll get it. You need a break. They probably do, too. If tracking everyone down isn't practical, "a good 'out of office' message goes a long way," says Louis Altman, owner of GlobaFone, a global satellite phone and service provider based in Portsmouth, New Hampshire.

Plan your vacation during the slowest time of the summer—or away from summer, if you have a summer business—and get all the important stuff done before your vacation so it isn't hanging there, worrying you while you're gone.

Automate What You Can 

It may not be the same as being around, but if you don't have any or many employees to step in while you're away, you could hire an answering service to handle customer inquiries and book future appointments while you're away, suggests Jennifer Martin, a business coach and work-life balance expert based in San Francisco.

"Your clients or prospective clients will appreciate a quick, professional conversation with a human being," Martin says. She adds that you might want to consider hiring a virtual assistant ahead of time who can cover for you while you're away.

And if your business is a service provider (e.g., massage therapy), Martin says you could set up an agreement to do an exchange of services with another massage therapist you're not competitive with. "You take on their clients temporarily during their vacation, and they can cover you when you are gone," she says. 

Decide How Connected You Want to Be

If you want to stay connected, think about that before the vacation. 

There's no kidding yourself. You're probably going to check email, and you want the ability to communicate with important customers, vendors and colleagues. You may enjoy your vacation more if you're plugged in—a little. What you don't want to do is assume that every inch of the planet is wired.

"Not knowing if someone is trying to reach you is like fingernails on a chalkboard," says Julie Fry of Making Care Easier, an online and mobile tool for families caring for elderly parents. She planned ahead for a summer vacation with several relatives and fortunately planned ahead, for example.

"The Berkshires are peaceful and serene. What they aren't is tech friendly," Fry says. "Twelve minutes away from our rental house, and I lost all cell phone, GPS and roaming capabilities."

But Fry had spoken to the landlord and had the Wi-Fi code, which helped immensely when she ran into cell phone problems; she didn't have reception at the rental house. But with the code, she was able to video chat, check email and conduct business fairly well.

Of course, there's a fine line between not being plugged in at all and being too plugged in. Fry is insistent that she had fun but admits she could have had a more restful respite. "Our dog Butter certainly enjoyed herself, and I relaxed after about 8 p.m. every night," she says.

Pay Your Employees

Sure, that sounds terribly obvious, but there are business owners who occasionally pay an employee a day or two late.

If you go on vacation and forget to pay an employee, you're going afoul of the U.S. Fair Labor Standards Act by not paying your employees on time, says Shelley Ng, vice president of product management at Ceridian Small Business Payroll, a human capital management services and technology provider, which handles payroll processing for small businesses throughout North America.

No Micromanaging

Josh Meah, COO of JackMyRep.com, an online reputation management and marketing company based out of Washington, DC, says that after you've set your checks and balances, it's not a bad thing to allow "a few gaps."

In other words, leave room for people to make mistakes and have to think for themselves. Doing that "will give your executive team an opportunity to step up and see that you really trust them," says Meah. "When people feel your trust in them, they will almost overwhelmingly excel, strive to not let you down and feel an even stronger relationship with you." 

John Crossman, president of Crossman & Company, a real estate firm with three offices in Florida and Georgia, has similar advice. He says that he has trouble letting go of work during vacations. Bringing in capable employees has allowed him to do just that.

"The most significant step was hiring more experienced staff [who have] been able to handle most issues while I am away," Crossman says.

The thing is, if you don't trust your employees to run the show while you're gone, maybe you have the wrong employees. And if you have the right employees, maybe they don't need you around anyway.

"GlobaFone often runs better when I'm not there, getting in the way of the people who do the work," says Altman, who once left his office for a week for the soccer games.

Actually Go on Vacation

That means really forgetting about your business for most of the day, every day, and remembering why you're on a vacation: You're taking a break.

Jen Moore, founder of Chicago-based Meez Meals, a DIY meal kit delivery service, says that since she launched her company in 2010, she has managed to take several European vacations—and she has made them true vacations.

Moore does business over email—"only during certain hours, like while my son napped, before heading out for the day and before dinner"—but otherwise, she stays away from email and keeps her cell phone shut off. "When we were sightseeing or traveling, I was in the moment. It was wonderful to have the phones actually shut off," she says.

Crossman struggles with that. He admits that he misses work when he's on vacation, and because he enjoys checking emails to see what's going on, he does. But he also tries to limit his checking email to when his family is busy with something else—like when they're all taking a nap. He also remains present online by scheduling some posts for social media during his vacations. "It helps keep me visible," he says.

But Crossman says that he is working on being the most visible with his family. He spent 10 days on a cruise with his wife and two daughters, admitting that he has had some vacations where he wasn't so present. But his mission on that vacation was to spend time with his family and relax.

"I have trouble turning off, but I am improving," Crossman says.

It's important to spend your vacation vacationing, says Michael Byrnes, Jr., president of Byrnes Consulting LLC, in Kingston, Massachusetts. "That quality bonding [with family] is often priceless," Byrnes says. "So, remember why you work so hard in the first place."

Read more articles on productivity

This article was originally published on July 16, 2014.

Photo: Getty Images 
Journalist, freelance writer