You Have A Brief Window To Take Working Vacations Before You Have To Return To Office

With the pandemic increasingly under control in the United States, more people vaccinated, and some offices gradually re-opening there’s a brief window where you can really travel and work at the same time. While work from home is likely to be more common than in the Before Times, we may not have the same flexibility in the future that we do right now. Become location independent, if only briefly. Go take a trip and work from somewhere else. Combining work and vacation is actually the best way to vacation anyway.

A couple of years ago Samantha Rosen wrote at The Points Guy that “nearly 70% of people don’t disconnect from work while they’re away.” She suggests that’s a problem and recommends that you “put your phone down and enjoy yourself once you do” take vacation.

It’s cliche’ that Americans don’t take enough vacation time and that we don’t really take off from work when we go. But totally unplugging is bad advice for many people. If you fully unplug, you may not get the greatest benefits from your trip.

The best advice comes down to: spend time planning vacations, take more trips, work while you’re gone, and experience new and unusual things.

  • Planning vacations contributes more to your happiness than actually taking them. You may need to take some of those trips to justify all of the planning time.

  • You get all of your relaxation benefits on the trip itself, so 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. 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. Not working at all on vacation may even exacerbate this effect of being stressed out when you 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 at making the trip right. That’s a big weight on you to deliver relaxation in a compressed period of time, especially if you’re planning for family or friends too.

    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. Longer trips can be worse, 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. That resets your appreciation for vacation. Work during trips, too, can help you re-experience the wonder of arriving in a new place. It feels fresher, compared to one vacation moment bleeding into the next. So consider staying connected.

    Working Onboard Etihad First Class, Abu Dhabi – Dusseldorf

  • Look for intense or unusual experiences, things you’ll remember specifically. You’ll get more lingering value out of the trip that has peak memories than just a general sense that you must have been relaxed but where did the relaxation go?

    View from Waku Ghin at the Marina Bay Sands, Singapore

  • Make travel part of the trip. And since planning contributes to happiness spend time working through contingencies so you know how you’ll handle things like missed connections along the way.

    Hopefully Emirates A380s Will Be Back In Full Force

Vacation itself is a modern invention, taking root over the past two hundred years. Ideas of prudence and work ethic embedded in Western religion frowned on it even to the extent that someone had the resources to stop working while they were still physically able to do so.

Middle class vacation is an idea very much mired in the industrial revolution, the idea of needing an escape from the drudgery of work, the notion that employment was miserable needing escape, and that two weeks in Miami Beach was the one thing to look forward to each year. It’s also influenced by Eastern notions of spiritual enlightenment.

The best strategy, for those who can accomplish it I think, is to find work that isn’t miserable but to still seek out new insights and experiences, to stay in touch at home while traveling abroad.

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, 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 »

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  1. Great article – I have never been stressed during vacation by keeping up with work on a very minimal level – I feel better knowing there is not a problem, than not knowing whether there is or not. Also agree you can take more trips or vacations if you stay somewhat connected – the office knows if there is something that is easy to answer that you might answer a quick email (even though not expected). Normally for me this is less than 5 minutes per day and I don’t mind at all.

  2. Thank you, Gary. There is much wisdom in what you wrote – even for us folk who are completely retired. Travel provides a break, even from our more mundane routines, and the experiences are everything. My wife and I often see places on television to which we’ve been, and for which there are fond memories and many stories. You are also completely correct that there is much enjoyment on the travel planning and the anticipation of the trip.

    May you and yours have a joyous holiday, and a 2019 filled with health, happiness and peace.

  3. I always stay connected on vacation. I hate the feeling of coming back and opening your email for the first time a in a week. I rather check in throughout the week.

  4. I agree with everything in this post. My husband and I travel at least once a month (it used to be every other week) and never call a trip a “vacation”. We’ve done that for years. Staying connected (and not putting up out-of-office auto-replies, so our clients never know) allows us to do that. Mornings are for work, afternoons and evenings are for exploring, and we never stress about what’s happening at our businesses because we are always connected.

  5. Absolutely agree with the post.
    For us business owners there is no disconnecting with the office.

    Planning the trip is it’s own reward
    ( I no longer call my trips “vacations”).
    This year I have taken over 60 days off over 10 trips, both domestic and international.
    Already planned 5 trips for next year so far.
    I would be more stressed if I did not connect with the office every 3-4 days.

