I've been at my current job for a little over two years, during which I've not taken a vacation or used much of my paid time off. I know that if I do, odds are I'll end up getting phone calls or emails for important issues that only I am able to resolve. I'm unfortunately involved in most operations and IT matters to some degree, as it's a small company.

Of course, a common suggestion is to find another job, but that's neither desired nor realistic.

How can I manage to get away from the office for awhile in a situation like this?

Edit: We now have another IT employee with whom I've been focusing on knowledge transfer, so there's redundancy on a majority of daily tasks. Taking a vacation in a week where I can reasonably expect few interruptions.

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    Take a cruise! No cell phone reception in international waters :-D Commented Apr 10, 2012 at 19:23
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    I can't help but notice that, in your question title, you acknowledge that you are doing too much: wearing too many hats. Are you planning to solve that? Commented Apr 12, 2012 at 21:33
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    Are you unable to delegate some of your tasks?
    – Burhan Ali
    Commented Apr 23, 2012 at 12:21
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    Why are you the only one able to resolve these issues? Commented Jun 1, 2012 at 7:43
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    Take a cruise? Funny. I've known people who got called back to work from a hunting camp in Alaska. In the US vacation is a privilege, not a right, and since your employer is still paying you for your time you are expected to be available at any point. The last time I had a job where I could actually be out of contact during vacation was when I worked as an hourly contractor, where I didn't get paid if I wasn't billable. In that case my employer didn't care - but at all other times the expectation is "if you're still breathing we own you". They don't call it "wage slavery" for nothing... :-) Commented Dec 13, 2015 at 20:19

13 Answers 13


Cross training is critical. You can get buy-in from your boss by explaining how he currently has a single point of failure in the systems you support.

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    Yeah, I'm a big fan of the "hit by a bus" argument. :)
    – Brandon
    Commented Apr 10, 2012 at 19:30
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    You can get buy-in from your boss by explaining how he currently has a single point of failure in the systems you support. Not all the time you can't... I know this from experience very well. Sometimes the company is just surviving and they can't afford to hire anybody else. Commented Aug 30, 2012 at 19:55
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    @maple_shaft if they are only barely surviving then they will surely go under if this crucial resource is unavailable. Commented Jun 10, 2013 at 11:44
  • @ThorbjørnRavnAndersen and I guess that's why the OP is asking the question?
    – o0'.
    Commented Mar 31, 2014 at 8:15
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    @maple_shaft The concept is "Cross Training" not hire someone new. If everyone else knows a little of what everyone else does then you have less to worry about. You CAN and should teach existing resources about diffrent jobs. It's not something that should be optional, you need to have 2-3+ people who know a job. What if 2 people are crossing in front of that bus...
    – Nick Young
    Commented Jun 8, 2016 at 14:20

I had the same issues as you. I started with a small startup where I was the only person who was incharge of the servers/code/development and so on. I was headed to Mexico for a trip and of course would not be available. What I did which worked for our company was I found someone who could handle things with the server in case anything went down. This person was "hired" as a emergency person while I was out.

I would suggest talking to the company and let them know that you need to take a vacation before getting burnt out of work and suggest that you bring in someone for a temporary emergency contact that can handle things like this.

Doing this would also give your company a point of backup in case something would happen to you. This way there is not one point of failure for something like this


This problem should never have arisen, so I suspect it will not get solve without drastic action. You need to create a crisis.

  1. Inform your boss of the problem.
  2. Request time to train coworkers and document key procedures.
  3. Inform them of a long holiday you will take in a few months during which you will be uncontactable.

If you do this you will force them to face up to the problem.

Also realise that you are not indispensable. As Charles de Gaulle said, "The graveyards are full of indispensable men."


It's tough, but there are several things to consider.

