19 Fun Things to Put on a Calendar

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19 Fun Things to Put on a Calendar

Do you want to better manage your time this year?

Are you looking for a fun way to add some spice and pizzazz to your calendar or planner?

Calendars are a convenient way to keep track of all the different meetings, appointments, activities, events, and functions that take place in your life.

But who says calendar entries have to be plain, boring, unimaginative, and uninspiring?

In this post, I offer a collection of nineteen fun things to put on a calendar.

Many of these items can be applied to your choice of paper and/or digital calendars.

There are a few items, however, that apply only to paper calendars. Trust me…you’ll know them when you see them!

And of course, feel free to use this short list as a springboard for your scheduling.

You might come up with your own customized list of items to add to your calendar.

Are you looking for a handy list of practical items to add to your calendar this year?

Be sure to check out my blog post, 40 Things to Schedule into Your Calendar.


Vacation time

Ahh, rest and relaxation! Seriously though, vacation time should be one of the top “fun” items on your calendar.

It doesn’t matter whether you’re taking a few days or weeks off from work or school, whether you’re traveling to some remote locale abroad or simply having a “staycation.”

You should plan your vacation time and take your full vacation time this year.

Personal time

Every now and then we need time for ourselves to take stock and plan for the future. You can think of this time as a type of “pause” button from the routine of daily life.

Personal time includes any time spent dealing with a family matter, recovering from a health issue, making a career or educational change, or just some time away from the hustle and bustle to rest and reflect.

Holiday dates

What holidays do you celebrate during the year? Take a moment to pencil in any local, city, state, or federal civil holidays, as well as any religious holidays or celebrations.

Don’t forget to add in ample time for holiday preparations, including shopping for clothing, hanging up decorations, preparing food, or attending services.

Party dates

It’s time to celebrate! Make sure you have upcoming birthday, wedding, anniversary, graduation, and other parties included in your calendar.

Be sure to schedule any necessary preparation time before and after a party, including time off from work/school, food and decoration shopping, gift shopping, and outfit shopping.

Sport seasons

Here’s a handy tip for both spectators and players alike: track sport seasons in your calendar.

You can add football, soccer, baseball, basketball, tennis badminton, ice hockey, stock car racing, horse racing, and more. If you’re really in the mood, you can schedule pre-season games and playoff dates, too.

Exhibit openings

What’s new in the world of traveling and limited-time exhibits in your neck of the woods?

Write down any and all appealing upcoming exhibits in your local history museums, art galleries, science centers, botanic gardens, historical societies, and colleges/universities.

Shopping outings

Love to shop? It doesn’t matter if you adore clothes, power tool, computer, antique, or candle shopping…it’s just one more thing to look forward to during the year!

Go ahead and add in any routine or special shopping trips, outings, excursions, and sales to your calendar, ASAP.

Inspirational quotes

Give yourself a boost of motivation and inspiration for the next twelve months by writing down different inspirational quotes in your calendar.

You can write in your current favorites, or find brand-new collections of quotes to learn from, and appreciate over the next coming year.

Funny sayings or phrases

Let’s face it: sometimes, you just need a laugh! Keep your funny bone tickled pink by jotting down a couple of in-jokes, witty anecdotes, humorous sayings, side-splitting short stories, or funny phrases throughout the year in your calendar.

You’ll have something to smile about year ‘round.

Personal sayings

What positive or encouraging sayings or statements do you want to be at the top of your mind, every single day, week, or month?

Write down a list of your top personal sayings or statements, and jot them down in various places throughout your calendar for a quick reminder and does of encouragement.

Goal dates

If you’ve planned a project for this year, make sure it will come to pass. Schedule in all of your work, school, and personal goal dates.

This can include the completion of that six-month long work assignment, the completion of your history term paper, or when you reach your weight loss goal.

Online courses

Did you sign up to take a continuing education, lifestyle, hobby, or other online course this year?

If so, take a moment to add the courses dates and sessions to your calendar. This way, you’ll have time in your calendar to take your course, and complete any related assignments or exercises.

Release dates

Stay on schedule when it comes to your favorite media by adding release dates to your calendar.

Keep track of the latest book release by your favorite author, see your favorite actor in their latest blockbuster movie, snag a signed copy of CD or LP by a beloved musician, or buy one of the hottest new fashions from your favorite designer.

Performance and show dates

Have you purchased tickets for an upcoming performance or show? Tuck those tickets away in a safe location and make sure the big day is on your radar!

Schedule in all of your arts, music, and entertainment performances, shows, concerts, plays, and events into your calendar.

Family or friend leave dates

Do you have family or friends who are working, studying, or serving abroad and/or traveling? Chances are you probably have their leave or return home dates etched into the back of your mind.

However, it doesn’t hurt to add these dates to your calendar, so you can adequately prepare yourself and your household for their return.

Special anniversary dates

Has it been a year since you quit smoking, five years since you ran your first marathon, or ten years since you graduated from college?

Keep the memory and your motivation alive by adding in a variety of personalized special anniversary dates to your calendar. You can include any number of work, school, personal, family, health, wellness, or lifestyle achievements and milestones.

Doodles, drawings, and sketches

Set your imagination and your pen or pencil free! Just grab your favorite writing implement and your paper planner or calendar and you’re good to go.

You can doodle in the margins of your calendar during breaks, make quick sketch of the room you’re sitting in, draw imaginative fashions or outfits, invent new cartoon characters, or draw a beautiful mini-landscapes in the blank spaces of your planner.

Physical items

Personalize your paper planner or calendar the old-fashioned way with little mementos and notes. You can add style and sparkle to physical calendars using any combination of colorful sticky notes or tabs, decorative stickers, washi tape, glitter, ribbon, and glue.

You can also affix personal ephemera such as concert ticket stubs, special thank you notes, fortune cookie fortunes, love notes, drawings, and other items to your calendar, too.

New paper planner or calendar research

If you love using paper planners or calendars, then you know how exciting it can be to browse through planners in July/August, and at the end of the year.

Mark your calendar to browse stores in person and conduct online research so you can find your next favorite planner in a timely fashion.

How about you? Which of the above items are you going to add to your calendar this year? Can you think of any other fun items that can be added to a calendar? Join the conversation and leave a comment below!

Create Your Own Customized Calendars

Create your own customized printable calendars from the comfort of your home or office.

These fully-compatible daily, weekly, and monthly printable calendars make it easy to plan your days at home, the office, and school.

Click here to learn more! 

Love using pen and paper to plan your projects, assignments, tasks, and to-dos? Looking for interchangeable daily, weekly, and monthly calendar layouts? Be sure to check The Order Expert's Calendar Printables!


Follow Rashelle:
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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