Goodbye Vacation Days! Here’s How to Pitch a Work Holiday to Your Boss

Kelly Konya Freelance Writer Coworker Blog

[Published on Coworker.com, January 18, 2018
Link to full article here.]

It’s okay to admit it: you’re still bogged down by set vacation days, paid-time-off, and other limitations of your work schedule that keep you from traveling. You may sit there and wonder how you can manage to set out on new adventures in exciting countries while still keeping your boss happy. The truth is, it can be done—if you simply pitch the idea of a ‘work holiday’ for the benefit of both your company and your own long-term fulfillment.

What is a Work Holiday?

A work holiday is a new concept. It is set to revolutionize the way remote workers actually work, free from any imposing restrictions of staying in one city. Much like taking a vacation, proposing to go on a work holiday gives workers the chance to occasionally work remotely by extending their stay in a new place beyond an initial short-term timeframe.

In many cases, it makes perfect sense for companies with the ability to have employees work remotely as a way to help utilize vacation days, and allow for vacation time to be integrated into regular days spent working. Location shouldn’t matter—instead, it should enhance productivity, and if that call for being inspired by a unique location, then bosses should see the value in giving employees the wings to explore.

Think of it like this: you have the opportunity to visit Ireland, working remotely and attending a weeklong conference in Dublin. You ask your boss if you can stay in Dublin for an additional three weeks, rounding out the month, and she says yes! In an instant, you now have the chance to experience the city for an entire month—living like a local, touring the city’s attractions, and finding a great coworking community in an energizing setting. This is a work holiday.

Kelly Konya Freelance Writer Coworker Blog

Benefits of Work Holidays for Your Company

Since improving employee happiness is a high-ranking priority on many startups and business owners’ to-dos, it will be valuable to companies to offer work holidays. Imagine all of the opportunities for your business that can stem from you taking a trip. In the eyes of your company, you can become a more well-rounded employee and individual, benefitting in the following ways:

  • You will improve your ability to communicate and general language skills
  • You can develop your independence and personality
  • You will learn new working styles and build international networks
  • You may improve your professional skills and gain new qualifications


By engaging in cross-cultural activities and interactions, you will garner powerful insights into international marketing and other successful business strategies while developing your own point of view. Such experiences may even spark ideas for new business practices for your company, which they will definitely want to hear.

Your boss should be quick to recognize how important traveling can be to your development as an individual and as an employee. In fact, travel is even linked to making better entrepreneurs, having a hand in boosting creativity, productivity, and encouraging problem-solving skills. People with international experience typically display more originality, inspiration, and are quick-thinkers. For digital nomads, travel is the answer to gaining a bicultural perspective and finding fulfillment in your work.

And, of course, there are many advantages for you.

Coworking spaces around the world present some truly matchless opportunities that will leave you feeling fulfilled, both on a personal and professional basis. Now, there are coworking spaces in wine country, in places with access to scuba diving, in cities teeming with startups, and many even offer accommodations through co-living coworking spaces. It’s easy to find your tribe, and it’s even better when you can stay with your new tribe for more than a few days.

By taking a work holiday, you can build a new “work-home,” or better yet, you can even call it your “vacation home.” There is an ongoing myth surrounding digital nomads that constant travel leads to unreliability, but wouldn’t you work better if you were able to finish your tasks and get excited about all that you could then explore? It’s incredibly rewarding to be able to stop into a pub where there’s live music on your way home, or to try new street food on your lunch break. These experiences won’t ever take away from your productivity—on the contrary, they will enhance it, leaving you more enriched and fulfilled after waking up in an exciting place.

In a much-discussed 2010 study by professors from Tel Aviv University, INSEAD, and the Kellogg School, researchers found that “travel and living abroad have long been seen as good for the soul.” So while your company is benefiting from your enhanced performance as you work from a new place, you can also guarantee that you, on a deeper level, will find a higher quality of life and boosted happiness. With a break from your daily remote working routine, you will cultivate gratitude, mindfulness, and the importance of living in the NOW.

With so many advantages to taking a work holiday for both you and your company, the next step is simple: pitch a trip to a coworking space in Dubai next time you touch base with your boss, and soon you will be off on your next adventure. Don’t forget your computer!

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