how to take a vacation when your work never stops

A reader writes:

The holidays are here, and I’m meant to be taking a week off for vacation. The trip is booked, it’s been approved months ago by my boss, and I’ve scheduled my requested time with an eye to our work cycle and done my best to get everything done and covered before I’m gone.

However, two days before departure, my manager said that perhaps I can’t go, as we are not as far along as she’d hoped. (It’s impossible to do a month’s load of work in three weeks, and while I attempted to get all of it done and create the minimal amount of stress and bother for those left behind, there is still work to be done of mine in that week I’m away that will have to be covered by someone else.) She says I can either not go, or be available during my leave at all times for work, or I can pay out of my own pocket for a freelancer to come in to backfill me.

There may be no way to save this vacation, but I wonder: how does one responsibly take some time off? I haven’t had a holiday in nearly two years for this exact reason; every time I try, there always seems to be more work or responsibilities that only I can attend to and that can’t be put on hold even for a weekend. How does a responsible employee in a management position get away for a break?

You can read my answer to this question over at Inc. today, where I’m revisiting letters that have been buried in the archives here from years ago (and often updating/expanding my answers to them).

{ 144 comments… read them below }

  1. CMT*

    Pay for a freelancer?! Whoa. My advice would be the work equivalent of DTMFA, which is why Alison is the advice giver, not me.

    1. Cat like that*

      I would love to hear Dan Savage tackle work questions. Even better, have Dan and Alison switch advice columns for the day. It would be glorious.

          1. wannabefreelancer*

            OMG I love the Savage Podcast and AAM and follow both religiously.I would be so happy if this happened.

          1. Katniss*

            If I’m lucky maybe someone will know what I’m talking about, but I always thought it would be awesome to have Alison on the My Brother, My Brother, and Me podcast. Or maybe on a work related episode of Judge John Hodgman.

          2. Katniss*

            That was meant to be a reply to Cat like that. D’oh!

            Also, you mean Dan Savage’s blog Savage Love? It’s up on The AV Club every Wednesday!

          1. Ask a Manager* Post author

            I think ummmmm is probably talking about stuff Dan has said about bisexuality. This likely isn’t the place to get into it but if you google Dan Savage and bisexuality, you’ll get the gist!

            1. olympiasepiriot*

              Over the years, he has changed a lot on bisexuality. Lately, there seem to be some accusations at him about being anti-trans, although I have found myself on his side when I’ve been a witness to the threads or events that get those accusations.

              1. F.*

                Or his comments on the Catholic faith. Are you sure he would be appropriate for a forum that is supposed to be for everyone in the workplace?

          2. anonanonanon*

            They’re probably referring to his repeated use of slurs against bisexual, transexual, and asexual individuals, as well as some of the incredibly misogynistic comments he’s made. Basically, there’s a feeling in many LGBTQA communities that he only supports white cisgender gay men, which isn’t all that surprising because the mainstream LGBTQA community and their straight allies have a problem of focusing on white cisgender gay men and pushing everyone else to the side.

            As Alison says in a comment above, this probably isn’t the place to get into it, but a lot of people view him as a bully, which is ironic in so many ways.

            1. I'm a Little Teapot*

              Yes. I’ve never cared for Dan Savage in general – but I do love DTMFA (and it is often excellent advice).

              I believe Alison’s equivalent is YMSAIGTC (your manager sucks and isn’t going to change). :-)

              1. anonanonanon*

                I can appreciate that he’s helped some people and I think the general idea of It Gets Better is good in theory (though it’s not without its problems), but I really dislike the idea that people flock to him as a prominent LGBTQA activist when he’s so cruel to individuals under the umbrella whose identities he doesn’t agree with. And his tendency of outing people is awful. Anyone who outs someone is honestly doing it for their own benefit and curiosity and not the benefit of that outed individual. It’s such an inappropriate practice.

                I haven’t read or listened to anything he’s done in a long time, so I can’t comment on DTMFA and I should probably stop talking about this in general or I’ll start getting myself upset.

                1. Katniss*

                  I agree with this. Not to get much further into it, but for someone who claims to be so progressive his ideas are often very old fashioned and he isn’t good at looking at other people’s perspectives. An example would be his constant desire to push open, poly, or “monogamish” relationship and his fondness of the implication/outright statement that no one is happy with monogamous.

                  On top of that, he’s just been slacking off on his column a ton lately, to the point where recently he responded with genuine requests for advice with song lyrics. And no real advice.

          1. Not me*

            He’s not great about bi and trans people sometimes. Apparently he’s had something to say on asexuality, too, but I’ve missed that.

            He also visited my area and was pretty unpleasant, tbh.

            1. AnonyMoose*

              My only claim to fame is that he once roller bladed in front of me (I was living in Seattle at the time). Yes, rollerblades. I was like GET OUT! I am so bringing those back into the rotation.

    2. Almond Milk Latte*

      Right? My first reaction was shouting WHAAAAAAAAAAAT at my screen.

