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20 Challenges to Help You Write Your Way Into 2020

Updated on May 19, 2022Writing Tips
2020 blog cover.jpg

It’s the end of the year, and if you’re like us, you’re looking toward 2020. If you’re having a hard time setting goals, or if one of those goals is to write better or get a hang of the writing process, let us help you get those creative juices flowing. After all, the greatest writing tip we can offer is just to write more.

Each day, from now until the end of the year, we’ll add a new, quick, manageable writing prompt. Try out one, or try them all, and share your efforts with us!

Write more, write better.
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December 31: Instead of New Year’s Resolutions, try New Month’s resolutions.

Start tackling your goals list bit by bit. Assign three small goals/tasks to yourself to accomplish in January. Do the same thing at the end of each month. 

December 30: Text your best friend and tell them what you like about them.

Your best friend rocks—that’s why they’re your best friend! Shoot them a text that lets them know what an incredible person they are.

December 29: Pull up your list of things you like about yourself and add five-to-ten more things.

That’s right, you have to come up with more good things about yourself! Good thing there are so many good things about you. Again, depending on the level of your self-esteem, you may want to turn to your friends to remind you what’s great about you.

December 28: Break down your larger goals into smaller tasks—about five per goal. 

No one accomplishes a huge task all at once. Break down these larger goals, like learning the mandolin, into smaller goals. For example, smaller goals could look like this:

  1. Buy a mandolin
  2. Research mandolin instructors.
  3. Choose one instructor and contact them.
  4. Learn two chords.
  5. Set up regular lessons.

December 27: Assign your smaller goals a due date, and mark them on your calendar.

Whatever calendar you use, whether it’s a paper planner or your phone calendar, set due dates for your small goals and set reminders for a week before they’re due. Space them out, so you don’t have to do them all at once.

December 26: Make a list of 26 goals for 2020, of any size and scope.  

These goals could be as small as “automate my credit card payments” or as large as “learn to play the mandolin.” Just write down 26 things you want to do, whatever comes to mind. We’ll get to how you can actually take action on them in the next few days.

December 25: Send personalized goodwill texts to two-to-five important people in your life. 

You wrote the paper letter, now write the digital ones! Pick some people you love and send them holiday goodwill greetings. Tell them why you’re grateful to have them in your life.

December 24: Brainstorm some rituals that help you relax, write them down, and do one of them.

For those who celebrate Christmas, these two days can be full of joy and full of family stress. Think about times you’ve been really, truly relaxed or clear-headed, and what it took to get there. Then, once you have them written down, try doing one of them. Now you have a list for future self-care days, too.

December 23: Write a real, paper letter to a loved one. Go to the post office and send it.

Sometimes it’s actually easier to express feelings of gratitude to loved ones when you write them by hand. Write a friend hello, tell them how you’re doing and what you appreciate about them, and send it to them by mail. You may need to ask them for their address, but that’s part of the fun! You might even get a pen pal out of it.

December 22: Write down two habits you’d like to start and two habits you’d like to quit.

This is where you can start really getting into the New Year’s Resolution spirit. Think about small habits you want to cultivate—meditating a couple of times a week, or meal prepping every Sunday night, for example. Then, come up with two things you do that you want to stop doing, like biting your nails or hitting “snooze” three times every morning.

December 21: In honor of the solstice, create a resource for bad days by writing down twenty-one things you like about yourself.

When times get rough, your self-esteem can take a toll. It’s hard to remember why you’re awesome when things are going wrong. So write down twenty-one things you like about yourself. If you can’t think of anything, consider asking your friends for ideas.

December 20: Write down ten places you’ve visited in the past decade and ten places you want to go.

Maybe you’re a world explorer and travel blogger, or maybe you have fun going to new places within an hour or two’s road trip. Write down some places you’ve been, and add any new places you want to go.

December 19: What are your nineteen favorite memories of 2019?

This one might take a little longer. Think back on your favorite moments this year. As with all of our challenges, they can be small moments. If this was a tough year, reflecting on these memories can help you get inspired.

READ MORE: Resources to Help You Improve Your Writing at Any Age

December 18: Make sure all of your holiday cards are written!

However you greet your family and friends for the holiday season, make sure you have them all ready to go! Stamp your letters, draft your emails, pick the cutest picture of your dog in her Santa costume and write that adorable caption in advance. It’ll save you a lot of stress in a few days.

December 17: Write down seventeen changes you want to make by 2029. (They can be small!)

Now that you know all of the changes you’re capable of, try writing down some prospective ones! These changes don’t have to be drastic, and can be differentiators from patterns you’ve had in the past, like maintaining friendships you’ve let flag a little, or improving your writing in small ways.

December 16: Write down sixteen changes in your life since 2010.

The changes that you note should be tangible, like changing jobs, moving cities, or connecting with new friends. The goal here is to show yourself that you’re capable of a lot of change, even if it doesn’t always feel like it.

READ MORE: How Writing Helps People Connect

December 15: Write down one-to-five new things you learned about yourself since 2010.

Think back to who you were ten years ago. Surely you’re not exactly the same person you were then. Write down some things you know about yourself now: That when it comes to accomplishing a goal you can really apply yourself, that you needed to make a career change, that you can’t sleep a full night if you eat dinner after 9 p.m., or that you thought you were a dog person until you ended up with a cat. 

December 14: Write down one-to-four new things you learned about yourself in 2019.

Just as you can always discover something new about your partner, best friend, or colleague, there’s always something new to learn about yourself. Did you discover a love for a new hobby? Did you encounter a new challenge that you surprised yourself in overcoming? (Grammarly learned some new things this year—check out five of our new features!)

December 13: Allow yourself to reflect on one-to-three goals you didn’t accomplish, and mark which ones you want to carry over to next year.

Sometimes we bite off a little more than we can chew—that’s okay! If we never set ambitious goals for ourselves, would we ever grow? So let yourself acknowledge the things that didn’t quite work out as planned—maybe you didn’t get your screen time down after all—and think about why. Do you want to continue trying for these goals in the new year, or have your life, situation, or priorities changed too much for it to be relevant?

December 12: Write down your two biggest accomplishments from this year.

Instead of jumping to ways that you could improve next year, give yourself credit! Think about and write down the two goals you accomplished this year that you’re the proudest of and why you’re proud of them.

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