Digital nomad, location independence, Remote work, Road trip

Top 5 Tips For Working Remotely While Traveling (on a road trip)

If you want to start working remotely while traveling but have no idea where to start, you’ve come to the right place!

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Whether you’re a burnt-out corporate worker, a college student dreading the cubicle life, or a remote worker itching to see the world, the work-and-travel lifestyle can become a reality for each and every one of you.

Here are my top 5 tips for working remotely while traveling on the road!

Tip #1: Solidify Your “Why”

Before you start working remotely while traveling, spend some time nailing down your “why” – AKA the reason you’re pursuing this lifestyle. There are a few reasons for this:

  1. People are going to doubt you. Hell, you might even doubt yourself. Having a clear “why” is critical to back up your decision to others and yourself.
  2. Working remotely while traveling is not easy. On days when your vehicle breaks down, your hotspot stops working, or you can’t find stable cell service, your “why” will keep you motivated.

Click here for tips on finding your “why.”

Tip #2: Get Comfortable In Your Job Before You Go

When you’re just getting into the remote work world, there are quite a few learning curves that you’ll encounter in the beginning.

If you’re new to the remote world, I highly recommend working in a stable environment for the first few months before hitting the road. This will allow you to work through the kinks and challenges before navigating the work and travel lifestyle.


Tip #3: Treat Every Week Like A Work Week

The biggest misconception about working remotely while traveling is that it’s all travel all the time.

But what you have to realize is working on the road is not a travel adventure that you weave work into when convenient; working on the road is a working lifestyle that you weave travel into when you can.

I often find myself working more on my road trips than I do at home because of the logistical work that goes into it. Before you can make any money, you have to find Internet, look for strong WiFi in various cities, make sure all your gear is charged, etc. This adds a few extra hours to your week, so make sure to keep that in mind. 

Tip #4: Plan Way Ahead

If you’re a chronic procrastinator, the work-and-travel lifestyle will force you to change those habits.

When you’re on the road, you’re going to encounter unexpected challenges such as broken technology, electricity going out, lack of cell service, etc. And without the proper planning, this could cause you to miss meetings and/or deadlines.

I highly recommend laying out your monthly calendar a week before the start of each month and write down every upcoming deadline, meeting, and event. From there, you have a clear idea of what’s coming and can plan each week accordingly. The farther ahead you do this, the more prepared you will be and the more free time you’re likely to have at the end of each week.

In the Work & Wander eBook, you will get access to sample schedules for different jobs that you can customize to your own. Check it out here!

Tip #5: Clear And Consistent Communication

Whether you’re already on the road or still planning your trip, make sure you are communicating everything with your coworkers, clients, and anyone else you work with.

Out of respect, I’d recommend communicating with your team before you make any drastic plans. You don’t necessarily need to ask permission (unless you do), but keeping them in the loop before, during, and after your travels will keep everyone happy.

Once you’re on the road, check in with them as often as possible and let them know in advance if you won’t have service on a particular day.


I hope you found these tips helpful and I can’t wait for you to start working remotely while traveling. Don’t forget to check out Work & Wander for the ultimate step-by-step guide (with exercises and resources) to start working on the road!

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