Travel While Working: How We Travel the World While Working Online [Tips + Tools]

In the past year, Robert and I have been working online and our careers have become entirely remote. As this was happening, I noticed that a lot of people were curious about how it was possible to travel while working online, especially if you don’t already have prior experience (we definitely didn’t!).

Before travel blogging, traveling the world and becoming “digital nomads,” we did completely different things: Robert worked as a bank analyst with a degree in Psychology and I worked as an executive assistant for a construction company with a degree in Human Resources. So, believe me, we had to start from scratch.

After two years of travel, one year of working online (half-a-year for me), and a ton of questions along the way, I decided it was time to share what we’ve learned and what our experience has been finding online work. If you want to travel the world while working from your computer – or would simply like to have more flexibility and work from home – this is for you!


Another note: This won’t be a long list of different types of jobs available for digital nomads. There are tons of lists out there already and they often gloss over the practical side of finding online work that we ended up discovering on our own. So instead, I’ll be discussing the sites and resources we personally used to find work.

Travel While Working – Definitions Before We Start


Freelancers normally operate their own businesses. Sometimes the term freelancer and independent contractors are used interchangeably, but there are differences. A freelancer is a self-employed person who pays their own self-employment taxes, works remotely, sets their own prices, isn’t in charge of anyone (technically speaking), and could ultimately work for as many clients as he or she wishes.

Independent contractor

Independent contractors are really similar to freelancers but typically work with one client on a long-term basis. They can also work through a third-party or an agency, and they may (or may not) be responsible for their taxes depending on whether they work for themselves or for an agency. (E.g., Robert is an independent contractor, works for only one client on a long-term basis, and pays his own taxes throughout the year.)

Virtual Assistant

If you took these two words literally (“an assistant… that’s virtual), you’d have a pretty solid definition. A virtual assistant, otherwise known as a “VA,” is a self-employed individual that provides professional administrative, technical, or creative services to clients. A VA can work remotely or from home.

Note: It’s easy to confuse a Virtual Assistant with a “remote secretary.” Like I mentioned above, virtual assistants provide different kinds of professional services and essentially help a client with a particular task or role for their business. Virtual assistants typically have a few clients at a time.


An employee is what we’re all familiar with – a “9-5” worker that often receives several company benefits (which vary depending on the country and company). Remote employees are also a thing; you work from home and receive the benefits the company provides you, as well as having them handle taxes automatically every paycheck.

Now that we’ve gotten that out of the way, let’s talk about the resources that can help you find the gigs that will allow you to travel while working.

Facebook Resources

While it may seem weird, most of our gigs and opportunities came in through Facebook (specifically groups). Whether because the grand majority of people aren’t looking there yet, or because there’s an immediate personal aspect to it, Facebook has been instrumental for us.


Guavabean is a Facebook page and group created by freelancers to help other freelancers (experienced or not) find remote jobs. (It’s also a portal for those who want to hire freelancers, too, if you’re on that side of the coin.) Join the group and subscribe for their weekly Friday newsletter chock full of great online jobs and opportunities.

Virtual Assistant Internship

Virtual Assistant Internship was created by Esther, an entrepreneur/virtual assistant who brought together an incredible community of women freelancers. Esther offers a paid course that I considered taking (but ultimately didn’t end up needing) – still, I would suggest you first visit her Facebook page, check out the free Masterclass she offers, and then subscribe to her weekly newsletter that alerts you of new remote job opportunities. In other words, explore and utilize the free options first before going the paid route!

Virtual Assistant Savvies

Virtual Assistant Savvies comes recommended from a friend and is the latest community I’ve joined. Abbey, a virtual assistant and entrepreneur herself, is the founder of this community. Expect to also find a strong base of freelancer/entrepreneur support here, along with up-and-coming job opportunities for VAs.  

Virtual Assistant Jobs

Virtual Assistant Jobs is a bit different because it doesn’t have a “face” or brand backing it… but it’s also where I got my first client. This is a community of almost 30,000 people offering and seeking virtual assistant jobs. And, as explained above, VAs come in all kinds of professional capacities, so don't discard these options if you’re a professional within a certain technical field!

Virtual Assistant Tribe Job Board

The Virtual Assistant Tribe Job Board is a community that’s similar to the above-mentioned Virtual Assistant Jobs but is about half the size. You may see less activity here, but also have a greater chance of scoring a gig if you see one that suits you.

Find Work Online Using These Webpages

If you’re looking for a higher percentage chance of finding a full-time/stable job so that you can travel while working, these next sites might be a better fit. These are most of the websites Robert would keep open on a daily basis to look for work while we were in Serbia, and it only took him 1-2 weeks to find a full-time job.

