Juggling a Day Job While Travelling the World

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Juggling a Day Job While Travelling the World

Since covid normalised working from home, the definition of ‘workplace’ has expanded dramatically. With employers realising there is money to be saved and efficiencies to be gained from letting staff work from home, jobs in many industries are becoming more and more flexible (unless you work at Twitter).

Around the world, employees with the travel bug are realising they no longer need to choose between their careers and travel. With just a laptop and an internet connection, seeing the world while holding down a job is becoming more and more achievable. It just takes some planning and an open-minded boss. Juggling a day job while traveling the world.

Industries with the most location-flexibility

The most flexible jobs are in industries that are used to working remotely, such as design, writing, and programming. In these industries, employees can often do their jobs just as well from anywhere in the world and remote freelance staff is commonplace.

Some of the most open-minded bosses are in the tech industry, where many companies have a remote workforce policy. These companies have long seen the value in having a global workforce that can work around the clock. So, they are far more willing to consider remote work arrangements, even for local staff.

Other industries that have embraced flexible work arrangements include education, healthcare, marketing, and customer service. These days, there are many jobs in these industries that can be done remotely with the right technology and a shift in mindset. This can include jobs like online tutoring, support desk, telemedicine, and social media management. When you take away the almost arbitrary requirement to be in an office from 9-5, the list of jobs that can be done from anywhere is practically endless.

Finding a job that allows you to travel

Looking for a job with enough flexibility to enable you to travel at the same time, will take some searching and a bit of patience. The number of remote and flexible job listings online is increasing. Searching job sites using ‘work-from-home’, ‘WFH’, ‘remote’, and ‘flexible’ keywords can uncover some hidden gems. Many sites also include entire pages dedicated to remote jobs, like this one for work-from-home design jobs.

Of course, finding a new job may not be your preferred course of action. If you love your current position and want to keep it while you travel or live abroad, you have two options – Save up a bunch of annual leave or sit down with your boss for a tough chat.

Convincing your boss to let you go remote

It’s important to tread lightly when talking to your boss about the possibility of working remotely. Going in with demands and ultimatums won’t achieve much. The best way to get the result you want is to go into it with a solid business case. If you can demonstrate to your employer that you’ve done all of the necessary research and have considered all of the ramifications, you’ll show your commitment to the business and instill confidence. Here are some points to consider before sending your boss that meeting invite:

  1. What is your company’s policy on remote work? If they have one, make sure you have read it thoroughly.
  2. What are the benefits of remote work for both you and the company? Make a list of both. Remember, businesses don’t like losing staff. Re-hiring is time-consuming and expensive. Use this to your advantage.
  3. How will you stay connected? – one of management’s biggest concerns will be communication, and how you will stay connected with your team. Elevate these concerns with a comprehensive list of the whens, wheres, and hows.
  4. Think about time zones and office hours – When will you be working and when will that cross over with your team members? Don’t leave this open-ended.
  5. Think about the potential downsides and limitations of working on the road. How will you mitigate these risks?

Juggling work and travel

Securing a remote job or convincing your current boss to give it a shot, is one thing. Managing your time and competing priorities while traveling, is another thing altogether. With all of the distractions of travel, finding the motivation to stay on task can be challenging. But if you’re serious about it, there are things you can do to ensure you don’t let your boss and the team down. Here are just a few:

Be Prepared

A little preparation goes a long way when balancing work and travel. Servicing your laptop before you go, stocking up on charging cables, and arranging international SIM cards, are all non-negotiables. Plan out your itinerary so you know where you’ll be working from on any given day and when you’ll be offline due to flights, so you can keep your team in the loop.

Be realistic

Don’t over-promise and under-deliver. Set realistic expectations with your team and manage your schedule accordingly. You need to enjoy the travel aspect too, so make sure to allow yourself time to explore.

Find a rhythm

If possible, find a routine that can be replicated from one location to the next. This will help you stay focused and eliminate some of the chaos.

Stay consistent

Make sure everyone knows what your working hours are when you’ll check emails etc. then stick to it. Your team will adapt to your schedule if it remains consistent.

Stay connected

Don’t forget about the people who still work in an office every day. Regular, scheduled check-ins, and collaboration via Skype or other video call services will keep everyone on the same page.


Visiting new places and experiencing new cultures can be an amazing growth opportunity. It can help people find meaning and promote diversity and understanding. The normalisation of remote work is a great opportunity for people to explore the world without sacrificing their jobs. Getting it right takes some careful planning and consideration, but the rewards can’t be overstated. Bon Voyage!

Featured photo by Andrea Piacquadio, courtesy of Pexels.
Joseph Russell

I am an award-winning app designer, design writer and founder of DesignJobs.com.au

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