When should you take vacation? A strategy

The week between Christmas and New Years, is the worst time to use vacation. The reason is that’s when everyone else will be away. When an office is quiet even the most stressful workplace descends into a calm oasis of interruption-free time. Showing up at work on those days feels like vacation, even though you’ll be paid for it. Of course often family plans demand when you take time off, but if you have a choice you should make it wisely.

I remember when I first entered the full time working world, I was clueless about how to best use vacation, and I followed the herd. This is foolish, as here in the U.S. the annual average vacation time is a measly 13 days (Compared to Italy’s 42 and France’s 37): a pittance if you include time-off needed for weddings, complicated mid-week errands, parole violations and alien abductions. Yet somehow more than 1/3rd of Americans don’t use all their vacation each year. Yikes.

The ideal time to use vacation is when there is peak value, in your own psychology, for escape (say, when you feel creative burnout). This rarely coincides with what everyone else is doing (or in the above case, is the exact opposite of what everyone else is doing), as weekend trips with friends or sports team schedules put heavy emphasis on using Fridays and Mondays, regardless of when it is you need relief.

For awhile I found choosing periodic Wednesdays or Thursdays, every few months, was the best possible value for a spare vacation day: like a happy hour martini, they provided a dose of relief at the peak of a stress, and neatly divide up the working life into more manageable pieces. Catching a matinee, having a late breakfast and wandering my favorite bookstore, going for a short hike, or shopping in the calm of a mid-week crowd, were all low key, super mellow, high value vacation days.

Taken to an extreme, this strategy falls apart: it’d be a mistake to take vacation only at stressful events, or to dodge your responsibilities (“Hey boss, are you ready to present at tomorrow’s presentation for the CEO ?”, “Oh, didn’t I tell you? I’m off tomorrow: it’s all yours”). The goal isn’t to avoid hard work, it’s to maximize the value of time off so you’re of most use when you are actually there.

Consider these factors:

  1. When do you need stress relief the most?
  2. Are you, your friends, or your family, driving the use of your vacation days?
  3. When are other people at work on vacation or away, calming the workplace?
  4. Can you offset your own schedule, arriving at work before/after your coworkers, to make each morning a semi-vacation, free of interruptions or high stress?
  5. Can you make part of your daily schedule include time at the gym, the bar, the coffeeshop, or with friends, breaking up every day with some kind of psychological reprieve?
  6. If work is really so unpleasant that you don’t have enough vacation to survive, perhaps it’s not the vacation that’s the problem, but the job itself.

So what tips and tricks for maximizing vacation days do you know?

28 Responses to “When should you take vacation? A strategy”

  1. brian

    I’ve found the most effective technique is to schedule 2/3 of my vacation at the beginning of the year, even if I don’t have any destination planned. That way even if I don’t have money (or time to plan) for a vacation, I at least have the break I need.

    I think a lot of people end up taking the end of the year off simply because they haven’t planned well to use it up during other months.

  2. Ric

    Scott – agree with your comments about the working between Xmas and New Year: I’ve only ever taken that off when I’ve absolutely had to!

    In Australia, we generally get 4 weeks vacation. I usually keep a 15 – 20 day buffer, have at least on 2-3 week vacation per year when we travel, and usually try and work a few long weekends by having a Monday and/or Friday off.

    Of course, the fact that I have a buffer indicates that I haven’t always taken my four weeks vacation in the year!

  3. Scott (admin)

    Back at Microsoft most of my managers didn’t care about reporting vacation: as long as I was getting things done, that sort of book-keeping was irrelevant.

    Same went for hours: I came and went without a thought, but it worked both ways. All the weekends and late nights balanced out the half-days, the arriving lates, and the leaving earlies. What mattered was my performance, not the hours, and it’s the right philosophy.

  4. Grigor

    Scott, you’re right about vacation at Xmas time.
    My family used to go to holidays in May or September. Our usual destination was seaside and those times of year are still fine for water activities (in Croatia, where I live). And much more quiet, without summer traffic jams, crowded beaches and so on, what is important for both my wife and me.
    But now, when our daughter goes to school we have to spend our vacation in the summer (at least 3 weeks out of 6) and we plan it at the beginning of the year.
    The rest we spend without any planning.

