how can I take time off when my team needs it more?

by Alison Green on November 22, 2022

A reader writes:

I like to take vacation during the popular times that everyone likes to — spring break, 4th of July, and Christmas. The problem is that the small team I manage also likes to take that time off.

We have a specialized skill set. My boss has no experience in this space — he’s in his job because he manages well, not because of expertise — so he cannot cover for my absence. Only my team can do that.

I get five weeks of vacation that doesn’t roll over and I haven’t even used two weeks of it. I intended to take the week between Christmas and New Years off, but a second member of my team requested that time off today. Giving up my vacation makes me want to cry. But I don’t see how I can deny letting my employee travel cross country to visit her family for the holiday just because I want to hang at home with my kids and watch TikToks. (And yes, I know I could take other times off for vacation but the popular times are when my kids have school/sports breaks. I struggle with taking vacation time just to sit at home alone, do laundry, and let work pile up at the office.)

My team is stretched incredibly thin due to budget constraints and there’s no line of sight for me to hire them help. Giving them time off to recharge is the one thing I can do for them but I really need that recharge time too. How do I enjoy time off with my family without being a selfish and crappy manager?

Whenever you manage a team where not everyone can be gone at once, you need a clear and transparent system for how time off will work, especially during peak desirable times. Some teams do it by seniority (not terribly fair but at least it’s a system), some rotate from year to year or holiday to holiday, some do first-come first-served (really not fair if you’ve got one person who always requests the most desirable dates really early), some ask everyone to submit their first and second choices of dates and try to make sure everyone gets at least one of their choices, and on and on. It sounds like your problem is that you don’t really have a system, so anything you decide is going to feel unfair to someone (whether to you or to your staff members). That won’t help you this time, but take the current conflict as a sign to get something in place going forward.

As for the current conundrum with your employee … ugh. Can you split the time between you? (That may or may not be realistic with a cross-country trip, of course.) But it’s also not totally unreasonable to decide that her request came in too late if in fact that’s the reality of it and if you’d claimed the time first (in a transparent way, not just in your head). Practically speaking, it wasn’t great on her end to expect she could give only a month of notice to get a week off during a highly desirable vacation period on a team that needs coverage.

Before you decide, though, take a really hard look at whether both of you have to be there that week. Will the workload that week really require it or is it slow enough that full coverage isn’t absolutely essential? Could you make it work if each of you agreed to log in remotely a couple of days, in order to make both vacations possible? (Obviously that’s not ideal and you’d only be doing it with the understanding that going forward you’ll have a better system.) Might someone else be willing to cover for you if you can come up with the right incentive (like a bonus, even if that requires making the case to someone above you)? Do you have the authority or the capital with your boss to say, “We’re all exhausted from unsustainable hours this year and our department is closing that week so we can all get a break”? Maybe none of these solutions will work, but it’s worth getting creative to see if there’s a way to solve it.

But again, you need a clear system so everyone knows how time off requests will be decided, so they can work within that set of rules in the future.

Also! Make a plan to ensure your vacation time won’t pile up like this next year, and make sure your team is doing the same thing too, which will probably require explicit assistance from you. You don’t just need time to recharge at the end of the year; you need it throughout the year too. (One thing to consider since you have a lot of vacation time that you might otherwise lose is to take a bunch of three- or four-day weekends throughout the year. They can be surprisingly beneficial and are short enough that you’re less likely to just be bored at home — and taking all your vacation time is a good thing to model for your team.)

Read an update to this letter. 

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  1. Prospect Gone Bad*

    There is a whole art of mastering workload that takes time. After 20 years in the workforce I finally realized that there is never a good time to take a vacation, so just started doing it (as long as it didn’t overlap a huge meeting or new product launch).

    I think your issue started in April or May when you subconsciously decided not to take time off. If you have five weeks vacation you most likely are going to “have” to take off quiet periods because you just have a lot of vacation time. I myself have niche tasks so I get it but I also think the talking point gets overplayed in various work discussions at times. At a certain point you have to be comfortable just telling people “widget sanding is closed this week” and see if you get pushback. Most companies realize they want to have it both ways – a role is niche but they don’t want to pay more people to do it, so they quietly learn to accept you taking PTO.

    Once I became a manager I realized the vacation coverage issue is something else that you need to start thinking about months in advance, as well as the niche role thing. If you are niche but also keep the company running, at a certain point, you just need to take time off. Or think long term and start training people in basics for when you are gone.

    2. Tio*

      Sounds like the LW really wants some very busy times off, but I think the LW is really getting in their own way with the thought that their team should always take priority when giving a request. LW, you need to be able to say “I had this booked already and we can’t have two people off, so I can’t approve this this time. Are there other dates you want?” You get to give yourself priority once in a while, as long as its not all the time.

      Alison’s point about the system is a really good one. LW needs to outline a system, have a meeting, and lay out that system. the system should include “must request more than X days at least Y days in advance”, i.e. Must request more than 2 days at least 3 weeks in advance or whatever system they want to implement. They can even give more consideration to the holiday season, and do something like “All requests for time off of more than 3 days in Q4 must be received by September 30th and will be assessed and approved on Oct 1st”. Adding team time off to the calendars can also help people manage their expectations in most cases.

      1. Anne of Green Gables*

        My workplace sets a deadline for requests for holiday-adjacent time off, to ensure we can still maintain needed coverage. We do this for Thanksgiving, Winter Break/Christmas, and 4th of July.

        1. GythaOgden*

          Not quite the same, but our employer mandates we give 8 weeks notice for longer trips. My trip in January will need a single week rather than two, but I wanted two days either side, since it involves a trip to America and I remember the few times I’ve been before needing a day or so to pack and a day to recover from jet lag. I arranged it in February and booked the days out by May, but I think that’s very fair — give people as much time as necessary to sort stuff out, particularly in client-facing jobs like property management and maintenance. I’ve had discussions here about ‘Why can’t you just get another person?’, but unfortunately, I am the extra person on our team and I still get the same 27 days holiday as everyone else.

          The one thing I couldn’t do in my role though is dial in from holiday! I’m not sure that it would be possible to take our franking machine away with me — that would be one heck of an excess baggage charge! Disneyworld might be the most magical place in the world, but I’m not sure even the Fairy Godmother could conjure it and the envelopes we need to send out up and whisk it back across the Atlantic.

      2. MJ*

        One former job had a 2x rule. For example you needed to give minimum of 2 days notice to take 1 day off, or 2 weeks notice to take 1 week off. Taking 2 weeks off was 4 weeks notice. Managers could be flexible if something unexpected cropped up, but for planned vacations we were expected to give the required notice so coverage could be planned.

        At another, education adjacent, job we were not allowed to take the two weeks before or the first two weeks of term off. New hires were told this during their interview. On the plus side, the office completely shut down from midday Dec 24th until Jan 2nd.

    3. tw1968*

      If there’s no budget for more people, and they won’t allow vaca to roll over (or at least PAY you for what you’ll miss, some companies do this)…then it MUST NOT be important to the company to have backup for you. You should all take the time off and let your boss know why. Unless it could cause someone to lose their life if you aren’t there, then you all need to be on vaca and when a “crisis” comes up, it will then be important to the company to have additional staff for coverage…or… it won’t be. Enjoy your vaca!

      1. Iroqdemic*

        “If there’s no budget for more people, and they won’t allow vaca to roll over (or at least PAY you for what you’ll miss, some companies do this)…then it MUST NOT be important to the company to have backup for you.”

        You just blew my mind a little. THIS EXACTLY THIS.

      2. Legal Beagle*

        It seems that the company would not be taking an unreasonable position by pointing out that OP could have taken all of her vacation without the need for additional employees or rollover, simply by scheduling at least some of her vacation during less popular weeks. OP seems to be electing to not take her full vacation if she can’t get the exact times she wants (which happen to be the times that everyone wants). I do agree that a more thoughtful, strctured approach needs to be taken toward divvying up vacation times going forward.

        1. doreen*

          It’s good that (unlike some people I’ve known ) , OP doesn’t take all the popular weeks and leave the rest of the team with unpopular weeks – but it’s also not the company’s fault that the OP only wants to take time off when her kids are on school breaks which also happen to to be popular times that other people also want. Thinking just about my kids’ school schedules , they had about eleven full weeks off from school. I don’t know how many people are on the OPs team or if they all have five weeks of vacation time but it seems that only one at a time can be on vacation. If the team consists of the OP and two other people, there’s no way three people can each take five weeks of vacation during the eleven or so weeks that are school breaks.

      3. Rose*

        I am finally in a job where it is pretty relaxed, we are definitely shutting down Christmas to New Years, it doesn’t matter who is off or on vacation. I also had a child not long ago. And let me tell you, work is such a low priority for me – I want to spend that time with my kids! And it doesn’t matter if someone doesn’t have kids…unless you’re literally saving lives or you’re being paid so incredibly as to make up for working Christmas, stop dude. Work somewhere else. There are chill jobs out there. And my vibe from the LW is she’s ok financially like I am and we’ve been in the working world for a few years. Your company could hire enough people so you wouldn’t have to stress about this – that’s their problem. Why are you missing time with your kids to make the CEO rich?

