How to Work Remotely While Traveling

I’ve worked on the road for years. This isn’t my first rodeo, and it’s why I chose to set out to start my own company. The freedom of working wherever, whenever. I’ve lived in Berlin, worked remotely from anywhere I travel, and called Beirut home for a while, a place where rolling blackouts were part of daily life, and still one of my favorite cities in the world.

The point? Working remotely sounds glamorous, but it’s built on experience, flexibility, and a high tolerance for WiFi roulette. It makes you learn how to adapt, and stay focused. It’s very easy to get distracted or want to spend your days enjoying the destination. It’s about balance and a strong work ethic.

The Freedom is Real But So Are the Trade-Offs

I’m about to head out for a month of travel, and I’ll be working the entire time. There’s no such thing as an out of office when you are the boss, and it’s your company. Client needs and deliverables still have deadlines.

The reality is that when you run your own business, whether it’s a small agency, consulting practice, or freelance gig, the freedom to travel comes with responsibility, planning, and sacrifice.

Things to Anticipate and Plan For:

Time Zones Can Be Brutal
Late nights or early mornings might be required to stay aligned with your clients or team back home. Build your schedule accordingly. Keep your computer on the time zone from home (don’t update it even if your computer asks you). Allow your phone to be the one that updates to the time zone where you are, so you can keep it straight when you’re navigating a few time zones. Remember about seasonal daylight savings, since not all countries do the same or change at all.

WiFi is Not a Guarantee
Vet your accommodations for reliable internet. Always have a backup hotspot or data plan. I’ve learned this the hard way, and had to pick up to move to another location on the fly if the cafe internet wasn’t reliable. I would have a hot spot to power my laptop typically and consider the amount of data I would need based on my work (if you work with video editing, larger files, etc. don’t skimp on data). Before you go abroad, check your options (read this AARP story) with your phone carrier, and see if you can arrange a longer term, monthly international phone plan. It can really add up with $10 a day plans for example.

If you’re flying, check which airports have Wifi and lounges you could have access to via your ticket, airline status, and Priority Pass with cards like Chase Sapphire Reserve benefits.

Identify Your Work Space(s)

Depending on where you’re going and for how long, you want to identify good ‘working spaces: a go-to cafe where you can always find a spot, wifi & electricity plug. Find a place to stay that has a desk, balcony or extra room if you need to seperate. Staying longer? Consider a co-working space, which is a great way to meet other people if there is good programming and perks. There are places that arrange all that for you like Noma Collective.

Boundaries Are Key
Just because you’re “away” doesn’t mean you’re unavailable, but it also doesn’t mean you’re on call 24/7. Set clear expectations with clients and colleagues. Make sure to turn off things like Calendly or make sure your time zone is updated to when you’re available. If your client(s) follows you on social media, make sure to address that you have made arrangements or working certain hours.

It’s Not a Vacation. It’s Work with a Better View.
I love this lifestyle, but it’s still work. The deadlines, deliverables, and daily responsibilities don’t disappear. Manage your own expectations and any activities you arrange around ‘working hours’ that you set for yourself.

Entrepreneurship is Risky, But Worth It
The ups and downs of running your own business are real. But so is not having to ask a boss for PTO or permission to live life on your terms.

Working remotely isn’t always as dreamy as Instagram suggests, but for me, the risks and reality were worth it to create a business and a life that doesn’t fit inside the typical 9-to-5, even though in my line of work, I never worked really within 9-5.

Follow along on this next travel stint at @TripWhisperer.