I spent a total of 10 weeks quiet vacationing all over the world without my boss finding out. Here’s how I did it.

• Tobi Oluwole quiet vacationed for 10 weeks in 2022 and 2023 while working remotely at a tech firm.
• Despite his travels, Oluwole managed his team effectively through delegation and efficiency.
• He says that quiet vacationing made him more productive at work because he was so happy.

This as-told-to essay is based on a conversation with Tobi Oluwole, a 30-year-old former sales manager at a Big Tech firm who recently relocated to France. His former employer is known to Business Insider but is not named for confidentiality. The following has been edited for length and clarity.

In 2022, I took a trip once every six weeks or so, but I only officially submitted two weeks of vacation time. Instead, I quiet vacationed for seven weeks — including a Euro trip with my wife. Before leaving my sales manager job at a well-known Big Tech firm in June 2023, I quiet vacationed for three weeks that year, only submitting one week of vacation time.

Over the course of 15 months, I spent a total of 10 weeks quiet vacationing from my fully remote job. I think quiet vacationing may be good for productivity; I was genuinely so happy while traveling the world, and it translated into my productivity at work.

I quiet vacationed to many places in 2022 and 2023

I grew up moving around — I was born in Lagos, Nigeria and then moved to Brussels; Atlanta, Georgia; Tennessee; Toronto; Ottawa; and Lyon — and always wanted to see more of the world. In June 2021, right after my wife and I closed on our house, we decided that our next priority was travel and do a European trip in 2022.

My wife also worked remotely for the same tech company, so we got an AMEX Aeroplan card, spent 2021 gathering 250,000 points, and banked them in August 2022 for our Euro trip.

Growing up all over the world, I had old friends in all these cities, so I spent a lot of time on my quiet vacations visiting with friends and family. I also officiated a friend’s wedding in Lisbon, did some sightseeing, and watched a Barcelona football game live at the Camp Nou stadium.

Here was what my itinerary looked like for quiet vacations in 2022 and 2023:

2022

• March: Cancun, Atlanta, and Houston
• April: Toronto
• June: Orlando
• July: San Francisco and Montreal
• August: Rome and Amalfi Coast
• September: Barcelona, Lisbon, Paris, and London
• October: Los Angeles and Vancouver
• November: Toronto and Austin

2023

• February: London, UK
• April: Punta Cana, Dominican Republic
• May: Cancun, Mexico

I was very efficient and didn’t want to draw attention to myself

I loved my job and my team, and I had the best boss. At the time, I was a sales coach, leading a team of eight people. I learned how to delegate, prioritize, and break down my tasks and assign them to the team members I trusted so I could hit my goal every quarter.

I always told my direct reports where I was, so they knew when I was on a quiet vacation, but my boss didn’t always know because if I told him, he would’ve likely made me submit my vacation days officially, which I didn’t want to do.

If I was the main contact for a project or it needed to be obvious that I was gone, then I’d officially submit time off. But if it was the beginning of a quarter, I didn’t have projects running, and I was working in the same time zone or within Canada, such as in Mexico, the US, Vancouver, and Toronto, I would just take a quiet vacation.

While traveling, I typically only worked two to four hours a day. On some quiet vacationing days, I had to work a little later to get things across the line, but I became very efficient. I didn’t want to draw too much attention to myself.

A quiet vacation day in Europe might look something like this: Wake up around 8 or 9 a.m. and eat breakfast at the hotel. Head out for lunch in the city and do some sightseeing like a boat tour in Amalfi or the Eiffel Tower in France. Return to the hotel around 3 p.m., which is 9 a.m. EST, and take meetings and work until 7 p.m. Then go for dinner with my wife and stay out in the city.

I kept Slack on my phone in case I was out and needed to respond. If my boss tried to reach me, which was rare, I’d respond within the day. Nothing was ever truly urgent, and my team and colleagues were also available.

I figured out pretty early on that at the end of the day, as long as the team was performing and my reviews were strong, I’d be fine.

My advice for people who want to take quiet vacations

Learn how to build systems that allow you to do your job more effectively but in less time.

As long as you are performing, you will have fewer eyes on you. I figured out that since we worked remotely, all I had to do was ensure that my team always performed well, and I could be anywhere in the world.

I’d figure out a system to automate messages or tasks. I’d block out time in my calendar to avoid random meetings being booked, ask teammates to send me notes or read the AI meeting notes, and take calls with a virtual background. Due to my deep trust in my team and the great systems we implemented, I cut all 1:1 meetings down from an hour to 15 to 30 minutes weekly.

I learned from another team lead to set up a daily revenue tracker so that everybody knew what number they needed to hit to ensure they achieved their quota at the end of each month and quarter. We also chose team prizes for exceeding each quarter’s targets — once, it was a Toronto Raptors basketball game and another it was a weekend trip to a cottage on the lake.

Learn how to get work done through people.

Whenever work needed to be done on the days I was quiet vacationing, I’d delegate as many tasks as I could to my team. I chose a team captain who stood in for me to run team meetings when I was out being a tourist and paired people up according to their strengths and weaknesses. This is why the team almost never missed our quota.

My team never felt frustrated that I was quiet vacationing while delegating work to them. In fact, my boss told me during my impact review that my team had only good things to say about me.

I did this through motivation and inspiration. When I was at work, I went over and above to make sure I supported my team and helped them make as much money as possible. When we had big goals or if our team was behind, I’d get on calls to close deals with them. I was very intentional about making sure they knew I’d be in the fire with them when I needed to be, which built lots of trust.

We wrote a team mandate together to define the team’s culture — for example, “We will exceed quota without experiencing burnout,” which meant I approved every vacation and trusted them 100% to achieve their goals.

I was also very close to them and spent time with them outside of work and we still do an annual trip together today. I showed them I trusted them by not micromanaging them, and whenever I was gone, they continued to perform like I was there — sometimes even better because they didn’t want to let me down.

Say “no” more often to projects that don’t align with your career goals.

This really helped me avoid playing politics or the career ladder game. If an opportunity didn’t serve my long-term goals or was too high-profile, I’d turn it down.

I turned down projects, stating I didn’t have enough capacity, and also just refused to attend non-essential meetings.

Build something you own outside your job

At that time, I’d built my LinkedIn audience to about 100,000 followers. I ran a career boot camp and marketed it on LinkedIn and also had multiple brand partnerships. I was earning about $5,000 to $8,000 a month outside my 9-to-5.

My company had a 90-day work-from-anywhere policy, but it required us to submit each location we were going to work from and I chose not to follow it. Having my own side hustle allowed me to not feel the pressure to follow all the rules. It also gave me disposable income to use for traveling and do all of this without fear.

Try to find a boss who values your productivity more than your physical presence, although that can be out of your control

I did sometimes get questioned by my boss and sometimes even higher-ups about my schedule and availability, but it happened rarely and wasn’t a big issue.

I was great at my job. My team always performed and they never missed their quarterly targets during impact cycles. I got very high performance reviews and glowing reviews from my direct reports. By the time I left my role in 2023, I had landed a 13% raise.

I left Big Tech and live life on my own terms

I left the corporate world before my 29th birthday in June 2023 to become a full-time entrepreneur and LinkedIn creator.

I moved to France with my wife, who also left her job at the tech company. We’ve visited 14 countries so far since leaving our jobs.

My goal was always to become an entrepreneur, and working at that Big Tech company was basically my MBA. Now I get to live life on my terms and continue traveling.

If you quiet vacationed and would like to share your story, email Jane Zhang at janezhang@businessinsider.com.