  2. Sheworkshardforthemoney*

    You need the time off just as much as your co-worker. Your reasons don’t matter, it’s time that you are entitled to take. This is something that your boss needs to manage.

    1. ThatGirl*

      Agreed, and also – only taking two weeks out of 5 allotted? is not setting a good example for your reports. Your mental health deserves consideration too.

      1. Miss Muffet*

        Also, you’re essentially working 3 weeks for free by not using that vacation, which is a part of your compensation.

        1. Kevin Malone*

          Right, it’s like saying you don’t want to get paid for a couple of weeks.

          It also is a really bad example to your employees.

          1. Zorak*

            And there’s no reason your home vacation time needs to be “sitting bored with the laundry” unless you choose it. Pop over to a museum, go to a movie, take a hike or walk, make an art, redecorate a room, have a home spa day, read a book in the park… there’s a whole world of possibilities!

            1. rebelwithmouseyhair*

              I get the impression OP has young kids, because that’s a time in the life of many women where “me time” only starts once they’re all fast asleep and ends the minute the first wakes up. I had the same attitude to paid leave: my kids hated the daycare centre they went to during the hols, so I would save my leave for the school holidays. You can get into a mindset where, if you do find yourself at home without the kids, you wonder what on earth you used to do with your time before you had them.
              Not saying this is a good or bad thing, just that it is a thing.

    3. M*

      I think you should both take it off. There is never a good time for a vacation. Also, speak with your boss and/or HR about creating a policy for vacation time.

      On my team we need at least one person in the office during working hours. For the summer we all go over our vacation plans in April/ May so we know who will be in the office. If someone needs to book it earlier they can send me an email and 9/10 I will say go ahead and book it and make sure I don’t take that week off.

      The last week of the year (Christmas to New Year) I close our department. This way no one feels they need to work, some do work a couple days but it’s WFH and totally up to them. It is part of our busy season, but it is the right thing to do for the team and if I need to work late in January to do that I am happy to do it.

      Vacation is a benefit of your job, take it. And like said earlier take short weeks if need be. Taking time throughout the year will help with productivity too. Good luck!

  3. Akcipitrokulo*

    Would your company be open to flexibility regarding rolling them over, on a one-off basis, given circumstances and on understanding you will put systems in place?

    On booking holidays – my job strongly encourages time off for the year is 75% booked before summer, and insists it’s all booked by 1st October – you can still change it of course (I had a family emergency so had to swap out one of my Christmas-New Year week for a day to deal), but everyone at least has it pencilled in, so you don’t have everyone needing to use it by the end of year.

    1. Hannah Lee*

      My company has done this on occasion. There is a standard “you can roll over up to 1 week” policy. But there are times when either more time can be carried over or employees get paid for accrued time that is over a week due to business reasons … eg a large order came in from a critical customer that the owners really want to fulfill before year end, and some people have a lot of accrued time they would lose at year end if the standard policy was stuck to.

      We track it throughout the year and managers try to encourage people to book time off throughout the year, but inevitably each year there are some people who have used up ALL their allotted paid time off by July and then are unhappy if they need to take time off or the owners announce a shut down between Christmas and New Years and other people who like to save ALL their time off for the end of the year when it’s not realistic given our business cycle for them to take 3-4 weeks off in December.

      1. Akcipitrokulo*

        Yeah – we don’t want you to *take* it by the deadlines, but it does have to be booked. But flexibly, so you can book in placeholder days.

    2. KHB*

      It sounds like there’s no reason to think that everyone won’t have more vacation time than they can reasonably take next year too – in which case, rolling over the unused time from this year doesn’t really do anything.

    3. Greg*

      Vacation management is equal parts art and science. We have our planning start in January. We have multiple stakeholders that have 5+ weeks of vacation so we always ask that those individuals take one week per quarter (avoids burnout and prevents any major build up of unused time). Vacation scheduled around school breaks is on a rotating basis. People at the top of the list get to pick one week and then go to the bottom. One person from each team per week vacation.

      We allow flexibility within the teams around these guidelines; lots of negotiating and side conversations happen before everyone walks in the room. We have a workforce that loves to hunt, so lots of summer weeks are traded for fall weeks within the team to get around the once per quarter.

      We have found that these transparent guidelines around vacation planning avoid most major arguments and most surprises. Everyone knows the rules walking in and no single stakeholder monopolizes the ‘good’ dates on the calendar.

  4. KHB*

    On the holiday week specifically, I agree with Alison that you need a system for how vacation time is allocated. It’s good that you’re thinking about accommodating your team and realizing that you don’t get to be first in line just because you’re the manager, but you also don’t need to be last in line just because you’re the manager.

    On time off in general, you’re each only one person, and you don’t owe your employer more than one person’s worth of work. If you’re chronically overworked and understaffed, would it be OK (as in, nobody literally dies) to let a few balls drop? If you keep pushing yourself to the point of burnout to get everything done despite not having enough people, that’s a great way to ensure that you’ll never get enough people.

    1. Janeric*

      I think this is a good point — it’s better to let a few balls drop early than to go full speed into burnout and employee loss.

    2. Cmdrshpard*

      I agree with this, if OP put her time off in a shared calendar or doc of time off requests as Alison said somewhere other people can see that is not just their own head, no need to give it up.

      But if it really was just I am going to take time off this week and didn’t let anyone know, even if OP planned/thought about it months ago it comes off bad even if the employee just put this request in.

      If I looked at the calendar saw no one had requested it and I asked for it and my manager took it instead I would be upset, but if it was marked as “manager off x dates” I would totally understand if I couldn’t be off.

  5. soontoberetired*

    Yesterday I found out the team we work with closest did their oncall schedule without considering who would end up with holiday coverage. The management person I was with and I both said, that is highly unreasonable, and you need to work things out that everyone takes a holiday time during the year, and someone isn’t stuck with taking 2 (they had 2 people with 2 holidays each so that did mean some people had no holidays at all). My group has for a long time on its own worked out who takes holiday coverage for the entire year sometime in january. That gives time for people to plan trips, etc, and make sure there’s people around.

    it is just being considerate to plan all this out before hand. Our planning is much better than our old manager who would try to stick me with every Christmas because I had no family aka children. I told her my parents would be shocked to find out they didn’t count as family.

    1. OP*

      OP here and this is exactly why I’m worried about denying the request. The requester is the only single, child free person on my team and I do not want them to feel punished for that! It’s really important to me as manager that they’re all treated fairly.

      1. MidMgr*

        I manage a team of 10, and run into similar issues on occasion, and we have a shared vacation calendar that tracks this time. Typically I handle it by one of 2 ways:
        1. Ask the employee if the dates can be adjusted (e.g. they haven’t paid for flights yet), and offer a shorter overlap by negotiating alternate dates for my own time and theirs. If this doesn’t work, see Option 2.
        2. Approve the time and take my own. Alert the people who usually interact with the team that we’ll be short handed date – date and please understand that response times will be slower during this time. (I actually announced that my staff would be unavailable this Friday, even though I do not have the authority to close the office. We’re “open” but unstaffed.)

        In either scenario, I don’t sacrifice my own time off though I may adjust it unless my plans cannot be changed. Unless your role is of the life-saving variety (as other commenters have mentioned), there is no real harm in just being short staffed for a week or two.

        On the topic of not taking your time throughout the year, I used to do that too. What I personally found was that the stress of carrying the banner for the team made me a worse parent for my kids. Once I came to terms with that and made it a priority to be there for the kids, no matter the cost to my job, I found it much easier to take my alloted time. The work was still there when I got back, and the team has never been resentful of me for taking my allocated time. It’s OK to use the time. You’ve earned it.

      2. Allonge*

        Having to take care of holiday coverage once is a thing that happens. A pattern is the issue.

        And it’s important that the whole team gets treated fairly, and that includes you!

  6. SC*

    Is there a chance that you don’t actually need to work that week at all? This is probably coming from a place of not understanding US norms as much, but where I work in the UK our business basically shuts down over that time period. I know some jobs require coverage for legitimate reasons, but some things can definitely wait.

    1. The OG Sleepless*

      When you work in an industry that shuts down during the holidays, it can be hard to remember that plenty of offices have business as usual and some are even busier. One of the many things I hate about Christmas is that my work is busier than normal, but most of the rest of my family works in education or finance and I’m surrounded by people who want to do lots of fun things and can’t quite remember that I can’t.

      1. Kevin Malone*

        Same – its the end of the year crunch, so actually that week between Christmas and New Years is super busy. We still have people off, just because…it’s the holidays, but there does need to be people there so have to limit it.

    2. ThatGirl*

      I’m wondering what kind of work it is — some jobs truly need to be done, even during the holidays (news reporting, healthcare, 911 dispatch come to mind). But other jobs, even if they’re *busy* during the holidays, it’s truly okay to let things go for a few days. It’s not life or death or a public good.

      And I think part of the answer is that the OP needs to figure out a fair way to prioritize time off requests including their own – but the other part is, are you TRULY unable to have two people off on a given day? What if someone was on vacation out of state and someone else got sick? Even in coverage-based jobs, sometimes the answer is “just do your best”.