      That’s why it’s Ask a Manager, not Ask a Latte.

    3. Leeza*

      Unbelievable. I wanted to book 3 weeks off recently and asked my boss when would be a better time to go, and she said that no time is good because we’re always busy and that I should just go whenever I want. Whenever someone on our team goes on vacation, the rest of the team picks up the slack it’s never been a big deal. Also, I live in Israel, where we are very into vacations. No vacation for 2 years? That’s unimaginable to me.

  2. AndersonDarling*

    Take vacations where there is no cell reception or internet, then you can’t be reached.
    Does the boss take vacations? Eeesh.

      1. fposte*

        Or it’s a culture where the boss doesn’t either and has a hard time grasping why that it’s a problem.

    1. NJ Anon*

      Exactly! Seriously, time to look for a new job! No one does my job when I am away. Oh well. Don’t forget the old line that when you are lying on your deathbed, you never say “gee, I wish I’d spent more time at work!”

        1. Ashley*

          I think there is a difference between “working” and “achieving” though. Achievement can be made in many different ways, lots of which don’t include work.

          1. fposte*

            But lots of them do, and plenty of people wish they’d done those.

            It’s not a big thing, but that’s one of those sayings that assumes everybody is forced bitterly into work and that nobody enjoys it, finds it satisfying, and relishes the outcome, and everybody likes babies better than Excel. And none of that is true.

              1. AnotherHRPro*

                I would love to see that post.

                I completely understand the mind set of work to live. I come from a family that worked solely to put food on the table and pay the electric bill. I get it. But that is not me and never has been. I enjoy work. I enjoy the satisfaction of a job well done. Of figuring out a problem. Of making something better than it was before. If I won the lottery I would still work. Maybe not this exact job but still a challenging and satisfying job.

                1. AnonyMoose*

                  Me too. :) I get super lazy and unproductive if I’m not spending part of my day work (yes, I rarely shower on the weekends and can usually be found on the couch reading….sue me).

            1. NJ Anon*

              Unfortunately, at least in my experience, most people work for a paycheck, not be because they love their job or are passionate about it. I might like my job and even enjoy it but would I much rather travel the world and see all there is to see? You bet! So yes, on my deathbed, I won’t say I would have rather spent more time at work. I’ll say I should have spent more time traveling. Just my 2 cents.

              1. Ask a Manager* Post author

                I think lots of people (although not the majority) work for a sense of accomplishment and impact, especially in the nonprofit world (formerly mine) and academia (fposte’s).

                1. fposte*

                  Yup. And also because I absolutely adore most of my co-workers and staff, which is no small thing, but that’s related to the mission anyway.

                  I don’t drag that fact out a lot here, I don’t think, because reading AAM makes me aware what a huge privilege and luxury it is to feel that way. People coming to AAM tend, understandably, to be people who are hoping to change their work, or get some decent work, rather than those who are delighting in their job. Some of that is an age bracket thing–even if you’re lucky early, it often takes a while to get a deeper security and satisfaction. But maybe it’s worth my making that announcement a little louder sometimes–that even if it doesn’t feel like it in your twenties or even your thirties, it can be possible to find real and deep satisfaction in your work.

            2. Elysian*

              I’ve never thought about it, but I like Excel a lot more than I like babies. Thanks for putting those two in juxtaposition for me!

                1. Jessica (tc)*

                  True, but now that you’ve presented the choice to me, the answer is very clear: Excel wins another round!

            3. Ashley*

              Understood and agreed. However, NJ Anon used the word “work” and you used the word “achieved”. I’m merely pointing out that those two are not synonymous. Achievement can be gained at work, absolutely, but it can also be gained outside of work. Satisfaction in a job well done, notoriety, success in the work world are all sought after and admirable, but not necessarily everyone’s life goals. Work does not necessarily equal achievement, satisfaction, or happiness. All of those things can be found at work, but also through many different avenues.

              1. Ask a Manager* Post author

                I don’t think anyone is arguing that achievement can only be gained through work — but that’s one avenue, and for some people that avenue ends up syncing up well with what brings them most or lots of fulfillment.

              2. NJ Anon*

                Indeed! If I won the lottery today, I would still work but not at the job I have now. I work at a nonprofit but not directly with clients. It’s not very rewarding at all. I would rather be on the “front lines” and am actually moving towards that goal. Then, I could say that I was achieving my goals through work. But not now. As one commenter said, they realize it’s a privilege and a luxury to feel that way and I agree.

            4. AnonyMoose*

              I happen to love work and view that my work achievements are my achievements (outside of my program volunteering but that’s more of a pick me up).

            5. So Very Anonymous*

              I’d also add that I’d like to spend more time at work actually achieving things, and minimizing time spent on things that feel like I’m just helping sustain a bureaucracy for the sake of sustaining a bureaucracy.

              1. So Very Anonymous*

                Whoops — that isn’t to say that I want to spend more time at work period… just that I’d rather spend the work time on things that feel more meaningful/”achievingful” than just bureaucracy-tending.