Note: He was able to leverage the prior 6 months of experience working part-time for a remote client just before this. He found a gig though someone we met while traveling that provided him with work similar to what you’d find in a Facebook group.

6 Websites for Finding Online Jobs

Open all of these, pin the tabs on your browser, and check them every day for jobs relevant to what you’d like to do on a full-time basis.







6 Tips for Finding Remote Jobs

  1. Redesign your resume and personalize it for the role you’re applying to, highlighting the qualities from previous jobs that would make you the perfect remote employee/contractor.

  2. When applying to certain gigs (especially ones on Facebook), I strongly recommend sending a short intro video (no longer than one minute!) introducing yourself to the potential client. Be authentic, brief, and explain why you’d be a perfect fit for the position!

  3. When applying to job opportunities in FB groups, try to attack the posts that don’t already have 30+ comments already (i.e., that aren’t filled with comments); go for the fresh ones and don’t wait to send whatever the job post is asking for – do it ASAP.

  4. Don’t lose hope – like any other kind of job search, it can take a bit of time, but consistency is key. Sit down as if you were working, but dedicate the hours to finding and applying for online jobs. It really won’t work if you’re applying to one or two opportunities every now and then.

  5. If you have some experience and work that you’ve already created, prepare a portfolio with some of your previous work even if it doesn’t directly relate to the role you have your eye on. If you don’t have material for a portfolio, contact your previous employers or clients and kindly ask them for referrals

  6. Once you get your first client, do your best work for him or her. As a “freelancer,” there’s a bit of pressure at the beginning to show them that they’ve made the right decision and that you’re the best candidate for the role. Surpass expectations and soon enough you’ll see yourself receiving referrals from that client. This is 100% how I’ve gotten the rest of my clients!

Tools for the Remote Freelancer That Wants to Travel While Working

Below are some practical tools that you’re likely to use if you decide to travel while working online. If you already know how to use some of these tools, it’ll make you seem more professional, make you more appealing, and save you time in the future of having to find a tool for a certain task:

Toggl or Clockify

Both of these are time-management programs for tracking the time you spend working. Most people I know use Toggl, but I personally like Clockify because I find it less buggy, especially after its most recent updates.


Asana is an application for managing projects – it’ll make your life much easier when working with a team online (even if it’s only 2 other people). The program looks and acts like a board that you’d find at a conventional office: you write tasks down on it and check them off as you (or the person you’ve assigned them to) complete them. To top it all off, there are due dates and organizational features that help tie it all together. Other project management programs that you could use are Monday or Trello, for example.


This is the go-to platform for team communication. Depending on the size of your team, you set up various chatrooms and channels for group chats and (hopefully) keep all work-related chat within the confines of the app.

Google Suite

You’re probably familiar with this suite of apps, but it literally pays to be well-versed with these applications (particularly Docs and Sheets). Use Google Sheets, Docs, and Slides to create and share your documents, or even modify them with other people in real-time. The easiest way to collaborate and put a document or organizational Sheet together is using Google Suite – so take some time to learn its nooks and crannies.


Dubsado is a CRM platform, i.e., customer relationship management program. This is useful for creating and sending invoices, contracts, and proposals, as well as creating workbooks, workflows, and keeping track of your work-related finances. It’s free for the first three clients that you input, so I 100% recommend that you use it from the beginning of your freelancing/contractor career to give your business a more professional appearance. If you need to add a 4th client, search Google for the latest promo code (I was able to save 30% off its usual price!).


This is another one you’re probably familiar with – andi if you are, you’ll know that it isn’t very complex. It’s a popular and often-used alternative to Google Drive/Suite and is mainly used to share documents.

Travel While Working – Something to Note

While I wouldn’t change this life (i.e., being my own boss) and the flexibility it gives me for anything, I feel it’s important to mention that often times, being an entrepreneur or self-employed carries more responsibilities than being an employee of a company. For example, you’re responsible for manually paying your own taxes (not just having them automatically removed) and you won’t automatically “get time off”. So, when you set your rates, you have to keep these “costs” in mind.

Then, you have to remember that as a “freelancer” or “virtual assistant,” there might be weeks full of work and others with little-to-no work – you’ll notice most when certain anemic invoices come in. Like I said, I wouldn’t change my position, but this journey has its pros and cons and it’s not all funny stories and sunset-filled IG photos.

We really hope these tools help you on your journey to becoming a freelancer, entrepreneur, online contractor, or digital nomad!