08/31/2026
Eleven years ago, I stood in a swimming pool with my arms stretched toward my three-year-old daughter. Grace was learning to swim. She stood on the edge of the pool, blonde hair draped across her face, staring nervously down at the water.
“Come on, Grace. Jump in. I’ve got you.”
She looked away from the water, glanced anxiously at me and said, “Dad, I don’t think I can. What if it doesn’t work? What if I fail?”
Reasonable questions from a three-year-old standing at the edge of something new.
With a little coaxing and a lot of assurance, Grace finally stopped focusing on what might go wrong. She bent her knees, brushed the bangs away from her face, shut her eyes, pushed off the side…and jumped.
Earlier this month, that little girl began high school.
And as our family enters yet another new season—two kids leaving for college and the younger ones racing toward milestones of their own—I’ve been thinking again about that pool.
About the ledge. About the hesitation. And especially about the jump.
Because some of the hardest transitions in life aren’t about stretching forward; they’re about letting go.
Letting go of the child as you drop him off at college. Letting go of the house that used to be louder. Letting go of friendships that belonged beautifully to another season. Letting go of a job, a role, a dream, a relationship or even a version of yourself that once mattered enormously, but no longer fits you.
Even when the change is good, there is grief in letting go.
We can be enormously proud of the young adult pulling away from the curb and still wish we could have one more afternoon with the little one who used to climb into our lap. We can be grateful for what’s next and still miss what was. We can know it’s time to move forward and still hold tightly to the ledge behind us.
Paradoxically, in order to embrace what’s next, we must loosen our grip on what was.
Maybe that’s why the questions of a three-year-old learning to swim still resonate with us.
What if I’m not ready?
What if I fail?
What if this next chapter isn’t as good as the last one?
My friends, as we get older, the edge of the pool remains. Yes, it looks different than it did when we were little. But we still want guarantees before releasing our grip, certainty before saying goodbye and proof that the next season will be good before allowing the previous one to end.
But life rarely offers those guarantees.
Instead, we are challenged to trust. To keep the faith. To celebrate what was, loosen our grip, shut our eyes and jump.
Eleven years ago, my little girl asked me, “What if it doesn’t work? What if I fail?”
Maybe today there are better questions for us: What if it does work? What if the kid you’re struggling to let go of discovers strength you never knew he had? What if the empty space created by an ending makes room for something beautiful? What if the next chapter isn’t better or worse than the last one, just different?
Let’s not allow our love for yesterday to keep us from jumping boldly into tomorrow.
We don’t need to see the entire landing or know exactly how the next season unfolds. We simply need enough faith to loosen our grip on the ledge, shut our eyes, and jump.
This is your day. And live inspired.
