7 **BEST* Tips for Traveling While Working Remotely || LGBT Travel Blogger

October 27, 2021

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Hey, friends! Today on the blog, I’m sharing my 7 best tips for traveling while working remotely. If you’re googling, “How to travel while working remotely?” then this guide is for you!

I started working remotely in 2011 (wow, ten years ago lol!), and I have traveled a ton while being a freelancer, part-time employee and as a (now) full-time business owner since 2016.

[Special thanks to Rah Foard for the photos of me in this post!\]

Traveling While Working Remotely

I started traveling and working remotely before the (not great) “digital nomad” term came about, so there weren’t a ton of resources out there.

Aaaand, to be honest, we’re still missing super actionable tips on exactly how one can be working full-time (either as a freelancer, employee or business owner) and travel.

“Have the flexibility to travel whenever you want!” sounds great!

……

But, uh, how do we actually DO THAT?

Like, how does one do the whole “traveling while working remotely”? What does one’s daily schedule LOOK LIKE? Below, I’ve shared my 7 tips, including an example schedule *I* use!

Note: This guide on traveling while working remotely is not about business travel – where you’re traveling, and the whole goal/point of the trip is to do work. Rather, it’s for folks out there who (like me) want to have our cake and eat it, too! This blog post guide is for folks who love to travel – and are trying to figure out how to travel on our while also working remotely on our respective laptops!.

Tip #1 for Traveling While Working Remotely: Have a Separate Place for Work

If you plan on traveling while working remotely, you need to be SURE to have a *dedicated* space for your work to take place.

And, no, a corner of a shared hotel room does NOT count.

Some ideas:

An AirBnB with an extra bedroom that will be used to take work calls & work only
Business center in a hotel (many hotels have a separate space with computers or a few small conference rooms that can be used by guests)
Co-working space in area you’re headed to
Getting a hotel suite with separate rooms that have doors (one big space isn’t going to work!)

This is very important. Even if you are traveling while working remotely with besties who GET IT, they may want to watch a movie when you need to be on a call. I recommend having a separate space (or your own hotel room) to work in.

Key Takeaway: Sharing a hotel room + expecting work to get done in that same hotel room is a recipe for disaster.

Tip #2 for Traveling While Working Remotely: Separate the Day with a Schedule

When working while traveling remotely, you’re going to need to learn how to turn “Vacation Mode” on and off.

I do this by working in the morning, and then spending the afternoon and evening playing and exploring.

Sometimes, I’ll work for an hour before bed.

Here’s what my schedule looks like for traveling while working remotely:

8AM – 9AM: Up and dressed with breakfast
9AM – 12Noon: Work
12Noon – 1PM: Lunch
1PM – 4PM: Explore & fun
4PM – 6PM: Nap and dinner
6PM – 9PM: Evening activity (sometimes includes dinner)
9PM – 10PM: Emails and work

You’ll notice that I don’t plan on working more than 4 hours a day while traveling. I find that traveling while working remotely means that I get *MORE* done in *LESS* time.

Parkinson’s law is the adage that “work expands so as to fill the time available for its completion.”

When I’m working, I’m super focused, following Parkinson’s Law. I get my work done more quickly, because I’m not derping around. I am super efficient, because I want to get out and play.

And, if I get my work done super fast – I shut down earlier for the day. I don’t penalize myself for working smarter/faster. Put another way, I write a list of what I want to get done in those 3 hours. If I get those items done more quickly, then I shut down my laptop and head out for an adventure!

Key Takeaway: Clearly separate work and fun, using lunch to do so!

Tip #3 for Traveling While Working Remotely: Make Sure Your “Travel Crew” Gets It

While working remotely, I have traveled a lot with friends and besties – and folks I’m dating!

One of the big issues that can pop up is your travel crew not understanding what it means for you to be working while traveling. Put another way, if your travel crew expects everyone to be on full-vacation mode with nary a laptop in sight, and *you* plan on overhauling the automations in your email marketing campaigns – the travel crew is NOT going to be pleased.

Make sure to be super clear when communicating your work + travel plans to your Travel Crew!

For this reason, I recommend completing the following checklist:

Set expectations for the trip, and ask your travel crew, “To be clear, I plan on working on this trip, which means I will be working X hours a day or by the pool. Is that going to throw off the vibes of the trip for you?”
Communicate *explicitly* how much you will be working each day, ie, “I plan on working during the mornings from 9AM – 12noon, and then spending the rest of the day exploring.”

Real talk, if you’re traveling with folks who also don’t plan on working during the trip…. It’s probably not going to be a great trip. They’re going to want to have fun, and it can cause friction and issues if you need to get work done.

Key Takeaway: i only travel while working remotely if my travel crew are working remotely, too.

Tip #4 for Traveling While Working Remotely: Stack Client or Work Calls the Week Before* Travel*

When traveling while working remotely, I find that it is SUPER HELPFUL to stack calls (ie “cram calls”) the week before traveling.

