How to Negotiate a Month of Travel from Work


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A few months ago I got back from Morocco where I had been living and traveling for two months.  Rather than quitting my job, I took a leave of absence so I could go back to my position when I returned.

This is the fourth time I’ve had an employer let me take time off to travel for a month or so at a time.  I wrote about my first two times in a previous post.

However in that post, I didn’t go into much detail about how I negotiated the time off.

Since then I’ve asked more employers for extended periods of time off to travel.  I’ve gained a lot of experience in the best way to ask in order to get travel time off.

So I want to go into more detail about what I’ve learned about getting a month or more of travel off from work.

Think Beyond Two Weeks

I’ve made it a point to explore the option of traveling for a month or more from just about every employer I’ve worked for.  It’s been quite enlightening for me.  It’s amazing how often you’ll get something simply by asking for it.

Of course it’s a delicate situation to ask for so much time off from work – rightly so.  You’re asking your boss to make an exception for you.  It should be done carefully so you don’t give off the wrong impression.

The last thing you want to do is make them think you aren’t dedicated to your job.  If you’re already on shaky ground, they might start looking for ways to dismiss you.

Personally I’ve never had an employer be mad at me for asking, but I can see how some might get upset with you.  I’d just be careful.

Ideally, there are three conditions you should try to have before asking:

  1. Be a valued employee.  If you’re in a great working relationship with your employer, they are more likely to bend the rules to let you travel.
  2. Try to make them need you more than you need them.  The proposals that worked best for me were in hard-to-fill jobs.
  3. Have great rapport with the person who will ultimately approve the request.  Ask that person directly for the time off when possible.

Also keep an eye out for slow seasons.  Does the workflow always slow down during certain times of the year?  Try and time your request around that.

How to Ask

Presentation matters.  How you introduce the idea of having a month off to travel is the key to the proposal’s success.

You don’t want to tell them that your request is simply to fit more vacation time in.

It’s much better to tell them that you were just presented with an opportunity you want to explore.  It helps your case if you explain it as an opportunity that came to you rather than you seeking it out.

This isn’t lying.  A month of travel really is a great opportunity.  All you’re doing is reframing your request from another perspective.

When I made my first request, I told my boss that a friend came to me and offered to take me along with him on his trip.  I made my case to him that it was a huge opportunity and I wanted to explore options.

Tell them you’re just asking to see if it is possible and you want their help to make it happen.  Say that you normally wouldn’t ask for so much time off, but the opportunity is too good to pass by without even looking into it.

Don’t say you’re completely committed, but that you’re just feeling things out at the moment to see if it is even possible.

By explaining it as a huge opportunity that came to you, you’re establishing two things:

  1. You’re in the exploratory phase and nothing has been decided yet.  Since you haven’t made any firm commitments, there isn’t much they can be mad about.
  2. It’s a unique circumstance.  This isn’t going to be a request you’re going to make year after year.

Be prepared to take this as unpaid time off or a leave of absence.

After you’ve made your case, you’ll probably have to wait.  Even when I’ve got a no, the supervisor took a few days to look into it.  In the meantime, be patient and wait for a response.

Whatever response you get back, this will be your one shot.  Get a yes and you’ll likely only be able to do this extended time off once (although I did get one employer to say yes twice).  Get a no and you’ll probably never get a yes from this employer.

After Asking

If you get a yes, you’ll want to continue your great working relationship with everyone.  This also means keeping in contact while you’re on your trip.  If you have access to emails while away, check it regularly and interact with people back home.

Keep reminding them just how valuable you are to them.  This will make it less likely for anyone to be upset that you’re traveling while they’re working.

There is definitely a risk to traveling for such a long period of time.  If you’re not willing to take that risk then I wouldn’t recommend trying this.  But if you’re like me and want to have more time to see the world than you’re getting, it’s often a risk worth taking.
photo credit: fotologic

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  1. The biggest risk for me would be not wanting to ever go back to work.

    I mean ever.

    I don’t think I could take a month off to truly live, and then return back to the grind.

    Best to just stay stuck in it until it’s time to move on.

    But props to you for being able to actually take that time and get out there. It takes guts asking your employer for that much time. Sounds like the reward is worth the risk though.