            6. newreader*

              I think an important point is that enjoying your work and taking vacation shouldn’t be mutually exclusive. I enjoy my work and find it fulfilling and satisfying – it’s not just a paycheck. But I also want to have some time away occasionally without having to be at my employer’s beck and call the entire time. I’ve worked in that type of environment before and it just bred resentment. My current situation allows me to take reasonable vacations. I generally still do some work during vacations, but it’s my choice and on my schedule. My employer respects me enough to allow me downtime during vacations and I feel much more appreciated.

            7. Connie-Lynne*

              My FIL is a retired NASA fighter pilot who trains astronauts to fly the space shuttle. Him and his coworkers DEFINITELY regret not spending more time at work.

              1. So Very Anonymous*

                Off-topic, but that sounds super-cool. My very first “real” job out of college was at NASA HQ, right around the time that the first shuttle post-Challenger went up. We all went into giant rooms with TVs to watch the launch… and held our breaths…

            8. bearing*

              I’m seconding that this would be a good topic for a post and discussion.

              I guess I’m not anywhere near my deathbed (I hope), but about 12 years ago I made a decision to stop pushing my thesis work through to be published (tl;dr: I had graduated and had already made the decision to stay home with my kids instead of looking for a job). I’m not sorry about staying out of the job hunt, but I still feel ambivalent about whether I should have spent more time “at the office” over the subsequent year and seen that work through to publication for a wider audience. It was a difficult decision then, even though it did make things easier on my family and my stress levels, and 12 years later I still haven’t concluded that it was the *right* decision.

          2. neverjaunty*

            I once induced a snit by replying to this with “And nobody ever complains on their deathbed that they wish they’d spent more time cleaning spit-up off the floor.”

            It’s one thing to point out that work shouldn’t substitute for a full life, and your employer’s loyalty to you goes as far as the profit margin; another to act like work is always meaningless and to be shunned.

            1. Polka dot bird*

              Why is the choice “work” or “babies” though? There are lots of other things you could be doing with your time.

              1. neverjaunty*

                In this particular instance, it was a dude rhapsodizing about how great it is that women prioritize family over the terrible rat race of the working world, totally missing the irony that he wasn’t exactly leaping at the chance to be an at-home dad. But that aside, you can pick your own things that nobody on their deathbed ever wished they’d spent more time doing, ranging from “losing their luggage at airports” to “having too little income to have a decent life”.

                1. Stuart*

                  Hi. Stay at home dad here – been SAHD for nearly 3 years now :)

                  Pet peeve: people who ask my wife about our son’s developmental stuff. They assume that the wife is the primary care giver and the husband is the primary earner. It’s kind of upsetting when they do that to us :(

    2. Connie-Lynne*

      It’s entirely possible the boss *doesn’t* get vacation time in. There’s still a lot of people out there who take pride in martyring themselves by not ever taking PTO.

      Which isn’t healthy either but could explain Boss’ weird ideas about vacation for her reports.

  3. Jane*

    This employer just sounds unreasonable. I work in a job where we sometimes have to work while on vacation (Biglaw), and sometimes people have to cancel vacations but cancelling isn’t the norm. If people where I work can figure out how to take vacations (often times with minimal workload during vacation), then I am sure people at any job can. Our work also never stops and there is never a “good time” to go on vacation. The issue is if your employer isn’t willing to put in the effort to figure out what to do, even with your help, then they are just unreasonable and there isn’t much to do other than eventually move on. Years without a vacation isn’t sustainable. You may be able to go two years, maybe even three, but after a while it just isn’t feasible.

    1. Biglaw spouse*

      This. There are expectations for people in Biglaw, and everyone knows what they are going in. They pay you an awful lot of money and expect you to be willing to check in and do a little work while on vacation. Plus the billable hours requirements kind of blur things anyway, since at least at my spouse’s firm no one really cares about official vacation days, just whether you get your work done and hit your hours target.

      My spouse just accepted a new job. It’s about a 50% pay cut, but with actual vacation time and no expectation that she’ll work evenings and weekends routinely. Neither of us can remember the last time she didn’t do at least a couple of hours of work on the weekend, and she was up until 3 a.m. earlier this week for an assignment, so it’s going to be a pretty big shift.

      If you didn’t know ahead of time that this is the culture and you’re not compensated accordingly, OP, find a new job.

    2. Bwmn*


      And if the company refuses to take this issue seriously, then what they’re saying is that ultimately they expect high turnover. While Biglaw may at least have the financial compensation factor, I used to be the only fundraiser in a small nonprofit organization. And I’m sure in lots for a number of roles where someone is the “only” – taking off a week or more at a time is often a challenge without any considerable financial compensation.

      Given that it was rarely possible to 100% off, my arrangement with my organization was that I usually took 3 weeks off once a year where even though I had to do bits of work here and there, the overall long period of time off ultimately ended up making it more restful. It also was easier for my organization to miss me once for a longer period rather than a few single weeks through the year.

