Team Leader’s Survival Guide To a Month-long Sabbatical

October 31, 2023

An opportunity to take a month-long leave is a great privilege, but can be a bit tricky for team leaders. Here’s a story of how it went for our Chief Customer Officer, Amit Kvint, and Content Manager, Dario Jazbec Hrvatin.

At OnTheGoSystems, anyone that’s been with the company for 7 or more years gets a special benefit – an extra, paid month of vacation they can use whenever they like. This is a great way to reward people who’ve been with us for such a long time and give them an opportunity to take a well-deserved rest.

We already covered some of the great sabbatical stories from our team members. Now, it’s time to see it from a slightly different perspective.

How do you take a month off when there’s a team of people depending on your leadership and a number of ongoing projects happening? Amit and Dario share some insights.

Amit Kvint, Chief Customer Officer
Dario Jazbec Hrvatin, Content Manager

What’s your take on sabbaticals? How did you choose when and how to take one?

Amit packed and ready


Anyone who has worked from home continuously understands the challenges it presents. Don’t misunderstand me – I feel privileged to have the ability to work from home. However, after doing so for over fifteen years, I’ve realized that the most significant challenge for me is knowing when to stop. After all, the office is always just a click away. That’s why the opportunity to disconnect for an extended period is such a tremendous benefit. I believe it’s crucial for maintaining a balance between work and life.

Personally, choosing when to take a break was straightforward. Summer is the most quiet time in Support, as many clients are also on vacations. And, since we (the family) decided to move out of our home in Cadiz, Spain, for a year, with my older son also just saying goodbye and starting his studies in Barcelona, I recognized that both my work and family would suffer if I attempted to manage these life changes while maintaining my busy daily work schedule. So, I planned my sabbatical to include ten days for moving preparations and the remaining twenty for settling into our new home. 

This turned out to be the perfect arrangement. They say moving is one of the most stressful things one can do, but I actually managed to enjoy (most of) it :-) 

Dario enjoying nature and wildlife


There is an incredible amount of information we need to process each and every day. And while it’s good to keep your brain going, I think from time to time it’s really healthy to just switch off as much as possible and let your brain take a sabbatical as well. By this, I mean, give it something different to experience in big quantities, like nature, arts, literature, music, and the people you love.

When it comes to timing, it’s exactly like Amit said. For us, summer is perfect as a lot of people are on vacation.

Some people used sabbaticals to also upgrade their skills, read books, etc. Did you do anything similar?


Apart from moving to another continent, I focused on physical exercise. I decided to try and re-establish a routine for biking and walking, a routine that I will be able to continue after the sabbatical month’s off is finished. This seems to have worked nicely, and I’ve managed to bike or walk around 10km a day for the last three months.

I also dedicated a lot of my time to family and friends, which is something that I tend to take for granted while working. 


I wanted to read only one book related to learning, which was about UX writing, a skill I’m working on these days. But besides that, I just wanted to use other parts of my brain for a while. :)

Also, I’m working on a new music album (I’m a singer-songwriter) so I spent a lot of time just thinking about the songs in my head and coming up with different arrangements and things I could do with them once I’m back in the studio.

Amit enjoying a quiet evening
Dario enjoying the great outdoors

As a team leader, many people and projects depend on you. How did you go about preparing for a month-long leave?


The first thing was to create a list of my tasks and responsibilities. Amir and Laura encouraged me to do that, and Amir was kind enough to review that list and help me organize it. The next very important step was to share that list with Alejandro, my deputy. With the other group leaders, I needed to communicate the fact that I would be away, establish who would replace me in what tasks and responsibilities, and then make sure it was very clear what they would need to do in different situations, both expected and unexpected. 

The role of deputy is very handy here – Alejandro and I had a few long sessions during which we went over all the items on the list. Alejandro took some responsibilities off my hands even before my vacation started, allowing us to create a smooth handoff and make corrections. Having a strong team that can support you, and especially a deputy that knows your role, is what permits someone that manages a team with many responsibilities and dynamic tasks to be able to take such a long vacation.

I am very grateful for that initiative and personally to Alejandro, Drazen, Marcel, Nigel and Ahmed M. who handled the different tasks of OTGS support system really well while I was away. 


