What If You’ve Been Asking the Wrong Question? | COTH Blog | Church on the Hill

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What If You’ve Been Asking the Wrong Question?

August 4, 2026 | Jeff Coleman

Read Time: less than 3 minutes

Every decision you will ever make starts somewhere.

Sometimes it starts with a spreadsheet. Other times it’s a conversation around the dinner table. Sometimes it’s a quiet moment lying awake at two in the morning while you struggle to go back to sleep.

Underneath so many of our decisions in life is another question we rarely say out loud, but it’s still shaping us: Will this finally make me happy?

It’s not a bad question. I mean, who wants a life characterized by misery? We all long for moments of laughter, peace, beauty, meaningful relationships, transcendent joy, hope, and work that really matters. Those, my friend, are really good gifts. The problem comes when happiness quietly becomes the measure of everything in and around your life.

A few years ago, when I was taking part in the Transforming Center, I met someone who seemed to have built the life that most people want. They had a successful business career. A beautiful home. Vacations that sounded amazing and looked picture-perfect. Every time we gathered in Chicago there seemed to be another accomplishment, another milestone, another reason to believe this would finally be enough.

One day over lunch, in the next to last retreat, he admitted something that caught me off guard.

“No matter what I achieve,” he said, “the satisfaction is short lived. It never lasts as long as I want.” So, he chased the next thing. And then the next. And so on.

If we’re honest, many of us know exactly what he meant. We tell ourselves that life will settle down after the promotion. After we find the right relationship. Once the kids are potty trained. After they get their license. After they graduate and leave home. After retirement. After we buy or build the dream house, lose those last few stubborn pounds, or finally get caught up.

You know what’s strange? Our finish line has an odd way of always moving. Maybe that’s why so many people who appear to have everything on the outside still feel so deeply restless on the inside? Which leads me to think the question itself isn’t big enough.

Maybe there is another way to think about the life we’re all secretly trying to build.

Jesus had a remarkable ability to expose the assumptions we never stop to examine. Repeatedly, he invited people to look beneath their ambitions, behind their fears, and beyond their selfish wants and wishes, not to take life away from them, but to show them a life they couldn’t find on their own.

The funny thing is it’s the same invitation he’s giving today.

This Sunday we’ll wrestle with one of the most common assumptions in our culture and ask whether we’ve been chasing something that was never designed to satisfy us in the first place. So, if you've ever found yourself wondering why getting what you wanted didn’t truly deliver what you expected, I hope you’ll join us. This one is for YOU.

Our conversation may begin with happiness, but it certainly won’t end there.

See ya Sunday on the Hill.

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