  • Often we think no one else can do what we do. If this is actually the case, then you (and the organization you work for) are in a bad place. What if you quit? What if you were injured/sick/long-term disabled? In the vast majority of cases, things aren't as serious as we might think.
  • In order to get out from under the "I can't leave because I have too many things to do" problem, you have to systematically train others to either take over additional work, or at the very least train a backup person/team who can manage things in your absence. Even if it just starts with a long weekend vacation (where the worst thing that can happen is only what's possible in 24 hours), you need to build redundancy under you.
  • Identify why you can't leave. What is it about your role that makes it so difficult for you to go anywhere? Is it because you literally hold the key to some lock box that cannot be accessed without you being there? Is it because key decisions can't be made without your approval? Is it because you're an expert at some key part of your job/office management that no one else is qualified or trained to handle? All of these situations have solutions: give someone else you trust the key while you're gone, give someone temporary decision-making power, train people around you to handle what comes up and give them your cell number in case something blows up.
  • Lastly, just try taking a vacation. You'll find a mix of things that come up, some of which aren't actually emergencies, some of which are. You need to get comfortable with the following things: taking the occasional phone call on vacation, trusting people to handle it (and not letting them get away with just calling you and dumping it on you), and not leaving your cell phone on all the time. Let things roll to voicemail, and check it only once every couple of hours or so.

You'll probably need to work up to the point where you can do this comfortably, but most people find that they've either made insufficient plans for their absence, or they don't trust people around them, or a combination of both.

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    Once every couple of hours?!?!? That wouldn't be a vacation, it would be a nightmare.
    – o0'.
    Commented Mar 31, 2014 at 8:18

We had this problem recently; a guy who'd been with the company four years, and had a wealth of miscellaneous knowledge, found another job. We had two weeks to try to suck all that knowledge out of his brain.

Need I add that several systems broke in various ways in the week or two after he left? (Something that had probably been happening all along, but we'd just never noticed because he always fixed them in his low-key way.)

Following this debacle, I installed a wiki, and we've been pouring knowledge into it. If my colleague asks me something, I tell him to look in the wiki. If it's not there, I tell him (or tell him who to talk to), and ask him to add it there after he finds out.

You need to do something similar so that no one person has a monopoly on company knowledge. Never taking a vacation is not healthy.

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    I attempted to get the company to adopt a wiki a while back, but was unsuccessful. Commented Jul 5, 2012 at 14:00
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    In what way? They refused to let you install it? Nobody would put information in it? I installed our wiki on our development server (which also contains our Git repositories and our Jenkins installation) so it wouldn't bother the server admins. As far as getting people to use it, the main thing is just to use it oneself, and to direct people there when they have questions. A wiki tends to catch on gradually, and gains traction when it has enough content that it's more likely than not that people will find the information they're seeking there.
    – user1602
    Commented Jul 5, 2012 at 18:46
  • @JohnStraka in that case, they deserve what they get, just take your vacation!
    – o0'.
    Commented Mar 31, 2014 at 8:21

If there is absolutely no back up for you, arrange to be contactable at certain times during the holiday or even certain times each day. Answer the phone then and only then - if necessary take two phones/sim cards so you can make and receive personal calls/texts outside these times.

This will give you the break you need and your employer the comfort they need that you are still available for support.

I would guess that most problems won't be so urgent that they can't wait until the next "contact time".

A better alternative is to train a few people within the organisation to do parts of your job. This way you spread the load and also, more importantly, the knowledge.


From what you are writing, your health may be in great danger, and if you ends up with burnout, the company will be out of your support anyway, and you out of your health. Your loss will be incomparably much more severe.

You should talk honestly to the company that the vacations are your indispensable right (we are not living in XIX century anymore) and you can't work much longer like that. You need to rest for yourself and your psychical wealth. The full rest need to swich phone off, vacations under phone are not real rest.

I know many people which are simply overused by the company. Once you accept to resign from your vacation plans, they know they can do it with you anytime they want. If you're in such situation, the change of work may be the only solution, however you should always try to talk first.


Most businesses have an off season, so take your vacation then.

