Why You Should Always Work on Vacation

Planning vacations contributes more to your happiness than actually taking them. You may need to go on vacation to justify all of the planning time.

Most people get all of their relaxation benefits on the trip itself. Don’t expect to be relaxed when you get back. We quickly snap back into the stress of daily life, sans any benefit from the vacation.

Go in knowing you’ll enjoy yourself while you’re gone, but don’t set the bar for “needing a vacation” that you expect to be reset, relaxed, and in a different place with work upon your return.

View from the Andaz Maui

Being on vacation can actually be stressful. We put pressure on ourselves to enjoy, quickly, in a compressed period of time. After all, unless you travel frequently, you only get one shot per given period of time and you have to make the most of it.

So take more trips. Don’t make them one-shot deals. Avoid the stress where each trip has to be perfect. Don’t try to do everything, it’s better to leave some sites unvisited and have some experiences left for the future. Leave yourself longing for more.

Overwater Villa at the Park Hyatt Maldives, Where I’ll Soon Return for the 5th Time

  • People actually enjoy trips more when they’re interrupted by real time, as counterintuitive as it seems. Many short trips get interrupted by returning to work in between. Stay connected, especially on longer trips.

    Working Onboard Etihad First Class, Abu Dhabi – Dusseldorf

    I work on vacation and so should you.

    • Some hotel rooms lack power outlets. I always bring a compact power strip so I can recharge all of my devices at once.

    • An air card or MiFi device is indispensable so I can even work in cabs. I like to travel above ground between an airport and my hotel so I can use the transit time from the airport to stay caught up on work, and enjoy my time once I get there.

    • I actually love staying caught up with work while I’m away because if I don’t, all of the relaxation I’ve accomplished is immediately wiped away by the deluge I receive when I come back.

    • I especially love traveling to Asia. Thanks to a 12-hour time difference, very little is happening the entire day that I’m on vacation, which leaves me free to enjoy without juggling any calls or crises. I get up early, check my email and respond by end of the business day in the States, then have the full day to enjoy myself without anyone trying to reach me or work hounding me.

    It’s worth highlighting that Nate Silver disagrees with me, he says that working 20% of the time eliminates 70% of the enjoyment:

    Do you work on vacation?

  • About Gary Leff

    Gary Leff is one of the foremost experts in the field of miles, points, and frequent business travel - a topic he has covered since 2002. Co-founder of frequent flyer community InsideFlyer.com, emcee of the Freddie Awards, and named one of the "World's Top Travel Experts" by Conde' Nast Traveler (2010-Present) Gary has been a guest on most major news media, profiled in several top print publications, and published broadly on the topic of consumer loyalty. More About Gary »

    More articles by Gary Leff »



    1. This is a tough one for me. I can’t actually work while on vacation at the moment, so I find that I spend more time on the blog and reselling business, and usually come out of a vacation feeling like I actually got ahead of things, only to get back to the office and sometimes lose that feeling. It definitely is timing based too – taking a vacation during a slower time (such as around the holidays, or summer), lead to less e-mail, than at a high intensity time. I think timing can make a big difference, even for folks that are unencumbered by school calendars, as counter-intuitive as that may sound.

    2. No. Work will be there when you get back no matter what, so why tend to it while you are supposed to be away from it? I can see it being a little different when your job is to travel, but I didn’t just spend a week in Maui so I could check emails or even think about work.

    3. Always work on vacation? No. The answer, of course, is it depends. It depends on the job, work situation, the location of the vacation, and personality of the traveler to name a few of the relevant variables. Any advice to a large and varied audience to “always” do anything is asking for trouble.

    4. Honestly, Gary, if you have so much to do that you need to work in the cab, then you should consider a career change, my friend. 🙂 Life is too short. One day you’ll be dead and wonder where the time went.

    5. I disagree. The problem is that Americans take vacations that are too short (a few days, 1 week, typically 2 weeks maximum) so there is not enough time to disconnect and feel truly relaxed. Part of this is due to our government and employers’ attitude/expectations towards “Paid Time Off” (the accountants have killed traditional vacation hours in most places where they can get away with not paying out accrued PTO if you separate from a company). If you are able to take 3-4 weeks at a time, do it and leave the business tech at home. I work for a European company and used to get mad at my European colleagues for taking their month-long holidays in July and August. Until I followed their lead and took one myself. It was amazing…I was so relaxed that when I arrived home, I had forgotten passwords, phone numbers, etc. (which is highly unusual for me). Sure, I had a mountain of email, but the funny thing is that reading thru the backlog, you see so many conversations about an issue where the people eventually arrived at a solution without your assistance, and often times it is what you may have recommended anyway. Life and business move on…at least within my company, people are used to covering for other colleagues during long holidays, so it is not overly stressful when you return. Ever since that first experience, I try to take at least one vacation block of 3 weeks minimum each year.

    6. CincyTraveler nailed it. I have found that you need a minimum of 3 weeks to really disconnect, so a 4 week trip (or longer) is ideal. That 4th week when you are really disconnected is awesome. Of course, in the US, taking such a long vacation is not feasible for many due to most US companies stingy vacation policies, but somehow I’ve managed to take 3-4 week trips for the last 10 years or so. Fingers crossed I can keep it up!