      1. Rain's Small Hands*

        Its more than those sorts of jobs. My husband worked in ecommerce operations – the post holiday season was always busy and always needed to be staffed – few people got days off over the holidays and he’d be available remotely even Christmas day. People shop online looking for post holiday specials as soon as the presents are unwrapped. I also worked in IT, and the holiday slow period was a great time to swap equipment or upgrade – fewer people impacted if something went wrong. And we needed to staff end user support – some people still worked through the year end – including those who don’t celebrate Christmas and enjoyed a quiet few days to get stuff done. Now I’m an accountant – and payroll needs to get run even if its a holiday week, invoices sent out, bills paid – all that still needs to be processed because people want to get paid on time – and because the holidays happen with a calendar year end, there is a lot of year end stuff that needs to be done as the year closes out – some which you can prep a little before December 31st – other stuff you hit the ground January 2nd to make sure everyone has their tax forms on time.

        1. ThatGirl*

          Oh, sure, those were just a few that came to mind. But honestly even on some of those you can get by with a skeleton crew.

          1. Ann Ominous*

            I’m not seeing how a skeleton crew would work in any of those particular examples – seems like they’d actually need to surge support instead.

            I agree with you that there are many cases that a skeleton crew would be fine, and businesses just keep going anyway out of habit or whatever, but I’m thinking about people whose work surges during this time.

            I imagine they must feel kind of invisible.

            1. ThatGirl*

              I worked in newspapers for four years and we always got by with skeleton crews on Thanksgiving, Christmas, etc. Now, THIS year probably a hospital can’t get by with a skeleton crew, but I would imagine in some places, in some years, they could.

              I also worked at a baking and decorating supply company for 3 1/2 years and Oct-Dec was hands down our busiest time, but we still made room for people to be off, and some things just went a little slower than others.

              Of course there are jobs where that isn’t possible, where important legal, regulatory, or health and safety things need to be done and you need a certain number of people to do them. But full staff over holidays is OFTEN (not always) a choice, not a necessity. My point is that we just don’t know which is the case here.

              1. Merrie*

                At the hospital, some shifts & departments are staffed to account for elective surgeries/procedures, so on weekends and holidays there’s less staffing on those shifts. But in instances where those aren’t a thing, staffing levels will stay about the same. I work overnights, and our staffing level is the same all days of the year. If the holiday comes up in your rotation, you work it. But at least I can hang out with my family before going to work in the evening.

          2. The OG Sleepless*

            I work in veterinary medicine! Pets get sick 365 days a year. A lot of teachers schedule their pets’ procedures for during school breaks. And not to be too gloomy, but for several reasons we do a ton of euthanasias this time of year. No skeleton crew here.

            1. ThatGirl*

              I did say *some*. And that it depends on the job. Our dog died on Dec 20 last year so trust me I’m grateful for vets who work around the holidays.

        2. CTT*

          Yeah, I’m a transactional attorney, and while very little of what I do is life-or-death, a lot of it is driven by the tax year closing and things have to get done by 12/31.

          1. Legal Beagle*

            Another reason to avoid having multiple people out during the holidays with a skeleton crew to keep things going is that it really, really puts a burden on the people unlucky enough to be on the skeleton crew.

        3. Professional Lurker*

          I worked in ecommerce returns department for a while. The week past Christmas was BRUTAL. Everyone scrambling to return or exchange their unwanted gifts.

      2. Ellis Bell*

        Every job I’ve ever had before my current one was at their very busiest at Christmas; retail, leisure industry, news, tourism… Though admittedly OP said nothing about it being a busy season, so it’s definitely worth considering mothballing things, or having fewer, or delayed targets if at all possible.

      3. doreen*

        but the other part is, are you TRULY unable to have two people off on a given day? What if someone was on vacation out of state and someone else got sick?

        Sometimes that’s exactly the reason you can’t have two people off on a given day – because maybe you can manage if one person is on vacation and another got sick but you can’t manage if two people are on vacation and a third got sick. And you could end up with one person on vacation and two getting sick – but there’s nothing you can do about that (other than not letting anyone take a vacation. )

      4. Ellen Ripley*

        I work for a very large company in manufacturing and R&D and we run 24/7, so a crew has to be there at all times. Turning all the machines off so everyone can go home is a huge deal and not likely to happen.

    3. LawBee*

      I have never worked at a place that wasn’t busier during the holiday season – when everyone else is off and has time to call us for “updates” and “status checks” and “I want present money for my kids”. It sounds lovely. One day.

    4. OP*

      There is a chance but I won’t know until like the 20th or so (manufacturing company so it’s dependent on what production is happening) So maybe this problem will be be taken care of but I’m appreciating the advice on avoiding in the future.

  7. Annonymouse*

    I think it so important for managers to model good work/life balance and be vocal about it. Whether it’s taking sick time, vacation, the afternoon off for a family thing, minimizing work out of hours (even if this is using the delayed send button on email) as well as working with their team who may need/want non traditional work hours..that’s the best way for companies to show if they really value work/life balance

    2. Fives*

      Yes! Last year in late spring, my manager said in front of me that they hadn’t needed to take time off all year like it was something to be proud of. It wasn’t. They had been a bear all year and did indeed need to take some time off.

      1. Important Moi*

        A manager I know, has already announced they will be available to work Friday, Saturday and Sunday (after Thanksgiving in the US). Basically, forcing the team to be available to work.

        Folks, we produce TPS reports (from the movie “Office Space”). It can wait.

    3. JustaTech*

      Yes to this!
      My husband is a manager and a couple of times I’ve had to coach him on being clear (but kind) about setting boundaries about weekends, evenings, and emphasizing taking time off.

      He had one employee who was so worried about taking any time off that they weren’t picking up a needed prescription because it would take half an hour in the middle of the day (and they were working so late the pharmacy was closed by the time they were getting out of work). “You have my explicit permission to take time off to pick up your prescription. Part of being a good employee is taking care of yourself.” (This person didn’t end up working out in that position, but they were able to move on with grace and their head held high, rather than running away in a panic.)

    4. OP*

      I know this. But my team does use all most of their vacation— I do make sure of it. My team member shuffled her last four days in this request.

      I’m do as I say, not as I do.

      1. Weaponized Pumpkin*

        So they’ve taken as much as 4 weeks of vacation already (assuming you have similar amounts) and you’ve not even taken 2?! Keep the days off!

      2. Uranus Wars*

        I am glad you allow your team time off – but you need to use yours too! This is a huge imbalance if they are using all theirs and you are not even using half.

  8. Just Your Everyday Crone*

    Some of this is that your team is stretched too thin, or, IOW, the company is under-resourcing its needs. You and your team should not be bearing the entire brunt of that. If others in the company don’t get everything they want or get it done to acceptable rather than excellent standards or get it with more of a delay than they’d prefer, that is a fairer result than you giving up your vacation time, even without any fault ascribed. If they company can’t afford more help, then they can’t afford perfection, and that’s a decision they have to make. They need to set priorities in terms of the work that needs to get done that are not “the employees burn themselves out.”

    1. Hannah Lee*

      “If the company can’t afford more help, then they can’t afford perfection, and that’s a decision they have to make.”

      That’s a great perspective.

      And LW might be position to look at times during the year that are usually the top vacation times and either close the department completely or let their ‘customers’ know that it will be a smaller crew so wait times might be longer and big/special requests will have to wait.

      It might not help them this year, but when planning for next year, some combination of strategically planned shutdowns managing staff to take time off throughout the year, and modeling that themselves, and coming up with a system to managing competing time off requests, may take the pressure off going forward.

      For this year, is it possible for the department to just be shorter staffed than usual during x # of days at the end of the year? Can LW set expectations with their manager to let that happen? And also let the staff that will be there know that it’s okay if they can meet every request, so they aren’t doing extra so others are out?

      As an aside, 2 things stuck out to me –

      First, that an employee is requesting a large block of time off during a popular time off period with very short notice. What’s up with that? Why didn’t they make the request sooner?
      And the second, which is likely out of the scope of the column, is that while preferring to take time off when you can share time with family is fine, defaulting to LOSE paid time off benefits when that isn’t an option, instead of taking the time off on your own, might be worth reflecting on. (It’s not either/or: Only 2 options: work or face time with kids. There are other worthwhile things to spend time on; you don’t need to spend the day home alone or doing menial housework … you could do … anything you want really. )

      1. WellRed*

        Maybe they didn’t think they could afford it. Maybe their spouse suddenly got the time off, too. Maybe grandma just got a terminal diagnosis. The bigger problem: the company either doesn’t realize it’s underpriced or doesnt GAF.

      2. Zorak*

        Yes to go to parts. It’s like people saying they don’t want to retire because they don’t want to just sit at home and watch TV all day. That’s a choice! The thing about not being at work is you can do pretty much whatever you want. Pursue creativity, relax, get into a new interest or hobby, learn something or take a class.

        One thing I do a lot on random PTO days is get ahead on life stuff, like Christmas shopping early or getting logistics done for a trip or a personal project earlier than needs be. Or tackle a backed up bigger cleaning project that’s kind of an all day thing so that I don’t have to do it on a Saturday.

        Point being: The world is within reason your oyster! don’t discount the value of days just for yourself to be yourself.

    2. Olivia*

      This is such a good way of framing this. Can’t afford more help = can’t afford to get it done as well as if you did have more help. That is a cost of doing business for the company, not for individual workers to shoulder in the form of not getting to use all (or even most!) of their vacation. And any company who doesn’t accept that is engaging in exploitation.