Ask to be contacted by e-mail, and only your boss can call you for actual emergencies (or a single person who has the capacity to judge if it truly is an emergency (server meltdown) or, as would very often happen, not one (lost files, lost e-mails, etc). Take your e-mails every other day, announce that's how you will work.

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    I disagree. A holiday is a holiday, not work at a different location. If you make yourself available, the problem will never be solved. Commented Apr 10, 2012 at 21:02
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    @Wikis The idea is to cull the influx of requests to just the absolute emergencies. It eases my mind when I'm on holiday to check my e-mails for a limited amount of time. That way I know the world is still going round without me.
    – MPelletier
    Commented Apr 10, 2012 at 21:43
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    I'm with @Wikis: Your employer has no right to expect you to be reachable or checking mail on vacation. Personally if I am contacted for whatever reason I no longer count that as a vacation day: I worked.
    – voretaq7
    Commented Apr 12, 2012 at 23:01
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    It's not a solution I like, and I'm not saying that whoever calls me during my vacation (or home time) wouldn't get an answer peppered with choice expletives, but it is a solution, and it can bring peace of mind.
    – MPelletier
    Commented Apr 13, 2012 at 4:07

I can very much understand this question. I am self employed and is very nearly impossible to take a vacation without conducting business. My best plan is to take an hour in morning and in evening. Leave a voice mail indicating response times. I've found this to work best.


I look to my father as an example here. He is the director of quality control for a large (international) flavor company, and is 100% busy at all times during the day. No products, from any of the company's 4 manufacturing plants around the world can ship until his department has tested and tasted them, and he has signed off on it. Thus, it's difficult for him to take any time off. However, he has flat-out refused a company cell phone or laptop, because his philosophy is that work time belongs to the company, and once he leaves work, that's his time, and the company has no right interfering. To that end, his lab knows that when he's taking a day or two off, he calls in twice (three times if absolutely needed). Once around 10, to make sure there were no issues the previous night. A second time around 1. And the third time around 4:30. That's it. Make sure there is someone who can cover your position, if only for a short time, and check in once in a while. Otherwise, once you go on vacation that's it.


So your reason for not taking the vacation is that:

I'll end up getting phone calls or emails for important issues that only I am able to resolve

So what? You'll be in that position until you trained up your colleague enough. You'll still be on vacation, and if you can deal with that it's better then not taking vacation at all. Just make sure to find a way which works for you. A coworker of mine is in that position and the way he agreed on it is that when there are issues we can send him a whatsapp message between 9 and 10 am. It works for him and we have to do it less and less.

It comes down to this: taking a vacation where you sometimes have to answer a text is better then not taking a vacation at all. You'll burn yourself out.

Just make sure it's the occasional message.

  • "Just make sure it's the occasional message." - at the time, that was the problem. It was not possible for the message to be occasional, and IMO a work-filled vacation is not always better than no vacation, and it's a waste to work when using PTO. This issue has long since been fixed for me though :) Commented Jun 8, 2016 at 11:55
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    I think it's all about how you manage to frame it. When your answering is regarded as you "doing a favor" instead of you "being on call" will make a lot of difference, because people don't generally like asking for favors.
    – Pieter B
    Commented Jun 8, 2016 at 12:04
I know that if I do, odds are I'll end up getting phone calls or emails for important issues that **only I am able to resolve**.

This is management's problem not to handle the staff and arrange to have backups for each employee. If you were out with the flu where you were too sick to handle inquiries, someone has to be able to take over.


While the situation is bad for you, it is bad for your employer as well, and needs fixing. I mean what happens if you quit? Have they given that any thought?

What they should do: Give you two days “holiday” where you are not at work (but nearby). See what happens. If the come to a point where they don’t want you, but absolutely need you, you return, fix the problem, and then you write documentation that would have allowed someone else to fix it, and your manager documents how much it would have cost if you had been gone for two weeks. (If it was a problem that someone else could have fixed, like the bosses printer runs out of paper, you just tell your manager and go home without fixing it. Because the whole point is finding the risk if you are not there).

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