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Traveling Long-Term: Living the Dream or a Waste of Time?

Traveling Long-Term: Living the Dream or a Waste of Time?
Ariana Arghandewal

For many folks, traveling long-term is The Dream. For some, the ideal scenario involves getting paid to travel while others are perfectly content working odd jobs at their destination in order to continue wandering. I myself spent four years working remotely, in two different positions – as a Managing Editor and then as a freelance writer/blogger.

What I initially thought was a dream come true became the opposite. I found myself depressed and feeling like my life had little purpose – not at all what you envision when you unshackle yourself from a day job.

Always on the Move

When most people envision quitting their jobs to travel long-term, their excitement stems from the perception that they are no longer beholden to The Man. No more working 9-5, worrying about office drama, annual evaluations and whether you’re going to score a small raise every year in exchange for your personal freedom. Traveling full time means freedom from that monotony and stress. Except, the novelty wears off eventually.

Travel can be exhausting, even if you’re staying at luxury hotels and flying first class all the time. Constantly going from one strange place to another can also feel unsettling.

Lack of Benefits

Another problem is the lack of benefits when you’re not employed full time. This may sound way too practical, but if you have the misfortune of spraining or breaking something, you’re looking at a huge emergency room bill for basic services. Unless you’re abroad when it happens, in which case your travel insurance has you covered. But even basic health services (i.e. health checkups) can become expensive. Aside from this, you’re losing out on retirement benefits that could really come in handy when you’re older and no longer able to travel as freely.

Skill Building

The biggest negative to long-term travel? While you’re certainly learning (languages, history, and about other cultures), you’re not always going to improve your marketable skills. When I returned to the workforce after four years of being a freelance writer, I suddenly had to relearn a lot of things: Windows, how to navigate different personalities at work, and various technological changes that I missed out on because I wasn’t using them in my remote job.


It was quite a challenge to adjust to working with others and having to answer to others. Which brings me to my most important point: Traveling long-term can get lonely, no matter how many great people you meet along the way. There’s something to be said for being in one place for the majority of your time. You build and strengthen relationships with family, friends, and colleagues. Those routines you dreaded can actually be comforting and grounding.

I don’t want to knock The Dream, but traveling full time can have negative consequences. I look at travel like dessert. It’s great after a meal (i.e. work), but if you have it all the time it becomes mundane and loses its novelty.


But I want to hear from you all. Is traveling full time your dream? If you’ve done it before, I’d love your feedback about what you liked/disliked about it.


[Image Source: Pexels]

View Comments (5)


  1. CaptHolic

    September 22, 2018 at 4:25 pm

    I am on the feeling lucky side of the fence.
    My job has me flying 100,000+ miles a year for the last 8 or so years.
    Luckily I do not suffer from some of the downsides you described as I still am accruing what you specified in your article as benefits. I also feel that my position has my skills adjusting with the times.
    As far as loneliness? With reference to friends it is my irregular schedule that does it to me not so much the fact I travel. Most friends are stuck in the Mon to Fri grind and their flash in the pan weekends are mostly reserved for their families. I spend 6 months on the road and the remaining 6 I have off, to spend waiting for my kids to get home from school…

  2. spamkiller

    September 23, 2018 at 10:32 am

    If you have a field that is portable, that is fine. Have laptop, can code while on a flight.

    In 2012, I got a cheap fare to Beijing. While in Beijing, I rewrote a the graphics decompression code on a remote access application so I could get decent throughput through the great firewall of China.

    In 2013 in Spain and on a flight back from Spain, I drafted a motion to dismiss.

    With a portable computer, a phone, and decent wifi, there is a lot you can do on the phone depending on the field you are in.

  3. ilcannone

    September 24, 2018 at 9:11 am

    Not only is this something that few are suited to but promoting it like some amazing way of life is misleading. Plus it’s just a way for the overentitled to show off and flood the internet with inane, hackneyed posts etc.

    Please don’t promote this.

  4. Dalo

    September 24, 2018 at 7:19 pm

    Ask Lucky about this .

  5. am1108

    September 25, 2018 at 6:55 pm

    Personally I think that I could easily adapt to traveling for work. I’d love to fly from city to city working from hotels and driving rental vehicles that the employer pays for. Especially while not having to put your own dime to earn airline & hotel status. And while I could not see myself traveling for work forever, I’d love to be in a position to do it for at least 20 years. I think the problems that Ariana is laying out is more from a Freelancer point of view especially- regarding lack of benefits.

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