      I’m sure this isn’t necessarily the norm, but the alternative option to coming up with some kind of solution can not be no vacations or forcing someone to personally pay for a temp.

    3. Green*

      Maybe this is why I’m in-house now, but I took my vacations during my BIGLAW years with zero work contact and I was on one of the worst cases in the history of biglaw. (Although “unlimited vacation time” = lies) I did once have to delay a trip by a day (which I agreed to, and it truly was case-critical), but they paid for my new flight to the location and a car service to drive me where I needed to go.

      In-house, I now take at least 4 weeks vacation each year with no contact and there has been no negative impact on my career. It turns out that stuff can wait until I get back or else someone else can handle it.

      1. Anoning it Up*

        I’m about to embark on a new BigLaw job, and you give me hope! I like vacations, and camping, and no contact.

        1. Green*

          Biglaw does suck. But! But! The best way to get an in-house job is to spend a few years in Biglaw. You can do it. Don’t stay too long. And try to set a few basic boundaries. Best piece of advice I got: “Who will hire you to advocate for them if you can’t even advocate for yourself?”

    4. AnotherHRPro*

      es, for some jobs there really never is a “good time” for someone to be off. The key is for the manager to value the employee more than the inconvenience of having them out. When some specialized members of my team are out, it is more difficult and inconvenient but I want them to have time away. They deserve time away. I don’t want them feeling trapped by work and their responsibilities here.

    5. Putting Out Fires, Esq*

      Hey, even us public interest lawyers have a hard time finding a good time to leave. Crime, as it turns out, doesn’t stop for the holidays either. Right now we’re struggling to figure out how to staff while half the misdemeanor unit is away on mandatory training. And that’s for training. Vacation? Psshaw.

      I’ve been in court all day every day these past two months, with client meetings afterwards. Office time is a rarity and time to visit jail is even harder to find. I won’t be able to do this kind of schedule forever. Luckily, once you’re out of the misdemeanor unit, the pace slacks off. Yes, the cases are bigger, but you don’t have two arraignment sessions a day every day to cover. Until then, I’m on my feet all day walking back and forth, trying to provide as much help as I can to about 20 people at a time, while fending off the rest. I’m just very fortunate that I have a husband who is understanding and makes dinner for me and gives me an hour of silence when I get home.

      This position is for the young. We were looking around the office for someone to step in as a supervisor, and all the parents gave a hard pass. The schedule is killer, physically draining. Court appearances are always good for keeping you on your toes, and the crowd control and face-to-face interaction reminds me most of my retails days… during the Christmas rush. It just sorta requires people who throw themselves into it, at least while they are there.

  4. Case of the Mondays*

    Practical advice from someone with similar job issues. This isn’t the way the world should work but what I have done to survive. Not the best, but keeps my family happy.

    (1) I work extra on nights and weekends the weeks leading up to my vacation to make sure all my non-moveable deadlines are met or as close to met as possible before I go. Yes, I realize hours wise that means I might not really be getting a vacation but it still allows me to be out of the office for a week.
    (2) I plan my vacations in advance so that I can try to make sure no deadlines are scheduled while I will be gone. Vacation is booked first. Then as I’m setting deadlines for things I tell people “sorry, this deadline has to be before or after X date, not on it.” If I get a surprise deadline for my vacation I try to move it. Usually things can get moved to before or after. This may require a judge’s approval in my case but can often be done.
    (3) I divvy up what is left among my colleagues. I usually have about 5 people each over seeing one or two minor things. So if I have a pleading finished but the client needs to review/edit/sign off a colleague can over see that process and getting the thing in the mail. I have even assigned such tasks to my boss before but ymmv on that.
    (4) 9 times out of 10 I continue to check my email twice/day while away and respond to any fires. The people covering for me can call me if they have questions about how to handle something. I have a laptop so I can remote in if I really need to get my own hands in something. Usually I spend about 3-5 hours over the course of the entire vacation on work stuff. If visiting family it is after dinner when people are just watching TV or early in the morning while others are still sleeping. I also work remotely while my husband drives or I’m on a plane as other examples.
    (5) I’m good at not sweating the small stuff. I don’t reply to every email. I let people wait that can wait.

      1. Bostonian*

        This depends on the person. Some people would rather do a few hours spread over the course of the week than come back to a massive list of unread emails.

      2. Witty Nickname*

        For me #4 is important for me to disconnect and recharge, rather than spend my vacation worrying that things aren’t getting done or about whatever emergency is waiting for me when I return. This way I can spend about 15 minutes a day staying in the loop, and hopefully keep things from becoming emergencies.

