Before You Decide To Take Your Job on the Road

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Whether you are interested in becoming a full-time nomad or just want some flexibility in your schedule to travel more frequently, technology has made it easier than ever to set up your office wherever you are. If the idea of working on the road sounds exciting, start now to take the steps needed to meet this goal.

The idea of sitting in a cafe or on the beach to work sounds enticing, but reality can be much different.

One of the reasons why travel can be so enjoyable is because you are leaving your real life behind. When you commit to working while travelling, real-life will creep into your experience. That isn’t to say you won’t enjoy your trips, but you must be realistic about how much free time you can spend exploring, how extensive your trips can be, and how important dependable, fast internet is to complete your work.

Think of what you do in an average day. If a good portion of your time is spent meeting with others, you need to consider time zones when making travel arrangements.

If your work is time-sensitive, you may not be able to completely unplug even if you don’t have any work pending.

Don’t let these things discourage you from taking your job on the road, but be sure you have clear expectations of what your job entails and how you can make it work long distance. Having an honest assessment of how capable you will be of completing your work while travelling will help you when it comes time to discuss the issue with your boss.

Arrange Your Finances Before You Leave

Even if you will be staying at your current job, you should be sure you have a rein on your finances before hitting the road. Unexpected expenses have a way of cropping up when travelling, and you don’t want to be stranded somewhere, unable to finance a solution. One way to lower your monthly expenses is to cut the costs of your education debt. By refinancing your student loans with a private lender, you can save money each month. This gives you more expendable income without the need to change your regular spending.

Speak with Your Current Employer

If you believe that your job is one that could easily be done remotely, talk with your boss. Different companies will have different guidelines, but most people who work in management would prefer to keep an existing employee rather than train a new one. Approaching your supervisor with this idea can be intimidating, but scheduling a time to talk and letting them know what you have in mind allows you both to size up the offer. They may not be able to give you a response immediately, but they should provide you with an idea of how likely it is you can remain there while working remotely.

Sharpen Your Skills

You may find that your company is not interested in giving you this freedom. If that is the case, you have to decide whether to move on or keep your job. If you are sure you want to travel, start sharpening skills that will help you land a new position. There are careers in nearly every field that you can manage remotely, from programming to marketing and more. When conducting your job search, make sure that the work-life balance sounds like it will work for you. Some jobs that are described as flexible and unlimited time off are truly that. Others describe the positions this way to ensure you are always available and the company doesn’t have to pay for accrued vacation time if you leave.

Develop a Timeline and Keep Track of Your Progress

If you are excited to start your remote journey, the idea of job searching or transitioning to a remote position can dampen your enthusiasm. If the idea seems overwhelming, start by laying out a plan. While you may not want to wait, there are plenty of things you can do to fill your time. Depending on where you plan to travel, you may need specific vaccinations. You should also spend some time getting comfortable troubleshooting basic issues with your computer. Even if your company is enthusiastic about allowing you to go remote, you won’t have IT support right down the hall. Also, take this time to streamline the paperwork of your life. Set up your bills on auto-pay. Visit the doctor and dentist. Find out what type of health coverage you will have when you travel. Narrow down your list of necessities to make travel easier.


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