How to Take a Vacation in Your First Year


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You deserve that vacation. You’ve learned everything you need to know as a new hire: your duties and responsibilities, your company’s rules and regulations and even your co-workers’ quirks (for better or worse).

So what’s holding you back from asking for a break? Are you afraid your boss and co-workers will think: “Oh, she’s a career gal now. Bet she thinks she can slack off whenever she wants?”

That’s not totally true. If you plan your vacation according to the steps below, you can enjoy it to the fullest, without feeling guilty about all the work you left behind: 

Wait at Least Three Months

According to experts, three months is usually enough for a new hire to gain her footing. It’s a good rule of thumb, but like all rules of thumb, there are exceptions.

You still have to figure out whether your company’s culture is vacation-friendly, for lack of a better word. For example, if everyone’s always firing on all cylinders, it might reflect badly on you if you leave your co-workers in the middle of a busy season. On the other hand, if the environment’s relatively laidback, and your hours are flexible, your boss probably won’t mind seeing your empty desk for a day or two.

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Inform Your Boss As Soon As Possible

The moment you’re 100 percent sure your road trip across the US will push through, tell your boss. Chances are she’ll appreciate more than your compliance with the rules, she’ll also appreciate your initiative.

If she seems to have reservations, try to compromise. Say something like “Okay, so (original vacation date) isn’t possible. How about (new vacation date)? Will that work for the team?”

No matter how you choose to phrase it, make sure you take your co-workers into consideration. You want to give your boss the impression that you’re the type who thinks things through – which is a good sign, as far as companies are concerned. 

Wrap Up Any Unfinished Business

Speaking of thinking things through, try to leave as little work for your co-workers to pick up as possible. That way, they won’t mind you disappearing on them next time, and you’ll avoid being labeled as the resident slacker.

In case you’re unable to finish your work on time, you can either:

  • Ask for a deadline extension
  • Offer to do your work remotely
  • Move your vacation to another date

Your boss would probably prefer the last one, especially if the work you’ll leave behind is urgent. So if you somehow accumulated a Burj Khalifa-sized workload a day before your vacation, try to finish all of your high- and medium-priority tasks before you head home.

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Prepare to Have Someone Pick Up After You

What if you can’t finish your tasks by the time? Use your charming demeanor and kindly ask for help. Think about what your co-workers might need from you while you’re gone. Then, hit up your office buddy, and say “Hey, I won’t be here on (date). If you need (what), you can get it from…” You can also print instructions for your co-workers, and leave it on your desk for their reference.

Be careful about delegating sensitive or confidential tasks. Either you don’t delegate them at all, or delegate them to someone who has the same level of clearance as you do.

Set Up Those Auto-Responders

Keep in mind that there are people who may need you, and aren’t aware that you’re on vacation – such as co-workers from other departments, and clients. For them, you can set up autoresponder email messages tailored to the recipient. Make your message brief, straight-to-the-point and polite. If possible, give them the name and contact details of the person who’s temporarily filling in for you, so they won’t feel left in the lurch in case of emergencies.

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Be Available (Within Reason)

If your company encourages remote work, they’ll probably email you even when you’re in the middle of frolicking under the sun. Naturally, this makes you undecided about whether to leave work at work, or whether you should treat your winter vacation as an extension of your office hours.

In that case, try a middle ground approach. Sift through your messages, sort them according to priority, and decide which ones need to be immediately addressed. Your boss will appreciate it if you try to work through at least some of your pending tasks.

Give Yourself an Extra Day Off Before Going Back to Work

You’ll need an extra day to psyche yourself back into work mode. If you’re anticipating two Burj Khalifas’ worth of work when you get back, that extra day will help you prepare physically, mentally and psychologically. Take a deep breath, wind down and look forward to another productive day ahead.

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Sarah Landrum

Sarah Landrum is a freelance writer and the founder of Punched Clocks, a blog dedicated to helping readers navigate the job search and work world to find happiness and success. She specializes in career advice but is also a health nut and DIY junkie with a passion for living life to the fullest. You can follow Sarah @SarahLandrum