How I Traveled Long Term (And Kept My Job) Twice


How I Traveled Long Term and Kept My Job

Two weeks is the golden standard of American vacations.  So when I had a chance to see Southeast Asia for a month, my first thoughts turned to my job.  I thought they would never let me off for such a long period of time.

But if you know me, than you’ll know that not only did I make the first month long trip, but I also made a second two month long trip the next year.  Each time I came back to work with the same employer.  So how did I do it?  All it took was some courage, risk and luck.

An Offer too Good to Miss

Shortly after I graduated college, I started working for an employment staffing company.  It was such a small business that soon I was on first name basis with the owner.  The work itself was dull and repetitive, but eventually I garnered a reputation for quick, efficient work.

After about a year, I became restless.  I was going through a routine that seemed futile and endless.  It was at this point that a friend asked me to travel with him to Southeast Asia.  It was as if he heard my restlessness and came to my rescue.

My only real obstacle was my job.  For this I came up with a brilliant solution: just ask for the time off.  I realize that two weeks is the norm, but I also realize that it isn’t written down anywhere.  There aren’t any laws about about vacation time.

I also thought I would ask the owner directly.  It’s best to get approval from the person who has the ultimate authority to make these decisions.  Asking for all this time off was the courageous part, the next part, his answer, was the lucky part.

He could easily have said no, but he didn’t.  Because I was such a good employee, he was willing to be flexible.  He had a big project coming up that needed staffing workers.  Coincidentally enough, I would be coming back from the trip around the time he would need people to work on it.  He said I could have the time off and work for him on that project when I came back.

So I made preparations for my journey in full knowledge that I would have a job coming back.  It definitely made me more relaxed on the trip overall too.  I ended up spending quite a bit of money so being able to go back to work right away and earn it back was comforting.

It ended up being good for another reason.  I was quite fully prepared to full-out quit and travel.  This trip was not something I wanted; I needed it.  So his flexibility not only saved me the trouble of finding work when I got home, but also saved him the trouble of finding a new good employee.

The Next Year

Of course, this isn’t the end of the story.  About a year after my first trip I was, once again, offered a chance to travel through Southeast Asia.  It was too good to pass up.  This time things were slightly different.  I wanted two months off to travel this time.

So I asked.  I told him I would be willing to work under the same arrangement as last year since I knew he would need people again.  The owner was once again very flexible and agreed to the terms.  However, I hit a snag this time.

The general manager of the company, who works closely with the owner, called me into his office.  He had a nice long talk with me about my plans and made it clear that I had permission to go this year and would be offered the position when I came back if it hadn’t been filled.  I knew the risks and decided to go anyways.

Another thing he told me was that they wouldn’t accept a vacation request like this ever again.  The message was clear to me that this would absolutely be my last long term vacation with this company.  I had no other choice but to accept these terms.

The End of This Story?

While I do admit that I had a lot of luck in this story, there’s certainly nothing special about my circumstances.  I think if more people were to ask for longer vacation times, more people would receive them.  Having a lot of flexibility really helps.  Of course I do realize that not all employers are so generous.  A few years later, I asked another employer for a month off to travel.  In that case, there wasn’t even a willingness to be flexible about it.  The answer was simply no.

It’s just a shame that the two week vacation is such a standard in the country.  Some workers are pressured by employers to not take any vacation at all!  But as long as you’re not in one of those situations and you find the courage, maybe you can be lucky enough to travel long term and keep your job too.
photo credit: archer10 (Dennis)

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  1. I too have been very fortunate to travel long term and have the same job. I am so lucky cause I get about 5-6 weeks off now (plus an additional 2 weeks of sick leave). Because of my hours I can take an 8 day trip without using an hour of vacation time. So if I go on a 2 week trip I only use 1 week of vacation time, and for a month long trip I will only use 3.

    I am beyond thankful to have one of the most stable jobs (absolutely no layoffs), and my boss allows us to be gone for up to 3 months on vacation (WITH PAY…if you have enough vacation time of course).

    It really doesn’t hurt to ask. My friend did just for this year and her boss also gave her the okay.

    • It really doesn’t hurt to ask. This experience showed me that you can often work around perceived limitations for your time off.

      You certainly do have a lot of flexibility for vacation time in your job. I know too many people that can barely get two weeks off at one time so I’m glad you realize how lucky you are. I’d take full advantage of all that time and put it to some great use. I know I’ve been very thankful for all the vacation time I’ve received.