  5. Pete Darby

    As a home educator and father of two under tens, we get to game family vacations a lot easier than most. The best so far was last year, for my mum’s 60th, we organized a mass family holiday to Eurodisney (sorry, “Disneyland Paris”, could that BE any more annoying?) in the second week of january…

    some parts of park “shut for maintenance” (no, shut so as they can cut staff bills during low season…)
    Sometimes, park so empty it feels like you’re in weirdzo post apocalyptic disney zone


    most rides have the option to go round again immediately in low season…

    Great personal attention from real life happy unstressed and not faking it french folks; when you’re english, you’re brought up to belive if such creatures exist, they sure as hell won’t be working in EuroDisney, where sincerity is only a hypocrisy away…

    As cheap as a disney residential holiday can get.


    But as for general strategy “When every other sucker is working” is a really good one, unless you absolutely, positively have to catch an event that’s on at a “peak vacation” time to get peak crowds.

  6. Greg

    Greetings Scott!

    I tend to agree with Brian above, if you schedule most of your vacation in the first half or first 3/4 of the year, you’ll be less likely to waste your vacation during the holiday slowdown (which I consider between Thanksgiving and New Year’s in the US).

    The other thing to keep in mind is that all time away from work is not created equal. Personal time, floating holidays, and the like are rarely transferrable from year to year, and are not paid out if you leave as vacation time often is. So there’s value in using vacation as the last of all your days off.

    One more blurb, Bren over at Slacker Manager (great blog) is a proponent of the Mental Health Day, or using a sick day to decompress, and often keep yourself from getting sick. He goes into detail here: (http://slackermanager.com/2004/11/mental_health_d.html). I’m not sure where I stand on that, I normally have enough vacation to use as Mental Health Days, and I would imagine if my manager weren’t as kewl as she is, she would probably frown upon an unexpected vacation day, where a sick day almost goes without question these days.

  7. Adam

    Scott, that’s definitely the way to have it. I’ve had positions like that in the past, and that’s definitely the way to do it. That kind of flexibility would allow for far more in the way of worker accountablity as well. If Worker X is taking of early, but getting everything done, who cares. But if worked Y is also taking of early but not getting their work done, then you know who to put the blame on.

  8. Tracey Rollison

    I’m also a home educator, and vacation scheduling was one of the draws of choosing it. We liked going to Florida the second week of January last year. It wasn’t too hot; it was plenty warm enough to swim; everywhere we went people were friendly and had a little time to answer the kids’ questions. Had we gone during the rush of summer or Christmas, it would have been stressful and rushed.

    We also like going places for fall color, but during the week, when most other people are working or their kids are in school. And we also like some more northerly vacations done during May or September, the week after rates drop, so it’s just as warm/hot and places are still set up for the peak season, but the rates aren’t.

    We both work for ourselves from home; but when one or other of us worked for someone else, we still tried to schedule things this way. At least we never had to worry about a school district’s schedule on top of our own work schedules.

  9. Pawel Brodzinski

    It’s essential to do things you like to do during vacations. E.g. I like from time to time a lazy day without going anywhere, besides the kitchen probably. However my wife prefer much active vacations and don’t recharge her batteries that way (we need to search some compromises here).

    If you can take longer vacations. Possibly a couple of weeks or even more. I know that few have comfort to do that, but the longer you’re off the further you’re from everyday work issues.

    If you can don’t check your e-mails and switch off your mobile. When you’re of try to be actually off. Don’t try to work remotely if it’s not absolutely necessary.

    And one general advice, but especially important when talking about vacations: don’t care about things which you can’t change.

  10. Johnny Simple


  11. Fam Wrkten

    Umm, with all due respect, I think we’d all be better off taking our vacation when things are quiet at Christmas. That way we don’t come back to an overflowing Inbox and urgent problems that are waiting.

    If we want our work to flow, we should work at the pace of the people and business around us.

    Much stress is induced by the difference between demands on your time and your available time. It’s made even worse with work-ahead/vacation/catch-up, work-ahead/vacation/catch-up, and so on.

  12. Scott (admin)

    Hey Fam: no doubt, it’s whatever works for you. This whole question depends heavily on:

    A) What kind of work you do
    B) When you do your best work

    What flow means varies a ton from job to job, and person to person. I always found the X-mas to New Years week super productive, since as a manager it gave me solid blocks of uninterrupted time so rare during regular working conditions.

