May: Simplify Month, Free Printable Calendar with Weekly Challenges

It's safe to say that we're all here on a journey to find joy in our daily lives. However, sometimes we get caught up in the daily grind and life becomes a little overwhelming. This month, we hope to help you slow down and simplify as you follow along with our Simplify Month challenges.

Simplify your life with a month of challenges from Fun Cheap or Free

So far this year, we've focused on cleaning up our wallets as we Focused on Finances. We've made a greater effort to grow and nurture relationships as a part of the February challenges. In March, we made an effort to get into better shape as we focused on fitness. Hopefully after last month, your house is feeling a little bit more organized! This month, we just want you to focus on being present and soaking up every single moment.

It sounds pretty easy, but we've found that slowing down, embracing the moment and keeping life simple is one of the hardest things for people to do these days. Especially for those who are constantly taking care of the needs of those around them… we're calling it:


So who is ready to take a few things off your plate? Keep reading to find out how to take a few baby steps to simplifying your life this month!

Simplifying can be a mighty big challenge.

May Simplify Month Challenge - It's Self-Care Week from Fun Cheap or Free

From the words of Eckhart Tolle, “In today's rush, we all think too much – seek too much – want too much – and forget about the joy of just being.” In order to really enjoy the present, we need to slow down and embrace the little things.


Step 1. Print the Simplify Month calendar – if you're not already on the mailing list, SIGN UP HERE to get the May calendar emailed to you.

Step 2. Follow along! Each week there is one main challenge for you to focus on all week. Plus a bonus challenge, tip or helpful habit to keep you focused half-way through the week. Then of course, wrap up the week with a simple date or family night to help keep you focused on the people that matter most.

Step 3. As always, adapt the calendar to work for your needs and help you get the most out of the monthly challenge.

Who is ready to join the challenge!?

Need a little extra encouragement? Brene Brown says, “It takes courage to say yes to rest and play in a culture where exhaustion is seen as a status symbol.” Have courage, my friend!

Since May starts mid-week, there is a Bonus Challenge before the weekly challenges officially begin. This is the perfect opportunity to sit down and take a good 5-10 minutes to think about what you want to get out of this month. We call it a “Thought Download.” Simply open a notebook, grab your favorite pen and start writing in response to the prompt!


It's time to get down to business. Choose 3 things to say no to this week that don't really fit your schedule. I know you might be a habitual yes person, but sometimes you just need to know your boundaries. If you're not used to saying no, it might seem awkward at first, but just remember that YOU matter just as much as the person you are saying “no” to!

Simplify Month Challenges - Baby steps to help you simplify your life from Fun Cheap or Free

There are many tough situations that we need to say no to, but don't know how. Here are a few ways to say “no” while still being kind:

  • “This week won't work. Do you have any time in your schedule to meet next week?”
  • “I'm sorry, but I can not do that this week. My schedule is already full.”
  • “No, that doesn't work for us.”
  • “I'd really love to help you out with that, but this is not a good time. Please ask again!”
  • “Thanks for thinking of me, but I have too much on my plate right now.”
  • “I'm honored that you asked me to go with you, but we already had plans.”

Bonus Challenge for this week is a super helpful habit to get into. Plug your phone in at 8pm and don't touch it for the rest of the night. Not only will this help you sleep better, but this will allow you a little time to unwind without any distractions, which means you might be able to get more done the next day!


Choose 3 things you can delegate to someone else this week – then get to delegating! We all have a lot on our plates, but we're surrounded by people that have skills. We don't have to do everything on our own. What can you easily delegate that will actually make a difference?

Here are a few ways that you can successfully delegate:

  • Ask kids to help around the house – check out this list of chores kids can do by age!
  • Enlist your family to help with dinner each night.
  • Hire a teenager to watch the kids so you can get some free time.
  • Find a carpool group you trust and take turns dropping the kids off instead of doing it every day.
  • This is a little out of the box, but Get Your Pretty On will take over the daunting task of deciding what to wear everyday! Let them hook you up with a wardrobe plan that is beautiful and easy to follow!
  • Have Walmart Grocery employees shop for, bag up, and load your groceries into your car!
  • Do a meal swap! Get together with some friends and make ahead several meals and swap them out. You'll all go home with easy dinners.

May Simplify Month Challenge - Delegate Week from Fun Cheap or Free

Bonus Challenge: Simplify meal time. Instead of running away with your hands up or crying in the corner during the most hectic and sometimes dreaded part of the day, make dinner easier! Take a few minutes and prep easy meals that your family loves. Use the crock pot, prep double and freeze for later, or have brinner aka breakfast for dinner. Do whatever you can to make your meal time easier and more enjoyable for YOU!


Take a deep breath because this one might be hard for some of you. Schedule 30 minutes every day this week just for you-time. Breathe! You can do this! It might be the last 30 minutes before you go to bed or it might be on your lunch hour, but take time for YOU this week.

