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Written by Ronald Poon

It sounds like the dream right? To be able to travel around Europe whilst working. To use up no annual leave, take lots of pretty Instagram photos and go surfing before your first meeting of the day (at 5PM Lisbon Time) 😎.

I thought so too! Until I broke down right outside the Royal Palace of Seville (in front of a bunch of tourists and my sister).

I wasn’t crying because of a lack of Tapas and Tarta de Quesa (Cheesecake) that day. I was crying because I felt like I could no longer give my all to both my job and the people I care about most.

I wish someone had warned me about the emotional elements of working while travelling — the sacrifices that are involved, the impossible expectations, and that dreaded feeling when you know that you’ve let somebody who matters to you down.

There’s so much more prep involved besides finding good wifi and the best Pastel de Nata spots! In this Innovation Insights article, I’ll go through 5 THINGS that I wish I knew before my first work and travel experience in Europe:

Part 1: The Practical Time Elements

1. Don’t assume that people know all your travel plans

One of the first rookie mistakes you can make is assuming that people know all your travel plans (just because you chucked all your flight information onto Google Calendar).

Mentioning what day you’re flying out during a more casual sync-up isn’t enough. You’ve got to communicate these things directly with your team.

It can feel sort of weird and uncomfortable to post on your group Slack channel that you’re taking the day off because you’re holidaying in Paris or Portugal. But it’s really important for your team to know these things! (so that they can plan their workflow accordingly).

Push past the discomfort and the awkwardness. Make things clear, very early on (not just to your team, but also to clients and account reps that you interact with frequently). They don’t have to know that you’re currently riding on the back of a scooter (or trying to chase down an overnight bus)… BUT they do need to know whether they’ll be able to get in contact with you for essential items and work tasks.

2. Communicate your work needs clearly with the people you’re travelling with

The flip side of this is to communicate your work needs with your fellow travel companions. Your best friend isn’t going to know that you have to attend a meeting at 6PM, unless you tell him that. Your sister isn’t going to know about all the important prep work you have to do, unless you gently inform her. We have to let the people that we’re travelling with know, well in advance, what our current work-related needs are.

The days when I felt more stressed or upset were the days when I wasn’t strict about these boundaries. I let others dictate my working schedule, because I wasn’t clear or firm about the space and time I needed.

Of course the people who love and care about you the most are going to want to spend as much time as possible with you. They’ll take every opportunity they can to show you around, or explore a new city with you.

With this in mind, it is crucial for us to list out our most important tasks for the day using a journal like this Productivity Planner. Once you’re clear about what you need to accomplish that day, you’ll be less tempted to squeeze in another activity and will feel more comfortable and confident saying no to the people you love.

3. Have the courage to ask for time off

Sometimes two days just isn’t enough to truly explore and enjoy a place! We need more time. And the only way we’ll ever be able to get more time is if we’re brave enough to ask for it.

I hesitated about whether I wanted to ask for a Friday off (around halfway through my trip). Usually, Fridays aren’t as client work intensive, so it WOULD HAVE been possible to fit in a full day of fun travel activities.

But I wanted that peace of mind that can only come from taking a FULL DAY off. Even if you have no client meetings, you’re still kind of expected to respond to emails and start preparing things for next week.

Once you switch off your phone and your mind from work, you can truly begin to take in and enjoy your surroundings. You’ll be able to engage deeply in conversations, ask more creative questions and generally feel more relaxed while roaming around a brand new city.

Part 2: The Emotional Side

4. Let go of the impossible expectations you have for yourself

You’ll never be able to do it all and that’s ok. Life is all about making meaningful sacrifices and decisions. Sometimes work will be your top priority. Other times exploring and having fun will be your main priority. If everything was equally important all the time, we would never end up doing anything meaningful with our lives!

Sometimes I feel like I self-sabotage myself emotionally by being too greedy with the things I want to do and accomplish. I want to learn Spanish in two weeks, I want to go surfing with my sister and I also want to work on exciting new business projects! When you’re travelling for just a few weeks there’s NO WAY you’ll be able to see it all, whilst still killing it at work. Something has gotta give — whether it’s your sleep, your work output, a really cool travel list spot (or perhaps your mental sanity… 😅)

It’s ok to feel overwhelmed! You’re definitely not alone in this! 💙 When you feel overwhelmed by all these impossible expectations, it’s important to just breathe and remind yourself that you’re doing the best that you possibly can. I did a bunch of breathing exercises with my sister, when I experienced my first remote-travel related breakdown.

Let yourself cry. Let it all come out. Sometimes the burden we place on ourselves is just too heavy for us to hold. When we learn to let go of these pressures and expectations, we create space for ourselves to experience more positive feelings such as: joy, wonder and excitement. Which leads me onto my 5th and final point…

5. Be excited by this unique and challenging opportunity

How often do you get to take meetings in a completely different country/continent? I literally got to host my weekly Wednesday committee meetings in a brand new city every week. One week it was Lisbon, the next week it was Madrid and the final week it was Cascais.

It’s kind of exciting to test your “time optimization” skills to their very limits. To see how many fun activities you can fit in a day, while still prioritizing the most important tasks and client deliverables. Tough moments improve what you can ultimately handle when you go back to your “normal life”. It’s like altitude training, but for your emotions/mind!

Looking back on all of this now, a month later — I recognize what a huge privilege it was to be able to go out with my best friend for dinner after finishing work. How lucky I was to be able to have brunch with my sister and girlfriend, before grinding out some emails at the Airbnb. How insanely spoilt I was to be riding on the back of a scooter through leafy pine forests (around Sintra) and stunning Atlantic Ocean Views (near Cascais) on a WEDNESDAY and THURSDAY!

I swear I don’t do a TENTH of the things that I did in those 3 weeks hopping around Portugal and Spain, during the entire time I’ve been living in Montréal (9 months). Travelling, whilst working isn’t meant to be easy. Adjusting to different time zones, fighting off jet lag and sleepless nights on overnight trains/buses isn’t meant to make your time preparing for client meetings any easier. It’s supposed to test you — to see if you can still nail it in an unfamiliar environment and get the work done (whether that be in a crowded cafe or sitting on a desk-less and chair-less Airbnb floor).

Summary

If I were to do it all again… I probably wouldn’t change too much in terms of work output or fun travel activities (my situation). The main shift or adjustment would most definitely be to my perspective and mindset. I would remain just as ambitious and excited but would make sure to truly lower and adjust my expectations. I would be just as bold (if not bolder) with my actions, but make sure that I carved out the mental space, time and freedom to actually go out and ENJOY it.

That subtle, fine and minute difference between ambition and expectation is a lot easier said than done. But through time and experience (and many more iterations of this fun/challenging situation), perhaps one day we might get this combination right — so that we can explore and discover more 🧭 — all whilst learning how to truly smile and laugh along the way ✨☺️