    • Trevor, I know what you mean. When you’re out traveling for long periods of time, you just want to keep going. It’s actually not that hard a transition to get back to what you were doing beforehand as far as getting back into work goes. What’s hard is there is so much more to see in the world and so little time.

      Now that I’ve seen the reaction to this post, I do think it takes a lot of guts. I don’t know how many people will actually take this advice, but it has worked for me. Maybe I do have a lot of guts to try, but the rewards have been sweet.

  2. I enjoyed reading your post.
    I think that I would not go back.

    • I’m glad you enjoyed it, Sandi. Yeah, going back is tough. The big reason for me is that I just want to keep traveling. There’s too much to see out in the world.

  3. Steve,

    Like the other commenters, I don’t know if I could go back to work after taking that much time off. Heck, by a month I could be settled in a new community living the good life (-;

  4. kaylee tietz says:


  5. kaylee tietz says:

    pretty basic common sense stuff. but a few things were very helpful!!!! :)

  6. You slacker you 😉

    Well, that’s one reason I’m glad I work for myself – I can do whatever the heck I want. My only boss is my customers. Right now I’ve only got a few, so I can do whatever I want :)

    Were you able to get the same employer to give you more than one leave of absence, or has it been a one trip, one job sort of thing?

    • Yeah, working for yourself would make it easier. The owner of one company I worked for took a month off here and there. It was easy for him to just get up and go. I had to do it the hard way.

      Most companies won’t do it more than once, but I did get one job to approve it twice.

      It’s actually not that hard to ask, but most people don’t think to do it.

  7. These days not a lot of people can take off for a month at a time. Vacations are quite expensive and if you go away for that long, most likely you don’t get paid at work. However, if it’s a cool opportunity to miss, I would definitely consider it. Life is too short to be always limited by the rules…

    • Yeah, it can be expensive, but that shouldn’t stop you if you want to travel. I saved a lot of money so I could go. It’s actually not too expensive if you go to an inexpensive country.

  8. I’m under the influence of no employer, but how does it feel to step back in the office after such an awesome time away?

    Personally I don’t think work should be work, if you love it that is. I’m only an amateur but wouldn’t somebody in that position just be given that extra urge to never return…?

    • It’s actually not too hard to go back to work. In my opinion, two weeks isn’t long enough, but once you’ve traveled for one or two months in a row, you’re ready to go back. When you’re out for that long, you get diminishing returns.

  9. I think this is a wonderful idea. For a valuable employee, it would be better to grant a temporary leave than have to replace them altogether.

    I’ve had some week-long vacations that have led me to realize how much I hate my job, and some longer trips that left me a better employee, refreshed and ready to tackle the challenges in a more creative way.

    You are right, though: You’ll never get to take a long break without asking for it.

    • I get the same way. When I travel for a week or two, I feel as if I didn’t really get into the travel mode. You feel rushed and can’t fit everything you want in. Even in some small countries, it’s hard to see it for just a week. On the other hand, a month or so of travel is more satisfying and I feel more ready to get back to work.

  10. Such a great post! I have a job where I get more time off than others, so I don’t have to negotiate for time. But this is so important for travel lovers who only get 2 weeks off a year!

  11. This is a great tip that I don’t see much on travel blogs. My partner-in-crime got his supervisor to agree to let him travel for one month to Asia and two months to Australia. It’s not always necessary to leave a good job to travel.

    • You never know what you might get if you just ask for the time away. I’ve often been surprised what employers are willing to do.

  12. I have a question, I just asked for two months off and got a yes, and they want me back but they want me to present it as resignation, is there way to do it so as to make sure they’ll take me back?

    • The first couple times I did this, they had me do the same thing. I had to basically quit with only the likelihood (not guarantee) of coming back. Although both times went smoothly and I got rehired quickly. The last time I did it, I was on a leave of absence – theoretically that should make it more likely to be hired back – although I wasn’t taken back. Complications got in the way and I had to find a job elsewhere. No matter what happens, either way, it’s a risk – it’s just a risk you have to be OK with taking.

      • Steve, thank you so much for your reply, I really appreciate you taking your time to respond. I will have to think about it now, I am a single mom and it’s not easy to throw 10 years of working in the same place.


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