  9. Uranus Wars*

    I’m with Alison – re-evaluate the workload and consider you both taking off. But also, while I appreciate when my managers work so I can have time off I also realize they need time off too and don’t want them to be cranky at me because they can’t recharge! It doesn’t matter to me if they are in their PJs eating a carton of ice cream or with family.

    I manage a few people and while I try to give them first dibs all the time on vacation I just realize there are times we might overlap a few days. And guess what? The building (and the business) are still standing upright!

  10. Daniel*

    Definite yes to three and four day weekends scattered throughout the year.

    It sounds like the unit definitely needs a deadline to submit requests for vacation time during the desirable seasons–maybe the start of October for Thanksgiving/Christmas/New Year’s and maybe the start of May for summer vacations.

    Also! Keep track year over year as to who has gotten what extended holiday leave in which years, so those who didn’t get it can get priority placement for the following year. Or something else along those lines.

    1. bamcheeks*

      Yes— and depending on the age of your kids, you can get some proper family time in there! Taking a Friday and a Monday off can mean you can pick kids up from school with a packed-up car, get somewhere for Friday night, stay til Sunday afternoon, and then get back late on Sunday night, take the kids to school in the morning and then spend the rest of Monday doing all the sorting out and laundry and stuff that you’d usually do over the weekend. It gets complicated if the kids have activities that they don’t want to / can’t miss, but if it’s stuff they can miss a couple of times a year it can feel like a much bigger break than it actually is.

      Alternatively, get into the habit of taking off a day, an afternoon or a morning here and there, and just doing something nice by yourself! This doesn’t solve the bigger problem of how to schedule the difficult school-holiday times, but you’ve got three weeks you didn’t use this year, you’ve plenty of time to play with.

      1. Kevin Malone*

        Plus, kids have TONS of time off of school. Long weekends, random days, random WEEKS plus summer break.

      2. MissCoco*

        Also depending on kids age and personalities, but we had one or two random days to “play hooky” with my mom every year until 8th grade/ high school when missing school was actually an academic issue. She had way more PTO than my dad, and those days are some of my favorite childhood memories. We never did anything big, but even for kids, there’s a thrill to being on vacation in the middle of the week, and now as an adult I am glad she set the example for me to use my benefits and to take pleasure in simple things like being able to spend an entire Wednesday doing whatever I please.

    2. Ellis Bell*

      I had a boss who was really on the ball with holiday allocation. He knew which weeks were typically the highest demand for our office, (Christmas week, new year week, and the two weeks smack bang in the middle of the school summer holidays) and he made us bid for them. He asked us to rate which of them was our top, second and third priority, or if we didn’t care for those weeks at all. At the start of the calendar year, he would ask us to submit those preferences, and to at least “pencil in” our entire year’s holiday allowance (you wouldn’t be held to it if you changed the dates as the year progressed, but it got you priority and helped people avoid dates you might want). In his words “I expect to see this done before the month end, because it’s good time management to at least plan to take regular breaks; what we do is so intensive”. You could of course book off solid dates, which he’d confirm, and there would be regular quarterly deadlines to either remove, or confirm pencilled in dates. Obviously there was still hot competition for the desirable dates, with lots of people asking for Christmas as top priority for example, but he was very clear that those people who completed their calendars first got priority there. You could still ask for short notice holidays if they were showing as free on the calendar, but you were unlikely to be stepping on any secret plans.

    3. Chinook*

      When looking at these scheduling issues, I am honestly curious if religious accommodations need to come into play as well? If I am a practising Christian (or even a twice a year one), then Christmas is a religious holiday. Does that mean I have to miss out on my religious practice this year because I got to go last year? Especially when there is no equal obligation for Thanksgiving (though New Year’s Day is a day of obligation for Catholics as well, making it 2 out of 3 in that trifecta). Does that ever come into play?

      1. Zorak*

        I think it’s a safe assumption that the place is closed on literal Christmas, unless it’s like a hospital or something. Usually between Christmas Eve versus Christmas morning services, people can find time to sneak the actual religious observance in there, but I would assume that for not working on Christmas Day that might be an accommodation to set up with HR. But outside of life-saving services that’s a relatively uncommon problem not having the day itself off, versus just not having people be able to take longer time off in those last couple weeks of the year.

        1. Zorak*

          I do agree though that if we’re talking about the day of, the alternating system would need to account for the fact that for a lot of people it’s not just choosing between different days to spend with family (Thanksgiving one year, Christmas the other), it’s the judge you win religious observance that’s important which can’t be switched with Thanksgiving.

        2. not a drama lama*

          My Mom’s church (which is not a particularly big Catholic Church) has 3 masses on Christmas eve, and 5 Christmas day. Any of those would fulfill your obligation.

      2. Aerin*

        I grew up Catholic, and even the most blowout Mass was less than 90 minutes. And my parish did Christmas services for about 30 hours straight (Christmas Eve counts) to meet the demand and people’s schedules.

        I suppose there are some denominations where you genuinely spend a full day at service, but otherwise you just go before or after work/school.

    4. Cheshire Cat*

      Yes to this! At OldJob, the rule was first-come, first-served for vacations over the holidays and the summer. Then one year an employee, without kids but whose husband was a teacher, put in a request early enough that she got the week between Christmas and New Year’s off. An employee with kids in school bullied the other person to give up her vacation time so the one with kids could take it instead. (This was at a public library, and lots of people came in over the holidays, so no more than x number of staff members could take vacation that week.)

      The bullied employee didn’t tell anyone else until it was too late to remedy that year, but the next year the director instituted the rule that no one could take off the same week in December two years in a row.

  11. Blue*

    If your boss is a good people manager like you say, then he should help you sort this out. You do not have to make these decisions in defeated silence in your head, LW <3

    1. Roobarb*

      Yes, OP you said they are a good manager. I’m sure they will want to know about this workload issue and help!

  12. Roobarb*

    Last year a department in my organisation sent an email that they would be closed due to staff leave, and nothing caught on fire. I think this kind of boundary setting is a great idea and sets clear expectations. I was so impressed they had taken the initiative, rather than each person’s out of office directing to the one poor soul left working in December!

  13. Lily Rowan*

    In addition to what everyone is saying about the future, for this year, could you take off (say) December 21-27, so you’ve got some time before Christmas when your colleague is still there, and only one day when you’re both out? (Assuming you have the Monday holiday)

    That at least would give you more of a break. (I am currently trying to figure out if I could take any of those days before Christmas, since the other person of my two-person team is on leave.)

  14. Llama Llama*

    I have started with the mantra, it is still going to be a dumpster fire if I am there or not. Can I fend off the flames? Sure. But it’s still going to be there so I will take the time my company has offered.

  15. Brain the Brian*

    Alison suggested this already, but is there any portion of your team’s work that can be done remotely? Obviously, vacation isn’t the same as working remotely, but if you can each take half off the week in however you want to arrange the daily/hourly work/vacation split — with your teammember handling the essential remote work from across the country while you do the essential onsite work locally (and spend as much time as possible at home with TikTok and your family) — that’s better than both working straight through it, forcing her to cancel travel plans, or missing your own family time at home.

    You could also ask your manager if one member or all of your team can roll over more than the standard allowance of vacation hours into next year — even if only for a month or two, during which you could schedule alternating vacation times to use it — because the current extenuating circumstances mean that you can’t use much of it. The answer might be no, but you won’t know unless you ask.

  16. Mockingjay*

    Where is your boss in all this? As Grandboss, it’s his job to ensure that 1) everyone gets to use their benefit – earned leave and as a corollary, 2) fix the staffing issue.

    OP, with the specialized skill set, you and your team have leverage.
    – Ask Grandboss to intercede for a one-time exception to the rollover rule, so you all don’t lose WEEKS of leave while a coverage plan is sorted. Vacation is a very expensive benefit to lose.
    – Don’t compare your vacation plans with your report’s plans. One does not have more value over the other. Vacation is whatever you enjoy doing. Being a manager doesn’t invalidate your need to take off – you earned a break as much as your reports did. Don’t invalidate your own worth.
    – A coverage plan is only the tip of the iceberg. I see tough issues with an unsustainable workload and lack of staffing. Don’t let Grandboss get away with “well, hiring is not in the budget right now.” All right then, let’s prioritize and drop some of the work until hiring is in the picture. Be firm. You and your team are not indentured servants to work all the time without a break. What good is earning weeks of vacation if you can’t take it? It’s no benefit at this point.

    If Grandboss doesn’t take steps for immediate relief for you and your team, I’d take that special skill set and look around for other opportunities. (You might not earn as much vacation with another company, but you could actually take it…)

    1. Brain the Brian*

      Bingo. I lose weeks of vacation that I can’t take at end of every calendar year because we’re chronically understaffed, and it’s plain exhausting. It’s not sustainable, it leads to burnout, and in your case, your boss should know that your team is approaching a breaking point (losing out on weeks of vacation due to workload is, by definition, approaching a breaking point). LW, at least ask — please.