        I have a very specific hierarchy around what emails get responded to while I’m on vacation though. I leave an out of office message with instructions on who to contact for what issues, and then:

        1) If it’s an urgent issue and I know the answer off the top of my head, I will respond.
        2) If it’s an urgent issue, but I don’t know the answer, I will respond and copy the person who can help (and include whatever info I do know either in that email or in a separate one to the person I forwarded it to, depending on the situation).
        3) If it’s an important issue, but not at the urgent level, I’m going to assume you read my out of office message and contacted the person who can help, but I’m also going to follow up with you when I get back into the office to make sure you got what you needed.
        4) All other emails, I am going to assume you read my out of office message and contacted the person who can help, and got what you needed, unless you reach out to me when I get back and tell me otherwise.

      3. Bea W*

        It also sets up the expectation that you’ll still be available and willing to work on your off time. It’s one thing to log in and tidy up your inbox, but once you start responding to emails it can just come back to bite you in the butt.

        I once sent a friendly hello and photo from an exotic trip I took. A co-worker took that as an open invitation to ask me a non-urgent work question, which was reasonable in her mind only because I had previously answered work email on other vacations. It totally rained on my relaxing parade. That was my harsh lesson in just being incommunicado because working defeats the whole point of vacation time away from work.

        1. anonanonanon*

          Yes, exactly. I’ve checked my email to delete anything pointless so I’m not swamped with a full inbox when I return, but responding to emails definitely means certain coworkers think you’re going to be accessible during the rest of your time off. No thanks.

        2. Elizabeth West*

          This. My previous job was as a receptionist, so there really wasn’t anything I could do remotely, though I did tell my boss and backup they could call me if any questions arose. At the time, I was dating someone long-distance, and every few months, I was taking a couple days PTO attached to weekends so I could spend time with him. Backup only had to call me once while I was out of state–he borked the FedEx login–and it only took a minute to refer him to my documentation. I did not check email while out because I had no way to do that.

          In Current Job, I can check email remotely, but I did not during the UK Trip #1. I’m lucky my company places a priority on people taking PTO, because while I volunteered to work remotely on UK Trip #2, I would have been super pissed if they had kept bugging me when I didn’t.

      4. Meg Murry*

        Yes, I have learned that if I really want to disconnect and recharge, I can’t open email AT ALL, because I’ll wind up reading all of it and tagging things to do when I come back or forwarding to people, etc and I just fall down that rabbit hole.

        Now I have the policy that my OoO says to contact my boss in case of an urgent situation, and if it really is urgent he will text or call me to get the most important details, or very rarely say “I need to you go respond to the email from Person ABC sent at X:00”.

        1. AnonyMoose*

          That’s me. And I totally tell myself that I am just going to ‘peek’ but then it’s two hours later and my heart is racing and I’m trying to figure out how to fix X while Husband is yelling from another room (or balcony) to ‘GET OFF THE LAPTOP’. Siiiigh.

      5. pomme de terre*

        Agreed. Checking work e-mail is a total relaxation killer, and possibly a sign that you don’t know how to delegate.

    1. ace*

      As I read #1, I thought “sounds like a fellow lawyer….” and then it was confirmed. Good advice!

      My #6 would be to make a quick chart for my assistant to check, identifying who gets what and who the interested parties are (e.g. opposing counsel on the Johnson matter is Bob Smith, so any correspondence from Smith should go to Associate Jones for triage).

    2. fposte*

      #2 is a really, really good point. Vacation comes under the “pay yourself first” rubric–if you wait and try to squeeze it around all the random appointments and meetings, you’ll never manage it. It took me a long time to learn that.

    3. Green*

      I also block off my calendar for the entire days I am going to be gone. Then nobody can add anything to my calendar. I also put it on my boss’s outlook as well, so she knows I’m gone.

      1. Hlyssande*

        Blocking off time is useful in general, not just for vacations! I do it for lunch as well and that cut the lunch meetings down to almost nothing.

  5. Bend & Snap*

    Seriously, new job. My previous boss would not approve vacation, or approve and then revoke it, or approve it and find a way to harangue me while I was gone, and always found some kind of “issue” that he used to spank me with when I got back. It was impossible to recharge, I felt sick with worry when I was finally out of the office and it was never, ever worth it.

  6. Eliza Jane*

    Did we ever get a second update on this one on the first go-round? The last comment on the post was from the OP saying she took the vacation in spite of her boss, and would update if she got fired. I’d love to know what ended up happening when she got back…

  7. NK*

    When I was a child and my mom worked a demanding job, she had planned a vacation for us and then all of a sudden they said it was too busy and she needed to reschedule. She was able to without losing any money, so she did. Then when the rescheduled vacation came up, it was the same story. This time, a portion of the vacation was nonrefundable. Mom said she would work if they really needed her to, but they would need to reimburse her for the money lost. Suddenly, they weren’t all *that* busy and we went on our trip.

  8. Angela*

    Maybe it’s just me (or my company) but it seems like this becomes more and more common as staff is cut to an absolute bare minimum. I know we’ve gone through a few rounds of layoffs here and my department has come down to just me, one coworker at same level, and our manager. The last time our department was downsized, they decided it was better for us to work 60 hour weeks than to keep our 3rd person. Since a “normal” week is 60 hours with two of us, time off has become a nightmare, but luckily my manager is one that recognizes time away is important and we are a tight knit team, so we just power through the insanity so the other can take vacation when it happens. We also plan the entire year of vacation in advance. That took some getting used to, as I’m more of a “I’m starting to feel burned-out, need to take a few days” within the next month or so person and not a “planned vacation” kind of person.

