9 Rules To Follow If You Work During Vacation

A working holiday might sound like an oxymoron, but there are actually good reasons you might want to sneak in some hours while taking your vacation.  A study shows that 47% of people feel less stressed if they don't completely disconnect from work. Another study found that more than 50% of workers find they're more productive when they can stay plugged in.  Just don’t over do it – holidays are a time to regroup and relax so that you can return to the office refreshed.  Peek these tips to help you check-in and check-out at the same time:


1. Before you leave town, remember to add an auto email reply that states you’ll be out of the office for x period of time, and include a contact person if there is an urgent work matter.  It will at least slow the number of people who expect you to respond and take the pressure off knowing that in an emergency, someone else will also be contacted to handle the matter.

2. Plan ahead and before you leave, decide which project(s) must be tackled while you’re away and then feel good about leaving everything else waiting until you return.  Print out and organize all the info you’ll need for that project so that you can work on it even when you don’t have internet access.  It may sound old-school, but you can’t always count on modern technology.


3. Speaking of modern technology, hope for the best but prepare for the worst. You may not always have internet access or it might be really slow.  I use a Mifi so that I don’t have to depend on hotel or airport Internet access and I don’t have to worry about security.  Also, bring an extra power-strip because often hotel rooms (especially quaint, older B&Bs or reconfigured manors) won’t have enough outlets for you to plug all your technology into.

4. Install a secondary browser on your laptop that doesn’t require quick Internet to load.  Strip it of most of your bookmarks, bells and whistles so that you can just boot up and perform basic work tasks like checking your email.

5. You can keep in touch via phone conferences if need be.  Just be prepared to find a quiet place ahead of time so you’re not calling in while marimbas play in the background.


6. Similarly, you may offer to attend a virtual meeting via Skype (or similar means).  Just remember that you don’t want to log-on to a virtual meeting sitting by the pool in your bikini.  So pack something presentable if you think that could occur.

7. Plan-ahead for your downtime. Check your itinerary and look for moments when you’ll have nothing to do.  For example, plan on working while you’re on planes or on buses.

8. Set limits as to what you will accomplish.  Don’t tackle time-consuming elaborate projects.  It's OK to delegate tasks to a coworker while swinging from a hammock so that when you return, you’re not faced with an overflowing inbox.

9. Set boundaries as to how much time you’ll spend working and during what hours you’ll be working.  During the rest of the day, be completely present with your friends/family or just enjoying your holiday.   Wake up an hour early to check email (especially if the time difference is in your favor).  Or, if you’re in the tropics, consider taking the hottest hours to sit in air-conditioning and work.  In my case, as much as my boyfriend will claim that he’ll be go-go-go on vacation, I know that he’ll be taking a siesta mid-day between his beer at lunch. I take that time to work while he’s snoozing.


Look, let’s face it – we all sneak moments while in the office when we check our personal Facebook page, or Pinterest, or order something off Amazon that we suddenly remember we need.  So if someone complains that you shouldn’t be working during your time off, just smile and offer to email them a cute cat-photo when you get back to the office and call it even.

Picthx weheartit



  • kylie rachel says:

    I’m living on my own, and I’ve got an apartment to pay so I have to work doubly hard. If I have to work on a holiday, as long as it pays the bills, then so be it, I wouldn’t complain, just as long as I have already planned it and not be bothered by outside forces like parties or unwanted guests and the like..

  • Shaye says:

    Working on a holiday means double pay. That’s what I think of when I work so I won’t get hassled for working when everybody else are outside tanning themselves…

  • Misty says:

    I won’t be working this Labor Day weekend, thank God. I’ll get to spend it with my friends before I get back to school 🙂

  • Arianne says:

    I’m actually going to work this Labor Day weekend, but – I’m gonna work at home 🙂

  • Nicky says:

    These tips and rules work out best for me, not only on Labor Day weekend but on all other holidays. Thank you!

  • Lauren Lim says:

    Lucky me! I don’t get to work this Labor Day! 🙂

  • Erin says:

    I survived! Yes, I had to work this Labor Day, but so far, I didn’t get bored because I was with my funny co-workers and we just decided to have a good time instead of sulking.

  • thanks for the tips here. I’d be sure to take this into consideration the next time my boss asks me to work on a holiday..again.

  • Johanna says:

    Glad that I was spared from work today 🙂

  • Olive Vega says:

    Mind if I share this with my colleagues? I know Labor Day has gone and passed but there are still other holidays ahead and I just want to remind my co-workers that working on holidays isn’t actually bad at all.. Thanks!

  • My kids don’t mind me working at home, at least they know that whenever they need help, I’m just a hand-wave away. So working on a holiday isn’t a big deal to me.

  • Patricia C. says:

    Thanks for this tips, I’d be sure to take note of these on my net working holiday! Cheers!