  2. Very inspiring. Well stay tuned because I will be doing the same thing, though I will be aiming for more like a year off. And I don’t even want to go back (but leaving the option open may be nice…)

    Nah, I will just peel out indefinitely. That sounds better to me! :)

    • I think that if you have the money and time than you should do the full year. I still look back on the traveling I did in this story and realize that I could probably have done a full year instead. I’m very thankful for the time I spent, but a year traveling would have been amazing.

  3. So this was your story on how you were able to manage traveling for a longer period.

    I work for an American company and we only have 15 days of vacation leave and we can opt to spread them across the year or use them in full. I prefer to choose the former.

    It’s really nice if you have an employer who understands your needs to get our of the office environment for a period of time. There’s a 50/50 chance so it doesn’t hurt to ask for that well-deserved vacation.

    • I don’t think my employer really understood my desire to travel for such a long period of time. He isn’t the traveling type. He did understand how much I wanted it though. It helped that our relationship was good and he just happened to have positions to fill around the time I got back. It worked well for both of us in the end.

  4. Hey Steve,
    isn’t it amazing how people (employees) are programmed to accept the fact that they are doomed to a pithy 2 week vacation per year?
    For two year in a row (while employed) my husband and i traveled to Europe for over a month each time. Now we’ve been living like vagabonds and planning a year long trip to France (crossing my fingers). Granted we are no longer working but still, it’s exciting….. People say we should go to Thailand but since i was born there and i’m half Thai it doesn’t appeal to me. But i would definitely go there for a month long trip if i had the opportunity..

    • Hey Annie, it really is amazing how employees just accept that they only get two weeks of vacation a year. Of course that is if they take the full time. Many don’t. In fact, one year I told some coworkers that I was traveling through Central America for two weeks. Many were amazed that I would go for that long. It was weird for me since I really don’t consider two weeks a long time for a vacation.

      You should definitely visit Thailand. I’ve been there twice and I love it there. There’s so much to see and do.

  5. Steve, When I was younger I told my boss I was leaving to travel the world indefinitely and explained to him why I had made that decision. He was understanding and wished me well. After almost 5 years of travel I returned home, and before I even arived in my home town I called him up and aranged work the following week as I was obviously broke.

    I have worked for him ever since, and he is aware that I am a person who likes to travel frequently, but I always try and plan my travel arround slow times in the business so its a win win.

    • Hey Jason, it sounds like you have a great setup at your job. It is kind of similar to what I had in this story. The job I came back to was for a yearly project that was short term so my employer knew he would need people for it around the time I came back. It was good timing for both of us.

      And even though I don’t currently work for this employer, I’m glad I’m still on good terms with him. His wife even helped me get my next position by writing a written recommendation.

  6. I think u were just hell lucky! The same as me, got a lot of time off to travel when I used to work as a flight attendant. Hopefully everyone could do it!

  7. That’s an awesome story. It’s a shame that Americans are not encouraged to take more time off from work. Two weeks out of a 52 week year is not much time.

    That’s why I am self-employed.

    • Being self employed really does help in getting time off. I knew one small business owner (different from the one in the story) who took off one month to travel through Norway. I’m not entirely sure if he would have let his employees do that, but I’m guessing no.

  8. Hey Steve,

    I liked that you took charge and asked. It doesn’t hurt to ask right? If they say no, then you’re back to where you start. No big deal.

    After your second trip, when you came back was the job still there or did they fill it?

    It is sad that the typical vacation is two weeks. What’s worse is that the employee feels like they have to check their work while on vacation. It’s vacation!! Don’t do any work. Don’t worry.

    • Hey Benny, after my second trip I did end up getting the job. It pretty much went just like the year before and exactly as I had planned.

      Taking charge and asking for what I wanted was the big lesson I learned from this experience. Sometimes asking for what you want is the easiest way to get what you want.

      I think it’s bad how employees take work with them on vacations too. It really defeats the purpose of going on one.

  9. This is the hardest part of travelling, I think – finding the right balance between work and play.

    The only reason why I would want to be French is to benefit the 8 weeks off per year…! I tried to explain a French friend how us North Americans only have 2 or 3 weeks per year, and boy was it not easy. He almost said we were victims of slavery!

    • I’ve had similar reactions from some Europeans too. They just can’t believe how little time off we get. It really does make it hard to find the right work/play balance. It also makes travel plans unnecessarily hectic since you have so little time to do everything.

