Unveiled: How to Work from Exotic Places without Your Boss’s Knowledge


The Secret Trips: Combining Work Obligations with Vacation Time

Imagine working from a mountain bar, sipping beer while enjoying a view of snowy ski slopes. Sounds like a daydream, right? Well, not for Connor, a British consulting professional who has been taking “secret trips” for the past five years. A secret trip is a work vacation that is not authorized by employers but is becoming increasingly popular among workers with inflexible contracts who want to fulfill their work obligations from more exotic settings and add a few vacation days to their schedule.

Connor, who is not eligible for digital nomad visas or work abroad programs, only works two days in person, usually on Wednesdays and Thursdays. She has devised ways to shoehorn as much vacation time as possible into her life, such as flying somewhere on Thursday night and working remotely on Friday, allowing her to enjoy the rest of the weekend in a new location.

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Taking a lightning trip like this may sound idyllic, but it is not without its stress and requires skillful management. Connor tries to bundle her meetings together for more flexibility but admits that unexpected phone calls or meetings can cause problems. To disguise her location, she also purchased a VPN to hide her IP address, giving the impression that she is still at home.

Despite these potential issues and logistical problems, the idea of combining work obligations with vacation time is becoming a priority for employees worldwide. The pandemic has given a boost to remote work policies, allowing people to experiment with their lifestyles and explore new destinations while fulfilling their work obligations. Besides, taking time off to unwind and change the scenery is essential for employee well-being and productivity.

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So, if you’re working with an inflexible contract, consider taking a secret trip. Just remember: be careful what you post on social media and adopt a “don’t ask, don’t tell” policy, choose places with same or similar time zones to the country of work, and plan accordingly. With a bit of smart planning and management, you can fulfill your work obligations while enjoying a much-deserved vacation.


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