    1. AnotherHRPro*

      I feel the same way. Over time we gotten leaner and leaner. What this means is there is no flexibility left in the system and it is harder to cover. When departments are small and people are very specialized it makes it challenging.

  9. hbc*

    I’m reading along thinking “standard jerk faux vacation policies,” and then the freelancer part came up, and my eyebrows raised higher than I thought was physically possible. I think I may have pulled something.

    1. Chinook*

      “the freelancer part came up”

      This is the only part that doesn’t surprise me because, when I was a teacher, it was negotiated into our union contract that if you took vacation time during the school year (or went to more than one professional conference during school time), you the teacher would have to pay for the cost of the substitute teacher to cover for you. It may have even applied if you called in sick too many times. I think it was a way to limit teachers to their assigned vacation times and because we technically didn’t get PTO because we are all exempt.

      1. blackcat*

        Yeah, that’s pretty standard. My old job, though, had the rule that if you got internal coverage (from other teachers giving up their prep periods), it didn’t count as a “personal day” or a “sick day.” This was GOLD for taking half days/doctors appointments/etc. I think it also fostered a general atmosphere of helping each other out as needed.

        But yeah, more than 2 personal days or more than 10 sick days, and the sub came out of the paycheck.

      2. MaryMary*

        I don’t know any teachers who have to pay for their own subs, but several schools make them responsible for finding their own subs. My mom retired a few years ago but likes to substitute every now and then. She is in high demand among her former colleagues and acquaintances. Everytime she subs at a new school, several people’s eyes light up and they ask if they can have her number.

      3. Artemesia*

        I was a tenure track assistant professor at a small college where a. my health insurance did not cover maternity (the national law kicked in a couple of months after the birth of my daughter — I was badly paid and so went to the local welfare clinic with sliding scale for pre-natal care and delivery and was delivered by whomever showed up that day — a man I had never met). They also provided zero maternity leave and I was required to pay for my replacement if one was needed. I tried to time the baby for early May to catch summer break and she was born in early April (we were more successful than expected getting the project launched) and so I taught a seminar starting two days after the birth and a couple of colleagues taught my undergrad classes the last couple of weeks of the semester. I graded everything.

  10. Les Nesman*

    Two years ago I cancelled a vacation because work was crazy. I had recently been given a promotion and was a little leery of leaving things a mess a month later. I didn’t say anything to my boss about it, and only mentioned it to another co-worker who enjoyed vacationing at the same spot and who asked why I hadn’t taken the trip she and I had discussed. Unbeknownst to me, she passed the word to my boss and at our next raise, I was given a bonus to cover the cost of a new vacation (I hadn’t lost money on the first one and they did know that). I’m still glad I didn’t go, the team I inherited had so many issues that I just finally resolved the last one this fall. Any vacations taken from here on out will be so much more relaxing!

  11. anonanonanon*

    This past summer, my manager said our team was too busy to take any of the vacation days we had scheduled, AND THEN went and took vacation herself, which was infuriating. Our department head gave everyone a week of comp days to make up for it, but it still really annoyed me.

    1. I'm a Little Teapot*

      Ohh yes, I’ve seen multiple emails demanding that no one take any vacation or even call in sick for the next x months, followed immediately by vacation or sick days by the same manager.

    2. hbc*

      Oh, man, a former manager here had every one in his department pull mandatory overtime for every day in June (one of the few nice months here). Not only was it due to scheduling mistakes he made in May, but he didn’t put in a single longer day himself and gave himself 4 three day weekends. Horrible.

      1. anonanonanon*

        That’s awful. This same manager at my company also took a week long vacation the day after major layoffs and impending layoffs in our department were announced.

  12. TheBeetsMotel*

    None of those options are acceptable. It should be a prerequisite of being in a managerial role that you deal with people’s vacation requests professionally and compassionately, and once requests are approved, unless the building catches fire, that person gets their damn vacation.

    “We always need you here” is a sign of poor management. If you were hit by a bus tomorrow, they’d find a way to cope. They can do so far more easily for pre-planned vacations, so there’s no excuse.

    1. MashaKasha*

      Came here to say this, re this being a sign of poor management and poor planning. What if OP hits the lottery tomorrow, are they going to tell her to hire a freelancer before she can quit? Or else what?

      I’ve worked in mission-critical environments, fast-paced, deadline-driven environments, most of the teams I’ve worked on were shortstaffed, and I’ve NEVER seen anything like this happen. There can be a vacation freeze during certain times of the year, but it’s announced months in advance and vacation requests for that time period are not approved. If a vacation has already been approved, it’s happening; the rest of the team somehow manages. This is how things have been at every place I’ve worked.