    I also think the vacation/catch-up cycle is a separate problem: there’s all kinds of tricks to making that transitions easier, but it has little to do with when you take vacation (it’s always an issue).

  13. Don

    I’m with those who read Scott’s original post and thought “that’s a mental health day, not a vacation.”

    I’m sure there are lots of personal differences in what it takes to re-create oneself. But I wanted to speak up in favor of the long vacation as something essential. I recall someone telling me that it takes at least 10 days to really leave work behind – that on only a week’s vacation some/many/most people are still spending significant time thinking about work – getting in to it or getting out. For me, I’ve felt this has generally been born out. I don’t find vacations of less than a week very restorative.

    Further to Scott’s comment about MS’s being very flex in their time accounting, there’s been a recent splash in the media about BestBuy’s flex time program that is formally enshrining this policy. One effect their noticing is that people are actually working more hours. Which in some ways defeats the value for the work, I think.

    At my company, vacation and sick time have been merged into “personal time”, another phenomenon that will lead to people hoarding “vacation” time for when they get really sick and skewing US numbers relative to Europe.

    I think one thing that makes it hard to take vacation in the technology industry at least is that we’re generally addicted to poor planning, crises, and individual heroics. I have a friend who wants to schedule her family’s vacation, but she’s afraid to because there’s a software launch purported to be at the beginning of the summer that she has to support. So she doesn’t feel like she can make plans ’cause who knows when that launch is actually going to take place.

  14. Scott (admin)

    Don: It’s a good point about the whole sick days vs. vacation days thing. In my limited experience I don’t really care: If I’m the boss, be home when you need to be home and at work when you need to be at work. As long as we agree on how what you’re supposed to finish and when, and you do it well, I couldn’t care less about the rest.

    But of course this gets complicated in support roles, or retail work, etc. So I admit there are zillions of special cases.

    And I do agree about long vacations. The policy missing I think is the unpaid sabbatical – Give me the option to go away for 3 months every few years without pay. Or perhaps a smaller option: I can get an extra 2 weeks of unpaid every 2 years. Something. I’ve never heard a good explanation from an HR person as to why these more creative options of what vacation is are so hard to create.

    But as far as your friend: it’s her manager’s job to protect her work/life boundaries. If she’s going on vacation or having a baby, the working world will survive without her. Postponing family life because a project might slip seems like a misguided set of priorities to me. If she’s afraid that she’ll be asked to cancel her vacation when it does slip, that’s something else – but it’s back to the manager to do his/her job and manage.

  15. Tom

    I also enjoy the quiet days around Christmas as working days. That’s a good time to get some work done and it saves your vacation days for times when you need some “decompression”.

    This year, I decided to start to work 36 hours instead of 40. That amounts to a long weekend (mini-holiday) every second week. I must say, that makes a big difference on stress levels.

  16. MJ

    I do a LOT of travelling and I find that anytime between April and June are the very best times to travel. what a child learns on vacations if you are going somewhere other than Disneyland, (which is hardly a vacation), they will learn more on that vacation than they will in a classroom. Hands-on learning is always more memorable than book-leaning. In fact the hands-on learning is far better because it enhances the “book-learning”. also, if you don’t have children therea re not as many people on vacation during this time, (unless you you opt for the “un”vacation at Disneyland), so you get better airfaires, hotel rooms and less chaos. the streets are less crowded and people are more willing to interact with you, (should you desire this feature). I never take a vacation during peak season.I just came back from the East coast. I live in L.A. and my airfare, (including taxes and tarrifs, all – inclusive) from LAX to Boston, round trip,was $201.00. But I went from the 16th of April to the 10th of May. I had a marvelous time!!!!!!!!!!!!!!

  17. Dilys

    It’s really difficult to say how to handle holidays the right way.
    I totally agree with Scott and take my holidays anytime, but not between xmas and new year, but I also think that Fam is right. Everytime I take off a week or two in spring or autumn, I am already afraid of thousands of emails waiting for me when I am back. So, it’s not really a holiday in that case.
    But, and that’s for me the most important point, if you can take holidays for 2 or 3 weeks, than do it. That’s the time where you really can relax and forget all emails and jobs.

