I’d be lying if I said the dream of working and travelling wasn’t a huge part of why I went self-employed almost 8 years ago.

One of the biggest catalysts? I asked my then-boss at a web design agency if I could work remotely for a month (this was pre-2020, remote work was not the norm). I even created a three-page proposal outlining exactly how it would work, how I’d stay on top of my responsibilities, and how to avoid potential issues.

I was so proud of it.

But let me tell you... HR were not having it. 🙃

They shut it down, fast. And honestly, that moment shifted something in me. I wanted more flexibility. I wanted the freedom to work from anywhere. I wanted to build something of my own. (and I guess the whispers about the company possibly going under helped a little too.)

So I quit.

Since then, I’ve worked and travelled across South Africa, Brazil, Portugal, London, Mexico, and more. I was chasing that romantic feeling, and yes, it had its moments. Like sipping coffee on a balcony in Barcelona, or watching the mist roll in over the mountains in Rio from a hidden Airbnb. I'd exhale and think, this is it.

But it wasn’t all dreamy balconies and ocean views.

There were also moments of frantically replying to a potential client three minutes before boarding a flight. Or whipping out my laptop to finish a homepage on the NYC subway. Or lying flat on the rooftop floor of an Airbnb in Mexico, scrambling to hit send before the Wi-Fi limit cut off. Or planning to make a website live at the airport - only to miss my flight because I forgot I needed a visa... seriously this happened… I know, I know - I’m rolling my eyes at past me too. LOL 😬

This is the truth about working and travelling: it’s not always glamorous. It’s not always organized. But with time, I’ve figured out how to make it work for me.

And honestly, having systems like my automated booking tool, email sequences, and preset onboarding flows through my website? Total game changer. It frees me up from the tedious stuff so I can actually live a little between client deadlines.

If you’re dreaming of taking your work on the road — or if you’ve tried it and felt like a chaotic mess - here are 6 things I’ve learned that I wish I’d known earlier:

1. SET YOUR PRIORITIES BEFORE YOU GO

Not every trip needs to be a full-on adventure or a full workweek. Decide: is this a longer stay where you’ll keep normal hours and just swap your home office for somewhere new? Or is it more of a working holiday — where work comes second to exploration (and maybe just helps cover the next Airbnb)?

Being honest about this upfront changes everything. You don’t want to spend 6 out of 7 days staring at your laptop in a beautiful place — but you also don’t want to overbook yourself with excursions if work still needs to happen.

2. PLAN YOUR SCHEDULE AND CLIENT COMMS IN ADVANCE

It’s so worth it to get ahead of your schedule — not just your flights. Let clients know if your hours are shifting, what to expect, and when you’ll be checking in. Clear boundaries = less stress.

Bonus: pre-schedule anything you can. I love using tools that let me prep social posts, emails, or client deliverables in advance. Future you will thank you.

3. LIMIT MEETINGS (OR TIME-ZONE THEM WISELY)

Meetings can be the biggest time suck — and timezone nightmare. If you can, replace live calls with voice notes, Looms, or async updates. If you do need meetings, set availability that works with your lifestyle.

When I worked from South Africa, I set meetings for Monday afternoons around 4pm. It gave me slow mornings to explore and kept my week from getting too fragmented.

4. BE REALLY HONEST ABOUT HOW MUCH YOU CAN DO

If you’re travelling for 7 days, you won’t see a city and finish a full project. If you’re somewhere for a month or two, it’s easier to settle into a rhythm.

The worst feeling is being in a place you’ve dreamed of visiting — and being glued to your laptop. So manage your workload and your expectations. It’s okay to say no to a client project or to an all-day hike. You don’t have to do it all at once.

5. CURATE YOUR SPACE - NOT JUST YOUR ITINERARY

This is something you can control… kind of. Make this romantic. An airbnb with a cute desk or table set up, strong Wi-Fi, a comfy chair and a quiet corner can make or break your work flow. Before you book, check actual photos of the workspace (not just the bed), and ask the host about internet speed.

Set yourself up for success by treating your “home base” like a mini office you actually want to work in. Or — if you’re craving café vibes — research local coffee shops and co-working spots ahead of time. That way, you can be part of the local scene and get stuff done without the Wi-Fi roulette.

6. FORGET INSTAGRAMMABLE. AIM FOR REALITY

The real gift of working while travelling isn’t the curated content — it’s the conversations with strangers, the chaos of navigating a new city, the perspective you gain from existing somewhere else. It’s the moments you feel a little out of control, a little stretched, and then — somehow — totally empowered.

This is how life is. Messy. Full. Unpredictable. And weirdly wonderful.

So no, I won’t pretend it’s always dreamy. But it is a damn privilege to even try this lifestyle — to exist in a time and place where this is possible, and to choose how I want to work, live, and move through the world.

…So no, I won’t pretend it’s always dreamy. But it is a damn privilege to even try this lifestyle — to exist in a time and place where this is possible, and to choose how I want to work, live, and move through the world.

And I’m sharing all this now because I’m in a different phase of life and work. The goal isn’t to travel and work anymore — at least not right now — but my gosh, I’m so glad I chose to do it when I did. These are the things I learned along the way, the moments that shaped me, and the tips I’d give anyone who’s thinking of doing the same.

I also can’t talk about this chapter without mentioning that a lot of it was done alongside my now-fiancé. We were both remote working and travelling — which was amazing and occasionally chaotic. (Ever tried finding a single Airbnb where one person needs total silence for meetings and the other one needs to screen-share with a client while frying an egg? Yeah.) Different time zones, different deadlines, different energy levels. But we figured it out. It taught us how to communicate, compromise, and create space for both work and love.

If you're someone who's ever dreamed of working while travelling - or you’ve done it and have your own stories - I’d love to hear them. Share them with me. What worked, what didn’t, what almost made you cry in a train station bathroom? Let’s talk.

As for me? This lifestyle isn’t what I’m called to do anymore. Buuut... who knows. Maybe I’ll take on the ultimate boss-level challenge next: working and travelling with a baby. (Pray for me and my future airport Wi-Fi.)

Teagan ♡