Lessons Learned from Work From Anywhere Week: Traveling with Coworkers

Many professionals will travel with coworkers at some point in their careers, typically for a conference or a work event. These situations can be potentially stressful when you have to navigate logistics, make decisions as a group, and maybe even share close quarters.

But combining work and travel can also be fun and bring people together. Take it from a few members of the Justworks team who spent the second company-wide Work From Anywhere week traveling with their coworkers. They packed their laptops, headed to places like Budapest and Cartagena, and spent a full week of remote work with their colleagues.

Traveling with coworkers offered these people the chance to strengthen relationships among colleagues and across teams, and helped the remote work feel more focused.

Needless to say, there were a lot of lessons learned. Here are the top five pieces of advice that the Justworks team picked up over a week of remote work:

1. Set Expectations

When deciding to travel with a coworker, it’s a good idea to make sure you’re aligned on what you want out of the trip. This will help you understand if you’re choosing the right travel buddy for you before you go, and set up the trip for success.

"Talk through travel and activity preferences ahead of time to make sure everyone is on the same page."

Laila Zouaki, a Product Manager at Justworks, learned in the past that just because you’re friends with someone doesn’t mean you’ll have the same travel style. Thankfully, traveling with a work friend to Colombia worked out great. “We had the same expectations regarding balancing out work and leisure, as well as budget,” said Laila. It made the remote week easy.

Alex Freschet, an Account Manager, emphasized the importance of keeping an open mind. “When traveling, especially with coworkers who you may have never traveled with, it’s best to remain as flexible as possible,” she said. “Talk through travel and activity preferences ahead of time to make sure everyone is on the same page in terms of how you want to structure your free time.”

2. Choose the Right Location

There’s more to a successful Work From Anywhere week than simply booking a flight to wherever you want to go. The one rule of the week was that everyone still had to be online and working during their normal Justworks work hours, 9am-6pm Eastern time.

Alex spent the week in Budapest, and she found the time zone to be a bit of an issue. “Next time, I would consider picking a location with a time difference more closely aligned with New York,” she said. “Although we were able to sightsee all day, Budapest is six hours ahead, so our work hours were 2-11pm.”

For Laila, the part that proved tricky was being online. As it turned out, good WiFi wasn’t as easy to find in Cartagena as she’d hoped. “It definitely disrupted some of our days to not have a good enough connection, as we had to rush to find a better workplace to be on time for meetings,” she said.

3. Set Clear Goals

Actually getting work done in a beautiful remote setting can be tough. We’d all rather take in the sights! As Laila pointed out, this makes setting clear goals a top priority. “Being in a different setting created a stronger need to constantly re-evaluate: what is my goal for this week, and what am I trying to achieve?” she said.

"It made it seem less like we were on vacation and more like it was a normal workday."

Omar McKenzie, an Account Executive, echoed this sentiment. He found that being with his coworkers while in Costa Rica actually helped him keep his focus. “Working next to the people I was with made things easier, because it made it seem less like we were on vacation and more like it was a normal workday,” Omar said.

Emily Masseo, a Customer Success Communications Manager who was also in Costa Rica with Omar, didn’t feel that the remote work was a challenge — in fact, quite the opposite proved true. “There’s something really inspiring about being in a different environment, let alone a different country, and accomplishing tasks you normally do from the comfort of your desk,” Emily said. “I felt a sense of empowerment and ownership that was refreshing, and it stuck with me when I got back.”

Related Article: How to Work From Home: Tips to Increase Productivity Outside the Office

4. Learn from Your Colleagues

A great thing about traveling with coworkers, especially those you don’t normally work with, is getting the chance to hear different perspectives. “It sparked a lot of conversations and impromptu brainstorming regarding our work, which was unexpected but very fulfilling,” said Laila.

Claire Sarsam, a Software Engineer, shared a house on Fire Island with seven other Justworks colleagues for the week, and learned a lot from coworkers who typically sit across the office. “I had a bug that I was completely confounded by, and an engineer who I normally don't work with spent an hour talking through it with me because he happened to be working next to me at the kitchen table,” said Claire.

“Teamwork was really apparent — when one of us was swamped, we’d all pitch in to help out,” added Alex. “We’d bounce questions off of each other and were way more open to talking over cases in our casual environment.”

5. Plan Some Fun Activities, Too

Part of the perk of Work From Anywhere week is of course to have fun and experience a new environment. While the remote work bonded these groups of coworkers, the non-work activities strengthened the relationships, too.

“Since we were two hours behind Eastern time, we still had some time to kill after the New York workday was over,” said Omar. “That allowed us to do things like go surfing or take a sunset ATV tour while still working a full day — a true work hard, play hard mentality.”

For Alex, everyone in her travel group lent their personality to the activities in Budapest. “One of my coworkers really values history, and we spent a day exploring the major attractions and museums,” she said. “Another teammate really loved lounging around, and going to the Szechenyi Thermal Baths was right up her alley. I’m a big foodie so I planned all of our meals and nights out. We all were open to new experiences, which made the trip seamless.”

“My group was all about chilling out at our Airbnb, going to the beach, and walking around the tiny beach town we stayed in,” said Claire. “I learned about people’s many hidden talents and hobbies, from being incredible at bluffing games to building amazing sandcastles.”

Combining travel and work helped these Justworks employees make Work From Anywhere week a truly memorable experience. Everyone agreed that the best part about the week was getting to know their coworkers better — even for those who were already close friends. In the end, traveling with coworkers can create tight bonds between teammates, and strengthen the relationships you bring back to the office.

“It’s funny, working full-time at a company where you spend nine hours a day, five days a week with people, you’d think you get to know your coworkers pretty well,” said Emily. “But through traveling together, you bond in a way that transcends what’s forged in the office.”