How Jessica Strategizes

How Jessica Strategizes

I spend each day with my four kids. We sit around the dinner table every night, I work to provide for the household, we do homework and assignments together, I paint fingernails and toes, give daily baths and snuggles and, even when I am completely exhausted after a long day, nightly reading. But if I am being completely honest, some days I am just going through the motions. I get trapped in my ever growing, never ending to-do list, and somehow get buried in the idea that my house always must be clean and I have to always have it all together.

So I decided that in 2019, one of my goals is to be more intentional with my family time—time I spend with my children and husband to reconnect, teach, and learn from one another. Some people may be reading this asking, “Just once a month, is that all of the time you are putting into your family?” No, of course not. But in the quest for being a present parent, I am choosing to set aside exclusive family time once a month. I want to better myself as a mother, and I know that these 12 special days will push me in the right direction.


Our List

As a family, we sat down and came up with a list of 12 things we would like to do together this upcoming year. We had to agree on each item, but also remember that there should be a certain balance of “service” and “self” on our list.

I encouraged and reminded the kids that not everything we do has to be extravagant and/or cost a lot of money. Having an outdoor play day and BBQ in the backyard is just as important and valuable to family time as going on an exotic vacation.

It’s also a gentle reminder to children that parents can be fun, uplifting, and engaged even when they are not on vacation. This is one that I need to personally work on. My children see me most relaxed and engaged when we are away from the home. I know that I tend to worry about the dishes, the house, and all the other “things” when we are at home. And I need to be better at being present at home.

To help facilitate the list building, I tried to think about things we already do together as a family and things that we have on our family bucket list. Once we pinpointed some of the activities we wanted to do, we identified how they tied into some of our core family values: fun, knowledge, service, health, simplicity, exploration, and tradition. This helps us keep a specific purpose in mind.

Here’s what we came up with:

January: Fun

Let’s kick off the year with some fun, shall we? Is there a better way to fight back the winter blues then fully embracing it? Snow Day here we come! Sledding, skiing, snowman building…you name it we are going to do it. Full disclosure—I don’t do well with cold weather, but I will for my kids!

February: Knowledge

Night at the Museum anyone? Ok, we won’t be going at night, but we are going to visit a family friendly museum for the day and learn something new together. 

March: Service

Let’s give back. Spend a Saturday together at a neighborhood or shoreside clean up. This will be a great day for us to teach the kids about caring for our local community. 

April: Health

The weather is warming up and it’s time to get out for a family hike. Let’s get our steps in for the day as a family. 

May: Simplicity

You don’t have to go far to have fun. Let’s pack a picnic lunch and ride our bikes to the park together. Frisbee, baseball mitts, soccer ball…you get the picture. 

June: Fun

Time for a backyard campout. It’s the perfect way to kick off summer. And even better, you don’t have to load the car up to go anywhere. 

July: Simplicity

Since we will be traveling during the month of July, we thought this would be a good opportunity for us to stay connected, sitting down together and writing cards to our family and friends back at home. We’ll let the kids take full control of this project—who, what, where, and when we will be sending these when we are abroad will be up to the kids. 


August: Knowledge

Let’s learn something new/try something new as a family. We have not decided what yet…so stay tuned. If you have any suggestions, put them in the comments below!

September: Exploration

Let’s visit a new place together. Is there anything more exciting than going somewhere completely new? Destination TBD. 

October: Tradition

We’ll make caramel apples together from start to finish. Make the grocery list, go shopping, prepare the ingredients, and create together. 

November: Service

Write “Thank You” letters to veterans and service men/women. We’ll gather up our sweets and treats from Halloween, as well as some other requested items for Operation Gratitude. This nonprofit is dedicated to lifting the morales of US Military, Veterans, and First Responders. You can find more information at

December: Service

Host a charity event to collect for the Toys for Tots drive. Our daughter has hosted a piano recital annually in our home for this charity. It is always a success and we love planning it together. The little kids are in charge of handing out the programs and collecting the donations at the door. My oldest and I work together to pick the songs she will be performing and practice for the recital. We all bake cookies together before the recital that we are able to share with our guests after the show. 

Our Calendar

Full disclosure: I’ve never done this. And by this I mean writing these down and sticking to it. This is a new journey for me. I am not one for making New Year’s Resolutions…because let’s be honest, do many people actually keep their resolution? That is why I am calling this a commitment. I’m making a commitment to my family and I hope that you find some way to make a commitment with your family this year too.

The next step is to schedule these commitments into your calendar and plan them! Since I’m a planner by nature, I put these all into our yearly calendar at the beginning of the year. I have a pretty steadfast rule about our family calendar: once it is in the calendar we are committed. However, with so many unknowns for other scheduling conflicts, it is easy for these to be pushed aside and then forgotten about. DON’T LET THAT HAPPEN!

For those of you that are not planners (it’s ok, I know many people are not!) you could write these down somewhere the whole family could see them, or set a monthly reminder on your phone to schedule your family day. Or you could write the 12 things down on small cards that you put up in your kitchen/or office area for everyone in your household to see. I am a visual person, and know that seeing it will keep me committed to it.

My family and I are so excited to go through our list this year!

About the Author


Jessica is the mother of four children nine and under, a wife, and a kindergarten teacher. She always wanted a big family and loves spending time with them, whether traveling or at home. She loves adventures, being outside, and all things Disney. You can find more of Jessica’s great ideas and insights on her blog,, and on Instagram @flyingwithfour.

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