  10. Steve,

    I am actuall lucky enough to be up for a sabbatical this year where I get a full month off with pay. Reading your story makes me want to do something productive with it like traveling. I was just going to sit around and get fat for a month. Traveling sounds a lot better. How do I get the money to get where I want to go because all of my desired destinations are expensive? Is robbing banks still illegal? lol! This was a great story. Thanks for sharing and reminding me how much my 2 week a year vacation sucks. :-)

    • lol, as far as I know robbing a bank is still illegal. Fortunately there are better ways to get money for traveling. My trips through Asia were actually very cheap. I went during a slow time so food and hostels were not expensive at all. But even if it wasn’t cheap, I would still have traveled.

      I think you’re lucky to be on sabbatical for a year. You should at least travel for a little while during that time. Personally speaking, I’ve never regretted spending money on travel.

  11. Niceee!

    Honestly I think either people are not in that intimate of a work setting or people are just too scared to ask, but to your point what if more people did. Travel is a time of growth. Exposure to new perspectives and philosophies – ideas that you can bring back with you to work. I’m sure when you came back from your trip whether you noticed it or not, there was some type of enhancement in your work.

    Wonder what would happen if more people were courageous enough to ask for what they really want.

    • I like to wonder what would happen if more people asked for long periods of time off. With enough people doing that, maybe vacation time would start to rise naturally. It’s hard to say.

      Travel really is a time for growth. I’d been exposed to so many new experiences and cultures. I saw the world in a brand new way and it excited me. I could tell that I’d changed for the better.

  12. Hey – I love the simple advice here. Don’t ask, don’t get. I find in corporations sometimes they are less open or you really have to shine amongst many other candidates to get the flexibility. However, a couple of people were able to take 3-12 month mini sabbaticals to either pursue a foreign volunteer opportunity or travel the world. The key is being willing to quit if the answer is no.

    After just coming back from London and Portugal for 10 days, I am trying to find a good use for my remaining week off. But also really thinking I want to travel more and have more freedom. Although I spent way too much money and appreciate the pay off factor. Trade offs, trade offs.

    • I think it all depends on the corporation. Some seem way more willing than others. I wish I knew how to tell which ones would be like that and which ones won’t. I guess that’s where being lucky helps. Of course, it’s just makes sense to ask. You never know. Plus, being willing to quit and do it anyways really helps. Either way, you get to do what you want.

      When it comes to traveling, I’ve learned that it is better to just do it when you can.

  13. In Europe, where people are free 😛 a month is standard for everyone. My co-workers in Spain were all scandalized when I told that we only get two weeks in North America!

  14. my employer generously agreed to a two month trip away from the office. I do continue to work, but remotely from a small town in Colorado. the time change allows my husband and me to end work after lunch and spend the rest of the day in the mountains. This will be our second summer out west. As I grow in my job and responsibilities I am a little more uneasy about being gone so long. I have planned a mid summer trip back home to work in our office for a week. I am hoping that these mountain escapes can continue even if not for the same extended amount of time. I can’t picture any other job that would allow me this flexibility.

    • It sounds like you have a good setup there. Working remotely is a great way to be able to spend your time where you want and keep your job. In fact, I know some people that work remotely and travel at the same time. That way they really don’t leave their work for any extended period. Seems to work really well. I hope you can keep what you have going.

  15. Dena Taylor says:

    I’ve known former coworkers who asked for unpaid weeks to add on to their regular vacation time and got it, this at a progressive coffee company. But it wasn’t the norm. But they asked and had an awesome time in Argentina.

    I’m self-employed and can and do take off when I want (after working a lot to save the money to travel). There is always a risk that I’ll miss a project opp while I’m gone but after building some solid relationships, I’m finding that some clients will wait work around my schedule. It surprises me every time and I’m truly grateful. Then again, I’d do the same for them.

    • It seems that being self-employed is a good way to take off the time you want. Of course the ones that seem to have trouble are the ones that have to work regularly with clients. So I’m glad you can make that work for you. I think you show that people can make it work if they want it to.

  16. One of my favorite thing about teaching is the fact that we have 2 weeks of in the winter, 1 week off in the spring and 2 1/2 months off in the summer. Having so much time off (despite the shitty pay) is a great reason to get into the education field.

