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How to Take a Working Vacation

Experts weigh in on everything from when should you try to get away to how to keep the heat from ruining your gadgets.
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This Friday summer officially got underway but you’ve probably been daydreaming about vacation season from long before that. And, as a business owner, also probably fretting about it.

Like everyone else, entrepreneurs love a good beach getaway or lazy Saturday BBQ with friends, but the warm months present particular challenges for business owners. How can you find time for a proper break? What sort of contact should you keep with your employees back home (and how much will disappoint the kids or annoy your significant other)? And should you leave that laptop at home or at least in the hotel room?

Thankfully, the experts have plenty of wisdom to offer.

When can I get away?

Short answer: never. Let’s be honest, there’s never a time when you calendar is truly empty, but that shouldn’t stop you from planning a vacation anyway, writes Alan Henry on lifehacker recently. "If you've been hoarding vacation days because it just hasn't been a 'good time' to get away from the office, stop. The truth is, most of our jobs are busy and hectic enough that there's never a good time, so think instead about the accommodations you can make so you can slip away to recharge," he chides vacation-starved business owners.

Not only will getting away help stave off burnout, but its also a good way to test out new ways of delegating work and communicating on the go with your team. If there are slow periods at your work, by all means aim for them, but get online already and book yourself a getaway!

How often should I check in?

Obviously, the answer to this is going to vary based on the person and the business, but there are some general principles to help you find a sane balance. It’s clearly a good idea for everyone to communicate when you’re going to employees as well as possibly customers and key partners as far in advance as you can and to make every effort to lighten your schedule for the days you’ll be away.

Experts such as Careerealism’s J.T. O’Donnell also suggest setting a fixed schedule for check ins so everyone is on the same page. "My dad was a pro at this," she writes. "He made it clear he would dial in at 9 AM every morning and that it would be the only time staff would get him ‘live’ during his vacation. They were always organized and ready with questions. Just because you have a cell phone on vacation doesn’t mean you should be picking it up whenever someone from the office calls... You can even send e-mails the night before to remind them you’ll be calling."

O’Donnell also stresses that when you’re sipping a cool drink poolside isn’t the time for any heavy duty coaching or tough feedback. "It’s one thing if you are in the office and can provide valuable feedback face-to-face. But, telling a co-worker in a text message or two-sentence cryptic e-mail from vacation that you weren’t happy with their work and intend to discuss it when you return is pure evil," she writes.

I’m addicted to my gadgets. What do I do?

Working vacations have gotten even more complicated since we’re all wired all the time. Exactly how much should you abstain from your smart phone? At what point will your travel companions start contemplating throwing your tablet into the ocean?

First, if this is a struggle for you beyond the boundaries of your vacations then consider putting some effort into redefining your relationship with you tech. But if yours is just garden variety gadget overload, take comfort in knowing you’re not alone. Everyone from veteran entrepreneur Noam Brodksy to VC Brad Feld has publicly come out as struggling to draw this line (Feld offers a creative fix for how much email to respond to in the same post) but as Brodsky notes, not taming your connection anxiety not only annoys your traveling companions but can also really hurt your business.

As a warning to "people who think they are taking a vacation when in fact they have simply moved their offices outdoors" he confesses that "for eight or nine years after starting my first business, I took breaks only when my wife, Elaine, forced me to... If the technology had been available, I would probably have been one of those poor souls sitting on the beach with a BlackBerry in one hand, a cell phone in the other, and a computer on my lap. Or I would have been doing deals while riding a ski lift up the side of a mountain. It took a long and painful trip through Chapter 11 to make me realize the dangers of becoming consumed by the business. Looking back, I could see that I had gotten in trouble in part because I had lost perspective."

Now he’s a firm believer in vacations -- real vacations -- so put down your phone already.  

No, you don’t understand, I love my phone so much that I’m worried my vacation may damage it.

This Mashable post is for you. If you’re concerned about water damage or temperature changes might do to your beloved gadget, it has solutions. Now, just make sure you’re as careful about applying sunscreen.

IMAGE: Marylka Yoe Uusisaari/Flickr
Last updated: Jun 25, 2013

JESSICA STILLMAN | Columnist

Jessica Stillman is a freelance writer based in London with interests in unconventional career paths, generational differences, and the future of work. She has blogged for CBS MoneyWatch, GigaOM, and Brazen Careerist.

The opinions expressed here by Inc.com columnists are their own, not those of Inc.com.



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