    2. TootsNYC*

      The fact that a freelancer COULD be hired to do her job means she should just go.

      She should document everything, and then just go.

      Holy Toledo, how much does a freelancer cost? I pay $35/hour, and that’s $1,400. It’s really not that much money in the scheme of things.

        1. Chalupa Batman*

          I took it as the company has financially reasonable options besides making OP skip vacation. $1400 is not a big deal for a medium to large company.

        2. TootsNYC*

          No, she shouldn’t pay for the freelancer.

          I mean for the company, it’s not that much money in the scheme of things.

          By “I pay,” I meant, “out of my department budget, of which I am in charge.”

          I don’t even think $1,400 should be that big a deal for anything but the smallest of companies. And maybe not even them; they should be factoring vacation coverage into their budget.

          And if their freelancers earn less, the coverage costs are less!

  13. Menacia*

    My coworker’s husband was in the same predicament. He could never take time off because the company he worked for was very small, and he was the primary. Well, years and no vacations later, he starts looking for another job, boss finds out, and fires him. Was probably the best thing that ever could have happened to him, because now he’s free to take time off, and really think about what he wants to do next. Not the ideal situation, but he and my coworker are in a good position financially, so it could have been worse. Of course now, his boss is frantically trying to get a handle on all the work that is now squarely in his lap. Talk about cutting off your nose despite your face!

    1. F.*

      Although they won’t fire me, that is the position I am finding myself in. Unfortunately at my age (mid 50s), finding work would be next to impossible. I have only 18 mos in my HR manager position and no HR degree, so I would have to go back to admin asst work and take at least a 20% pay cut, which is unsustainable.

  14. Temperance*

    This is timely – my work has been crazy, so I was planning on coming in to work today, but my boss told me that I need to stay home instead. I only used 3 hours of PTO, but it feels great to detach for a day.

  15. Renee*

    At my last law firm I was the only associate with two partners. The junior one was especially good at taking responsibility for tasks and then dumping them on me as the deadline approached. I ended up becoming the primary brief writer and was constantly writing furiously on deadline. I had no scheduled vacations for more than two days at a time in two and a half years while the partners each had at least 2 month-long vacations a year (and I couldn’t take vacation while either of them was out). The outcome – I got extremely sick with a chronic pain disorder and a collapsed immune system, and my doctor took me off work without notice for a week to see if it helped (it didn’t). I went back to two extremely pissed off partners who pulled me into an office and lectured me about stepping things up. I told my doctor what had happened, and he pulled me out of work indefinitely. After a couple of weeks of temporary disability (hallelujah for living in Cali), I realized that my good health was fundamentally incompatible with working with those two a-holes. They fired me when my doctor would not certify me as able to return to work by their deadline, and all I felt was blessed relief. I’ve never gone back to working for a law firm in my community and I never will. If you can’t take a vacation, it may be time to evaluate your career choices. I’ll never put up with that kind of BS again (and with benefits I am making about the same amount of money anyway).

      1. Renee*

        Unfortunately I don’t think this is atypical of the work culture in a lot of the firms here. I’m sorry you had to deal with a-holes too, and I hope you’ve ended up somewhere much better. The happy ending for me is that my job now is super laid back with a nice group of people, and they think I’m a rock star because I can juggle like crazy and nothing stresses me out. What they don’t know is that there is nothing here that even comes close to the pressure I dealt with at any law firm.

    1. neverjaunty*

      I’m imagining what happened when they suddenly realized nobody was doing their work for them.

      1. Renee*

        I was friendly with the support staff, and they said it was crazy, in large part because a lot of the clients were unhappy I was gone. As a special schadenfreude-y treat, the intern they brought back a few weeks later after she had passed the bar quit law entirely after about a month of working there.

  16. Workfromhome*

    The option to “take vacation” but be accessible for work should never be accepted. Vacation means you don’t work. Taking vacation but still responding to email calls etc is just “working offsite or taking a long lunch break”.

    I take at least one week a year in a place where there basically is not cell or email.

    Any other vacation I take I set an out of office that says ” I’m out until X and will have no access to email or voicemail. If you have an emergency please contact XXX. If you require a response from me by email please resend your request on X when I return.”

    I create a vacation folder in my email so I don’t see ANY work emails on my phone.
    When I return I scan through the folder in case there are any documents I might want to keep but any questions or enquirers I assume they solved or asked someone else unless I recive a new email.

    People often say that client or their company would never accept that but after doing it a few times I noticed that 99% of the emails that came in while I was gone were either solved by other means (if it was critical) or it really wasn’t that important and I never got a follow up email.
    If I am truly so critical that you can’t go a few days without me you are not playing me nearly enough. If I’m that indispensable then I must be very hard to replace and you wouldn’t want me to find another job because I’m ticked over not taking any vacation..if I’m replaceable then you should be able to replace me while I’m on vacation.

