Our Family Has Weekly Calendar Planning Meetings—Here's What We Do (and Why It Works!)

I love a good checklist. What I love more is checking items off said checklist, and sometimes even cheating by adding a couple I just completed for that quick hit of accomplishment turned motivation for the next item. And what I appreciate even more is teaching my kids fundamental organizational skills that will help them navigate the journey ahead in school, career, and life in general.

Now that I’m a mom with a mental load that weighs heavier than I ever could have imagined, I value my planner, calendar, and checklists more than ever. I’m not going to lie and write that my kiddos have the same sentiment. Let’s just say there’s a heck of a lot more fun out there beyond scheduling. But I know they’re storing tips I share somewhere in the back of their minds for when they’re ready. Or at least they’re kindly humoring me.

Every (or nearly every) Sunday, our crew begrudgingly gathers at the dining room table for our weekly Family Calendar Meeting. This is when we map out the week on our giant kitchen calendar. Everyone is required to bring the following:

Respective planners/agendas/calendars (our collection ranges from PTA-published spirals to perfect-bound books to digital apps)
Any events that are happening or projects, deadlines, goals, or chores that must be completed this week
At least one contribution to the week’s meal plan
A fun activity to propose for the week
A source of gratitude or inspiration we all have to agree on (this has been a quote or a special event, but, most often, it’s our dog or my husband’s 104-year-old grandmother)
As few complaints about this exercise as possible

The table is strewn with multicolored markers, crumpled flyers from backpacks, snacks and drinks, and of course, the great big calendar. Everyone calls out or adds items in their designated color: carpool duty, school tests and projects, work meetings and deadlines, rehearsals and practices, plans with family and friends, volunteer commitments, which of the kids’ friends are sleeping over this weekend, and more. As our children grow, their social lives seem to take up more space than ours, and I love that.

Try out your own version of this meeting now. Perhaps it will help you ease into back-to-school season. Or start a family meeting about something other than planning! The ritual and routine (and blessing) of gathering for a shared purpose have value no matter the topic. I’ve heard family dinners are a timeless favorite.

I suppose that in each of these planning meetings, I have a vision of the blank canvas that is the calendar transforming into a colorful masterpiece of all of us having it together. In other words: a representation of the executive functioning skills I am determined to impart to my children. It sounds ridiculous, but I tell them that the collaboration, problem-solving, strategic thinking, and accountability developed in these conversations are mere examples of soft skills that will help them:

Develop and maintain self-esteem
Excel independently and on teams
Pursue talents and interests
Manage their time from middle school to college and beyond
Find success in future jobs
Contribute to their communities, and
Nurture their families and friendships

Though my daughter has picked up a love for highlighters and both kids amaze me with their ability to prioritize the fun in life while upholding responsibilities, I admit that no one but me loves these sessions. We may continue with them, just as they may disappear as teenagers’ priorities change. The kids may never even remember my attempts at these meetings.

Yet I pray that when they are all grown up, they will have skills surrounding both mental and physical organization for personal and professional success, that they actualize and grow from the thoughts and ideas in their minds rather than get stuck in anxious swirling and spinning, that they create and thrive in their environments rather than settle in where they are placed.

And when they look within, they see a sense of self rooted in positive values like kindness, honesty, and gratitude.

And when they look in the mirror, they feel a sense of self uplifted by positive beliefs like confidence, respect, and ambition.

And when they look at their desks, they live a sense of self guided by positive practices like grounding, responsibility, and, hopefully, a sprinkle of calendar planning.

I am no expert in parenting or organization, but I am confident that we are building a foundation. And I do know preparing our kids to design and achieve their dreams—and giving them skills to do so—is and always will be at the top of my endless to-do list.

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Ilana Lipson Cohen

Ilana Lipson Cohen counts her blessings as a beyond-full-time working mom who has the romantic notion that she can cook like Ina yet appreciates the reality that TJ's is the most brilliant source of dinner. Find her on LinkedIn or on Facebook at Holding Hands Forever.