Take a Permanent Working Vacation

by Brian on July 18, 2011 in Location Independence

One summer during college I was doing an internship at a corporate law office in Tokyo and I met a lawyer there from Los Angeles who was on a “working vacation.” This was a new term to me at the time, but it seemed like a shear genius idea.

Many of us would like to travel the world, live in exotic places, and meet new and interesting people. But we have no notion of what that might actually look like in real life.

We might have a few vague images in our heads of airplanes, hotels, and pictures of us in front of well known landmarks, but actually describing it in concrete detail is another matter.

Would you be in New York, Tokyo, Paris, Mumbai, Melbourne? What would you be doing? Learning French, visiting ancient temples, watching a play on Broadway?

Even say you had an idea of where you might go and what you might do, isn’t long term travel expensive? And how would you ever get that much time off from work? And what about the kids (if you have any)?

The easiest way to keep your finances afloat during extended travel is to make income from an online business, but as I hinted at the beginning it’s not the only way.

It might be time to redefine the way you look at “traveling the world” and consider a working vacation.

Redefining Travel

Even if your aim and interest is long term travel, you probably have an unhelpful notion of a “vacation” in your head.

At some point in your life you’ve probably been on at least one three day, four night type of trip where you crammed as much sight seeing into the few days you could as possible then came home exhausted and wishing you’d had more time. Perhaps you even shed a small tear when your credit card bill came that month because the trip cost so much.

Long-term travel–the kind that lasts months or years–is not the same thing as just taking a long vacation. It requires different strategies and a different plan of action.

Instead of just taking a short trip someplace, you’re going to actually be living there as a resident.

Instead of a hotel, you’re going to want to find an apartment or a house to rent.

Instead of a pile of cash that you’ve saved up to pay for the trip, you’re going to need a way to keep earning money while you are there.

Instead of seeing 3 museums and 6 national monuments a day to “get it all in,” you’re going to have a lot more time to space out your sight seeing and get to know your new locale and its people on a much deeper level.

In fact, this goes much deeper than taking a trip. Really what we are talking about here is moving to a new city, or a bunch of new cities. You’ll be gone for a long time, possibly forever, so you’ll either want to give up your apartment / sell your home before you leave or make arrangements to sublet it.

Finding Work For Your Working Vacation

Of course if you are going to go on an extended working vacation, you need some work to do to keep paying the bills.

If you’re lucky, you might work for a large company that has a branch in your new location that you can transfer to. Or if you work for a more flexible company, you might be able to continue doing your current job remotely. If neither of those options work for you, you can simply get a new job in the city you are moving to.

New employers will often want at least a 1-2 year commitment, and I find this is well suited for long term travel. If you live in a place for at least a full calendar year then you get a chance to experience it during all the different seasons, all the different holidays, and all the different local eccentricities.

That said, like any other job, don’t spell out in your interview that you are only looking for a 1-2 year job. When I’m interviewing for jobs in a new city I usually just say that I’m moving there and plan to live there for the indefinite future–because it’s true. I don’t know how long I will be there. For all I know I will really fall in love with the place and want to stay for 5 years, 10 years, or longer.

I’m not going to pretend this is the easy part though. You have to look hard at your priorities here as there will most likely be a trade-off between career and your desire for long-term travel. Achieving very high levels of career success often means being involved at the same company or at least in the same network of contacts for a long period of time, which is usually not compatible with frequent moving.

However, if you’re making a livable income now, no matter where you go you should be able to find work that meets your basic needs and leaves some left over for play. If you move to a city where English is not the native language, you can usually find decent paying work teaching English if nothing else.

Living in New York: A Personal Example

For the past decade of my life I haven’t lived in any city for longer than 2 years at a stretch. I don’t really think of myself as “traveling” so much as just moving to a new city. Though in all that time I’ve never stopped feeling like a tourist.

Most recently I’m finishing up a 2 year stretch in New York. Prior to that I spent time in Los Angeles, Seoul, Tokyo, Yokohama, and Silicon Valley.

When I first moved to New York I was actually unemployed and in the process of shutting down a failed online store. Everyone wanted to know how I was going to get an apartment and pay my bills without a job–so did I.

With about 6 months rent in the bank and a co-signer, I was able to negotiate my way into a studio apartment just outside Times Square. It was about 4 nerve wracking months before I actually landed a job in the city–in retrospect not too bad considering that we were supposedly in the middle of the worst economic downturn since the Great Depression.

Now that I had regular income and the bills were taken care of, I was free to explore the city. And explore I did. I’ve been on bus tours, walking tours, boat tours, and helicopters tours of New York. I’ve been to the Statue of Liberty, Ellis Island, Governor’s Island, Coney Island, the Empire State Building, Central Park, Battery Park, and more.

I saw the New Year’s ball drop 20 feet from Carson Daly in Times Square, then watched the exodus from Times Square from my roof top. I saw the Macy’s 4th of July fireworks from my rooftop as well. In the winter I saw Christmas displays at the shops at 5th Avenue, and in the summer I saw a performance of Shakespeare in the Park.

All in all, I’ve seen and done far more in New York City than I could have done on a short vacation trip. By actually living here I still have essentially a “normal life” except that the tourist destinations are located right in town instead of a plane ride away. Instead of cramming them all into one day, every weekend or two I go explore a new corner of the city.

The experience is actually much deeper than just seeing the sights in a new city. It’s experiencing an entirely different way of being and viewing the world as a “New Yorker.” I’ve also been able to work in online advertising on Madison Avenue, which gives me somewhat of an affinity to the show Mad Men. Sometimes I even light-heartedly tease my friends for living in New Jersey.


So often we get our heads stuck in the sand and think something can’t be done or will be way too expensive for us to ever afford it. Long-term travel needn’t be that complicated.

The “working vacation” I have described here is in many ways simply “moving to a new city” by another name. Something that many people and families do all the time–and so can you.

Moving to a new city gives you a new launching pad to explore not just the touristy items in the city and near the city, but the experience of a different way of living. Once you’ve had your fill the option is yours to stay, move back where you used to live, or go someplace entirely new.

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