  18. Nemo

    What happens if you’re at the point where the thought of taking vacation makes you sick? I detest my job, but I can’t afford to quit. I have vacation accrued all the way to Mars, but as far as I’m concerned, anything that ends with coming back to my job is not worth doing. The only “vacation” I’m looking forward to is death. I’m basically a one-person second shift, and I want to die. I’m not going to look for help. I’m not going to talk to a counselor or take anti-depressants. I don’t want another job. I just want out. And that means the only vacation I want is the permanent one.

  19. Finding Nemo

    Nemo, I don’t pretend to have a fix-all answer and am in no way a professional, so take my advice with this in mind. But my suggestion would be to just TAKE the vacation time, and take it SOON. Do something during that time that will bring you joy. Block out the job completely while you do so. Simply pretend it doesn’t exist. And hour by hour during that vacation, enjoy whatever it is you’re doing at that moment. It may be hard right now to imagine what could bring you joy, but take the time away from the job to look for it. You may surprise yourself.

    There are other things I think you should do, but I won’t go into them since it sounds like you know what they are.

    I am CERTAIN that there are people in your world who would be devastated if you took a permanent vacation, so while I’m not much of a pray-er (is that a word?) I will desperately hope that you don’t make that choice.

    Best of luck.

  20. Braden Kelley

    Nemo – If your job is really that bad then make a change plan. If you can’t quit for financial reasons, start simplifying your life to reduce outgoings, improve your cash flow and save up money so change is possible. Start thinking about what you would like to do, and what incremental steps might be needed to get there, including one small enough that you can do it today. Start one the path, and find someone to talk to about taking the second step on the journey to achieving a job you would enjoy. Finally, consider identifying someone who does a job that might interest you, introduce yourself and use some of your vacation to just go and shadow that person, helping them out in whatever small ways you can during the day (and be a silent observer the rest of the time) – a working vacation. Devote yourself to learning and preparing, and pursuing the small steps, one at a time, that can get you there if you persist.

    The change may not be immediate, or even easy, but you must persist.

    Today is the best day of your life, because today you can make a change.

  21. Scott Berkun

    Hi Nemo:

    Saw your comment and wanted to get to it right away. Tried to email you, but the address you left appears to bounce.

    I realize you say you don’t want to talk to anyone, but then again, you left a comment for me. And I’d say, you should talk to a few more people who know more about this than I do.

    – You can email the folks at http://www.samaritans.org at (jo@samaritans.org)
    – You can call 1-800.SUICIDE 1-800-784-2433 in the U.S.
    – Or just start here http://www.suicide.org

    Very much hope to hear from you again,


  22. Steve

    Nemo: The wiley Odysseus of Homer’s epic, and the Jules Verne captain from 20,000 Leagues Under the Sea both called themselves “Nemo.” Yes, it means “No One”, but they were both independent and resourceful people. They followed their own path, and for them, the name really means “Unique.”

    Be resourceful, wiley, independent, and unique. We all have time to die. The hard part is the living without following the crowd.

    Also before you check out, check this out: The Joy of Not Working. http://www.thejoyofnotworking.com. It’s a book for the retired, but the premise is that anyone can retire: don’t wait until you’re old.

    You’re probably too smart and creative to be stuck in a job, so just quit working and start living.

  23. Theresa

    I’m trying to get my family to look forward to an all member included vacation. We’re all grown and we’ve never done this before. It’s really rough for me to even want to undertake. I can imagine what they’re going through. I’m printing out your article. It’s written out in a thoughtful and sensitive to the subject way: I hope it helps and quiets them down as much as it quieted myself down.

  24. Mary-Lee Henson

    Last summer, my girlfriends and I went on the most relaxing vacation in the Florida keys. We found an incredible rental in the awesome Ocean Reef Community in Key Largo. Elaine knew Bob from Swenson & Ecuyer Realty and he found us this perfect condo right on the breathtaking Marina. Bob and his team provided excellent concierge service, that catered to our every needs. We did everything… scuba diving, tennis, sailing, golfing, etc.. The experience was amazing! You should check them out at http://www.swensonrealty.com or call 3053673600.

  25. Tom Geist

    We have holidays that often fall on a Monday. So if I take the Friday off before it, I have two weeks when I only work 4 days…. plus I get a 4 day weekend.
    And let’s be real here, if you are an hourly worker with duties that you have to get done, at times you have to squeeze more work hours into the week the days before or after you come back to work. So, if you end up working 36 hours on 4 of the days you still have the full day off that week but only have to use 4 hours of vacation time. Make sense?



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