Fancy working while travelling around the world as a digital nomad? While the idea of taking off to see the world seems to be very tempting, you may feel trapped by the insoluble dilemma over how to get away easily and at the same time keep your job. Truth is, you may not have to make that decision because you don’t necessarily have to quit your job to be a digital nomad. Here are some tips:

Make use of what you have

Even if you are required to work 9-5 every day and are not able to take a long break throughout the year, it is still possible to have a short one. It’s time to break the common mindset that remote work is equivalent to being away from home all the time.

Research suggested that the average trip length for approximately 50% of the digital nomad is less than 15 days. That is to say, you don’t need to be away for a long time to be a digital nomad, short-term travel works as well.

Indeed, there are plenty of potential resources to make use of. Check your company’s policy and you may surprisingly find out how close you are to being a digital nomad.

Holiday extension + unpaid vacation 

Find a freelance job when you are free and travel during holidays. A recent survey suggested that more than half of Americans did not take their eligible vacation last year. What a pity! If you are among those who haven’t taken full advantages of vacations, try to break the habit and start by marking your calendar and getting ready as early as you can. Although the duration of the holiday is short, you can still make the most of it providing everything is well-planned.

Besides, you may try to apply for a holiday extension or negotiate for several days of unpaid vacation with the company. Even if you add on just two or three days, together with a long weekend, it can last for a whole week and that is perfectly enough for a short trip.

Sabbatical scheme or company retreat

If there’s a sabbatical scheme in your company, that’s perfect! Instead of merely going on holiday, use this as a chance to have a sneak peek of the digital nomad life.

If, unfortunately, there’s no sabbatical, take note of the time when there’s a company retreat or any chance to ask for a short break. Although you may always have to follow a certain routine, don’t feel constrained. Chances are always there and you need to make an effort to find them.

Take a career break

If you prefer to travel for a long time to experience the digital nomad life to the max, the best way to keep your job is by asking for a career break.

I know, it can get tricky when it comes to negotiation. However, apparently, there’s nothing to lose by trying to negotiate. Following the trend of maintaining employees’ work-life balances, more companies are willing to accept an employee’s request for a career break and for a flexible schedule. With that being said, what should you do to successfully convince your boss?

Timing is very...very important

Ask yourself honestly, am I eligible for a career break? What have I done for the company? You know it may be impossible to get a career break if you just start working, so take time to think about it before you make the move.

As I said, timing is extremely important. Apart from your own eligibility, does your company has enough staff to cover for you? Is there a lot going on right now? If the answers are yes, maybe wait to ask. Choose an appropriate time when it’s not so busy and your boss will be more accepting of your proposal.

Be well prepared!

Bear in mind that you are planning to leave the company for a while, you should be aware that this is not solely about you. Any change to a contract of employment needs to be taken care of by the company with much consideration. Hence, the company needs to know why you want to leave and why they should keep a position open for you. You ought to give them enough reasons to look at it.

Before the actual negotiation, it’s a good idea to send a proposal and ask for a proper meeting. Give them a detailed presentation that is sincere and serious to show them the importance of this career break to you and more importantly, how it will benefit the company when you return. Prove that you are taking this seriously and they will consider it carefully too.

Ask for remote work


If things don’t end up as how you expect and you cannot take time off work, maybe you should just try to ask for remote work.

This may be the best way if you happen to do work that does not necessarily require physical attendance, such as accounting, graphic design, programming, etc...Technology has advanced so much that it has created possibilities for various jobs to go location-independent. Moreover, there are tons of advantages for both the company and you if you work remotely. But as I said in the last tip, be prepared and talk about it seriously with your boss. Don’t forget to suggest a trial period if your boss seems to hesitate as it can moderate your request and give you both a chance to evaluate the effectiveness.

Still not working...

If these tips have not seemed feasible, perhaps you need to figure out the reason. Are you in a position that is nearly impossible to be absent? Is there a lack of proper vocation scheme in your company?

If you have tried everything and it still doesn’t work, don’t give up, you can always try again. Or, consider changing to a position with a more flexible schedule.

Another way to deal with this is by starting to do other small projects alongside your work, for example, freelancing in your field. Develop this “side hustle” gradually as it can help you get familiar with working remotely and may provide you with an alternative when you decide to pursue the digital nomad life but can’t keep the job in the future.

Last, but not least...

Being a digital nomad can be eye-opening and life-changing, yet it is not just about adventures and having fun. A successful digital nomad needs to be independent and to be able to face difficulties and ambiguities. Hence, being a digital nomad is never easy and keeping your job may be that first big challenge along the way.

I genuinely hope that my tips can enlighten you and help you manage to embark on this amazing journey! Good luck!