Twenty Twenty Fun: A Year-Long Quest for Challenges, Celebrations and Commitment

Jenna Miller
5 min readFeb 8, 2021
Watch the video introduction of this year-long challenge and follow along for monthly updates.

The year 2020 is one I will never forget, but one I am trying hard to move on from. Yes, it did strip me of my college graduation and my plans to get a cool first job in a new city. But yes, it also brought me romance, lots of family time and a new career path.

So I thought, since I don’t really have a steady job (I am a freelance writer and podcast editor who breaks even with rent), and since I am obsessed with challenges, why don’t I fill the year with challenges?

And my boyfriend, Casey, being as incredibly supportive as he is, decided to take on this year of challenges with me. So we mapped out the entire year with monthly challenges, and within those months, we have weekly and daily challenges. We have challenges that we are completing together and challenges that are specific to our own personal goals.

Along with each challenge, we will be reading a book to go along with the monthly themes and doing a weekly book club where we discuss the books because we are just that cute. Be jealous.

To give ourselves incentives to actually complete the challenges, we owe a dollar for every missed challenge and $2 for each repeat offense. We are also each putting $5 away at the end of each week into what we are calling our Fancy Fund. At the end of the year, all the money in the Fancy Fund will go toward a fancy dinner and a night at a fancy hotel.

Let’s get to the breakdown of each of the months. I’m going to start with a very vague overview of the year’s challenges and will be releasing a more in-depth summary of each month as the year goes on. So hopefully that gives you some incentive to keep up with our journey and follow along.

January: Joy, Joints and Jobs

This month, we are focusing on daily yoga and gratitude practices, applying for jobs for Casey and for me, expanding my freelancing business by picking up new gigs.

February: Family and Friends

This month, we will be calling family members weekly, mixing up date nights and trying to schedule online activities to do with friends like virtual game nights, Zoom wine tastings and maybe even watercoloring sessions over FaceTime.

March: Money

This month is all about saving money and figuring out our finances. This will mean budgeting and for me, getting a business account and LLC set up. For Casey, he’s looking at getting a new car at the end of the season, so budgeting for that.

April: Amen

We are both Christian and thought it would be good to dedicate a month to strengthening our faith and diving deeper into scripture. This means daily devotionals and weekly sermons/church services.

May: Miles

The word miles will mean many different things this month. Miles fit into a fitness goal to run everyday and it also fits into our big move across the country, meaning miles of driving. We are hoping to have enough time to hit some national parks and cool cities on our way to our new home.

June: Journaling

This month is pretty self-explanatory, but our goal is to journal everyday and the journaling cannot be work-related. No to-do lists and no brainstorming story ideas or lesson plans. This is purely to integrate a positive mental health practice.

July: Just Write/Just Golf

This month will look a bit different for each one of us. For me, I have been wanting to start writing a book, so this month, I am challenging myself to write everyday. This has to be creative writing and cannot include my time spent journaling. Casey will be dedicating time to practicing golf and playing in tournaments.

August: Adventure

This will be a really fun month for us. We make weekly dinners, so for this month, we will make foods we’ve never made before and we will also switch off planning unique activities for each week.

September: Snap and Savor

During this month, our goal is to slow down and be present. We want to take a photo each day to capture it and we will enjoy each meal without any screens. At the beginning, in the middle and at the end of this month, we will fill out an hourly chart tracking how we spend each moment, so we can be more aware about how we are filling our time.

October: Organize

This month is all about decluttering. Our closets, our home and our phones will all be squeaky clean by the end of this month. We plan to deep clean each area of our home, donate our old clothes, unsubscribe from emails and services we don’t use anymore, delete photos and old emails and go through household items to see if we can get rid of anything.

November: No Waste

This month, we are going to try and reduce our waste. We will steer away from getting takeout, or if we go out to dinner, we will bring our own take-home containers. We will also try to limit waste by using metal straws, reusable Ziplock bags, cloth towels instead of paper towels and wool balls instead of dryer sheets. We also want to participate in a local trash pickup or some sort of local sustainability organization.

December: Digital Cleanse

For this month, we will limit our TV time to three hours a week and we can only watch TV on weekends. We are also limiting our phone use to only 45 minutes of social media per day between the hours of 8 a.m. and 7 p.m. with no social allowed on the weekends.

So there it is. A year filled with challenges and lots of fun (hopefully) and maybe a year of change. I am so excited to see what this year will bring, so please follow along with us on this wild journey. Goodbye 2020, hello 2021!

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Jenna Miller

CEO and Founder of Just Better Media, LLC, a media company dedicated to providing you with creative services that are just better than the rest.