It was pretty simple to prepare things before I went away, but it did take some time. I wanted to make sure that Kathy, my deputy, had a list of priorities for critical content-related tasks during my time off. I also needed to make sure the same was clear for other members of the team so Kathy could lead them properly.

I also switched all my usual stakeholders meetings to her which I think was interesting for her. But besides having a great deputy, it was straightforward because the rest of the team is very responsible.

OK, so what amazing things did you do on your sabbatical?

Amit experienced peaceful strolls


The first week was dedicated to revisiting our area. As it was August, I went to the beaches of Cadiz daily, visited old friends, and spent time with my family.

I spent the next three weeks walking and biking throughout the state of Wisconsin, visited many lakes, rivers, and mountains, and strolled through the neighborhoods of towns and cities. 


My wife, daughter, and I used 1 week to go to a house that stands alone in the middle of a forest. This house is located in the Slovenian mountains (village of Borjana) and it’s surrounded by incredible nature. We had a pristine small river 5 minutes down the hill from the house. It’s as much in the heart of nature as it gets.

Directly after that, we drove to the Croatian island of Cres for another two weeks. I’m from Croatia originally, and this island is really close to Slovenia, where we live. We stayed in Lubenice, an ancient tiny village on top of a hill overlooking the sea. It’s a big island and we spent the whole time exploring its different places, beaches, and villages.

Dario captured a unique strike of lightning

Were you able to switch off from work completely and just enjoy your time?

Amit spending time with his family


In the first week I checked work daily, though I tried not to get too involved with what was going on. After that first week, I saw that things were going well and I managed to disconnect and focus on my personal goals.  

Dario spending time in the heart of nature


I also needed time to stop thinking about work and checked on things in the first week. But then, I realized that my team was on top of things and that I needed to just let go. And it was as important to my team as it was for me.

After the sabbatical, how was the transition back to work? Were there any surprises waiting for you?


The transition back was smooth. For the most part there were no surprises, but we did recognize some areas for improvement. Mainly, making sure that in times of high workload in support, everyone on the team knows how to prioritize and focus on giving clients the fastest, best solutions. Alejandro and I had a few meetings right after I was back to make sure some issues that we did not anticipate were handled properly.


Everything went smoothly while I was away, so there were no emergencies or surprises waiting for me. But it was a new experience for both my team and myself, so we did learn thanks to it. I think it helped us realize how important each part of the team is and how being organized is crucial to avoid issues and stress.

Amit on a kayaking trip
Dario taking in the beauty of wild horses

Is there anything you would do differently when it comes to planning longer leaves?


The most challenging thing for me was letting go. I tried leaving a very “clean table” before I left for my vacation. If I ever get to do it again, I’ll try to start the transition even earlier, so some tasks can be distributed before I am away. Apart from that small detail, I think the planning proved to be successful. 


I would definitely try to stop checking up on things from the start and let my deputy and team handle it all.

Did you notice any impacts on yourself or your team after this experience?


The first impact was on me – I came back with a lot of new energy and new ideas.  

Another big impact was on the team. The support system, including internal workflow, and processes we put in place proved to work well, and the support group leaders and Alejandro had the opportunity to take ownership of my tasks successfully.  


I definitely came back rested and more relaxed. But even more importantly, I think we all learned to appreciate each other and our roles even more than before. 

Amit taking relaxing summer strolls
Dario exploring the island of Cres, Croatia

Any other advice you would give to other team leaders considering a sabbatical?


Preparation and trust are the keywords. You need to make sure everything is in place before going away and that it’s not all just in your head. Create a document with what you do daily and make sure it’s clear enough so someone else can take over. Then, trust the people you leave the tasks with.


Just do it (but prepare beforehand). :) 

How Sabbaticals Make Us Better Leaders

At OnTheGoSystems, we see sabbaticals as more than just extended breaks; we see them as a way to find new and fresh insights on our work.

Stepping away for a month might seem daunting, but sometimes, it’s the distance that gives us a clearer perspective. Of course, it’s important to plan ahead and make sure the team and projects are not left in the dark while the team leader is away.

Our experience shows us that a short-term absence leads to long-term gains: refreshed leaders, empowered teams, and a culture that values well-being. 

So, if you’re contemplating taking a sabbatical, remember—it’s not just good for you; it’s good for the whole team.

Come Work With Us

Are you interested in working with a globally distributed team that encourages growth and advancement? Are you ready to harness the power of technology for a better future?