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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.

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?

Top comments get re-tweeted!

  • I honestly think that it really depends on the individual. Some people can unplug completely and be content while others will feel more stress that way (as you stated above). For the ones who will feel more stressed I agree with creating pockets of time and focusing on what is important. You need to make sure that you aren’t missing your opportunities for relaxing or spending time with the ones you love. So figure out what’s going on during your vacation and figure out some times to slip away to a coffee shop to do a little catch up at work. For the most part, a lot of people are also on vacation and you won’t be doing a lot of business during the time. But catching up on a few things, tying up a few loose ends or responding to the occasional e-mail isn’t going to hurt anyone. It’s all in moderation.

  • Mieke van Son

    Honestly, I am pretty much always connected. I do take my time to relax but I really don’t feel stressed whether I’m connected or not. My clients know what to expect and I think that’s the most important thing.

    We add mini-vacations at Virtual Assistants USA as well. We don’t always do this around the official holidays because most clients actually need more help during these times. I do always tell them we do not work full time but as Deanna Cox already stated in her comment, answering an occasional email or helping out someone in need when they really have an emergency isn’t going to hurt.

    I personally feel proud of my service, motivation in this respect. It makes my clients feel good and it gives me an edge above others. Or at least that’s the setup.

  • Steve Westrop | WORK[etc]

    I’ll be connecting daily, but aim to keep it minimal – I’ll relax more knowing everything is in hand than wondering what will be greeting me the next day. I’m amazed – perhaps jealous – that some people are able to walk away from their desk/laptop for two weeks and not think about it. Does it show that they don’t take business seriously, or that they’ve taken it seriously enough to know it’s all covered?

  • Robert W. Bowles

    Good read, some food for thought. For me the best way to enjoy a vacation to ensure I have the right people to handle my responsibilities…that they have been properly trained and I have planned appropriately. When I have done this, all goes well. When I leave in the spur of a moment with no foresight or planning, not so enjoyable for anybody.

  • Ash Shilkin

    You’re a legend Dan. Always seem to have great practical advice. I have been wondering how to take time off without taking time off over Xmas. This is awesome.

    • Vrm Staff

      Couldn’t agree more! love it!

  • Vrm Staff

    Love this! Its really hard for driven people to completely unplug because we love our companies and that’s what makes us great at what we do and keeps us inspired! I love the idea of having pockets of time to check in on things over the holidays! I will totally be using these tips this year! One of my life mantras has always been that creativity on a schedule is always safest! Great stuff! Keep them coming!

  • Ben Nighswander

    Great post. I have struggled with this in the past. It’s important to me now that I can review emails once per day and stay informed, but not take any action unless necessary and enjoy family/friends. Not always the easiest to do but very important to take time away.

  • TechGro

    Being self employed, it is imperative for me to stay connected. However, one must be able to control customer expectations and take the necessary time away to be with family and friends without them feeling like work is more important…

  • Jonathan Hickman

    I always feel busier when I go on vacation! If I am at home and receive a telephone call, I really do not notice it much, but I do notice when I am on vacation. Being an entrepreneur as well as working an steady job can be quite stressful sometimes. It is important to take a day here or there and turn off the phones and computers. (Okay, okay… maybe not turning off the phone but letting it go to voice mail for a day instead!)

  • Arturo Garcia Cifre

    I agree with Mieke, I’m allways on!, I really don’t feel stressed whether I’m connected or not. My clients and work mates know what to expect and I think that’s the most important thing.

  • Ryan Powell

    Left the phone in the car during christmas visits, only way to check out for a bit.

  • laura

    I turn off my devices during important bits of vacations.

  • Thomas Lawler

    I try not to work on vacations / holidays, but work always seems to follow me wherever I go! We have a smaller team and sometimes we just don’t have the man power to survive with multiple people out of the office.

  • Tony T

    After working from home for a few years I had to learn how to separate work from home, let alone work from vacation. It is important to maintain a balance between them. I don’t think I have ever gone cold turkey away from work, but having limited connection by staying in the loop of things relaxes me knowing that I wont go back to work behind and more stressed.

  • Steven Kennedy

    I like how simple it is to just check in and see how things are going with out spending a lot of time.

  • mbwahli

    As a control freak, it’s so difficult for me to not know what’s going on with any of our clients. The learning point for me came when my husband made a comment about how uptight I become when I’m checking emails during my “off” hours. I am having to learn how to set boundaries and delegate so that I can enjoy my time out of the office, be it during the holidays, or even just in the evenings. A happy husband is better than a clean inbox.

  • Michal Brenneman Wahli

    As a control freak, it’s so difficult for me to not know what’s going on with any of our clients. The learning point for me came when my husband made a comment about how uptight I become when I’m checking emails during my “off” hours. I am having to learn how to set boundaries and delegate so that I can enjoy my time out of the office, be it during the holidays, or even just in the evenings. A happy husband is better than a clean inbox.

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