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I take a week of 'vacation' every month to travel the world without telling my boss — and I'll keep doing it even if I get caught

Business Insider logo Business Insider 12/6/2022 insider@insider.com (Fortesa Latifi)
A stock photo of a woman in vineyards in Italy. Marco Bottigelli, Getty Images © Marco Bottigelli, Getty Images A stock photo of a woman in vineyards in Italy. Marco Bottigelli, Getty Images
  • With the rise of remote work during the pandemic, some workers are choosing to travel and live abroad more.
  • Insider recently spoke to a 38-year-old who travels for a week each month without telling their job.
  • "I used to only travel once or twice per year," they told Insider. "But I've found a way to make my love for travel and my job work together."

This as-told-to essay is based on a conversation with a 38-year-old who works in the publishing industry. They spoke on the condition of anonymity to protect their career, but Insider has verified their identity and employment. The conversation has been edited for length and clarity.

I have a secret. Since May 2021, I've been taking vacations for at least one week every month without telling my employer. I just bring my laptop with me, find a neutral background, and call in from wherever I am — whether that's Iceland, Portugal, or Colombia.

I realized last year that I could travel while working

After I got vaccinated in the spring of 2021, I knew I needed to travel. The pandemic had been difficult for me, like it was for everyone. I ended a relationship with the person I thought I was going to marry, and I found myself looking around and thinking I needed some change. 

Once people started getting vaccinated and borders began opening again, I took my first of many trips, to Reykjavik, Iceland. After going to Iceland and seeing that it was possible to work from another country without anyone from my job knowing, I just kept doing it. 

Every month, I work for about a week from somewhere around the world

I went to Guatemala and Costa Rica and Spain and Yellowstone and Morocco and Norway. At my job, we only have to be in the office one day per week, so I usually go into the office that day, leave on a flight that night, and return the following week in time to go back into the office. And no one's the wiser!

I used to only travel once or twice per year because I was so constrained by my limited vacation days. But now, I've found a way to make my love for travel and my job work together. I know I'm not supposed to be traveling around the world without telling my boss, but I feel like the pandemic shifted my priorities. 

After seeing how much the world changed and how fragile life really is, I knew I had to start spending mine the way I want to

My mom always says: "In life, you either have time or money." I've usually found that to be true — except now, when I seem to have found a way to have both.

It feels indulgent in a way, but then again, I should be enjoying myself. Why not? Plus, the publishing industry infamously underpays its employees, so I feel like they kind of owe me.

Sometimes I wonder what might happen if a plane crashes, and no one at work knows where I am

The other month, I was on a really short flight to Nantucket. I scheduled the flight to be during my lunch break and worked in the airport up until boarding. When I was on the flight, there were some issues with the plane. We had to circle the airport a bunch of times before landing. 

I remember thinking: "Please don't let this plane crash, because then my boss will find out I wasn't actually working from home." I know I'd be dead in the case of a plane crash so it wouldn't actually matter, but I was just thinking about how everyone at work would think I just disappeared. Then, eventually, they'd find out I was killed in a plane crash, and they'd be like: "But why was she on a plane during her lunch break?" 

Once, on a transatlantic flight, I remember thinking that if the plane crashed and I died somewhere over the ocean, I wouldn't be able to explain what I'd been doing. Luckily, none of those situations have ever happened.

My motto is: If you ask for permission, someone might say no

But if you don't ask, it's kind of like no harm, no foul. If anyone ever did find out I was traveling while working, I would just act like it was a one-off thing. And then I'd keep doing it.

Do you have an interesting story about working remotely, with or without your job's permission? Email Fortesa Latifi at whatsyourstory920@gmail.com.

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