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Working on holiday: Why we all do it and how to stop it ruining our time away from the office

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If you’re reading this as a freelancer, let me ask you bluntly – how many times have you got into an argument with your significant other while on holiday because you “just can’t ignore” that email or that phone call?

For me, it happens almost every time. Indeed, I remember a recent holiday to Disney World where I was thrown out of the room by my wife and forced to work in the hotel lobby amidst hundreds of giddy holidaymakers. It was miserable but it’s a scene that’s become commonplace among freelancers.

Because, while the flexibility of freelancing can be liberating it also brings challenges that can impact both your personal well-being and professional output. Nowhere is this more apparent when you’re meant to be switching off and enjoying yourself but just can’t bring yourself to activate that out of office mode.

Why Freelancers Work on Holiday

Freelancers often find themselves working during holidays due to several reasons. The nature of freelancing, which lacks the structured boundaries of a traditional job, makes it difficult for many creatives to fully disconnect from work.

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There's also the fear of missing out on potential opportunities or letting clients down, leading so many to bring their work along on vacations​. Some freelancers might also feel the need to maintain income stability, especially if they’re concerned about work drying up during quieter periods​, which can and will happen.

It’s a vicious cycle of asking yourself “what I am missing out on?” and constantly glancing at your pocket, wondering if you should just give your messages a quick glance. Because you just know that quick glance will turn into an “I’ll just nip back to the room for a second.”

The Drawbacks of Working in Paradise

Despite the obvious benefits (keeping the revenue stream running, not missing out on any golden opportunities), working while on holiday can have significant downsides. The most obvious is burnout.

Vacations are crucial for recharging creative energies, and without a proper break, freelancers risk their long-term productivity and mental health. Also, working during a holiday can dilute the quality of both the work and the holiday itself, leaving freelancers feeling neither fully rested nor fully accomplished​.

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You have to ask yourself if you’re really doing your best work when your mind is elsewhere and your family are becoming more and more enraged at your absence.

Strategies to Mitigate the Negative Impact

  1. Plan Ahead: Effective planning is key to avoiding the need to work while on holiday. By communicating with clients in advance and setting clear boundaries, freelancers can better manage their workload. Completing major projects or delegating tasks before taking off can help ensure that the holiday remains a true break​.
  2. Set Boundaries: It's essential to establish firm boundaries regarding availability. Setting up an email auto-responder and sticking to it can prevent the temptation to check in constantly. Uninstalling work-related apps from your phone can also help maintain these boundaries​.
  3. Delegate or Outsource: If possible, consider delegating tasks or hiring temporary help to manage urgent client needs during your time off. This not only allows you to rest but also ensures that your clients' work continues smoothly​.
  4. Use the Time Wisely: If working on holiday is unavoidable, try to schedule specific, limited times for work and stick to them. This can help in maintaining a balance and ensuring that you still enjoy your vacation.

Final Thoughts

Working while on holiday might be a necessity at times, but freelancers must manage their time more carefully when they’re meant to be recharging their batteries. By planning ahead, setting boundaries, and ensuring they take genuine breaks, freelancers can protect their well-being while still meeting their professional obligations.

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Whether I take my own advice or not, however, is another matter entirely... I mean... I'm working on holiday LITERALLY RIGHT NOW!

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