  17. Mike B.*

    The only acceptable excuse I can think of for revoking someone’s approved, paid vacation would be that literally no one else can perform certain tasks that aren’t sufficiently complete and can’t be put off. But that’s clearly not true if a freelancer is capable of doing the work, so the company should have been prepared to hire one on its own dime. There’s something seriously wrong with either the culture or the finances of this place.

    I would think “pay a freelancer” is a non-starter, since that’s in effect docking a salaried employee a week of pay when she has PTO days. There’s unfortunately no law against “we don’t care what we told you or what plans you’ve made; work these days or you’re fired.” Most companies just don’t do it because it’s hard to keep employees in that situation who have a choice in the matter.

    1. TootsNYC*

      Also–OK, so some work didn’t get done in advance–can’t ANYTHING that people do while she’s out be put off until she gets back?

      That’s how I’ve handled most vacations–work like crazy before; play catch-up after. And we all cover for one another, because what goes around…

  18. Sidenote*

    Sorry Alison, but BOO to the autoplaying, large video before the comments. It is SO BIG! and I really hate autoplay videos. They mess my browser up all the time. :-(

    1. Ask a Manager* Post author

      Over the next few weeks, I’m going to be experimenting with some different ad formats (in part because traffic is slower right now than it will be in January, so this is a better time to do it). It shouldn’t be auto-playing sound, though — if that happens to you again (with auto-play sound, not just auto-play video) and you’re able to send me the URL it clicks through to, I can have it blocked. Unfortunately I can’t track it down without the URL.

  19. Nanc*

    My feeling is if I dropped dead at the bus stop on the way to work, the company would soldier on. Therefore, they are capable of soldiering on while I’m on two weeks vacation.

  20. The_artist_formerly_known_as_Anon-2*

    If the work never stops – then TAKE your vacation and then – and worry about the consequences.

    Some years ago I was planning to take a vacation in July. In April – I asked – and was given permission to take two weeks. I emphasized it because we were going to Europe/UK and airfares, car rentals, hotels were non-cancellable.

    So I bought three plane tickets. I rented a car through an agency in Britain. I rented two places. I paid.

    Then they call me into the office and ask me to cancel. I said “I can’t”…. they begged me to. It was their problem, they were supposed to delegate someone to back me up – and the delegatee didn’t want any part of it. So – “we may be able to cover the cost of your cancellations”….

    OK – three plane tickets, that was $1800. Car rental, that’s $500. Four nights B&Bs, that’s another $250.
    “Hmmm… 1800, 500, 250 = $2550. Plus 30 percent — hmmm…. that’s $3315, plus, it will cost you an extra week…”

    “What’s the 30 percent for?”

    “TAXES. If you cut me a check for $2550, I’m going to lose a lot of money because that was all post-tax bucks I laid out. You want me to go home and tell my wife and daughter that the trip of a lifetime is cancelled – that’s one thing. But to tell them we have to eat soup for awhile because you won’t cover my losses….”

    End of story. Well, not really, but there’s a dinner-table story that followed this. For another time.

    1. TootsNYC*

      It was their problem, they were supposed to delegate someone to back me up – and the delegatee didn’t want any part of it.</i.

      Umm, boss, how about you fire his butt? Because, well, you're the boss, and you just delegated.

  21. MaryMary*

    At OldJob, I knew of a woman who postponed her wedding (!) twice (!!) because of critically important projects. When I left OldJob, she was three levels above me even though she’d only been hired about a year before me. Last I heard she was continuing to work like crazy and rise through the ranks. More power to her, but a large part of why I left is that I didn’t want to work for a company where the culture made stories like that legendary instead of insane.

    1. Ruffingit*

      That is sick. Makes me wonder if that marriage ended in divorce when she finally was able to get married since she was likely spending so much of her time at work and postponing time with her husband for work.

  22. el_g*

    Ugh, this is my life. I’m the only person that runs my area of my department, so my boss hates to approve any time off and always freaks out the day before I’m off. Doesn’t matter if I take one day or two weeks, she freaks out every time. Then when I return all I hear about is how hard it was for her to handle everything while I was gone. It makes me feel horrible every time. I took my first international vacation this year, giving six months notice and it took 3 months and lots of negotiation to get it approved. Sometimes I don’t bother asking for time off because the process is such a headache.

  23. NewDoc*

    Due to retirement/staffing issues, there was a period of time at our hospital where there was only one surgeon who could do heart transplants…when he went on vacation they would have a plane on standby at our local airport to go get him in case a heart became available.

    Fortunately for me, I’m not a highly specialized surgeon, and residency is actually really good about honoring our vacations (of course, they are built into our schedule a year in advance, so there’s that…)

  24. WorkerBee (Germany)*

    Probably too late to the party. Tomorrow I am leaving for my vacation and for the first time I have someone cover / work on parts of my job, so that I won’t come back to a massiv pile of work. This is huge and I should be happy. But for whatever reason I am more worried that the new coworker can handle it. Did I train her enough? What if she makes a huge mistake? If you can’t tell, I am for the first time managing someone.. Help!

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