As a consultant and career coach, I do my darnedest to do ALL of my calls for 2 weeks in 1 week. I pretend that there are NO call slots open for the week or two I’ll be traveling, and I work longer days before traveling to get calls out of the way.

That way, I’m not juggling with iffy wifi or in a space that’s not conducive to calls. (I realize this not be doable for some folks, but that’s ok! I’m writing this post to share my experience.)

Note: Never trust the WiFi will work!

I still might have a couple of calls while I’m traveling and working remotely – but stacking calls is much more effective.

Key Takeaway: Try to do all of your calls or zoom meetings the week before traveling.

Tip #5 for Traveling While Working Remotely: I don’t tell people I’m traveling

As a travel blogger, this can be complicated, lol. Many of my clients follow. me on Twitter or Instagram , so they know I’m traveling.

Because I travel 1 week out of every month, I don’t tell clients I’m traveling – because I don’t want them to think I’m unreliable.

For a lot of people with good boundaries, they won’t want to bother you while you’re traveling – which can be an issue! That’s lost business.

If you do have to tell folks (ie you’re a salaried and remote employee), you can use a script like, “For the month of April, I will be working remotely from Costa Rica and Nicaragua.”

For the month of April, I will be working remotely from Costa Rica and Nicaragua

^^^Notice, the word “traveling” isn’t in there. If I want to communicate that I will be traveling and NOT working, I use the word “vacation.”

Key Takeaway: Be careful in how you communicate your travel plans – and with who!

Tip #6 for Traveling While Working Remotely: Focus on Longterm Work

When traveling while working remotely, i recommend using the trip or time to focus on a longterm project that keeps getting interrupted at home.

For example, you might focus on business or work tasks like:

Quarterly or yearly reports
Content calendars or campaign planning
Budget proposals
Writing a lot of copy, for an ebook, email series or blog posts

I like to do a lot of work that is “thinking intensive” while traveling. Working in a new setting helps me see things from a different perspective. It’s like a reset button for my brain.

Use the new space to “reset” your brain!

Now, you may find the opposite to be true for you! Maybe you’re wayyyy more efficient at tackling other tasks when traveling while working remotely. Don’t be afraid to experiment!

Key Takeaway: Be strategic about the kind of work you do while traveling. Test out different types of work, and see what works for you.

Tip #7 for Traveling While Working Remotely: Get Your Tech Right

When traveling while working remotely, it is SUPER HELPFUL to have your technology and gadgets organized.

I’m a self-described “ADHD Squirrel,” so organization is not my jam.

That said, I have found that doing the things below to be super helfpul:

Pack ** 4 ** iPhone Chargers: 1 for next to the hotel bed, one for my backpack or purse, 1 for my checked bag and 1 for a car (if I’m not renting a car, then this just floats around!) I buy 6 at a time for $9.99, link here!
2 Phone Charging Banks: This might sound excessive, but I recommend packing 2-5 phone charging banks before your trip. Ideally so you can use 1 per day (ish). I find that I do not remember to charge these bad boys, so it’s helpful to pack multiples.
Car Charger: I throw one of these in my purse, even if I’m not planning on renting a car. These can be used in a lyft in a pinch!
Laptop Purse: I love love this $40 laptop purse I got from Amazon. It has made traveling while working much easier.
Laptop Backpack: I also love the Knack Bags line of laptop and travel backpacks. These are super handy for folks who pack light or don’t want to check a bag.

Basically, the idea here is that I pack EXTRAS on PURPOSE (including 2 hairbrushes, lol) so that I don’t waste valuable time digging through a bag. I just purchased a packing cube set, so stay tuned on whether or not those actually help me be more organized while traveling and working remotely!

Key Takeaway: Bring more tech than you would when going on vacation.

Bonus Tip #8 for Traveling While Working Remotely: Meet with Clients & Potential Clients

Ok, so this might not be as applicable to people who are full-time and salaried remote employees.

Buuuut for my self-employed folks and business owners, I think that it’s always a good idea to figure out how to turn a trip into a write-off. Or a partial one!

The laws vary on this, and I’m not an accountant or CPA. I read about these strategies in this book, and then I asked my accountant about how to strategize best here!

For instance, I prioritize where my clients live when choosing a new place to visit. I love exploring new cities (and countries!), and going where my clients are located can help me choose where to go.

Key Takeaway: Consider strategizing on trips and travel to maximize tax write-offs.

Traveling While Working Remotely – Wrap Up

Alrighty, those are my tips on traveling while working remotely. I hope that this guide has helped you figure out how to explore new places and airports while also making money!

If you have tips that you think I should add to this post, feel free to reach out to me via Twitter or Instagram DM (or email, if you prefer!). I love connecting with other folks who love traveling.