How to Ask for a Two-Week Vacation

How to Ask for a Two-Week Vacation

Written by Alexandra Baackes on

Alexandra Baackes is a traveling writer, designer, and underwater videographer. She is currently in her fifth year of living as a full-time nomad—follow along on her website.

How to Ask for a Two-Week Vacation

How to Ask for a Two-Week Vacation

To some people, asking for two weeks off—and getting it!—is a total breeze. For the rest of us, requesting that many vacation days can make us a nervous wreck! Getting the getaway time you deserve doesn’t have to be scary: Get expert advice on asking for a two-week vacation—without offending the boss.

You’ve chosen a destination, picked up a guidebook and researched plane tickets, accommodations and activities—so what’s left? For many of us, the biggest obstacle standing in the way of our next great adventure is requesting the time off we need to make the trip a reality. It can be such an intimidating proposition that many of us wait until the last minute to ask our boss, or worse, actually avoid taking a dream trip because it would require too many days away from our desks. But despite the most common fears (ie, that we’ll look lazy or uncommitted to our work, or that we’ll be easily replaced) most superiors would be surprisingly understanding of our desire for an extended break—if only we would ask them! The key to making a successful request is knowing exactly when and how to approach the subject. Follow these tips and guidelines culled from career break experts—and you’ll seriously up your odds of getting out the door and on a plane in no time flat.

Time Off Tip #1 Know Your Rights

Before you approach your boss, review your employee manual or contract to be clear on how much time off your employer has committed to giving you based on your tenure with the company. While it’s always possible to ask for more time off than what you’re officially owed, it always helps to come to the table prepared with the info your higher-up needs to make a decision.

Time Off Tip #2 Have a Strong Pitch Prepared

Have you always dreamed of traveling to South America to hike through Patagonia, or visiting Kenya to volunteer? If you want the extra days to take a once-in-a-lifetime adventure, be sure to share your passion and your plans with your boss. While it’s not necessarily his or her business what you’re doing when you’re off the clock, most people want to support their employees’ extra-curricular goals. Even if you’re just planning a getaway to rest and recharge on the beach, that’s reason enough to take a longer break—studies show that workers who truly unplug (that means no smart phones!) during a long break tend to be more productive when they return.

Time Off Tip #3 Choose Your Dates Wisely

An accountant will have a hard time going on safari in the middle of tax season, no matter how strong their pitch or how pleasant their boss. Request your two-weeks off during a time of year that’s not in the middle of your profession’s busiest season!

Time Off Tip #4 Plan Ahead

Request the time off as far in advance of your vacation as possible—this makes it possible for your boss to plan for your absence. Outline how you will get your work done ahead of time, or who will take over for you (and, if absolutely necessary, how you will check in from the road). Make it clear that your preparedness will mean your vacation will not have a negative impact on the office. Note: You may also want to make your case to the boss on a day when his or her schedule isn’t jam-packed, like Friday morning (if possible, check his or her calendar through your company’s online meeting scheduling system or an assistant).

Time Off Tip #5 Put It In Writing

Follow up on your meeting with management by putting your request into an email with dates and details clearly outlined. While you may be acutely aware of the days you’re planning to be away, others can easily forget what you told them—or what they actually agreed to. Keep the email on hand, and send a reminder a few weeks before hand so there’s no last-minute confusion on your whereabouts.

Time Off Tip #6 Be a Class Act

Once you have received final approval, be sure to thank your manager for his or her understanding. If it seems appropriate, bring your co-workers and boss back a token gift from your travels. And most importantly, be sure to enjoy your adventures so you can come back refreshed and ready to work!

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