by Jeroslyn JoVonn
October 8, 2024
A former tech employee shares tips on how to quietly vacation while on the clock.
Meet Tobi Oluwole, a former big tech employee who spent ten weeks vacationing from 2022 to 2023 but only officially reported three weeks of vacation time.
Now a full-time entrepreneur and LinkedIn creator, Oluwole is reminiscing on the weeks of traveling he used to do while still on the clock working for a major tech company. In 2022, he traveled every six weeks and only clocked two weeks of vacation. In 2023, Oluwole quietly vacationed for three weeks but only reported one week of vacation time.
“Over the course of 15 months, I spent a total of ten weeks quiet vacationing from my fully remote job,” he told Business Insider.
“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.”
This growing trend among remote workers, known as quiet vacationing, involves employees taking time off without informing their boss—an alternative to the quiet quitting movement.
How Oluwole managed to vacation without his job knowing, as a remote worker, there were specific processes he had to take and consider before taking flight. He outlines these considerations in five tips he shares for other remote workers who want to add more quiet vacations into their work week.
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,” Oluwole says. “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.”
Oluwole developed a system to automate messages and tasks and would schedule dedicated time in his calendar to prevent random meetings from being booked. He had teammates send notes, or he would read the AI-generated meeting summaries and use a virtual background for calls. As a manager, he still had a team to look over, which he successfully did by implementing effective systems, such as reducing all one-on-one meetings from an hour to just 15 to 30 minutes each week. He also established a daily revenue tracker to keep his team informed about the targets they needed to reach to meet their monthly and quarterly quotas.
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,” Oluwole shared.
“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.”
His team also enjoyed the task delegation and had “good things” to say about Oluwole’s management style. He credits this to the motivation and inspiration he provided his team through support and financial reassurance.
“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,” he explained.
Quality time he also helped. Oluwole spent time outside work with his team and even planned annual trips with them. He also avoided micromanaging, which motivated them to continue working hard even when he wasn’t around.
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,” Oluwole said. “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 refused to attend non-essential meetings,” he added.
Build something you own outside your job.
While working at a major tech company, Oluwole actively side-hustled on LinkedIn, building a following of over 100,000. He promoted a career boot camp on the platform and secured multiple brand partnerships, earning between $5,000 and $8,000 monthly in addition to his day job.
“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,” he said.
“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,” Oluwole said.
Due to his strong performance and his team’s ability to meet their quotas, Oluwole received positive performance reviews, resulting in a 13% raise at the tech company. After enjoying ten weeks of quiet vacationing throughout the year, he left the company, relocated to Paris, France, with his wife, and transitioned to working for himself full-time.
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