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.
At Roundtrip once you have worked here for five years, you are eligible to take a four week sabbatical. I recently hit that five-year milestone, and took a four-week sabbatical—my first real break in years, and one that gave me space to truly step back and reflect.
I has set some very firm rules for the time: No emails, no Slack, no notifications. Of course the team could get a hold of me if they needed time, but after a fun and eventful five years I was looking for time to reset and return back with fresh energy. Stepping away from the daily demands of Roundtrip’s operations taught me three valuable lessons about the importance of rest, career growth, and perspective.
1. The Importance of Unplugging for True Rest
We have a 24/7 Contact Center, so while you may log off for the day, you’re always one escalation away from not being off. A normal day pre sabbatical would consist of checking Slack and email multiple times after core hours, before bed, and then first thing when I wake up. I didn’t realize the extent of how much my days were driven by notifications until I silenced them.
It took about a week to reset myself, but removing the apps from my phone helped to achieve that goal. In those newly discovered quiet moments, I found real rest—not just the absence of work, but a reconnection with family and deeper thinking. Without the constant pull of emails and alerts, I had space to reflect on what truly matters both personally and professionally.
2. The Value of Clarity Breaks in Your Career
In operations, it’s so easy to be reactive—solving problems as they come, and putting out fires. As much as I strive to be strategic it never seems like you have enough time in the day to get there. To truly move the needle on strategic projects you need the time — dedicated time — to get in that zone and think about where you want to go and what you want to do.
Stepping away for the four weeks forced me to zoom out and ask bigger questions: Where am I adding the most value? How can I stay ahead with what seems to be constant new ‘best practices’ with process and procedures. And then most importantly getting time to think about: Where do I want to be in 3, 5 and 10 years? The clarity that came from this sabbatical was invaluable. I was one that typically subscribed to the adage of progress can be achieved through sheer will and pushing harder but this break showed that progress is made though taking breaks long enough to zoom out to see your bigger picture and end goal.
3. Reframing My Perspective on Customer Support & Call Centers
Prior to Roundtrip I spent most of my career in vendor management, and process improvement operations type roles. I always wanted to be agnostic of the business line and specifically If you had asked me five years ago what I didn’t want to be known for, I would have said: “the call center guy” But over my five years at Roundtrip and with dedicated time to reflect, I’ve really seen what Customer Support and Call Center teams are: Value Drivers for the business.
These teams aren’t just answering phones or emails, they’re shaping the entire customer experience and are often the first and most frequent touchpoint for patients navigating complex healthcare systems. A well-run support team doesn’t just resolve issues, it builds trust, drives retention, and ultimately improves patient outcomes. My sabbatical helped me see this function not as a back-office necessity, but as a strategic advantage.
Stepping Away to Step Forward
The perspective I gained from this time away was just as valuable as the rest I got from unplugging. I was able to trust my team and coworkers to continue to lead us forward in my absence and was able to return with a new revamped perspective about where we are headed in 2025 and beyond.
I returned to Roundtrip with renewed energy, focus, clarity, and a greater appreciation for the role we play in shaping healthcare experiences. If your organization offers a sabbatical, it’s really tempting to feel like it’s too much work to prioritize taking the time away. If you’re still considering whether or not to take yours, I really can’t recommend it enough. Sometimes, stepping away is exactly what you need to step forward.
Phil Montanez is Roundtrip’s Director of Operations. Phil oversees end-to-end operational execution, including service delivery, capacity management, vendor performance, and cross-functional coordination. He plays a critical role in ensuring that Roundtrip consistently delivers reliable, scalable, and high-quality solutions to health system and public-sector partners. His work focuses on performance management, reporting, and continuous improvement, equipping him with a disciplined, metrics-driven approach to operations.