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How to Successfully Ask for Vacation Time Off

Are you ready for a vacation? Yeah, so am I. If you’re in the corporate world like us, you know that vacation is a necessary aspect of any full-time job. In fact, many people who work full-time do it in part so that they can afford awesome vacations. Sadly, many people don’t take as much time off as they have available. Even worse, some people don’t travel as much as they’d like because they’re afraid to approach their boss and ask for vacation time off.

That’s crazy talk.

We know that it can be scary to approach your manager and ask for a few days off, especially if you’re relatively new at the company. Everyone (myself included) is worried about getting that dreaded one-word, soul-crushing email back that reads “NO.”

To help you navigate this tricky situation, we’ve compiled our main tips below. In this guide, we’ll help you navigate the nerve-wracking task of asking to use your vacation days. We’ve even included our exact email template you can use to ask for vacation time off with your boss.

Perform Well At Work

In order to gain the trust of your boss and the people around you, you have to gain trust and rapport at work. The tried-and-true method of doing this is simple: be a high performer. Each job has different performance standards, but whatever yours are, aim to blow them out of the water. If you do this, your boss or supervisor will be more likely to give you what you want. Doing this over a long period of time will set you up for success when you go to your boss to ask for vacation time off.

Write A Clear, Persuasive Email

The most crucial step when you ask for vacation time off is, well, actually asking for vacation time off. If your boss is as busy and preoccupied as most, you’ll probably most effectively do this by writing an email. I basically always use some form of the following email when I ask for time off.

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“Dear [BOSS NAME HERE],

I’m emailing to put in a request to take the week of September 7-14 off for an international vacation. While I’m traveling, I will have very limited access to email, but will plan on checking it once a day in case anything urgent comes up. To ensure that things run smoothly while I’m gone, I have set up the following coverage:

  • [PERSON A] will run point on all of the incoming requests from vendors
  • [PERSON B] can serve as the point-of-contact for internal stakeholders for my project
  • [PERSON C] will run the training on the new software we are implementing and will be available to answer any additional questions

Please let me know by EOD today if this plan works for you. Thanks!

Best,
Kay”

It’s that simple. If you spell out all of the steps and precautions you’ll take to make sure things go business as usual while you’re away from the office, you’ll be more likely to get the magical “Yes, of course!” email that you’re not-so-secretly hoping and dreaming of.

Plan Far, Far in Advance

I know, I know. If you’re anything like me, you probably love to take advantage of cheap, last-minute flight deals and procrastinate until the last minute to book anything. Trust me, I get it.

However, if you are really nervous about asking your boss for time off, and you want to maximize your chances of success, asking for time off far in advance is the best way to go. This gives you time to plan around your days off, and gives your boss the peace of mind that there’s still some time to work around your absence. If you throw your vacation on the calendar one week beforehand, it can seem like it will be nearly impossible to gather an effective coverage plan when you leave.

 

Don’t Take Too Many Separate Vacations Back-to-Back

When I’m planning out my annual travel calendar, I try to space out my vacations so I’m not taking several days off during the same time of year. Avoiding stacking your vacation is a best practice across the working world. Not only does this limit your ability to use vacation days during other times in the year, but it also comes off negatively when you’re gone for long periods of time. Moreover, your boss will begin to notice if you’re taking a bunch of back-to-back trips within the span of a few months and start to say no. Be sure to space out your vacations to maximize your chances of getting your days off approved.

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Know What You’re Willing to Negotiate On

No way, you’re probably thinking, I don’t want to negotiate on taking my vacations. And you shouldn’t.

However, you should probably be willing to be at least a little flexible, especially if you’re in a really demanding job or if it’s your very first vacation. Compromise can mean things as little as checking emails once a day for anything urgent, or offering to work on the plane over to tie up any loose ends. It can mean not being accessible by email, but possibly being accessible by text. It could also mean, in the case of extended hiking or camping trips, that you let your boss know when you’re going to be off the grid completely.

The Bottom Line

When you ask for vacation time, you might be worried about an undesirable answer. However, if your boss trusts you, you write your email in a clear and concise way, and you’re willing to plan ahead, your chances of getting a “YES” will be much, much higher. Try out this expert formula before your next vacation and watch the magic happen!

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How do you ask for vacation time off? What are some of your secrets to doing it successfully? Share your thoughts in the comments!

Kay is a full-time media professional located in Washington DC who takes every spare day of time to travel the world. In the last year alone, she's visited over 10 different countries and taken a dozen short trips in between. You can typically find her wandering the streets of a city, taking ridiculous self portraits, or hiking a mountain somewhere. Connect with Kay: Facebook | Instagram | Twitter

7 Comments

  1. This was always the scariest for me and it’s so stupid! All of your tips are great though. I don’t really have any secrets other than everyone at works knows I’m obsessed with traveling so I think they kind of know a vacation request is just always looming LOL. Maybe, “Let your love of travel be known” would be my advice. 🙂

    • Thanks for commenting, Ashley! Totally feel you there – I definitely make my love of travel known at work too 🙂

  2. I must confess I have never experienced the amount of angst and stress that seems to have motivated this post. In all my jobs we usually had work scheduled in advance and took our leave around that. Now our department normally does a leave roster a year in advance, and in my department it ensures that only one person is off at any one time. Most people take 4 weeks at a time but I tend to split mine up and take two weeks at a time, usually 6 months apart. If my irritation or stress levels are high I may take a few days in April and September too.

    • Thanks for your comment, Razena! You’re so lucky to get 4 weeks off work! Most people in the US, especially young professionals, get two weeks or less off of work, including sick days. Many employers here actually disapprove of people taking them at all. In my last job, I wasn’t allowed to take more than one week off work at a time, EVER. So, I’ll say that it’s less a matter of angst and stress and more of a matter of realistic expectations and helping people get around them 🙂

  3. Yes, thank you! Such a helpful post because I HATE asking for time off especially after asking for two weeks off in a row and getting a talking to about how that was too much time at once.

  4. These are all great tips! I’m very lucky that my current job has unlimited vacation but it has the weird side effect of making me hesitant to actually ask for the time off. I’m so conscious of wanting to not be seen to be taking advantage. I think it helps that I typically take me trips in spring and fall while most people do a summer vacation.

  5. I never have trouble asking off for vacation because my boss likes me and the work I do, but my husband who is a manager with unlimited PTO always has trouble! How is that possible?!?! We deal with this struggle consistently, especially because we have Tuesday-Wednesdays off. This year has been full of weddings, graduations, family reunions and welcoming a new born baby. So every time he comes back from a three day weekend and needs another one off, everyone at his office is like, “oh hey Adam, going on vacation again?”. Even when we take a two day trip on our days off people give us a hard time about enjoying our life. Drives us crazy! We even do your first tip, perform well at work – my husband works 11+ hours, whereas his co-workers leave work early, yet they give him hard time about going on vacation…. It is such a shame that asking off for vacation is so difficult and stressful.

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