    • That’s part of what I think I’ll like about being a teacher. Of course, many teachers don’t actually get all that time off. There are a lot of meetings and setup you have to do at the end and beginning of each school year. I hear it all depends on the district you’re in. But I know in the end that you get more than two weeks so it is still good.

  17. Hi Steve!

    You just never know what answers you might get if you don’t ask the questions, right?

    How great that you rely on seeking to be your guide, instead of blindly accepting the sometimes arbitrary rules that often make up company policy.

    I’m sure you had wonderful adventures – that may have never happened if you didn’t have the courage to ask for what you wanted.

    Terrific message here, thanks for sharing!

    • What’s weird is that I didn’t even know what the company policy was on time off. I just assumed it was two weeks when I asked. I was right, of course. But what’s strange is how I knew that without even having to look. It’s just been drilled into workers that they get two weeks that they don’t think to ask for more.

  18. I think it’s great when you find employers who are able to accommodate the needs of their employees. My company has been accommodating for me in the past, not about travel, but other things. I like your advice about not being afraid to ask.

    • It’s great to have an accommodating employer. It’s just good to know that they’ll be flexible to your needs. I have that now and I feel very fortunate.

  19. Hey Steve,

    I commend your courage and assertiveness. This post reminded me of the biblical quote, “ask and you shall receive”. It’s probably unlikely that everyone would have the same luck as you, but then again you never know unless you ask!



    • Hey Sean, I often wonder how many places would give their employees as much time off as I got. From some of the comments I received on this, it seems as if there are other workplaces that would do it. I guess most people won’t know until they try.

  20. It’s so great that you found ways to travel and keep your job. I think a lot of people wouldn’t even be brave enough to ask their employer for the time off. I’ve always been self employed so can take as much time as I want – without getting paid, of course, which is the downside. I know a lot of Americans only get one week vacation time. That is so wrong.

  21. Yet another reason why I seek self employment. 2 weeks off is far too little for my taste.

    I would understand why anyone would get the sense of feeling trapped and all. Wow I could definitely never live like that. I’ve been fairly fortunate in my working situations.

  22. That’s great! I had a similar experience when I wad offered a fulltime job but then decided I wanted it to be part time freelance. We negotiated the best arrangements and I stayed there for a while! It never hurts to ask.

  23. In my previous non-profit jobs, I had 22 days a year of personal time that allowed me plenty of time to travel. At my new job, I don’t have vacation for a whole year but that didn’t stop me from going to Hawaii when I had the chance; I just took unpaid leave. I get that you can forfeit being able to move up in the company if you are seen as a person that isn’t “dedicated” but that matters less to me than just enjoying life!

  24. Sounds like you need to think a little bit “outside the Box” and look into becoming an Expat. I wanted to travel and applied for a job on an island in the South Pacific in 2001. My one year living abroad plan turned into two years and a transfer to islands in the Atlantic. I spent 3 to 4 years on various islands in the Atlantic along with a decent amount of time in the Caribbean. Floated resumes for about a year and landed a job in Asia. I have been in Asia for about 6 years and met my wife who is from the Philippines about five years ago. We will end up in the Philippines for the long haul eventually but will always travel. We are looking at a few opportunities in Europe and may go there a few years first before we decide to move permanently to the islands. One of the great things about taking jobs overseas is that the standard paid vacation plan is about 30 days. There is a job site called “career jet” and if you Google it you will find the link. I did not want to clutter your blog with a link. What I do is use the site to find jobs and when I apply for them I then search the company that posted the job and apply to their site directly if they have other positions.

    If you love spending a lot of time overseas becoming an Expat is the way to go. You actually get the time to not just experience a new culture but live it. Look up “Foreign Earned income exclusion” on the IRS website if you are a U.S. citizen. If you are another nationality your tax break could be even better. As a U.S. citizen you get about a $90K tax break. A lot of jobs overseas pay more than they do in your home country. Part of the reason is that, for example, a U.S. company will have positions they need to fill with U.S. citizens. Finding U.S. citizens willing to live overseas and be able to handle a different culture is not as easy for them as you may think. I started my one year excursion 10 years ago and it ended up turning into my life.

    If you are from a country other than the U.S. I am sure you already know how easy this is.

  25. Aaaaaaaaaaaaaaaaaan this is why I am ready to leave my job and this country. Time to live my friends!

  26. I have been planning in my mind a trip for Dec 2012 and I hope to request three weeks off.

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