Hey, we get it: asking to take a vacation can be kind of intimidating. Even if you’ve proven yourself to be a valuable asset to the company (the Anderson deal probably would have closed anyway, but that sweet Powerpoint presentation you put together definitely helped seal it) and you get along great with your boss (they’re the one who dubbed your Powerpoint skills “sweet”), you might be worried that any serious time away might hurt your standing in the cubicle power struggle or that requesting some vacay might make it look you’re not a team player.

So you don’t bring up the whole time off thing (you’re fine just taking off the days the office is closed on federal holidays) or even bother to use all your vacation days. You’re not alone. An astonishing 41% of Americans didn’t take a single vacation day in 2015! And more than half of all Americans (55%) didn’t use all their allotted vacation days.  


Lots of people fear that taking time off will hurt their relationship with their employer, but according to career expert Ellen Reeves, author of Can I Wear My Nose Ring to the Interview?, it’s not so much the time off but the request that matters.   

“When and how you ask makes all the difference in maintaining a positive relationship with your employer,” Reeves explains, adding: “If you’re afraid to ask, ask yourself why you’re afraid. Are you asking at the last minute? Have you let work slip lately or missed a deadline?

Reeves also points out that taking vacation time is essential not only for your health, but also the the health of the company you work for. So taking the time off that you deserve is a win-win situation that should be at the top of your to-do list!

Here are some rules to play by that should make it easier for your boss to say yes to that vacation, according to Reeves.

Know Your Company’s Policies


When asking your boss for time off, you need to properly understand your company’s rules regarding vacations and time off.

Schedule a meeting as much in advance as possible to talk about time off with your employer; make sure both of you are up-to-speed about how many vacation days you are allotted and how many you have left to use.” Reeves says.

Whether it’s formal or informal, knowing the rules sets the stage for a positive conversation. Reeves also says that it “helps to know what the unwritten office rules are about taking time off are as well as official office policy.” Get a feel of the office culture to determine what’s appropriate when it comes to taking time off.  

Give a Heads up as Far in Advance as You Can


Giving as much notice as possible is not only thoughtful, but it will help you ensure a nice long break that is stress (and email) free. Providing plenty of time for your boss and coworkers to prepare for your absence is all that matters. Even if you forgot about your cousin’s wedding and had to book a last-minute flight, your employer does not want to hear details.

“If you went ahead without asking and bought a last minute, non-refundable ticket, that’s not the employer’s problem,” Reeves explains. “People are juggling schedules and dropping a last minute getaway on your boss isn’t exactly ideal.”

Make Your Absence as Painless as Possible


Vacations are not something to fear, they exist for a reason. Your boss doesn’t want you having any workplace groans and grumbles or seeing you completely stressed out. The truth of the matter is: your boss actually wants you to take time off!

“All your boss cares about is that your work is going to be done in your absence and that you’ve laid out a plan with his/her approval,” Reeves says.

Assure your employer that there will be as little disruption as possible. Who can you delegate your work tasks to? Are you willing to be contacted in a crisis situation? Understand who bears the burden when you’re gone and craft a vacation proposal that your boss can’t refuse.

Ask, Don’t Tell


There is a very important distinction between a demand and a request, and when asking for approval, one is much more effective than the other. Casually telling your boss that you’re going to be out of the office for the week is not the way to go. Asking for vacation time takes advance preparation. According to Reeves, you should approach the situation respectfully and “don’t just mention it as you bump into each other in the hallway.” She also suggests putting the agreed upon request down on paper (or probably, in an email). Even if you happen to be best buds with your boss, always be diligent and schedule an appropriate time to request and discuss time off, then follow it up with an email.

And One Final Point to Remember . . .

Enjoy Your Vacation!

Having time off from work is a great way to recharge your batteries and can actually make you better at your job! But remember, as Reeves puts it, “When you’re on vacation, you’re on vacation. When you’re back at work, be back at work.”


Do you have any tips for asking your boss for time off that we missed? Let us know in the comments!

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From Australia, skateboarder/explorer.