Life can become overwhelming at a fast growing startup, even at the best of times. Thus, it was no surprise to learn that after two years with Bench, our lead Product Designer Kyle Thacker needed to get away. Far, far away, in fact.
In April, Kyle embarked on a six week trip that would see him work remotely from Paris, Rome, Florence, Venice, and Milan.
The underlying motivations that inspire entrepreneurs to travel and work from afar are varied. And while the work-remote experience is beneficial to some, it doesn’t always end well for others.
Curious to learn how working remotely has influenced Kyle personally and professionally, we spoke with him at the halfway point of his trip.
What compelled you to embark on a six week workcation?
I lost myself for a while, creatively and personally. I let small moments consume and define my thoughts. My perspective narrowed. I decided to make some changes in my life. One of those was to broaden my perspective through travel. The goal wasn’t to travel for the sake of traveling. I had specific personal goals and perspectives I was searching for.
Could you elaborate?
Impatience and transience are things I struggle with, largely because I work in a digital medium where everything I create never lasts more than six months. I wanted to travel somewhere that was the opposite of that. I decided on Italy, a country thousands of years old, famed for its architecture and artwork. I also wanted to escape the grey of winter and go somewhere warm. Turns out it still rains in Italy though…
The length of my workcation was defined by my goals. It had to be long enough to feel less like a trip and more as though I was living somewhere else.
Tell us about your design process.
I work on a wide range of projects at Bench, so my process is constantly changing. Flexibility is a requirement in startups. Often you’re working with people from different departments, and you need adapt to different working and communication styles.
One quality that I consistently enforce in my process is iteration. From the problem definition to an interface component, we work to quickly manifest ideas, continually iterate, and reflect on decisions. This takes place at different scales, sometimes it’s on the whiteboard, or in Sketch, and sometimes it’s week or month long projects that requires fearless reflection. We’ve decided to step back from projects we’ve been working on for months to really question if we’re heading in the right direction.
Did your routine change dramatically when you started to work from abroad?
I was initially worried that the time difference would be an issue. However, it’s actually turned into a benefit. My daily routine is almost the opposite of what it is in Vancouver. I wake up, have breakfast, work for a bit, then spend my day exploring whatever city or area I’m in. I return to work in the evenings, to make myself available for the team.
There have been a few nights where I’ve stayed up working past 1:00am, only to wake up again at 5:00am to catch a bus or train. Even though I’m in Italy, I feel a responsibility to my team to be available and support them. I can make a few sacrifices.
What benefits have you derived from remote-based work?
I’m a supporter of the occasional environmental change. It provides a reset. I would also say that working remote for an extended period has afforded me the opportunity to feel less like a tourist and more like a local. I’m not spending my days running from tourist spot to tourist spot. I’m grabbing my laptop and heading to a cafe or a park for a bit.
Do changes in your location influence your relationship to design?
That’s an interesting question. Changing your environment shifts your perspective. When you travel, especially somewhere completely different from where you live, there’s an unfamiliarity present. It forces you to look at everyday things deeper than you normally would.
How does remote work affect you psychologically?
I’ve had a lot of breathing room to think about problems. My workday isn’t interrupted by shoulder taps from well-meaning co-workers. I define how my day is structured.
Of course, being separated has its challenges. We have an incredible culture at Bench, so I’ve missed out on different events that I wish I was around for. I miss the ability to chat quickly with co-workers whenever an idea or thought arises suddenly. I miss running into people in awkwardly narrow spaces, or talking through a design challenge over lunch.
What tools are essential for remote work?
As a designer, a laptop and a decent wifi connection is about all you really need. Bench’s flexible “work from home” culture is supported by tools like Slack, Flow, Github, and the Bench app. Because working offsite is pre-established in our work flow, it’s easy enough to work from abroad.
To keep in touch with the team, I communicate through Slack, sometimes email (stop emailing me), and Flow. There’s a nine-hour time difference between myself and the people I work with. I use Flow to keep track of my team without having to constantly prod them for updates at weird hours.
I carry my camera around wherever I go. It’s a small mirrorless camera. I enjoy watching everyone lug their giant DSLRs around narrow tourist spots. Also, Spotify. I’ve spent numerous days in a park in Rome listening to music and working.
Cultural differences and language barriers often amplify problems experienced abroad. Do they challenge your ability to work remotely?
The language barrier was difficult for me at first. I’m quite a shy person, so to spend six weeks in a country where you don’t speak anything more than pleasantries is a challenge. At first I would keep to comfortable environments, working from a Starbucks in Paris over a local coffee shop.
Eventually I grew more comfortable and challenged myself. People are just people, and more often than not if you’re friendly and kind, they’ll reciprocate. Now I walk reasonably confidently into a local restaurant and have a meal. I still speak essentially zero Italian, the one phrase I’ve picked up purely from hearing everywhere is “Selfie stick?” I’m not sure how far that’s going to get me.
Do you think all companies should offer employees the flexibility to work remotely?
If it’s feasible, then sure. We’ve become so mobile that there are very few barriers to working remotely. It allows people to integrate their work responsibilities into their own way of living. That goes a long way to improving wellbeing.
Has your time away affected your ability to enjoy fixed-location work?
The experience has inspired me to find more of a balance between the two. I was putting off vacation and travel because I worried that being away would negatively affect my work, or my team. That was the wrong perspective.
A workcation is a great opportunity to explore and mix up your lifestyle. It’s too easy to get run down and complacent doing the same thing every day in the same environment.
What advice would you give to other entrepreneurs considering a remote-based experience?
If you plan to travel while you work remotely I suggest you spend time in a single region or only a few cities, rather than jumping around to different places. You’ll miss out on things if you’re constantly on the move, and you’ll resent having to work if you have to choose work over doing something you want to do. Also, use Airbnb or rent apartments. You’ll have more space to work, probably a kitchen for meals or snacks, and you’ll feel less like a tourist.
If you’re oscillating between working remotely and staying put, it may help to stop looking at a desk in an office as the sole location where you are “supposed” to work. I’ve worked from airports, train stations, on trains, buses, cafes, in queues, in parks, in public squares, and even at a desk (briefly). Plenty of tools can help you work from anywhere. Pick up your laptop and go.