Life On the Road: Is Working Remotely Really For You?

There are a lot of people who like the idea of living life on the road and working remotely. Whether it’s traveling solo, with your partner, or means taking the kids out of school, people of any age can benefit from traveling across the globe, exploring other cultures and getting a worldwide education.

Perhaps you’re sick of your office job, hate where you live, or simply aren’t one to be stuck geographically in the same place for long. There are lots of reasons why traveling constantly may sound appealing to you.

With more options for working remotely, running an online business, or picking up flexible work, more people are choosing to live the nomad lifestyle.

But traveling all the time working remote jobs can also be hard work.

So, how do you know if a life on the road is really for you or not?


Lack of Home Comforts

If you’re a bit of a homebody, you may want to rethink your plan for a life on the road. If you like to come home, slip into a bubble bath and catch up on the latest Netflix series, you should probably stay put.

Life on the road means you’ll never be in the same place for long.

If you’re traveling in a van, camper, or trailer it could be days before you have access to plumbing or a high speed internet connection. Yes, you have the option of staying in hotels, but that can become very expensive, very quickly.

It can be hard to work remotely if you can’t stay connected. Video conferencing, conference calls and even simple data entry will require internet service. Without access, your plan to escape the office environment and work from anywhere might mean you’re working from coffee shops or coworking spaces instead.

For a lot of people that defeats the whole purpose of remote work.

Although today’s technology will allow you to stay in touch with family, friends, and your coworkers and employer, you may have to make frequent stops to charge your phone or connect to Wi-Fi.

On the other hand, not being connected 24/7 might work to your advantage. Without the constant interruptions of the internet, you could benefit from increased productivity and overall job satisfaction.

Limited Supplies & Space

When you’re on the road, you have to travel with as little as possible.

For remote workers, this means you’ll need to get used to living with only a few essentials personal items. If you’re someone who likes to get dressed in different outfits each day, for example, the traveling life may be a disappointment.

Working from home, even in a non-traditional sense, also means setting up a remote office or work space. When space is at a premium, this can be a real challenge. Your designated working space might double as the kitchen table or your kids craft corner.

Without the typical office setting of a cubicle or desk, your productivity can suffer. Particularly if you are also dealing with interruptions from your family members that are living on the road with you.

This is also a challenge for jobs that require office supplies. Traveling with a printer, boxes of files, or an ergonomic chair might not be feasible.

No Permanent Residence

There are perks to having a permanent residence. For instance, you’ve always got a place to park your car. When you’re out on the road, you may not know where you’ll be parking from one day to the next.

Similarly, when you’re at home, you have a permanent address where you can receive your mail. If you don’t have an address, you can use a trusted friend or family members home as your mailing address, or get an online post office box.


Making Money

Just because you’re out on the road, it doesn’t mean you won’t have expenses and bills to pay. You’ll need to maintain your vehicle, pay your phone bill and buy necessities like food, clothing and gas.

Unless you have a hefty savings account, you’ll need to be creative when it comes to making money while traveling.

With advanced preparation, it’s possible to set up passive income streams so your that your work day might only be an hour or two, leaving you plenty of time to enjoy the sights and local culture.

Otherwise, there are numerous jobs that can be done remotely, depending on what it is you want to do.

If you can get a fully remote job like being self-employed as a freelancer or work virtually as an online customer service representative, you can easily work at home, no matter where that home is.

If you are more impulsive, it is possible to find temporary job opportunities that allow you to work anywhere you choose to stay. You can find these types of jobs through sites like Flexjobs, online job boards, or searching terms like “gig jobs”, “side hustles” or “work from home jobs”.

Just be sure to watch out for those work from home scams!

However, relying on trying to find a job at each different stop you make may lead to increased burnout. You may not do well with this work arrangement and end up back home sooner than you think.

No Set Schedule

A lot of people want to work from home so that they have a flexible schedule. For the most part, you get to decide what your workday looks like. You can plan your working hours around when you are most alert, focused and will do your best work, opposed to having a set work time of Monday-Friday, 9-5.

You also don’t have to worry about your daily commute, which I’m sure any one that works remotely will agree is a huge advantage.

However, this open work schedule is also one of the biggest challenges with working remotely.

If all employees are in different time zones, a meeting or a video chat might fall outside of their preferred work hours, and might interfere with the work life balance many employees are striving for.

It can also make it too easy to work all the time instead. So be sure to set aside time for yourself to get out and experience what other parts of the world has to offer.

That is, after all, the whole point of a life on the road, is it not?

Working remotely while living on the road isn’t for everyone, no matter how stress-free it may seem. If you are willing to give up some of the luxuries that a home and traditional job provide, you can experience everything other places in the world have to offer.

YOUR TURN: Is a life on the road something you’re interested in? What kind of remote job would be most appealing to you? Would you work at all while traveling?

Leave a comment below and let us know!

Amanda Kay, the founder of My Life, I Guess, provides valuable career advice and support for anyone striving to make a living and, more importantly, make a life. Whether it's navigating job searches, learning new skills, overcoming unemployment, or dealing with debt, My Life, I Guess has been a go-to resource for career guidance and financial stability since 2013. Amanda's expertise and relatable approach have been featured in trusted publications such as MSN,, Yahoo! Finance, the Ladders and Fairygodboss.

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