How to Plan a Vacation and Still Get Ahead

The day you got hired, a human resources representative probably detailed a long list of benefits that came with your job. Remember those 10-or-more days you were supposed to use for vacation?

Have you used them, or are you like the 30 percent of Americans who do not use all their vacation time?

We get it. Work can be busy and stressful, and the thought of stepping away for an extended period of time might make you nervous.

Aside from all the work you imagine piling up, you might imagine that it could hurt your chances of getting that big promotion.

It’s time to let go of all of the preconceived notions that come with taking time off, though, because most of them are false. As long as you’re planning your getaways the right way, you can do it without getting behind in your career.

Which is good, because there are so many benefits to skipping town from time to time — and one is coming back refreshed, so you’re a more valuable employee.

It’s a win-win.

If you’re ready to hit the road, here are 12 tips to help you plan and prep for your trip so you won’t miss a beat or drop the ball:

1. Plan It Right

You probably know the time of year that work is busiest and when it tends to wane. That means you also know the best time to schedule your vacation.

Try to find a lull in your schedule, as well as in your department’s, so your time off is more likely to be approved. More importantly, though, you won’t be leaving your colleagues in the lurch — heading out of town when you’re needed most wouldn’t make the best impression.

2. Make up for Your Absence If Need Be

Sometimes, you do have to take time off of work for a set event. Weddings, graduations, retirement parties — all of these come with dates that can’t budge, even if they come at a busy time of the year.

In this scenario, you could provide your boss with a pre-vacation work plan to get yourself ahead, as well as a coverage plan for while you’re gone. Make it clear to your boss that you’re only going at this time because you have to and that you’ll go to any length to make it work for everyone.

With this type of prep, your boss will have a hard time saying no or faulting you for requesting the time off — they’ll also likely remember your dedication later on as well.

3. Wait for the Opportune Moment to Request Your Vacation

You might not have access to your boss’s Google calendar, but you probably know when they are doing some serious work — in fact, you’re likely all working together on whatever project it is that’s stressing your boss out.

Clearly, this is not the time to ask, “Hey, can I go on vacation?” Wait for a breezy week when it’s easy to schedule some face-to-face chat time to discuss your plan for how everything will go without you.

4. Answer the Big Questions

Once the dates of your vacay are approved and ready to go, it’s time to start prepping for your own absence. Who should you notify of your impending time off? Who will be your clients’ point of contact? Who needs to be rallied to step in on your big projects?

Think of any and all questions that need to be answered before you’re out of town so no one else has to scramble to figure out the answers while you’re away.

5. Update Any Relevant Procedural Information

You obviously know how to do your job. Depending on the structure of your company and the specialty level of your position, you could also be the only person who knows how to do it.

So, before you go, it’s a great idea to update any training or work manuals you use(d) to better understand and complete your tasks. If that doesn’t exist, jot down some pointers, reminders and other pertinent information for the person filling in.

You should also write down any passwords that someone would need to get into your computer, filing cabinets, etc. All of this works to minimize the chance someone will have to call you while you’re out of town — or note your absence in a frustrated way.

6. Don’t Be Afraid to Delegate

Unless you’re a manager — or have a managerial instinct — assigning jobs to others might feel foreign and weird. But, you gotta do what you gotta do to go on vacation, so delegate your to-dos away.

You can put your mind at ease by delegating the right way. Make sure you are clear in your instructions and put your tasks in the hands of those you trust most.

7. Communicate Your Absence

It doesn’t matter your line of work — you’ll need to let people know you’re going to be gone. Start informing your colleagues, clients and other relevant people between one and two weeks before you head out.

A couple days before you leave the office send a reminder email to your department.

And right before you leave, add a more general out-of-the-office message that will auto-reply to your emails and update your voicemail for any missed phone calls.

8. Tidy up Your Workspace

Whether it’s a cubicle or a corner office, your workspace is a reflection of you. Make sure yours is presentable before you head out so anyone who walks past or pops in for any reason will see that you’re organized and on top of your work — and they’ll be able to find something if they need to in your absence.

9. Tie up Loose Ends

The pre-vacation time period is a great opportunity for you to finish up the tasks and projects you’ve been meaning to finish, but haven’t gotten around to. You won’t want to come back to the same long list of to-dos, so make a point to work hard in the weeks leading up to your getaway to check everything off. Set goals each week, or each day, to finish up certain projects. Give yourself a little reward to keep yourself motivated.

10. Stay (Somewhat) in Touch

So many sources will tell you not to check that e-mail under any circumstances while you’re away, but it might actually cause more anguish. In fact, some believe checking in periodically can improve your peace of mind while you’re gone — you’ll know for certain you haven’t been needed for anything important.

It’s your call to make depending on the nature of the vacation, and of your work.

Make sure you’re checking in no more than once per day and going at a reasonable clip, though — replying to only those red-flagged notes. Everything else can wait, and your out-of-the-office reminder email will do all the talking for you.

11. Trust Your Coworkers

This idea goes along with the importance of delegation, but it’s necessary to trust your coworkers emotionally as well. Take a deep breath and remember your colleagues work alongside you for a reason: They’re very much able to take on the tasks you’ve left behind. Don’t worry about bad things happening while you’re gone because your team has your back.

12. Come up With Your Return Strategy

Finally, somewhere in your preparation, you should make sure the week after vacation is an easy one. Don’t try to stack meetings, conferences, presentations, etc. Instead, give yourself time to get back into the groove before doing anything drastic.

I always try to take one day with no meetings, or even return mid-week, so I don’t get overwhelmed when I return to my desk.

When you do jump back, that refreshed, post-vacation brain will make you more creative and productive.

If for no other reason than that, get out of town and use those vacation days!


Are you planning a vacation? Let us know all your tricks for staying on top of work while you’re away in the comments!

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How to Plan a Vacation and Still Get Ahead

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Sarah Landrum is the founder of Punched Clocks.

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