To give some context: I'm 21 and I've worked in IT fields since I graduated from HS, I was hired at this company last June for a 4 months fixed-term contract, I was usually assigned to a wide range of different operations since I'm the only IT guy of the department. Eventually they extended my contract for another 8 months because I started working on an important project.

Out of my work life, I'm currently attending a training course, at a local catholic foundation, to become a missionary. Basically, this group, holds this course for 9 months, while in the summer they become unavailable because they actually go on missions with the people that attended the course during the year, most of the missions occur in August and last an entire month.

I'd really love to leave and go for a mission but I don't know how to bring this up to my boss for a couple of reasons:

  • The law in my country expects fixed-term contracts to last no more than 1 year, therefore if the company wanted to keep me they won't be able to extend my actual contract but have to switch to a new one;
  • I'm afraid they will think I'm too pushy if I hurry them to take a decision, but at the same time I don't want to find it out too late;
  • Asking for a month of vacation may appear a bit 'extreme', I don't want to sound pretentious as it could negatively affect their opinion and my chance to stay in this company.

So my question is: How can I let my boss know that, in case they'd want to rehire me, I'm going to request for a quite long vacation period, without sounding pushy or pretentious?

  • They may be more likely to give you that length of time if you take some of it as unpaid, for example 2 weeks paid 2 weeks unpaid. But I suppose it depends on your company as to how many holiday days they give and how many you have already taken, as well as if you are on vital projects
    – Uciebila
    Commented Feb 28, 2019 at 11:20
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    In case they don't want to rehire you, they don't need to know what you will be doing, you don't need to request something for them.
    – Bebs
    Commented Feb 28, 2019 at 13:19
  • @Uciebila: In Germany minimum requirement by law is 4 weeks of paid vacation per calendar year. The company can´t deny that, and they can only deny / shift to a certain date if they can proof important economic reasons. I believe it´s somewhat similar in Italy.
    – Daniel
    Commented Feb 28, 2019 at 13:19
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    @Bebs: In case they rehire him they also don´t need to know what he is doing in his own free time. All they need to know is when he will be available for work and when not!
    – Daniel
    Commented Feb 28, 2019 at 14:53
  • @Daniel, I agree. If they want to extend him, they need to make it know quick especially for august when it should be considered as normal to go on holidays.
    – Bebs
    Commented Feb 28, 2019 at 14:58

3 Answers 3


Split it up into steps.

Find out if they are going to give you another contract first.

Once you find out, when signing or negotiating your contract. Bring it up and simply say that you wish to take a month's holiday off for personal activities.


This is a twofold question, really.

It all depends on the relationship you have formed with your boss and company.

In the UK if you have worked for a company for over a year, some of them will offer you the opportunity to take "sabbatical leave", unpaid leave for a period of up to 1 year where your position is left available for you.

Ask for a meeting with your boss and ask him what the prospects are for the contract renewal.

You should have in your current contract a notice period, if you are outside of the notice period, then not much you can push for, if you are already within that period just remind them of that.

When you are told that the contract is being renewed/you are being made permanent explain that you would like to be allowed 1 month off unpaid as you are planning on leaving for a voluntary mission.

This is usually well regarded when asked and some employers would even sponsor you (at least in the UK).

  • The mission thing could backfire. If you want to play it save you can always go with a neutral Something else planned for August. Depends on the relationship and how well you know your superiors.
    – Daniel
    Commented Feb 28, 2019 at 12:50

Here is what I would do: Nothing!

At some point they will come to you to talk about extending your contract or not. IF they don´t want to extend, you have no trouble at all. If the want to extend, you just tell them that you have already taken commitments elsewhere so you can´t give them August. If that´s okay with them you are happy to accept another contract which leaves you free for August.

That way you don´t push at all, you let them come to you. You are also not pretentious, you just have made some other plans they now need to take into account.

You are in a much stronger negotiation period if the already decided (and planned) that they want something from you.

Don´t worry to much about putting them in a hard place with their projects. They are professionals, and they thought securing your workforce was less important for them than potential costs of termination, should they not want to continue with you. Else they would have given you a regular contract (with vacation days). You don´t ow anything more than you signed for!

PS: If time runs out, you can just remind your boss that you need to talk about your availability, should they want to keep you around, as you already began to make plans for the time after. Then again, you let them come to you...

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    This makes it sound as if OP isn't interested in staying within the company
    – Twyxz
    Commented Feb 28, 2019 at 12:19
  • @Twyxz: Why? This is just normal business at least where I live. Somebody offers you work, if you like it you take it, if not you leave it - if you have conditions, you put them forward at the right time and see if you reach a mutually beneficial agreement...
    – Daniel
    Commented Feb 28, 2019 at 12:42
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    BTW: If OP comes now, he is in a weak negotiation position. He is the one with the wishes. If he waits till they ask him, he is in a stronger position. They want and need him, now. He can put his vacation as anchor.If they don´t want to continue with him anyway, asking now about vacation arrangements won´t change that!
    – Daniel
    Commented Feb 28, 2019 at 12:55
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    @Twyxz: Did you not read the Question? His contract ends in three months! They have to come to him in that time frame or he is out of work anyways!
    – Daniel
    Commented Feb 28, 2019 at 12:58
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    @Moondane: I´m not sure if I understand your question correctly, then. You promised in your contract to work for them until 05/2019. You planned to do some other Activity in 08/2019 Correct? They never asked you if you would be available to work for them in August nor did you in any way offer that to them. If and when they ask you about your future availability, it´s easy to say sure, let´s go on, but not in August ....
    – Daniel
    Commented Feb 28, 2019 at 14:50

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