  17. SarahKay*

    I’m in the UK so get five weeks also, and in the past I’ve also struggled to use it all. In that case I can highly recommend using some of it as single days, either to make a long weekend or on a Wednesday to have two really short weeks.
    Because it’s just a day the email / outstanding tasks don’t pile up in quite the same way as they do over a whole week or fortnight. Plus you get the day to do something nice, whether that be a trip out (midweek, so usually places are quieter) or just a totally you-day at home reading (insert leisure activity you prefer) in peace and quiet.
    Outside of that, we also have coverage requirements so popular holidays are done by rota – if you had last Christmas off then you’ll usually need to work the next two, etc.

  18. Ann Onymous*

    I also struggle to use my vacation because I get bored at home. What I’ve started doing that’s worked well for me is being intentional about using (at least some) of my 1 day vacations for fun things. This year I explored the hiking trails at a nearby state park and visited some local museums (which have the added advantage of being less crowded on weekdays).

    1. Hlao-roo*

      Yes, I typed up this brainstorming list of how-to-take-vacation time as I was reading the letter. Hopefully some of these suggestions are helpful to the letter writer:

      – Are there any long weekends/days off that your kids’ school has that your work doesn’t (I’m thinking MLK Jr Day, Presidents Day, Veterans’ Day)? Would you be able to take those days and enjoy the long weekends with your kids?

      – I know in the summer, everyone wants a week off at Memorial/Independence/Labor Day, but there are several other weeks of school summer vacation. Can you take one or two of the non-holiday weeks instead?

      – Using vacation to create long weekends on days when your kids are in school: if you have a spouse/partner, can they take those days off too and you can have a “date day:” go out to lunch, go to a museum/the movies/wherever?

      – If you don’t have a spouse/partner, or they can’t take Fridays/Mondays off: do you have friends who work different schedules/are retired and could meet you for lunch on a weekday? Or are there things you like to do that your kids/partner don’t like? One-off vacation days are perfect for that day hike/museum exhibit/event that you’re the only person in your family who enjoys it.

    2. M*

      I also did a few days in the middle of the week. Flying and hotels are usually cheaper in the week and it’s surprising how nice a two night short trip can be! I took a train and stayed somewhere once and when I lived overseas I would take short week breaks and visit other countries on the cheap.

    3. daen*

      I do a lot of staycations, and while I don’t necessarily feel bored at home, I have sometimes struggled with feeling like I’m wasting vacation time. I’ve learned to combat that by scheduling one “must-do” for the morning of and one “want-to-do” for the afternoon of every vacation day.
      Usually, my “must-do” is some kind of chore I’ve been putting off, and by I try to pick something that takes an hour or less to complete. That way I have the rest of the morning to bask in the glow of accomplishment while doing nothing in particular.
      My “want-to-do” thing is usually something like “go for coffee with a friend who has a free afternoon” or “read all afternoon” or “do nothing until I’m sick of it.” Not gonna lie, there is something about scheduling do-nothing time that makes it feel like a reward and self-care instead of time-wasting and immoral self-indulgence…

    5. Caramel and Cheddar*

      Thank you for pointing this out, because I struggled a bit when I got to this line in the letter: “I struggle with taking vacation time just to sit at home alone, do laundry, and let work pile up at the office.”

      I think a lot of people think vacation is primarily for doing *fun* things, like traveling or hanging out with friends or whatever one’s definition of fun is. But if you don’t have those things to do, that doesn’t mean you shouldn’t/can’t take vacation either. I know it’s tougher for parents who are probably also trying to schedule vacation for when they need childcare as well, but I think most people would benefit from re-framing vacation as “this is time I need away from work” first and foremost.

      1. Zorak*

        Yes vacation doesn’t literally mean a vacation where you go somewhere. It’s just time for your Life, which presumably encompasses multitudes. (Even if some of those multitudes are just petting the cat and binging a new TV show!)

  19. The OG Sleepless*

    We’re having this very issue in my office right now. There are three people who can do my particular job: my boss, me, and my one peer. If one of us is on PTO, the other two either have to pick up extra days, or each of us can work like crazy on our normal days. The nature of our work means that Thanksgiving and Christmas weeks are particularly busy and emotionally taxing, and we do not have an end-of-year slowdown. So what did my boss do? Two years in a row, she hasn’t planned her PTO days well and she has two weeks left. Last year she just peaced out and left us holding the bag for the last two weeks of December, and this year she breezily informed us that she was taking both Thanksgiving and Christmas weeks off. (Side note, the year before that I worked a bunch of extra days in December because my peer coworker was on maternity leave.) Um, what? After much negotiating, she grumpily agreed to modify her PTO a bit.

    I insisted that we sit down in late summer next year and map out everybody’s remaining PTO for the rest of the year to keep it fair. Fool me once, and all that.

  20. Michelle Smith*

    You need to talk to your people. I don’t know how big your team is, but not everyone values all holidays the same. I used to work in a field where we were required to have staffing 18 hours a day, 7 days a week, 365 days a year. No exceptions, no options for shutting down. What worked for me was talking to my peers. My family lived 500 miles away. Taking two days off for Thanksgiving was useless to me, because with travel time, it wasn’t enough time to really spend with people. My family is also Christian and celebrates pretty extensively for Christmas. I worked with Jewish colleagues who didn’t care at all about Christmas, but wanted to spend time with family during their important holidays and Thanksgiving. So we worked out a system where I worked Thanksgiving for them and they worked Christmas for me.

    Seriously, you may find that this problem goes away if you’re able to talk to your people, figure out what their priorities are, and then manage the leave schedule accordingly. Yes, of course, it would be nice to get a week off for every major holiday, but since that’s not realistic find out what people really want to prioritize and see if you can work out a reasonable compromise.

    Also, you need to take your vacation. All of it, since it doesn’t roll over. It’s fine if you want to take time around your children’s breaks from school, but it sounds like you’re not doing that. I’d rather you take a week off when they’re in school or camp than lose that time altogether. You need rest and time away from the office! Maybe consider doing a staycation, just for you, where you are home resting, watching movies, and taking care of odd things around the house that you otherwise would never have time for. You’re literally throwing that time in the trash right now as we speak, so why not just use the weeks regardless? If you can’t justify using it just for yourself, use it to set an appropriate example for your people – that just because your department is understaffed doesn’t mean they have to sacrifice their mental health and well-earned benefits for the good of the company.

    1. Allonge*

      Your second paragraph, totally! I have a colleague who is also sooooo careful about making sure that she takes leave when it Really Makes Sense, that she ended up with an (exceptionally allowed) 50+ days of PTO…

      …for 2020. Of course then COVID came and taking leave made even less sense, but still she would not take a few days here and there, because ‘what if the weather is bad’. Is it better to just not take any leave at all?

    2. Miss Chevious*

      This. I manage a team or seven, and because of differing priorities about holidays and events, I, the boss, am off between Christmas and New Years this year. Almost all of the rest of my team prioritized other events this year, and won’t be on PTO during that time. That won’t happen every year, of course, but communication with the team is key to making sure everyone gets some of the days that are important to them, and everyone gets ALL of their PTO.

      Some of the team celebrates different religious holidays, some of them have kids and prioritize spring break or summer break trips, some of them prefer to have time after each quarter close, some of them have family traditions around other holidays, like Thanksgiving or fourth of July or their anniversary or whatever, that are more important to them.

  21. I should really pick a name*

    Not addressing the current conflict, but some suggestions on handling your own vacation in the future:

    1. Deliberately spread it out through the year to make sure you actually take it, and aren’t stuck with three weeks at the end of the year. Halfway through the year, you should have used up half your vacation.

    2. If you can’t get the popular times, be okay with taking your kids out of school for a week once a year to get out of the house.

    3. Give yourself long weekends. That might feel less like sitting around at home doing laundry

    4. Coordinate vacation time with friends so you can do stuff together during the day while your kids are at school.

    1. Not Australian*

      Give yourself long weekends *and plan something*, even if it’s only a movie or a sports event or a brief visit with family. Make every day off count for something; make them days to look forward to – and back on – with pleasure.

      1. Hannah Lee*

        Exactly.

        There was a little underlying theme in LW’s wording, approach that hints at them devaluing themselves or at least prioritizing others, doing stuff for others over things that just involve them. (feels bad scheduling vacation if a team member wants that time off, doesn’t see value in time off just by themselves … feels they have to save it to spend with family, or forego it completely if that’s not an option)

        If they are in the US it could be the “idle hands are the devil’s plaything” stuff that got handed down through the years from the Puritans and seasoned with a hefty dose of toxic capitalism. The “why would I take time off to stay home and fold laundry” comment when there are a gazillion different things LW could do when they aren’t working – at home, out and about, alone, with other people, planned or spontaneous, jumped out at me. Museums, sporting events, movie or play matinee, rehearsal days/open studios at music schools, lectures at local historical sites, sitting in on a class from your local adult ed group, exploring coffee shops, local neighborhoods, waterfronts, parks, reading, staring up at the clouds, baking bread, trying your hand at coffee roasting, Netflix, TikTok, volunteering, catching up with a friend or acquaintance, spiritual practices of your choice, listening to music, dancing in your living room, slapping on a facial mask, or going to a spa, sipping a drink in a local hotel lobby, browsing the aisles of a local hardware store, stopping in at a shop or garden center or spice shop or sports equipment shop you’ve always wanted to check out, counting the # of steps it takes you to walk a mile, practicing skipping or hula hooping or finger painting or some other thing you haven’t done since you were little, reading poetry, writing poetry, conducting an assessment of whether you prefer a mid-morning nap to a mid-afternoon nap, going through your contacts, friends family, acquaintance lists and picking 3 to send a quick note to, etc etc etc.

