Though there are many ways to save money on the cost of travel, making money while traveling is what ultimately makes a nomadic lifestyle possible. If you’re a worldschool family or you want to become one, then finding remote work is essential. There are many 9 to 5 jobs that could easily be done remotely using the right tools and if you have one of these jobs, it will be up to you to figure out the logistics of how to do your work online before approaching your boss to pitch the idea. 

How to Work Remotely as a Worldschool family

No one knows your job like you do! If you want to convert an existing in-person job into a remote gig that will pay the bills while you’re traveling, you need to be a top performer at your workplace. If you’re an excellent employee with an impeccable reputation for your performance, your boss won’t want to lose you. Use this to your advantage when you pitch the idea of working online. 

Do Your Research

According to recent research, about 70% of professionals worldwide work online at least one day of every week. And all this remote work is done using software and online tools to streamline the process. Before you go talk to the boss about working remotely, you need to do research into the online resources that are available to make your job do-able via the Internet so you understand these tools. Don’t go into a meeting with the boss expecting for your boss to come up with a way to work with you online. Rather, get to know what’s available! Tools like HubStaff or Slack make it possible for online employees to seamlessly stay integrated with the rest of a team. But every job is different, so think about what kinds of online tools you’ll need to work remotely. Put together a portfolio of the tools you would use and be ready to demonstrate how easy they are to use. 

Focus on How Remote Work Can Benefit the Company

If you’re hoping to do remote work, you need to get used to the idea of managing your own time. And while you’re at it, start thinking as though you’re your own boss! This will help you sell the idea of remote work to your company’s leaders. Think about the company you work for and how they would benefit from not having you on-site. How does the company save money? For example, if you no longer require an office-space, the company could pay lower rent by having you work from home. And research has shown that remote workers are often more productive when working from home. 

When you make that first appointment to discuss remote work with your boss, you need to have a list of at least three (or more) ways the company would benefit from changing your in-person job into remote work. Steer clear of talk about how you would benefit from working from home or at the very least, talk only about how these benefits would ultimately translate into higher profits for the company. 

Start with a Trial Period

Approach the transition from in-person to online work as a period of experimentation and learning. Start by trying to work from home 1 day of the week. Work out the kinks in the process and then ask for 2 days per week working from home. It could take some time, research, and effort to find the right online software to make remote work possible, but be patient and work toward your goal in stages. This will give your boss time to get used to the idea of remote work and as that happens, you can continue to remind him/her of the various benefits to the company of having you work remotely full-time.

Explain Your Remote Work Plan

When go in to talk with your boss, have a plan in hand that includes a transitional period where you work from home for just 1 to 2 days per week. Explain your motivation for making this change (you wish to homeschool or worldschool your children—they’re only young once, after all), but don’t dwell on how remote work will benefit you. Rather, simply explain the reasoning behind why you want this change. 

When you create your remote work plan, make the process of transitioning as simple as possible for your boss. An simple and elegant action plan that would be hard to say “no” to is what you should have in hand when you go in for that first appointment to discuss remote work with your boss. 


Working remotely as a worldschool family is ideal because you can fund your journey as you go along rather than having to save money for many years to do time-limited travel. At the Devela Worldschool Community, we offer work opportunities in exchange for housing and a small food stipend. Contact Jennifer Shipp at for more information.

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