  • Taranee says:

    I believe there’s another holiday next week? Columbus Day, if I’m not mistaken. And it’s been announced in our office that it’s a non-working holiday, so I am pleased that I won’t be working on that day. Yay!

  • Keanna says:

    I’m gonna be on another working holiday next week. Good luck to me! I’ll keep your tips in mind, Heidi. Thank you 🙂

  • Macy says:

    Leaving an auto- Away responder to my e-mails had proven effective to me, because my contacts then know when to expect me to come back when on a holiday or wait till I become available.

  • Steffanie says:

    Sometimes I want to strangle my boss when she asks me to work on a holiday. Seriously?! That’s the only time I’ll get to have fun and not worry about my job. But sometimes I really cant refuse especially when my budget is at stake. So with a heavy heart, I do go to work on holidays most of the time.

  • Celeste says:

    When I’m asked to work on a holiday, I just look at the bright side. That is, at least I get paid double during that time, that’s what I always think of.

  • wenamhine says:

    These are great pieces of advice. I plan to relax and take a day off on the next upcoming holiday and I want to plan ahead and make sure nothing’s left behind so that when I get back to work, everything’s in place.

  • Sophia says:

    When I have to work during vacation, I always make sure I bring my laptop with me so my boss or whoever needs my online services can contact me via Skype. That’s how we communicate

  • wenamhine says:

    I actually worked during Labor Day! Talk about loyalty at work and literally celebrating on this day, huh!

  • Faye says:

    Glad that I don’t have to work when there are holidays, that’s what I made sure whenever I look for a job..

  • Bernadette says:

    I assure you, no one’s really happy to be working on a holiday, because it is supposed to be the day one could relax and indulge.

  • Pamela says:

    I love holidays because that’s the time where I allow myself to stay relax and free. So just in case I am told to work on a holiday, I would surely frown and get annoyed. But if my job is on the line, I would rather work my butt off and do my job and take note of your ideas and suggestions.

  • Rakeesha says:

    Super thankie for this wonderful suggestions!

  • Wena says:

    I’m so glad I don’t need to work when there’s holiday. I could spend a lot of time for myself on my extra free day 🙂

  • Helga says:

    Working on a holiday is never fun. I’d rather stay at home and binge-eating than to work on holidays 🙁

  • Franceska says:

    How lucky for those who won’t be working on holidays! I am so jealous!

  • Margaret says:

    There’s another series of holidays happening in the next two weeks and I’m glad I won’t be working in the office. Yeah, totally cool!

  • Abby says:

    Oh well, congrats to those who are able to have a good time and not work at all during the holidays.. Yes, this is me, a feeling kinda jealous…

  • Misty Dew says:

    Well, that’s my story… working on a holiday, yep, that’s me. So I’m just making the most of it, socializing with friends afterwards. ‘Till the next working holiday!

  • Shailene M says:

    Oh, lucky you all who didn’t have to work on holidays. Me, here I am stumped at the office, whiling away and making the most of what I can do while working… on a holiday.. 🙁

  • Honestly, I envy those who get to go out and have fun during the holidays, not thinking of work at all. Me, I’m stuck in front of my computer lounging on my desk. ha!

  • Kandy Gurl says:

    Oh my gosh! I soooo envy those who will be able to enjoy their holidays away from work. Me? 🙁 I wish I were somewhere else!

  • MJ Walters says:

    I am sooo jealous of those who can take a day off from work because of holidays. Me, no can do. 🙁

  • Mabelline says:

    Thanks for these tips. I sure need to de-stress for a while because I have been working on holidays and it wasn’t productive at all…

  • Shauna says:

    Well I must admit, I easily get jealous of those who could spend their holidays free from work. I wish I could do the same.

  • Mabel Hastings says:

    I wish I could do these when I’m working on vacation. Ahh… For once, I want to quit my job and go on Paris and spend my holiday there instead of working!

  • Mabel Hastings says:

    In the next few days, I’d be left alone again at work while my peers go on vacation. How I envy them. Thanks for the tips on how to enjoy holidays at work!

  • Nilda Gustin says:

    Thanks for these great tips for when working on a holiday. I also often do some light work while I go on a holiday with my family. It’s okay to be busy at some time. Although I haven’t done those Auto-Away messages and planners to ease up my job when I return. I might do that soon.

  • Jillian says:

    Oh I’m so jealous of those who will be able to spend the holidays abroad or even just be having staycation. Me, I’ll be stuck at work until Christmas eve. My only consolation is, I have some of my friends who will be with me.

  • Gina DeGarmo says:

    I guess I am lucky this year because I am not working during the holidays. Finally have some alone time and pampering time.

  • Madison says:

    Love all those tips, Would really enjoy my vacation though if I were not working.

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