How to Schedule Your Vacation Time

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How to Schedule Your Vacation Time

Are you in need of some well-deserved vacation time?

Do you want to schedule vacation time for yourself this year as soon as possible, and most certainly before the year is through?

Sadly, it’s not uncommon for people to not use their yearly allotted vacation time.

Workers may have several days, and perhaps even weeks (or months!) due to be used, but for some reason they forget, ignore, or choose not use their vacation time.

This is a problem, not only from the perspective that vacation time is literally being left on the table, but that people are not allowing themselves to rest and relax from a busy daily routine.

If you’ve been meaning to schedule your vacation time for a while, but haven’t yet done so, then this is the post for you!

Consider this your vacation time assignment for the week. 🙂

In this post, I offer five simple steps to help you schedule your vacation time into your calendar.

Let’s get that vacation time planned right now so you can take a much needed rest from your work.


How to Schedule Your Vacation Time


Determine your vacation allotment.

Do you know how many vacation days you are allotted each year?

Some people know this number off the tops of their heads, while others have a vague or general idea.

We’re not going to leave anything to chance, so you’re going to do a little bit of detective work to determine exactly how many vacation days you have available to you at this very moment in time.

Where can you learn details about your annual vacation allotment? You may have to dig up your employment contract or employee handbook or log into your timesheet application or program. You can also contact the human resources department or get in touch with your supervisor.

When researching your vacation days, you should inquire about all details. This includes any existing vacation days that need to be used; perhaps you have accrued several vacation days from last year, or years prior. You’ll also want to find out how many vacation days you’ve accrued and used thus far in the year.

Check-in with others’ schedules.

If you’re planning on spending your vacation time with friends or family, you’ll definitely want to make sure your schedules are in sync.

Before contacting others, first decide how many total vacation days you want to take, followed by which weeks and months of the year you’d prefer for your break.

If you’ll be spending your vacation with friends, your partner, or significant other, check your work and school schedules to see which months and dates would be potentially good fits.

Do you all have a sufficient number of days to schedule a reasonable vacation? Who has a more restrictive schedule, and who has a more flexible schedule?

Find a balanced schedule that works well for everyone. Be sure to make note of any and all potential dates.

If you are in a household with school age children, roundup the school vacation or holiday schedule for each child. Then, block out their vacation and holiday schedules on a calendar. Compare these dates with you and your partner’s vacation allotments.

Do you have sufficient number of days to cover the length of the children’s vacation time? Who has a more restrictive or flexible schedule? Which weeks and months look more conducive to taking a family vacation?

Again, be sure to make note of any and all potential dates.

Propose vacation dates to your supervisor.

Once you’ve identified a few vacation dates, it’s now time to officially propose those dates to those in charge at your workplace.

Depending on where you work, you may have to fill out and submit a vacation request form to your supervisor and/or human resources. You may also need to directly email your supervisor or schedule a phone call or meeting with your boss to discuss further.

Be sure to specify the number of days you’d like to request, as well as the exact start and end dates of your vacation time. This might look something like, “Five days: Monday, December 21st through Friday, December 25th.”

Vague periods of time such as “the second and third weeks in October” or “the last week in August” can be extremely confusing and potentially misinterpreted by others. Those periods of times, for example, could potentially mean the last full workweek, the last workweek, the last few weekdays in the last week of August, and so on.

You want to get the exact amount and duration of vacation days you’re requesting, so be extremely specific in your start and end dates.

Schedule your vacation time into your calendar.

Congratulations! Your vacation time has been approved. Now, all you need to do is to physically schedule your vacation time into your calendar.

You’ll have a written record of your vacation days, and won’t accidentally schedule an event during this time.

If you use a single calendar or planner, this can be done in just a matter of moments. Block out all of your vacation days, starting with the beginning date and finishing with the last date. You can type or write in “Vacation,” for each day of your break, or write in the word “Vacation” across the span of several days.

If you use multiple calendars at work and/or home, such as shared a digital calendar, wall calendar, paper planner, and desk calendar, you’ll have to take a slightly different approach.

Simply write down the dates of your vacation on a piece of paper, and make a list of each of your calendars at home and the office. Then, update each of the calendars with your vacation time, one by one.

Reschedule standing appointments or meetings as necessary.

Lastly, it’s a good idea to double-check your calendar to make sure you don’t have any standing meetings or appointments during your scheduled vacation time. You don’t want to needlessly inconvenience others, or incur an avoidable penalty or fine, if you can help it.

Take a few moments to review your calendars and jot down any events that will need to be rescheduled, cancelled, or postponed. Then, pick up the phone or send an email to reschedule each appointment for a later date.

Don’t forget to remove the original appointment from your calendar once you’ve finished rescheduling it. Now you can start your vacation preparations, whether that means getting organized for your travels, crafting that travel itinerary or tidying up around your home for a relaxing staycation.

You’re well on your way: the countdown to your vacation has begun!

How about you? Have you scheduled all of your vacation time for this year? If not, which of the above steps do you need to start or complete? Join the conversation and leave a comment below!

Want to master time management? Check out The Order Expert’s Guide to Time Management, a self-guided eWorkbook designed to help you learn basic time management skills.

If you want to take your time management skills to the next level, learn more about my time management coaching.

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Rashelle Isip is a New York City-based professional organizer and productivity consultant who helps people get organized so they can stress less, have more fun, and be happier at home. Her work has been featured in Good Housekeeping, Fast Company, Cosmopolitan, The Washington Post, Business Insider, and The Atlantic. Get access to her free guide, 10 Simple Ways to Make Your To-Do Lists More Effective, by clicking here.
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