        4 or 6 or 8 hours of unstructured time with no “have to right this minute”s? Oh boy, you could find at least a weeks worth without really trying.

      2. nona*

        Or plan to do nothing. Everyone needs that recharge time to just be idle for awhile.

        Though, that could be a plan to not have a plan, so that someone doesn’t try to plan it forward you.

        1. Hannah Lee*

          Hah! That’s happened to me before … I’ve scheduled a day off with no external plans, and happened to mention it to some others … and there’s one relative that hears I’ve got free time and will show up unannounced to spend time with me, or come up with something to fill my time. I can say no, but I’ve found it easier to just not let them know when I’ve scheduled time off.

        2. Zorak*

          Yes! Planned idleness feels so much more refreshing than less conscious idleness where are you stare at Twitter and the time vanishes in an instant.

          But a day where you fully unplug except for music, take a walk and slowly drink a cup of tea? Poiiifect.

    2. Aerin*

      A while back we coordinated with some friends to all take a week of vacation at the same time. We played board games, watched movies, went to the arcade at 10am on a Wednesday when we were the only ones there, and otherwise just lived like teenagers on summer vacation. It was *glorious*. 11/10 would do again

        1. Aerin*

          Probably not for a little while, since half the group is in grad school right now and we’re planning a big international trip next year. But I’m hopeful that we can manage it again in the next couple of years.

    3. Llama Llama*

      I am getting to the point of taking my kids out of school in order to take a vacation. My busy times are always during their time off. I have ultimately determined that the kids will be fine being out a week.

    4. MidMgr*

      When our kids were quite young and in daycare until 5:30 pm, date night was difficult due to lack of childcare and funds. So, my spouse and I would schedule a random weekday off together so we could reconnect as adults. The kids never lost any time with us, and we were able to still spend time together on our own terms.

      1. OP*

        That would be great if my husband got paid vacation! We are on completely different ends of the spectrum.

  22. KP*

    The idea that requesting vacation off a month in advance isn’t enough time is really hard for me to wrap my head around. Maybe because I’m in a role with moving deadlines/priorities…but I often don’t know if I’ll be able to take vacation until about a week before. (Big trips are different, but I often take a vacation day or two with only a few days’ notice)

    What happens if you both take the vacation, and the work just doesn’t get done? What’s the worst that’s going to happen if the deadline is pushed? I’m not saying to go rogue. But, I think it’s worth a conversation with your management that your team is stretched so thin you are unable to use your benefits. They haven’t staffed appropriately, and it shouldn’t be on you to bear all the consequences of those decisions.

    1. Nancy*

      Asking a month in advance makes sense when it is the week between Christmas and New Year’s or another popular vacation time.

    2. Zorak*

      Everywhere I’ve worked has very prominent rules around never buying airline tickets until your vacation time is approved, and if you’re buying airline tickets a month out they’re going to be pretty dang expensive.

      At my former job time around the holidays got “released” in September and that was when you could submit request, although they were also judged against everyone else’s requests for the same days.

      It definitely depends on whether you’ve got a coverage based job, which being so understaffed it sounds like they all basically do. I believe my current company has people submit their requests in late September early October as well.

      1. KP*

        That’s interesting. If my work makes me cancel my vacation for a business need, they have to reimburse my plane ticket.

        Our vacation requests aren’t as strict as most places, I think. But at the same time, feeling like you can take vacation is an entirely different matter. I still have nearly 3 weeks. Every time I tried to take it, something dumb comes up.

    3. fhqwhgads*

      I took it as not enough notice because it is both: the most popular time to take off (end December) and a coverage-requiring role, not that a month notice at other times of the year would always be not enough.

  23. Aspiring Chicken Lady*

    New Years Resolution definitely has to be a better time off planning system. Do other depts in the office handle it differently? Can you work with HR to come up with a strategy that will fit nicely with the employee handbook?

    And yes, I am also a huge proponent of the 3 day weekend (and 4 days are amazing.) I take at least one a month and basically do nothing — just quilt and grocery shop and cook and nap. I don’t need fancy travel to keep my balance, so I keep balance by having days off to look forward to. And it reminds folks that we all get to use the time we’re given.

  24. CommanderBanana*

    Also, this is a general reminder that “generous vacation time” isn’t a perk when you’re discouraged from taking time off or on a team that is so lean that you can’t take time off.

    1. Philosophia*

      Exactly. Long, long ago, I worked for a nonprofit that underpaid its office staff even for that city, but in purported compensation granted four weeks of annual vacation right off the bat. Guess what: taking even a week of vacation was met with pushback from the workaholic executive director. (I took vacations anyway and bore with the consequences, for as long as I could tolerate that and the other working conditions.)

      1. CommanderBanana*

        Yes, my org likes to tout their generous leave policy. It is generous, but god forbid you try to take time off.

  25. I should really pick a name*

    Practically speaking, it wasn’t great on her end to expect she could give only a month of notice to get a week off during a highly desirable vacation period on a team that needs coverage

    Kind of disagree with this. If it’s a month out and no one has the time booked yet, I’d say it’s fair game.

    1. M*

      If this time of year is always an issue I do think a month does not give enough time. But they need to come up with a policy for Holiday time off if they need coverage.

      1. I should really pick a name*

        But if it’s a month out and no one has booked it, what else are you supposed to do?

    3. Critical Rolls*

      This is kind of unclear in the letter, but it seems like OP had herself penciled in for that time, so it wasn’t actually un-booked. But the lack of a system/communication may mean it appeared that way to the employee. But but it’s on OP to value her own time off enough to hold that space and say that leave has already been approved for that time frame.

      That said, a month before this holiday is… another holiday! I ask my staff to get their requests in early enough that I can get back to them before we have to deal with leave around Thanksgiving.

      1. Zorak*

        It’s also possible or likely that the employee wouldn’t assume that she and OP her manager could not both be out at the same time. It seems like that’s a symptom of the understaffing rather than something that’s obvious to the position, so she probably figured that if no other employees on her level had the time off, she should be able to get it off whether or not OP was there.

          1. Manic Pixie HR Girl*

            In this case, I think it is okay if you say no, or ask her to modify it! You already have someone approved to be out at that time. Most people know if they want holiday time off they need to plan further in advance for it because it’s popular for a reason. And I don’t think it is unreasonable, if she pushes back, for you to say you’re not willing to give up your planned week because otherwise you’ll lose your time. Maybe next year she’ll plan more in advance.

            I know you say you feel bad saying no, and I get it because I would too, but it sounds like you’ve maybe canceled your time off before so others could take time and now you’re sitting with almost 4 weeks you’re about to lose. Don’t do it.

          2. Teapot Wrangler*

            Then I’d say totally fair to say “Both X and I are out of the office then so we can’t have you out too. Next year, I’ll make sure you get the time if you want it.”

  26. Aerin*

    I find it a little odd that OP says “the popular times are when my kids have breaks” as if that’s an unfortunate coincidence instead of the exact reason those times are popular for vacation…

    With five weeks to take, a team that requires coverage, and everyone wanting the same times, there’s very little chance you’re going to be able to take vacation exclusively during school breaks, that’s just the reality of the calendar. You’ll have to get comfortable with taking long weekends or getting paid to bum around the house, because otherwise that time and money is just going to waste.

    1. Legal Beagle*

      Yes, this would likely be an issue no matter how many people they hired. Not saying that everyone wants the holidays off, but generally holidays and school vacations tend to be popular for fairly universal reasons!

    2. OP*

      It’s more of how do I take some, not all of them.

      It’s just very hard to not be “on call” if I’m home alone. I typically take a long weekend and work at least half a day if I’m home by myself.

    1. GarlicMicrowaver*

      Only suggesting this because there doesn’t seem to be a workable solution except to sympathize with your employee and do the best you can do to take care of your needs. Work toward a better/rotating system for next year.

  28. Roscoe da Cat*

    I would second all the comments about work out a system for next year. It will cause much less resentment if there is a clear way to do this, because then no one expects last minute requests to be granted (and they know what last minute means).

    As for right now – frankly, you sound burnt out, OP. I think you take your leave if you already scheduled it and you really need it. BTW – it doesn’t matter what you do with your leave as long as you feel good at the end of it.

  29. LDN Layabout*

    There needs to be a system in place and you as a manager need to be bringing up popular holiday periods proactively when it comes to cover.

    Not everyone can plan far in advance, but I know for our team the first ‘heads up, please think about this’ for Christmas came in August/September. Then we all filled in excel spreadsheets with ‘want off’/’would like off’ days blocked off to allow the managers to check if we needed any further cover.

    Once that got booked it, it still allowed for later requests/changes because management knew what 95% of the staff were doing.

  30. a tester, not a developer*

    My area has an on-call approach to the big holidays. One or two people commit to responding to any urgent requests, with the assurance that if they have to do any actual work they’ll get banked time to use later.

