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Entrepreneur’s Guide to Surviving any Holiday

Listen to popular business advice and they'll tell you the only way to relax is to go cold turkey and disconnect from your work.  But for entrepreneurs this approach is often the cause of even more stress.  Find out how we manage to stay connected yet still come back from a vacation refreshed.

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Taking A break

At this time of year every second business guru will tell you how critical it is to really unplug for the holidays.

Turn off your mobile, unplug your Wi-Fi and leave your laptop in the office.

They’ll claim this is the only way you can really recharge, and if you don’t do this you are in some way cheating on your friends and family.

I know this advice isn’t right for me, yet I still feel  guilty for not falling into line and staying unplugged.

There is actually nothing more stressful for me, than not knowing how everything is tracking. There is always that dread of returning to work to face thousands of unread emails, or worse, battling what two weeks ago was a tiny issue but by now has grown into a major headache.

I want to feel good about everything whilst I am away – I want to see that we’ve had new sales and that my team who are still scheduled-on are getting results in my absence.

Deny me access and I’m going to be miserable and edgy. And I know I’m not alone in this behavior.


79 percent of those surveyed admitted to taking their work-related device with them on vacation…

According to the Mobile Messaging Study by Osterman Research a whopping 79 percent of those surveyed admitted to taking their work-related device with them on vacation and almost 50 percent admitted to travelling up to 10 miles to check work emails on vacation. Even our friend, Nellie Akalp at Mashable agrees with me, Entrepreneurs holiday tips

Don’t get me wrong, I’m not suggesting that vacations and time with family are not important.  I’m saying tranquillity and inner peace for entrepreneurs or managers comes from being connected…not disconnected.

We need to embrace staying connected, avoid being made to feel guilty and not be pressured by those around us to act differently.

So how do you strike the balance of enjoying the good things in life while keeping your business humming and stress levels below a five?

Writing the recipe for next year

For anyone in business whether you’re an entrepreneur or employee, a handy way to free your mind for a vacation is to put things down on paper.

Before you shutdown for the year, take some time to jot down some key tasks or areas of focus for the upcoming year. This will quieten down that annoying little reminder that goes off in your head every couple of days. You know the one, it’s the voice that constantly says to you “you mustn’t forget this when you return” or “you mustn’t forget that next year“. The voice that makes relaxing almost impossible. Plus doing this gives you a handy to-do list so you can hit the road running on your first day back.

Schedule pockets of time

To avoid being the focus of icy stares from your S.O. (significant other) make sure you don’t give into the temptation of stuffing turkey into your mouth with one hand, whilst tapping away on your iPad with the other.

This means scheduling a dedicated time each day to quickly check in. A quick half hour in the morning before anyone wakes up is all it takes. If you struggle switching-off from work mode, then an evening check-in after everyone is asleep is going to work better. Or if you’re like me, you could do both.

Once you’ve finished your check-in, remove all temptation by keeping your devices out of easy reach!

Focus on what’s critical

Use those pockets of time wisely or they’ll quickly take over. To do this you must identify and draw out what lies at the very core of your business’s success. For me there are two things, a) keeping our customers happy, and b) making sure these happy customers are paying us.

As long as these two things run smoothly, then if I’m honest with myself, everything else can wait until next year.

So, what I actually do in those 30 minutes is scan the Customer Support activity list in WORK[etc] to make sure there’s no blowups, then run WORK[etc] billing and double check we’re getting cash through. Once those two items are done it’ll be vacation time for the rest of the day.

Avoid temptation and strip away the rest

Devise a way to shield yourself from issues that are not critical. Again, I use WORK[etc] activity streams to monitor the customer support issues and billing, that way there’s no risk of getting sucked into the hundred or so unimportant emails I know will be waiting on my inbox.

Your Team Needs more than just Christmas off

Many people will match up public holidays and earned vacation time during the Christmas period to get themselves a two or three week break. But what about the rest of the year? This approach can end up leaving you a solid 49 weeks of back-to-back work in some countries.

So starting next year, we’ve devised a “take-it-or-leave-it” schedule that allows everyone in the frontline teams to engineer a good four day weekend around every Monday public holiday. This is as simple adding the Friday or a Tuesday to that public holiday and suddenly everyone has a few good mini-vacations lined up throughout the year. (I need to divulge this isn’t my idea, I stole this from Cameron Herald’s book, the BackpocketC.O.O)

So how do you get through the holiday season? Are you a believer in being completely unplugged, or is keeping some connection critical to staying relaxed?

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