Dear Lifehacker, When's the best time to take a holiday? Some people say the summer is the best time to get away, but that means higher prices and school holiday crowds. And what about work? Should I just go, or wait for a quiet time when nothing is going on? Help! Thanks, Gotta Get Away
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Dear Gotta Get Away,
The short answer to your question is that it's always a good time to take a holiday! The longer answer is that you have a little legwork to do to make sure that it's a suitable time for your employer, and also a good choice for you so you'll be able to actually relax and enjoy your time away without worrying about work while you're away. You want to make sure you do a little prep while you're planning your getaway so you don't work your fingers to the bone in the days leading up to your holiday, and you aren't miserable your first few days back.
Plan First, Then Ask Your Boss
If your workplace needs to hire a temporary replacement when you're not around, or you know that being away will make a significant impact on your colleagues, you'll want to plan your holiday a bit more carefully than if you know they'll just make do without you for a week. Think about a time that works best for you to get away first -- have a few candidate days or weeks in mind before you go talking to your boss. Then ask your boss which of those times works best for them.
A difficult boss might tell you that they can't have you gone during any of those times. If that happens, don't let that be the end of the conversation -- make sure they suggest some times to you that work best for them. Be assertive, and change the conversation from "you can't leave now!" to "when can I leave, and what should I do to make it easier for you while I'm gone?" For many of us, there's just no "good time" to take a holiday, so stop waiting for one and set down a time.
Any Time Can Work
Some people will tell you to wait for a "slow time" at the office. If your work has busy and slow periods, then definitely take advantage, but recognise that you'll be competing with everyone else for leave during those slow times. Getting in early helps. Some people say you should wait for a big project to conclude before taking a holiday, but there are merits to slipping away in the middle of a project, as well.
Cost is another factor. While you might occasionally score a last-minute bargain, advance planning is generally a better way to pay a reasonable price. You'll also have the advantage of more choice.
Whether it's the middle of the summer or a holiday getaway, the most important thing about timing is when it's good for you, and when you can get away without making life terrible for your coworkers (and subsequently, for yourself when you get back).
We've discussed how to hit the ground running when you get back from holiday, but some of it requires prep before you even leave. It's vital to make sure everyone knows you'll be gone, be clear that your work is either covered or can wait until you get back, and to make your home and office comfortable places to come back to before you go. Arrange coverage well in advance of your holiday, and do a little extra work every day leading up to your leave so you're not crunched in the last two days before you take off.
With a little prep, you can clear your desk before you get away without having to work heaps of extra hours just to make sure everything is just right before you go. Finally, if you're really worried, there are ways to work on holiday without missing the point of a holiday entirely , although we'd strongly suggest avoiding all work if you can.
However you choose to do it, take your holidays. Your leave is part of your compensation. You wouldn't leave your salary on the table just because it wasn't convenient for someone else, right? There's no reason for you to do the same with holiday and paid leave.
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