I take a week’s “vacation” every month without telling my boss

  • With the advent of remote work during the pandemic, some workers are choosing to travel more and live abroad.
  • Insider recently spoke to a 38-year-old who travels for a week every month without telling him his job.
  • “I used to only travel once or twice a year,” they told Insider. “But I found a way to combine my love of travel and my job.”

This essay is based on an interview with a 38-year-old working in the publishing industry. They spoke on condition of anonymity to protect their careers, but Insider has verified their identities and employment. The interview has been edited for length and clarity.

I have a secret. Since May 2021, I’ve been taking at least a week’s vacation every month without telling my employer. I just bring my laptop, find a neutral background and call from anywhere – Iceland, Portugal or Colombia.

I realized last year that I can travel while working

After getting vaccinated in spring 2021, I knew I had to travel. The pandemic was difficult for me, as it is for everyone. I ended a relationship with the person I thought I would marry and I looked around and thought I needed some change.

As people started getting vaccinated and borders reopened, I made my first of many trips to Reykjavik, Iceland. After I went to Iceland and saw that it was possible to work from another country without anyone from my job knowing about it, I just kept going.

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

I went to Guatemala and Costa Rica and Spain and Yellowstone and Morocco and Norway. In my job, we only have to be in the office one day a week, so I usually go to the office that day, catch a plane at night, and return the following week in time to go back to the office. And nobody is smarter!

I used to only travel once or twice a year because I was so constrained by my limited vacation days. But now I’ve found a way to combine my love of travel and my job. I know I shouldn’t be traveling the world without telling my boss, but I feel like the pandemic has shifted my priorities.

After seeing how much the world had changed and how fragile life really is, I knew I had to start living my life the way I wanted to

My mom always says: “In life you either have time or money.” I’ve usually found that to be true – except now that I seem to have figured out a way to have both.

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

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

I was on a really short flight to Nantucket the other day. I planned the flight during my lunch break and worked at the airport until boarding. When I was on the plane, there were some problems with the plane. We had to circle the airport a few times before landing.

I remember thinking, “Please don’t crash that plane, because then my boss will find out I’m not working from home.” I know if a plane crashed I’d be dead so it really wouldn’t matter, but I was just thinking how everyone at work would think I’d just disappeared. Then eventually they would find out that I died in a plane crash and they would say, “But why was she on a plane during her lunch break?”

I remember once on a transatlantic flight thinking that I couldn’t explain what I had done if the plane crashed and I was going to die somewhere over the ocean. Thankfully, none of these situations have ever happened.

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

But if you don’t ask, it’s like no harm, no foul. If anyone ever found out I was out at work, I’d just pretend it was a one-time thing. And then I would move on.

Do you have an interesting story about working remotely, with or without your job’s permission? Email Fortesa Latifi at [email protected]

Leave a Reply

Your email address will not be published. Required fields are marked *