  31. T*

    I previously worked in a similar team where there were only two of us who could do highly specific work. We were in a department made up of similar teams.

    A spreadsheet was kept which tracked alternating groups determining who got dibs on taking specific days off (high-demand vacation times like around holidays). Wider spans of time, like across summer vacation, was more ‘first come first served’ because some people (especially people with kids, or family members working in the school system, etc.) have a greater need for that time than others, so it wouldn’t make as much sense to alternate.

    It worked out very well based on my recollection. Within our little two-person group we would sometimes negotiate and trade holidays from what was on the spreadsheet if it was necessary. We just had to keep our manager posted on what we agreed and whether we wanted the spreadsheet changed to reflect it (so that the swap would carry over, in the reverse, for the next year).

    I’m sure there are people who could find something to complain about in that system, because there are people who can always find SOMEthing to complain about with any system, but it sounds better than what you’re doing right now, LW.

    And with that many weeks you probably also need to consider using a good portion of it for single days off, making long weekends for yourself etc. If you really value using those days off for family time, maybe check your kids’ school calendar for those scheduled half-days that schools sometimes have throughout the year, and take a couple of those off. Or even (if this works for your kids and where they are in their schooling) take a day every year when the kids can afford to miss a day of school and let them stay home and hang out/go out and do something together. My dad did this with us occasionally when I was in school and those are some fun and special memories for me and my siblings.

    1. GythaOgden*

      Yeah, we divvy things up this way too. It helps that all three of us are either child-free or have someone available to watch kids (my supervisor’s husband is the stay at home parent) and that none of us really care about those spare days between Christmas and New Year, preferring to take holiday at other times. (In our case it’s mostly staycation.)

      It would be difficult to have an infinitely recurring series of relief receptionists just so we didn’t have to accommodate each other, but in practice many teams operate this way and so it’s not an unusual situation to have to deal with. Certainly, no-one should have to deny themselves time off at any time of the year, but holidays and other things do need to be shared sensibly so that people can use their time. (And over the course of my career in the UK I’ve never been able to bank leave; then again, I’ve never had any trouble using it up having weeks off when I barely have to get dressed. Because of the pandemic, January marks my first actual trip since February 2020 and I’m excited…but have some days still to use after that.)

  32. WheresMyPen*

    I was surprised when you said you had kids that you hadn’t even used two weeks of your vacation. Obv I don’t know how old they are, but even if you can’t get the 4th July off, why not take a couple of separate weeks off during the summer vacation or spring break if they’re at school? Sometimes you just have to be selfish. My team is always really busy with schedules, but she usually takes 2 weeks off during the summer and we all prep really hard for it so that we can manage ok with her gone. She also usually pops on to her email a few times a week to make sure that nothing’s on fire, and sometimes it’s annoying when there’s something only she can authorise, but we manage and I’d rather that than her burn out or resent not getting family time. I know there’s not much you can do this year, but in January start planning how you could use those five weeks to make sure they’re not wasted. If you spread it out over the year the impact on your team won’t seem as big as if you’re trying to cram three weeks into the last month of the year.

  33. Ms. VanSquig*

    Oh my gosh, me too. I want to be home during school vacations, not when it’s me and a pile of laundry. I hope you’re able to establish the system you need to get a break. It feels a little like the announcement on the plane about putting your oxygen mask on before helping others.

  34. Ann Ominous*

    “I struggle with taking vacation time just to sit at home alone, do laundry, and let work pile up at the office.”

    OP, you’ve gotten great advice about options on how to take the time – I’d also add that you should consider taking time off to do things you want to do that aren’t (1) alone or (2) laundry!

    Go tour your city and visit whatever things people go see when they visit there, get on meetup and sign up for a day hike, see what workshops are available in your area (in person or online) to learn a new skill or practice an existing one, go to a coffee shop and read for a few hours, grab a friend and take a spa day together….so many options for you!

    I think maximizing the time would help the 3- and 4-day weekends to feel more restorative for you.

  35. Clobberin' Time*

    How convenient for your company that it ‘compensates’ you with vacation time you don’t actually get to use because of the staffing constraints that your company also imposes. They’re effectively cheating you out of your compensation.

    Short term, work out a system, but long term, you all need to push back. Either the company stops working on a skeleton crew so that you can all use the vacation time (which, I can’t emphasize enough, is part of your pay for this job!) or it admits that the five weeks is BS and works out something else, like a bigger paycheck.

  36. lilsheba*

    “really not fair if you’ve got one person who always requests the most desirable dates really early” That’s me – I do that due to the last job I had where we HAD to plan time off at the beginning of the year, and so now I plan my whole year in advance at the beginning.

    ” One thing to consider since you have a lot of vacation time that you might otherwise lose is to take a bunch of three- or four-day weekends throughout the year.” THIS!! I do this when I plan for my whole year ahead. I have tons of 4 day weekends through out the summer and in December. I do that because it is more refreshing through the year and it’s also more fair than taking off an entire week here and there and leaving my work for others for that whole time.

    1. Baby Yoda*

      4 day weekends are the only way I take my time anymore. It’s great and the work doesn’t pile up as bad when you are only actually gone 2 days at a time.

  37. Peppercat53*

    I was on a team that did seniority picking for years. I highly recommend NOT going that route. It sucks especially on a team that has very little attrition. I was stuck not being able to take additional time off around the holidays (I got the usual holidays off but couldn’t take the connecting days in between off) for years and years. The person who I couldn’t overlap with on time off always took those days off to be with their kids. I get that she wanted to be with them but I also have a family and wanted to be with them too.

    1. Aerin*

      Our group corrected this issue by breaking up our seniority-based vacation bids (which we do for the whole year at a time).
      First round: You can bid up to five days, only one of which can be holiday-adjacent.
      Second round: You can bid up to ten days for the whole thing (so minus whatever days you bid first round).
      After that it’s first-come, first-served, and can be submitted on very short notice as long as there’s time available. You can also request days and then retract them later if you don’t end up needing them.

      So now even our newest folks have a chance to give themselves an extra-long weekend, and people can generally stake out the big preplanned trips comfortably in advance. I suppose it disadvantages people who aren’t willing/able to map out their whole year in advance, but honestly, the only way you can balance the “we need people here vs. nobody wants to be there that day” issue is with sufficient planning. You can’t just wing it and hope for the best.

    2. Quickbeam*

      I worked at a state nursing facility which had high seniority staff. One nursing aide had been there for 40 years and was the only one who could get the Christmas to New Years week off. Ever. Her coworkers had 35+ years in and had never had a Christmas off. It was a horrible system.

  38. Seeking Second Childhood*

    Something I picked up from an old CO worker. Once I had enough vacation time to do it, I started reserving every school holiday and early dismissal as single or half days. Family summer vacation comes from what’s left…and if I need an extra break during the year I surrender some time between Christmas & New Year to others in our not so stretched team. Because that time period is actually quite pleasant to use for catching up on admin.

  39. Keyboard Jockey*

    I want to challenge the notion that your team needs it more just because you aren’t traveling. Your team needs you to be rested and well-functioning. A burnt-out leader ends up funneling far more crap down to their direct reports than they realize. You make more mistakes that affect your team, and you have less creativity to address problems with when you’re stuck in firefighting mode all the time. (I have been that leader, and will be forever grateful for the employees who pulled me aside with “you’re more effective for all of us when you stop prioritizing everyone else’s wellbeing over your own.”)

  40. Turkey Gobbler*

    My department used to have a “take whenever you want” philosophy, which ended up with everyone taking off around holidays and me being stuck to do the necessary work. Once I took over, I made a policy that people had to check with me so I could ensure it wouldn’t have an outsized impact (tiny office with an inflexible schedule), so having more that 2 people out at once gets dicey). I also asked everyone to submit their requested holiday time off to me and I’d coordinate it. I was transparent about why we were now doing it this way, and got lucky enough that people were willing to flex plans that weren’t set in stone so everyone got their first choice. It may not always work like that, but being transparent means that my team is now coordinating with each other to figure out coverage when things are flexible (instead of dropping it all on me) and I get to take off around Christmas for the first time in 8 years.

  41. Emily*

    Are you going to be able to easily replace people if they leave? I’d assume no, and if that’s the case, that’s part of your pitch when you talk to leadership about the need to make changes that result in your team (and you) being able to take vacation time. Whatever they’re envisioning for the bad things that will happen if there isn’t coverage due to people taking PTO are going to be much worse if you lose employees because they were burnt out and frustrated at not being able to actually use this part of their compensation package. There’s no scenario where long-term your company keeps stretching everyone this thin and still retains them.

  42. The Other Dawn*

    In addition to needing a system to handle vacation requests at busy/desirable times, you also need a system in place for cross training if you don’t already have that. At least one other person, preferably more, should be trained on some essential tasks so people can take time off, whether it’s vacation or sick time, without worrying the business will come to a grinding halt or things will fall through the cracks.

    In every company in which I’ve worked and managed a team, cross training has been one of my biggest priorities right out of the gate. At my current company, we had plenty of people in the department (too many, in fact…), but everyone was completely siloed in terms of systems permissions (unnecessary) and also didn’t have the knowledge to do other tasks even if they HAD the permissions. That created a huge bottleneck because everything had to flow through one person who was already overloaded. Until I got the department to a point where people had the systems permissions AND the knowledge, I had to scramble to figure out how certain things would get done anytime someone was out unexpectedly. I was not a fun time for me, but we got through it.