  6. Totally agree. I thought I was weird. If I don’t get a vacation every month or so, I feel deprived. It’s usually short, but I know I’ve got plans already in the works for the next one. Still like my work, too. Maybe your best column yet!

  7. Add another to agreement. As mentioned, it’s not the planning itself, but rather having something to look forward to that drives a lot of people.

    And I know for a lot of us, not having to return to a fire is much more relaxing then wondering/worrying and possibly coming back to an emergency.

  8. “Make travel part of the trip” Totally agree on this! I love aviation everything, so I go out of my way to book flights I will enjoy. Like a couple years back, I flew from the US to Japan via Finland so that I could fly on a BA 747, then a Finnair A350 then a JAL 787. Sure it took longer, but it was much more enjoyable than a single 777 flight!

  9. This all just sounds like sour grapes by folks who are unfortunate enough to have jobs so demanding that they can’t be completely disconnected for a couple of weeks…or who are simply workaholics and/or control freaks.

    I feel sorry for such people. They don’t really know what they’re missing.

    I have a high-paying professional career, but I have zero interaction with work while I’m on vacation. My office doesn’t expect me to have, either. I don’t think about my job while I’m gone. We all cover one another’s work while someone is out such that no one has any concerns about something falling apart while they’re gone or coming home to a “fire”. Even if something developed while I’m out, so what? I’ll deal with it – not the end of the world.

    Some of us actually DO come back from trips with a long-lasting refreshed feeling and with different perspectives on things, including work. If I didn’t, then that would defeat half the point of taking such journeys for me.

  10. This is a good philosophy. Thankfully I work somewhere (and for someone) who doesn’t really care how much time I take off. I probably take 5-6 weeks a year, but maybe only two of those weeks am I “fully” disconnected. I really don’t mind. It’s amazing how efficient you can be on “vacation”. As someone else pointed out, I will set aside time I need for “work”, and spend the rest of the day and night exploring or just enjoying where I’m at. It’s almost like I’m working from home, but home happens to be a vacation destination.

  11. Disagree with the article unless you are business owner (which Gary is). If you are a manager or executive in a company,and you can’t disconnect other than checking email “occasionally” for fire drills, you haven’t developed and empowered your subordinates properly.

  12. Very good article, and I agree completely. Of course, this works differently for different folks and different jobs.

    To the folks who either just disagree or “feel sorry for such people,” you may want to consider that some of us *want* to stay connected while away, or just general weekends. It may not be about *have to*.

    As others have said, we take a fairly large number of small trips. I like knowing what is going on with our project and my team. I like having input even while away.

    Could I disconnect completely for those few days and let someone else “handle it?” Sure. I just don’t *want* to because I like it.

    So, for those who feel the need/desire to disconnect, maybe consider that you might be in a job that you don’t enjoy enough to want to stay connected. It may not be me that you should feel sorry for.


  13. Everybody is different, and needs to understand how/if a vacation works for them. I don’t think any one batch of advice can be best. For me, I realized it takes 2 weeks off to really disconnect, such that you are really “on vacation” by the 3rd week. I find 4 week trips are best in that regard. Shorter trips are fun too, but I find I don’t quite get the same effect. Unfortunately, logistics dictate we only take that big 4 week trip every other year. But there’s plenty of shorter trips in between.

  14. I’m happy this works for you, but I disagree with most of it.
    Please understand that a lot of us cannot take shorter trips, and don’t want to. If I pitched to my boss that I would be out a few days a month, every month, he would ask me why I wasn’t taking a longer trip. Additionally, as I’m not a huge fan of long flight, I don’t want to fly 12 hours to spend 2 days somewhere, turn around and do it again.
    I will also say that my boss requests we disconnect during a vacation. There are many reasons for this but the biggest is that this wouldn’t count as “work.” So if I take 5 days off and spend the equivalent of a half day dealing with stuff, my job will not count this as a half day worked. I was on vacation and chose to handle things, so I will not get to travel more.
    My boss also doesn’t like the idea of us being available 24/7 regardless of circumstances that comes with expecting people to respond to things while on vacation. Yes, things come up, but we prep in advance so everyone knows we are gone. Someone else has to handle it or you have to wait. I really appreciate this approach as I don’t want to have to check my e-mail when I’m on a trip. This policy came because I was in the middle of the Sahara Dessert and people were expecting me to answer e-mails. I simply didn’t want to(also not sure how I could have made that a short trip).
    I also disagree with your conclusion that you will be in a different place with your work when you return. I always get this feeling, even if I am just taking a day off. I think it’s because I am disconnected from everything. I come back feeling better able to handle things and happy to have some time away. I can’t imagine I would have that feeling
    Again, happy for people who can do this, but I don’t agree with your conclusions.

