Reflections After Rest: How Trusting His Team Allowed Sze Hui to Relax

At Roundtrip, we offer employees a four-week sabbatical after five years because we believe that sustainable work requires space to step back. This post is part of an ongoing series reflecting on what time away from your desk reveals about trust, teamwork, and the energy we bring to work every day.

When Roundtrip first announced that employees would be eligible for a sabbatical after five years of service, I wasn’t actually sure I’d be around to take the company up on the benefit. The average employee tenure at a startup is under three years, and I figured that my career would go in a similar fashion.

But before I knew it, the time had come, and this past April, my manager and I began to start planning for a month without me. We documented all of the things that I do, looping in all the folks that would step in for me as I was out of the office. We also worked to make sure that all of the external stakeholders I communicated with on a regular basis knew that I would be out of the office, and who to contact in my stead. By the time I shut my computer down at the end of June, I felt good about leaving work behind, confident that my teammates would keep things rolling while I was out.

Life Away from the Inbox

Over the month of July, while CAD integrations, implementations, and production support tasks rolled in at home, I was in Europe checking off my bucket list. I had real Belgian waffles in Brussels, watched Tadej Pogacar storm his way up the Montmartre on the last stage of the Tour de France, and discovered in Vienna why crisp apple strudels are one of Julie Andrews’ favorite things. I’d also had the opportunity to take care of a few more mundane things, like help my daughter through a correspondence economics and personal finance class.

Oh La La to Oh No No

The one thing I never knew was on my bucket list was to hear an actual French person use the phrase “Oh, la la” in real conversation. This achievement happened on the side of the Avenue Jean Jaures, in the suburbs of Paris. Turned out, there was a different Avenue Jean Jaures inside the city of Paris itself…and I was already 10 minutes late for a boat tour. “I went to the address you selected in the app,” said the Uber driver. “Oh la la, you are supposed to be at 211 Avenue Jean Jaures, Paris.”

As we trudged our way back through Paris traffic to Gare du Nord, I looked at Google Maps to see how we got the address for the meeting point for our boat tour so wrong, and discovered that I’d been hit by an issue we see from time to time in the Roundtrip app:

This moment was probably the lowest point in my sabbatical, but even in the low points there is a silver lining. On reflection, it helped me build empathy with the care managers who depend on the Roundtrip platform on a daily basis, and I was still in Paris, so even this low moment can’t be all that bad.

Return to Work

When I came back at the beginning of August, I was a little apprehensive. What, exactly, would be waiting for me when I opened Outlook and Slack back up? But as I started to work through email, I realized that I should never have been worried. My coworkers are all rock stars, and had kept everything moving nearly as smoothly as they would have gone if I was still here.

I think I spent the least amount of time I’ve ever spent working back through email coming back from a vacation, because I found that anything older than a week I could just mark read because it had been taken care of. I’m deeply grateful to Roundtrip for the opportunity to rest and recharge, and even more grateful to my teammates who helped to make sure that the transition back in was easy.