    7. Wow such a timely post. Just returned from a week in London/Abu Dhabi/NYC and a couple of Etihad First Class Apartment flights. Was having this exact discussion with my wife while away. It is difficult to put it down for a week and I generally feel better if I stay connected than if I don’t. The time zone difference is huge. I actually find Europe makes it worse (people working back home into the evening Europe time) and thus Asia helps me relax more – same as Gary.

    8. Love your last comment! We love being in Bali. I get up return emails and a call or two and I’m done for the day! It is awesome not to even think about my phone for the rest of the day.

    9. I think the answer to that question depends on career field, lifestyle and a whole lot of other factors. I check email and my phone while on vacations. I generally leave my work behind. However, I know that work will be waiting when I return so my philosophy is shorter and more frequent vacations. I feel very lucky to be in a career position to take two 1-week vacations and two 10-12 day vacations each year. Anything longer than about ten working days and I will become stressed. While I love vacations, at some point I begin to miss my own bed and life back home.

    10. I didn’t even read the article.
      Just the headline turned me off
      A post only an American could write 🙂

      No Aussie or European would agree with you. And they all die happier 🙂

    11. I think it depends on the nature of one’s work. I catch up on e-mail and reading and such but don’t do much else. I mostly see patients, and/or need concentrated time to write, and that’s not going to happen on vacation. It is nice to keep with my e-mail, but that’s about it.

      Regarding folks like Lucky working all the time on vacation, that makes me laugh. His job is to take fancy flights and hotels and write and photograph about them. I can see why that’s always working, but in the grand scheme of things, dude, that’s not such an important job.

    12. I wholeheartedly agree with the post title. Gotta work on vacation, which is one the reasons why (unlimited) suite upgrades rank up there among my most valued elite perks. I have creatively, as my plan B, pitched for complimentary suite upgrades on the premise that I am a “very serious academic”, who does a lot work on the road, so that the extra room/desk space that a suite offers makes working and, hence, the stay, much more enjoyable… 😉

      I usually need some R&R when I return from a vacation!

    13. I agree with the point being made that vacation should be vacation, and you should just unplug and relax. But with the reality of US leave policies, I find it better to do some work. If you work half-time on vacation, you can take twice as many trips or stay twice as long. And I’d rather be working on a beach than working in the office!

    14. In the past 15 years I’ve had one vacation that I haven’t needed to do any work on, usually I’m the only one on call so I just keep an eye on things. But that also has meant that I’ve worked hard to build out notifications when when my intervention is needed so really the only headache is bringing the work laptop on the trip.

      I’m lucky now to work from home = work from anywhere. Summer after this I’m sure we’ll disappear somewhere for a longer amount of time, my family can go play without me when I need to work. And if it’s somewhere like Hawaii I’ll just work my normal hours and then play during Hawaii hours.

    15. Agreed on the taking more trips and/or not deferring and compressing all the expected enjoyment into a small window, but I disagree otherwise. Unless my employer is paying for my room, I expect to enjoy it the way I want to, and that doesn’t involve work. Life is short.

      The only exception would be self employed or travel bloggers. So I see why the author has this perspective.

    16. I find it takes me about 3-4 days to completely lose the feelings of ” i must check email, I wonder what’s going on…” Once I’m out of that mode, it ‘s very easy to relax.

      Agree with others, Asia sees ideal. I was recently in Australia, and it was perfect. I could wake up, see what happened the previous day, respond to what might need a response, and be on with my day.

      One other “benefit” of working while on vacation (which is where I thought this post was going) is you can write-off some of the costs of your trip as un-reimbursed business expenses (assuming you itemize).

    17. Umm I must admit, I’m a little surprised at some of the comments. I would love to take a longer break, but the US based industry I’ve been in throughout my career wouldn’t hear of it. I once worked at a company where you started on day 1 with 4 weeks of vacation … and no one dared take it. “You don’t have to use it all” as one boss said. It’s in the back of peoples minds – and I’ve actually heard bosses say about other people – essentially, if we can do without you for two weeks, we can do without you permanently. It’s related to the comment above ‘reading thru the backlog … the people eventually arrived at a solution without your assistance’. That’s scary to me. So its self preservation to stay somewhat connected.

    18. @DCS — I don’t know you or your background but do sincerely admire your persistence in pushing you suite upgrade process!


    19. Very true. I decided to take some time off to clear my head last year – went to Thailand by myself to do literally nothing work related. While I never got bored, I did manage to avoid doing anything work related. I did “work” however – by focusing on writing for my blog and my online t-shirt store so in some regard I did work. The only difference was that work I was doing was something that I actually enjoyed doing as opposed to my normal job of being a lawyer!

    20. What type of aircard works internationally? I’m looking for one that would work in France/Germany/UK… and do they come with adapters for using w/ tablets?

    21. @Lindy I have an unlocked wireless router. I either buy a local sim card for it or Gigsky and buy one of their prepaid plans for the country i am in

    22. @ GaryLeff
      Gary – Thanks for mentioning GigSky.
      We’ve recently updated plans and coverage for GigSky SIM and we are integrated into iOS for the new iPad Pro 9.7″ with embedded SIM, as well as on Apple SIM for iPad Air 2, iPad mini 3 and mini 4 wi-fi + cellular models.
      Our website, blog and press page have a wealth of info.
      By the way Gary, there’s a new GigSky SIM that includes 100MB of free data – if you have the original SIM – you can get the replacement SIM sent to you for free. https://blog.gigsky.com/gigsky-sim-just-got-even-better/

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