  43. Keymaster of Gozer*

    Second biggest debate we have each year here is over holidays. We do have to have staff over the holiday period (24/7/365 industry) but a reduced amount.

    About last year? I think, I was not taking any time off because my staff were heavily impacted by lockdown, had kids that needed looking after, couldn’t come to site etc. so I covered for them (I may be IT manager but at heart I’m a techie).

    I nearly burnt out. And when I did put in my holiday request I took the time off and yep, the work fell by the wayside for a bit. There was no way around that.

    We have a ‘first come first served’ policy for leave, but a rotating ‘here’s who’s on call on Xmas, New Year etc’ bank. If you’re a senior tech you’re going to have to do one of those shifts.

    There’s every year a discussion of ‘means testing’ holiday requests (e.g. people without children shouldn’t be able to request time off over school holidays unless the parents on the team aren’t booking it off) but I always, always shoot it down.

    Me sitting at home watching YouTube vids and taking over the world with my armies (I play a lot of Civilization) is just as equal to the person who wants time off to go on holiday somewhere.

    And frankly, one thing I learnt during this whole pandemic is that you cannot be a good manager without a break. Your mental health is important!

  44. CoverageIsntAlwaysAThing*

    When I take time stuff just sits there not getting done. I’ve taken 3-4 day weekrnds which I paid for with 12-13 hour ays the following week. I took 8.5 days berevement (not all officially as berevement time; it was that long to sit Shiva) and came back to all of that work plus the added bonus of having no clue of what was going on at the company. Having coverage of any sort at any time sounds lovely.

    Unless it’s life threatening or going to cause utilities to go down or somesuch, I say take the time on all sides and deal with the overload when you’re back (if at all possible).

  45. Jane*

    If two employees cannot take time off at the same time, then the company is understaffed and/or the department isn’t cross-trained enough. Sounds like OP’s boss needs to start learning about OP’s role so he can cover when OP is out. Ridiculous.

  46. Quickbeam*

    OP, this letter speaks to my status at my last job. My boss was a good manager but not licensed to do the functions the team handled. We had to cover her desk and each others. Time off got super competitive with things like “who has kids” weighing in more than it should have. What we needed was a float person who wasn’t jammed with their own work and everyone else’s emergencies. I retired before they got on board with that.

    1. Luna*

      Yeah, that’s an upside to not having kids. But also downside.
      It’s just a conundrum. Like, you really don’t mind helping out in a pinch because you know having kids is an extra responsibility and you know that some can’t leave their kids home alone all the time during vacation* (Depending on age), buuuut… at the same time, there’s always this tiny feeling of resentment that you are being ‘punished’ for not having kids, so obviously you are free to cover whenever.

      * Aside from the age thing, you can do things to keep kids out of the house or so, at least part of the day. Like my elementary school was conveniently located right next to a childcare, so lots of kids were registered there, obviously. And they tended to be open half-days during vacation times, so parents didn’t have to take time off or worry about leaving the kid alone at home with only the TV or so. And stuff like summer camp, for example. Get them outta the house, and your hair, for a week or two, haha!

  47. OP*

    OP here. Thank you Allison for answering. Great advice here and in the comments. I replied to a few and look forward to reading the rest.

    And I appreciate the suggestions about planning my time off better and setting more parameters for the team. I want everyone to be treated like adults so I’ve been hesitant to do it but I’m seeing that there are reasonable ways to do this.

  48. Skytext*

    When I was in management for Walmart this was the worst. We got 2, 3, or 4 weeks based on length of employment, and you had to pick it at the beginning of the year. And it went by rank and seniority: first the Store Manager got his weeks, then the Co-Managers, then the Assistants in order of seniority. So of course I was at the bottom with my measly two weeks and almost no weeks available (because of course there were big blackout periods like the holiday season and inventory time).

    I always thought it would have been much, much fairer if we still went by seniority, but only picked ONE week at a time. For instance Store Manager goes first and picks his most-desired week, then each manager. Once everybody got a chance at their first pick, then the second week. Then third and fourth. It would’ve been much better than them gobbling up weeks just because it was available but not of any importance, but was MY first choice and I couldn’t have it.

  49. Nancy*

    The holidays and kids’ breaks are always the popular times. If coverage is still needed during those popular times (ie, you can’t just close the week between Christmas and New Year’s) then you need a set plan in place so everyone gets at least some of what they want, and no one is stuck always working the same holiday.

    Use the rest of your time during the less busy and more unpopular times of the year so you aren’t losing it. Go to a museum, go hiking, read in the park, plenty of things to do besides laundry!

  50. Wendy*

    Regarding my current employer…

    I always ended up being scheduled to work on Thanksgiving Day.

    But for this year I submitted a day off request for Thanksgiving Day months in advance because I will be out of town on that day

  51. Manic Pixie HR Girl*

    There are already a lot of good suggestions here.
    What we do in my office (and I’ve seen in other offices as well) is we do summer vacation requests in April/May, and holiday requests at the end of October.

    The rule for Summer is, if someone puts in after the approvals have gone through, the line supervisor checks it against coverage in their unit, and if it’s either for a full week or more, OR a Monday/Friday, they kick it to me not for approval, but awareness. If it is causing a coverage issue, they’ll kick to me for final approval/disapproval. (If it is a day I am going to be working anyway, for example, I try to say yes.)

    For holidays, essentially same rule. We used to include all of December in that but realized that was silly and just left it to Thanksgiving week and the 2 weeks around Christmas/New Years. As it is, we ARE much slower at those times, so it is OK for us to have a skeleton crew on Black Friday (yes, we’re open then), and Dec 24/26 or Dec 31/Jan 2.

    By using this system, for times when we know more people are out we can make arrangements to ensure the work is completed, and there’s a general expectation among staff on how to handle. Also, in this circumstance, your employee would have known that to get that time she would have needed to ask for it sooner, and there were no guarantees.

    I am also the one who often volunteers to work at these times – my family is local and I don’t have kids so I genuinely don’t mind it! But I ensure I take my days at other times. I am team Take Your Week because I think you need it, and approach your boss about having 2 people out at once at specific times. Not being able to overlap time off is not sustainable for any team.

  52. Goldenrod*

    YES, it is so important for time off to be fair! For years, I worked for a terrible boss who, whenever I asked her for time off (and it would definitely feel like I was asking for a favor), she would say, “Let me check first to see if Gary [her partner] wants to go during that time.” And if he did, I would have to make another plan! It was so unfair.

    One year, there was a special holiday cruise my mom invited me to, but it overlapped with her planned vacation. BUT it was by far the slowest week of the entire year (summer, in an academic office). That’s why I love that Alison included this:

    “Before you decide, though, take a really hard look at whether both of you have to be there that week. Will the workload that week really require it or is it slow enough that full coverage isn’t absolutely essential?”

    My crappy boss could have EASILY said, you know what, we can both be gone that week, it’s fine. But instead, it turned into World War 3. Man, she was the worst!

  53. TeemieBopper*

    Man, I can’t even comprehend not using my PTO, especially when it doesn’t roll over. Only a certain number of our accrued hours roll over year to year. Betcher ass I’m taking four day work weeks the rest of the year so that I don’t lose any of it. PTO is part of your compensation. If you don’t use it, you’re working for free.

  54. Luna*

    At my job, it overall is a case of first-come-basis for time off, though there is a note that employees with school-age children do get more consideration during the school vacation times. But we also don’t have three months worth of Summer vacation, in Germany they take about four to six weeks, with the end-of-school/start-of-school date shifting later as you go further south, with the most south ending school in late July and the next schoolyear beginning about mid-September.

    Personally doesn’t bother me too much, as long as people communicate and are willing to discuss times they take off, though there is always a teeny tiny bit of envy that coworkers with school age kids can ‘easily’ get several weeks off in July or August.
    But, at the same time, my employer also said a few weeks ago that it was time to prepare and plan your vacation days for the calender year of 2023, so… early plans and setting things in stone, I dunno if that’s how it’s done in the US or even specifically your place. Or if it can be done that way. (I already wrote down in pencil my plan to take time off next November, for example!)

    One thing you could do is the general standard of rotating things. Like you take the week between Christmas and New Year’s off this year, but will work that time next year.
    I’m doing something similar myself, especially since I work retail. I will gladly work Dec 24th (Christmas in Germany, most stores are only open until 2PM, anyway), but I will have Dec 31st off. In turn, I likely will work New Year’s next year, but have Christmas off.

  55. Spruce*

    If your manager is her position because she is great at managing, then this is the exact kind of problem you should bring to her. Not to ask for cover, but to help come up with a fair system in which every gets their time off. That’s the kind of things good managers will do, but she won’t know you need help with it until you ask her!
    She may think of out of the box solutions you haven’t considered! Maybe there’s some budget for a temp working or a contractor. Maybe she can argue for a system in which a small work from set up can be put in place and you only do one hour for urgent work during your children’s holidays, while the rest is mostly off. Maybe she can get an exception from HR to make sure the time you can’t get off while at least be paid out. Maybe there’s something else as well! The key is that you don’t know until you loop her in.

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