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Before the Calendar Becomes Boss

Posted by Jake Mills

August has a way of speeding everything back up. Vacations wind down. School emails start multiplying. Practices, meetings, homework, and packed lunches loom. The family calendar that had a little breathing room suddenly can’t be read from the “week view” because every day has that little “see more” beneath an already long enough list of events.  

You know the feeling. 

You collapse into bed, brain fried, body heavy, so tired. So excited to drift off to blissful sleep.  

But you can’t.  

Your mind won’t shut off. The to-do list scrolls like a news ticker behind your eyelids. Tomorrow’s meeting. The birthday you forgot. The supply list you still haven’t finished. The practice schedule that conflicts with everything. The laundry still in the washer. 

The house is quiet except for the hum of the dishwasher and the buzz of your phone lighting up again. You scroll mindlessly, not even sure what you’re looking at. Like a moth mesmerized by a floodlamp.  

You put your phone down and close your eyes, but still no dice. The day is over, but it’s still running laps in your head. A race between today and everything on the agenda for tomorrow. Today’s finish line has just become tomorrow’s starting line, and you’re about to hit repeat with no stop in between. 

Repeat. Repeat. Repeat. Until you catch yourself complaining about how busy you’ve chosen to be. Until you’re at your wits’ end and so you force yourself to take a beat.  

But it doesn’t last long. Because in that tiny moment of exhale, you say, “It’s just the beginning of the school year. Things will settle down soon.” But deep down, you know how this works. Back-to-school becomes fall sports. Fall sports become the holidays. The holidays become winter activities. Then spring comes barreling in, followed by graduation season and summer. Every season promises the next one will finally be calmer. 

Before we rebuild the machine for another school year, we should admit something: it’s not a season. It’s a system. We are a people in constant motion. Rarely at rest. 

We run from school to practice, practice to dinner, dinner to homework, homework to bedtime—scrolling, posting, planning, producing. We chase progress and call it purpose, but most of the time it feels like running on a treadmill—lots of sweat, but we’re not really getting anywhere, you know? 

It’s not a new problem. “My people have committed two evils,” God says through Jeremiah. “They have forsaken Me, the fountain of living waters, and hewed out cisterns for themselves, broken cisterns that can hold no water.” (Jeremiah 2:13) 

The problem is twofold: we’ve walked away from the Fountain and built our own wells. We’ve stopped drinking what satisfies and started digging holes that leak. We keep the machine running while the soul dries out. That’s why we’re so tired. That’s why we’re so thirsty. 

The Cisterns We Build 

In Jeremiah’s day, cisterns were man-made pits meant to catch rainwater. Once cracked, they filled with mud, mosquitoes, and disease. Our versions are sleeker: productivity, image, control, approval, activity. We promise ourselves, Once school settles, once soccer ends, once the holidays are over, I’ll slow down. But when the dust settles, we just pick up a new shovel. 

And you want to know the worst part? As we build another school-year schedule, we’re not just deciding where everyone needs to be. We’re teaching our families what matters, what gets protected, what gets sacrificed first, and where we run when we’re empty. 

It’s not just you digging in the desert for diseased water by yourself. Your kids are drinking what you dig up and learning how to dig for diseased water themselves.  

The Ache of the Chase 

Solomon called it “chasing after the wind” (Ecclesiastes 1:14): movement without meaning. But here’s the haunting part of Jeremiah’s image: God’s people weren’t atheists. They still talked about Him; they just didn’t trust Him to be enough. So they built backup wells…and ended up drenched in activity while their souls died of thirst. 

I mean, you can feel it building, can’t you? The weight of everything you’re carrying? 

The calendar full of good things that somehow leaves you hollow. The sense that if you stop moving, everything might fall apart. And I can hear you getting upset, listing the reasons… 

You don’t get it, Jake. I have to do all this. 

If my kids don’t make the team, take the lesson, join the club, and keep up academically, they’ll fall behind. 

If I don’t volunteer or attend every event, people will think I don’t care. 

If I don’t say yes at work, I’ll be passed up. 

If we leave open space on the calendar, we’re wasting an opportunity. 

It’s just the way it is! 

It’s the soundtrack of modern life: carry everything or lose everything.  

So before every square on the fall calendar gets claimed by competing, color-coded events, maybe we should stop and ask: What are we carrying that God never asked us to pick up? What are we expecting this next school year to provide that only Jesus can give? 

The Fountain We Forgot 

But the good news is that God doesn’t just expose the problem; He offers an invitation: “Come to Me, all who labor and are heavy laden, and I will give you rest… My yoke is easy, and My burden is light.” (Matthew 11:28, 30) 

It’s like He’s saying, Lay it down. Rest with Me. Bring your family into My rest. I’m the Fountain of living water. Stop digging. Just. Come. Here. 

You don’t have to search for water. Living Water came down. The Fountain took on flesh and allowed Himself to be drained on a cross so you could finally rest. The water that costs you nothing cost Him everything. 

The Better Way 

So what does it look like to live fountain-first? Start by naming your wells. Where do you run when you’re empty? Trade performance for prayer, hurry for honesty, the endless scroll for a slow walk. 

Maybe it looks like not checking the school email, work email, sports app, or social feed until you’ve checked in with God. Maybe it’s protecting one night a week for slow conversation around the table instead of filling every evening with another activity. 

These small refusals are how the Fountain wins back ground from the cisterns. 

Here’s a radical one: before the fall calendar fills up, protect a weekly protest called Sabbath. Gather and worship with your church. Close the laptop. Silence the notifications. Share a meal. Let your family see that stopping isn’t laziness and Sunday worship isn’t one more activity competing for space. It’s part of how we remember who actually gives us life. 

It’s not laziness; it’s loyalty. You’re declaring, God, You’re the Source. I’m done digging. 

When You Start Digging Again 

And when you fail—and you will—don’t go back to the cistern of shame. Return to the Fountain. Jesus still says, Come to Me, all who labor and are heavy-laden, and I will give you rest… you will find rest for your souls. (Matthew 11:28-29) 

The invitation isn’t for the well-behaved; it’s for the thirsty and broke. 

Rest is still available. The Fountain hasn’t closed. 

So before the backpacks are packed, the practices begin, and every square on the calendar gets claimed, come back to the Fountain. Don’t just ask, “How will we fit everything in this year?” Ask, “What kind of family—and what kind of people—are these rhythms forming us to become?” 

The calendar will fill. The pace will increase. But Jesus hasn’t moved. 

Come to Him.