Working while traveling? My tips to find balance and flow
What I’ve learned so far in my search for a successful work/travel balance
With most knowledge work making the full transition to being remote-capable in the past year, it feels like traveling while working is more doable than ever. Nothing is stopping us from getting our work done on the go, in another time zone or from a remote beach, as long as it has a strong wifi connection. A work/travel hybrid model is appealing to many who have spent most of their workdays tethered to a fixed office. Doable and appealing — yes — but not without proper thinking and planning.
Let me sketch a picture for you:
New city, new country; you wake in a new bed in an unfamiliar bedroom. At that point, you’re not exactly sure where you’re going to work that day: is it going to be in a coffee shop or the dining room table of your in-law’s living room with kids running around? Nothing sounds appealing and you truly aren’t sure about all the unexpected demands that are going to emerge. It’s overwhelming.
Another day, you’re moving around between meetings. You have one meeting on the Upper East Side, then you have another meeting down in Chelsea. There are three hours in between. This isn’t your hometown, and you’ve got to get stuff done. There are a bunch of emails to get out. And at the back of your mind there’s all this strategic work you need to do that requires deep thought to be delivered. You don’t manage to get anything done; you just about tread water.
It’s tough.
This can be okay for a day or two, but what happens if you’re moving around for a few weeks?
This was my reality the past few weeks. I was on a trip with my partner, and even though the expectation was that it was a working trip and not a true vacation, the constant underlying feeling of anxiety and disappointment that I was behind on my work and letting people down tinged the enjoyment of the time I did have when I wasn’t working, whether on a hike or out for dinner with family.
The trip was three weeks and only in the last week of it did I manage to find a way to make something work.
Since COVID started, more and more people are looking at extended trips to work from the far flung corners of the world or just to migrate from the city to rural living.
Having been a nomadic worker for the last decade, I wanted to reflect on this most recent trip and share some of my practice, failures and new learnings to help you make the most of your nomad life.
Manage Expectations
The hardest part of this trip was being misaligned on expectations with everyone around me. My partner, her family, my co-founder Sruli, the rest of the team and my friends. This caused me the most unrest and day to day challenges.
When you are in your normal structure and flow, implicit expectations are normally sufficient for everyone involved in your life, your family, coworkers and importantly yourself. It’s understood what hours everyone is working, when dinner will be, and your general availability.
When this shifts, it becomes your responsibility to realign all of these — if you skip this first step, it just comes back to bite you the whole trip.
Don’t underestimate the power of a quick conversation to align on what amount of time you’ll be working each day, your general schedule, what amount of flexibility you’ll have, and how people can best reach you.
Create Structure
Having some sense of structure is key: some anchors in my day that keep me stable and grounded while I’m working.
For me on this trip, I made sure that there were three hours of the morning that were unmovable and I’d use to have a daily stand up and check in with my colleagues.
Organize your day so you consolidate meetings and create space for deep work. Do this in your scheduling. Don’t be scattered. Don’t plan stuff all over the city when you’re moving around. Prioritize really creating a good hierarchy and structure for your day. For example, if your trip is a sales trip, then you have to build in proper time to do leads prep.
While part of the joy of working while traveling is being in a new place, I find creating clear boundaries allows me to enjoy it best. Work hours are work hours, allowing me to better enjoy my leisure time when I have it.
Plan Ahead
Plan the night before for anything happening the next day. Where are you going to work from? What’s that space going to look like?
Depending on where you’re working from, try to have a fixed, portable setup. I have a laptop stand, a keyboard, a mouse and a webcam — all of those pieces come together to make me really feel like I’m in Joshua’s workspace. It helps me arrive in work mode to have that ritual of setting things up and starting to work. Through that, I’m already a big step into the headspace I need to be to achieve work.
Make achievable goals
During this trip, I found I needed to feel like I’d achieved something every day. If I felt like I was just treading water and not being successful, that day could throw off the rest of the week.
As long as I know that even if I’m only working for a few hours one day, I’ll have done some meaningful work or made progress on something important to me, that can change the rest of my day.
Because just as much as being effective and productive while you’re traveling is the goal, you also want to feel that you’re enjoying yourself in your downtime. If you’re a digital nomad or you’re balancing work with any other priorities in your life, you want to be able to switch off from work too. The switching off is what’s really important to make sure that you when you’re switched on, you’re really on.
Be realistic
Working while traveling is not the same as working at home or in your day to day office space. You’re kidding yourself if you think it’ll be exactly the same. Whether it’s the time zone shift, getting distracted, having other priorities, or a bad night’s sleep in an unfamiliar bed, there’s always something that will throw you off a little.
That’s normal, and it’s ok! Just make sure you’re going into the trip being realistic with what you need and want to accomplish during that time.
Don’t try to keep every reoccurring meeting on the schedule. Have an idea of what you need to get done during that time frame, and what can wait until you’re back to normal.
Take time to rest
When we get back from a trip, there’s always the temptation to jump back into things, just kicking off another tiring cycle.
I feel best when I create time and space to get a proper night’s sleep, do my laundry and grocery shopping, and do whatever else I need to in order to make sure my days at home are back in the right routine and rhythm. Travel back on a Saturday instead of a Sunday, or take a half day off.
A slower pace can lead to a healthier mindset that is overall more effective for getting back in my normal work day.
All of the above applies not only once you’re on the trip, but more importantly, before the trip begins. Don’t cut out these important steps — they’ll help make sure any work/travel trip feels invigorating rather than exhausting.
Josh is the co-founder and CEO of Groove, the first online coworking platform that helps you feel more supported and focused so you can work with purpose. We’re on a mission to help creative workers around the world accomplish remarkable things.
Groove is in beta, but if you’d like to join the expanding trial and try a new way to work socially while working alone, send us a message to join our pilot.