Simplify Your Month Challenges - Reflect and take some time for yourself. Challenge from Fun Cheap or Free

Understandably, there might be huge obstacles to this task, but you deserve the time, friend! Put it on the calendar, find a friend to trade babysitting with, or wake up early – you are worth it!

Here are some affordable self-care ideas:

  • Read a book
  • Read a magazine
  • Paint your nails
  • Take a bubble bath
  • Catch up on your favorite show
  • Give yourself a facial
  • Call a friend and catch up
  • Meet up with a friend for lunch
  • Go on a walk
  • Exercise
  • Paint
  • Craft
  • Take a nap
  • Get outside for some Vitamin D
  • Do something you used to love as a kid
  • Trade massages with your spouse
  • Listen to your favorite music
  • Sit alone in the quiet
  • Journal

Bonus Challenge: Set aside a “power hour” to take a nap or do something for your soul. You might want someone to join you and that's okay. Whatever you do, make sure it's life giving and brings you joy!


For the last challenge of the month, we're encouraging you to take something that is weighing you down… and tackle it! This might be the hardest challenge of the month, but you're going to feel like a million bucks when you're done. 

Simplify your life by clearing the air - a simple challenge from Fun Cheap or Free

Interestingly, these things can be weighing you down in two different ways, physically and mentally. Physically, you might need to go through your junk draw or that one scary corner in your closet. Mentally, you might need to mend a broken relationship with a friend or loved one.

Either way, take some time to think of the things that you feel are weighing you down and try to fix them. Call that friend or family member and make amends. Letting whatever it was that was bothering you go will make you feel so much better. Likewise, you'll feel a lot better when you don't have to search through 5 million items to find a AA battery in your junk drawer! Whatever you do, take note of how you feel before and how you feel after you tackle it!


Each weekend be sure to make time for the important things like family time and date night. We encourage you to keep your family activities super simple this month. Go out for ice cream or make a treat together. Make an extra effort to connect in simple ways like game night, which is fun and encourages friendly conversation.

We are also challenging you to schedule in a “do-nothing weekend” where you literally clear your schedule of all outside obligations and relax together as a family. Sounds crazy… but these kind of weekends will save your life as they allow you to recharge and deepen emotional connections.

When all is said and done, just remember these words from Greg Mckeown – “Instead of spinning your wheels trying to get everything done, focus your effort on getting the right things done.”


Be sure to take a minute to do another thought download and reflect on how your month went. Reflecting now will help you see how far you've come and might help you decide to make a few of these challenges into habits.

What did you enjoy about slowing down? We'd love to hear all about your month and what you learned about yourself in the comments!


    • AvatarFunCheapOrFree says

      If you go to Step 1 under the Simplify Your Life section, you’ll find the SIGN UP HERE link that will have it emailed to you!

  1. AvatarNina says

    This is absolutely perfect and exactly what I needed to hear.
    I’m super excited to give this a go.
    Thank you so much
    As always, you hit the nail on the head.
    Love love love all the posts you do.
    Nina from Cape town

    • AvatarFunCheapOrFree says

      Nina! That is so nice to hear! I hope that it goes well for you, you’ll have to let me know once the month is over!

    • AvatarFunCheapOrFree says

      I would hope that it would help! But you should talk to a professional if you’re struggling with depression, there’s no need to try to battle it on your own.

  2. AvatarJanice Hiler says

    I didn’t get an email this month. Thanks for writing out the goals in the blog so I can incorporate from there!

      • AvatarJanice Hiler says

        It came a week late on the 7th. Just checking here was enough as I wrote what I needed into my planner. 🙂 Thanks for doing this!

  3. AvatarSara says

    Hi Jordan,

    You amaze me, as a mother of 6?! i love how you organise and handle stuff, you know life is not perfect but you just roll with it. Since i’ve seen a couple of your video’s, i’m so inspired.

    i would love a little bit more help with your block schedule. I’m recovering from a depression and it has helped me a lot. would you please tell me when you make them for you. Like do you make them on the computer day by day, or once a week on paper? that would help me out a lot!

    many thanks!

    an admirer from Belgium

  4. AvatarCeri Howe says

    I get the emails—but it won’t let me print anything—it redirects me back to the post and keeps asking me to sign up? (even when I am getting there from the email link)Am I doing something wrong?

    • AvatarFunCheapOrFree says

      I’m so sorry that you’re having problems! I’ve let one of our ladies know, she’ll be emailing you to get this figured out. Thanks for letting us know!

  5. AvatarBrittni Almaraz says

    I just wanted to stop by and thank you. A sister from church had sent me a link saying that I would just love your blogs and she was right. I am a mother of 5 boys and have a ton going on with working from home and trying to run our business. I relate so much to your videos and truly appreciate all of your knowledge. Have a great day.

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