  15. @brp
    I just want to understand something. Are you saying that I can’t truly enjoy my job unless I want to connect with it throughout a vacation? So if I want time just to myself, happy in the knowledge that others in my office are handling things, I secretly don’t like my job enough to have it? I just want to understand as that is a completely different metric than anything I have every been led to believe…

  16. @beth,

    No, that’s not what I meant- although I can see how it may have come across that way.

    This was in response to comments that seemed to imply that it is not possible to be OK with “working” while on vacation and we’re somehow missing things.

    One things is for sure- if one does not enjoy his/her job, said individual will not be OK with connecting while on vacation. Little debate on that.

    The converse, of course, is not necessarily true, but certainly could be, and worth individually exploring.

    What is certainly untrue is that it is “sour grapes,” or otherwise not possible to be perfectly happy with this in an occupation where one enjoys being connected. For people like this, it’s not about whether this “counts” as work time. It “counts” as time off, but I can still enjoy dealing with work things for part of the time while on vacation and not worry about how it will “count.”

    But, sure, it’s definitely possible to enjoy the job and not want to connect while away. I work here with people who do just that.


  17. Since my mobile phone will be online most of the time, I’ll still skim the emails to get a rough idea of what’s going on, but will only respond to urgent emails.

  18. @ Beth, I’m pretty much with you. Obviously we both like more adventurous trips, which take longer and get you farther from reliable wifi, rather than lounging at a resort. I just booked flights for an African safari yesterday.

    It’s an opinion piece, food for thought. Obviously there are lots of assumptions about the readership, their types of jobs, their personal preferences, their modes of work, what style of vacation is most enjoyable for them. Many people already are back at their worksites full time and many will never return. So the brief window idea applies to only a certain segment of readers.

    I really don’t need to work when I am on vacation. I check my work email periodically to see if anyone died, but I can fully let go. Others are in different situations.

  19. Rented a beach house in San Diego a month ago, my boss stressed that he didn’t want me doing anything and that he’d take care of it all. Though I argued I took his advice and the only stress I had on vacation was wondering if all was well. But he didn’t call me for anything. I got home to find he’d been pulled hard one direction and had done nothing for my things, I had a week’s worth of work piled up, now people and customers were angry and waiting. Late nights ensued, all stress relief from vacation was gone and I was worse than before. This all could have been avoided with 2 hours of work each day, now instead I had over a week of over work and tons of stress

  20. I only have 15 weeks vacation a year, and plan tp retire as soon as I hit 50.
    Not a day do I spend doing work while on vacation.

    Yes, I could be making more money working 50 weeks a year and retire at 65…. but why? Life is short.
    Feel sorry for those who
    a) never take vacations
    b) when they do, they still do work.

    Unless you are working for yourself, and your livelihood depends on you making money, what job can possibly be worth that?

  21. @Bob,

    “what job can possibly be worth that”

    How about a job that is rewarding and fulfilling and where checking in even while on vacation is a positive addition to the day. From what you posted it sounds like you may be working at something that is more of a chore than an enrichment. In a case like that, I definitely see the value in tuning out when on vacay and retiring earlier. Not all of us, however, are in careers like that.


  22. My job is enriching and fulfilling – for the 35-38 weeks I do it, but its not my *entire* life.

    There needs to be a disconnect.

  23. We’ve been ordered to return to work full time on May 24th. The joke’s on them because I’ll be on vacation that week. (one of the benefits of working from home the past year was that I accrued a lot of vacation time – and I plan on using it!)

  24. I took a working vacation in Hawaii last December. It went so well I went again in February. Then everyone else figured it out. Now you can’t get a decent hotel rate in Hawaii, let alone rent a car.

    I think your revival of this post is at least 3 months too late.

  25. @Bob: If you “only have 15 weeks vacation a year,” please let me apply for that job when you retire.

  26. @Bob,

    I do disconnect. I stop work at a reasonable hour each day and don’t check email. And only rarely on the weekends. I don’t need several weeks of disconnect. So, there does not “need to be” for me, although there may be for you. Vive la difference!


  27. Sadly, this ship has sailed. We have almost 2 million USA airline enplanements today. The time to have taken “working vacations” was when everyone was irrationally scared. Now prices are generally too high to justify working away from home. Sorry. Be braver next time.

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